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Ghosts of WIP Past, Present and Future

October 3, 2019

Happy 5th Anniversary Insiders! Join us on a journey through the program’s years.

Windows Insider Podcast Episode 24


JASON HOWARD: Welcome to the Windows Insider Podcast where leaders from Microsoft and Windows Insider discuss tech trends, careers, and innovation. I'm your host, Jason Howard.

This is Episode 24: Ghosts of WIP Past, Present, and Future.

But first, if you're not yet a Windows Insider, head over to the Windows Insider website, insider.windows.com, and register for free. Insiders get access to upcoming Windows features before they're released to the public, plus exclusive opportunities to experience all Microsoft has to offer. All right, on to the show.

Let's kick this episode off by saying happy 5th anniversary to the Windows Insider Program. In honor of this exciting birthday, we've put together a special super episode, and by super, I mean both content and length.

Our special guests will be taking us on a journey through the years with the Windows Insider Program. Think of it as our version of “A Christmas Carol.”

First, we will be joined by a familiar face, Brandon LeBlanc, to take a look at the history of the program and how it has evolved over the past five years. Then, we'll talk to Amanda Langowski, who will walk us through the present state of the Insider program and preview builds.

And finally, we will look out to the future of the program which we see as you, the Insiders. One of our many outstanding Insiders, Jeremy Sinclair, will be joining us to talk about how he makes the most of the program and what he thinks the bright future of the Windows Insider Program and Windows 10 looks like.

Without further ado, I am excited to welcome our first guest, Brandon LeBlanc. Welcome to the podcast, Brandon, and of course thank you for serving as our ghost of the Windows Insider Program's past today. Well, you know, even though we all know you're an integral part of the present and the future of the program as well. So, real quick, can you introduce yourself?


JASON HOWARD: I mean, I gave you your name, but like, can you tell those listeners out there, kind of, what you do here at Microsoft?

BRANDON LEBLANC: Yeah, so I'm a senior PM on the Windows Insider Program team, and I do a lot of the magic behind the scenes on making sure that we are communicating to Insiders on the things that we're giving them and the changes and updates we are making to the program. That's kind of it in a nutshell.

JASON HOWARD: That's definitely oversimplified.

BRANDON LEBLANC: Yeah. In addition to yelling behind the scenes on, you know, Teams, getting them to address feedback and things that we're hearing on social, specifically around like features. I don't do a whole lot of the, as you know, bug tracking and bug troubleshooting, because, I mean, I can't even troubleshoot my own bugs. But yeah, that's kind of it in a nutshell.

JASON HOWARD: Yeah, I mean, it is a lot of work to get, because there are so many teams that are contributing into each build of Windows. And so, one of the things that you did, you know, kind of in the past and obviously it's a process that is still used, is creating a unified place each week where we say, hey, this is the build that we're launching, tell us what you know of, if there's potential bugs, are there new features you introduced, are there changes that you made, to try and streamline some of that so that we can take some of the most salient points and put them in the blog post.

BRANDON LEBLANC: To make things a little bit easier than going and having to fish between different teams, I've created an alias internally.

JASON HOWARD: And what's that alias called?

BRANDON LEBLANC: It's called WIP Avengers, because I'm a nerd, and it has representatives from a lot of the major key teams. And every week, I ping them and say, here are the plans for the flight, and then they go in, and they just add their stuff into a Word doc. And it seems to be working well.

I mean, granted we do sometimes occasionally miss some things. You know, we're human. You know, it's a big product. There's a lot of code being checked in, and so, you know, we try to hit all of the things that we need to hit to tell Insiders about, so they can use it and give us feedback and all that.

JASON HOWARD: So much like myself, you've been doing this for quite a while, like you've been around since the team was, in essence, initially put together back in, you know. When did we formally come together as a team? That was in, what, 2015? But, I know both of us were working on that stuff even before then.

BRANDON LEBLANC: Yeah, so, I worked really closely with Gabe when the program first launched, and we started, you know, releasing builds. He had no one to write. It was, I mean, literally him, and then there were like teams responsible for flighting, but there was no one available, or no one was given the responsibility of writing the release notes.


BRANDON LEBLANC: And because at the time I was the editor-in-chief of the Windows blog, they were going to be making the announcements on the Windows blog, so it felt natural for me to write that content.

And so, Joe did the first blog for the first build, I believe, because that's when he introduced Gabe as the head of the program. And then going forward, I just took it upon myself to work with Gabe on writing the stuff that was in the flights.

That time, we weren't flighting as quickly, but every time we did flight, I remember I would always go to Gabe's office and sit there on his couch, and it would be like we would be there, hit the button, do the tweets. It was all just less formal.

JASON HOWARD: Yeah. (Laughter.)

BRANDON LEBLANC: And just like, I mean–and sometimes they'd change and like I'd get a text from Gabe like, "You need to get over here, we are about to flight." And I'm like, "Oh, I'll be on-on my way." But I mean I had a lot of fun.

That was my first like deep integration into like the engineering world. Because before, I was on the marketing and PR side, and I had a lot of integrations with engineering there, but it wasn't as deep, it wasn't as technical and nerdy, and I kind of felt myself kind of flourishing a little bit in that area.

So, it wasn't until like 2015 where Gabe realized as the program was-was becoming more and more important to building Windows 10, put together a team. He was like, hey, you want to come over here and-and do the release notes? And I had been doing the Windows blog for a long time.

JASON HOWARD: Nice little change of pace.

BRANDON LEBLANC: Yeah, it was more focused. I get to focus in the engineering world. It would have been really silly for me to pass that opportunity up, so I took it.

JASON HOWARD: Yeah. I mean, it's interesting, like, because my story is almost identical, but down a different track, right? Because even to today, you're still working on the comms side of things, working with teams or whatnot.

My side of things was more on the engagement and troubleshooting side, where after we started putting out flights, like I originally spent a lot of time in the Answers Forum, and Gabe kind of spun up the whole, hey, we're gonna be on Twitter thing, right? It felt a bit like an intentional accident, right? I know that sounds weird, but it's like he would go make an announcement, you know, and it just, naturally people started being drawn to that space, because of the nature of how Twitter operates. I can give quick feedback, I tend to get faster responses, things like that. So, Twitter kind of became a thing.

And randomly, like, I had a Twitter account, but I had literally never tweeted anything, right? I had created it to do some hardware testing back in the day. And so I logged in one day and I saw, you know, Gabe replying to things, and there was something that I knew I had information on, and I was just like, well, I hope Gabe doesn't get upset, I'm just going to tweet back, right?

And so, I tweeted back and got–you know, got the little like, and you know, all that kind of stuff. And you know, next time I saw Gabe he was like, "Hey, thanks for helping out, da da da da da," and the next thing you know, he's looping me in to conversations, and I'm going in and doing troubleshooting and, you know, guiding folks to, you know, please file feedback, let's look at the logs, things like that, things that I'm still doing today.

And, you know, at the same thing is, you know, right after we launched Windows 10, as we were working in that next cycle, when the team got pulled together, Gabe was like, hey, you know, I'm pulling together a formal team, it's going to be the Insider team. I know, you know, you've been doing a lot of work in this space, I definitely need somebody to continue doing this type of work, would you be interested in, you know, coming over to the engineering side and-and doing a lot of what you're doing now?

I was like, sure, why not, right? It was work that I enjoyed doing, and, hey, you know, kind of like you said, you know, I'd have been crazy to turn down the opportunity. So, I did, and then, you know, I've been in the engineering role ever since.

And a lot has changed in the past, what, now it's, you know, five years since the first build went out? It's hard to imagine how much has evolved over the course of time, between how we flight builds, the communications process, the number of Insiders that are involved in the program, right?

Some of the stories that we could sit here and talk about, just, I don't know, like, for me personally, like I'm going to ask you a few things specifically here in a moment, but like, one of the things that I reflect on is like as we've done travel, right, and gone to other cities in the U.S., countries outside of the U.S., the folks that we've met along the way, like this has been some of the eye-opening experiences that I could have ever have asked for.

BRANDON LEBLANC: I think, if I could summarize, really generally what the program has evolved to, it's truly evolved into a community. Doing the things that you just mentioned, where we are talking to people in person, like hearing the stories of how important the Windows Insider Program is for them, that's been amazing, like traveling and hearing their stories, whether it's how they're using the Windows Insider Program in their business to just them personally like why it's so important, how they love engaging on Twitter, for example.

You know, you were mentioning Gabe and Twitter. Like it was a happy mistake or an accident, only because he saw how amazing the engagement was with our deep fans, because they were–they were seeking us out and wanting to have that conversation.

It’s been crazy, because I remember back in the day, when we were flighting less quickly, we were like once a month, you know, pulling together the notes, you know, the messaging and stuff. It took a couple weeks. And then as we moved to this-this cadence of trying to go weekly, like, that was an interesting challenge.

JASON HOWARD: (Laughter.)

BRANDON LEBLANC: But now, like, I feel like everything is moving kind of as it should, but like that was, you know, if I could look back on that, that was like, oh my gosh.

JASON HOWARD: It's a–it's a significant change. So, you mentioned obviously that being–that you didn't necessarily call it being hard, right, but, I mean, it no doubt was, right, it was a difficult change to kind of navigate through.

So, looking back historically, right, so you got five years’ worth of stuff to kind of pour over in your head. What do you think one of the hardest moments that we've kind of surpassed or worked through in the past five years? Like, and I'm sure there's obviously more than one story that can be told here, but what's something that kind of sticks out in your mind, and do you think we did a good job of handling it?

BRANDON LEBLANC: The challenges that we're facing over the last year of multiple releases at the same time being flighted, that has been a bit of a challenge, trying to explain what build is part of what release and going into what ring. But it's a-a good challenge, but it's certainly a challenge, and making sure that everything is communicated in a manner in which it makes sense. And sometimes we don't do that.

The recent 19H2 stuff, we didn't do a good job initially of communicating it, and I spent literally a week with the team working out, like the best possible way we can explain this to–that will make the most sense to the broadest set of customers. And then we released an updated text to a-a 19H2 post.

Those are some of the biggest challenges, I think, whereas before it was more of just a single release and a build going through the ring progression, and then, you know, we would finish that release, move on to the next. Now, we're finishing a release, but we've already moved on to the next.

And just rolling with the changes that the engineering teams are pushing out as they find more efficient ways of building and releasing Windows. Just making sure that we're following that train and-and communicating that out to Insiders, it's been a challenge, but it's been a really exciting challenge. Like I've had a lot of fun-fun actually dealing with that. Yeah.

JASON HOWARD: (Laughter.) Yeah, the listeners out there, obviously you can't see Brandon's face, it's that–it's that mixed bag of fun look where it's like, yeah, it's-it’s fun–at least I'm interpreting this right, you can tell me if I'm right or wrong, Brandon. It's like it's challenging while you're going through it, but once you've kind of come out on the other side and you've got a plan put together, it's like, okay, like that was an interesting challenge.


JASON HOWARD: It was different than, you know, some of the way we've had to do things before, or you know, a different process we've gone through, and knowing that you've got something productive and you know, hopefully beneficial to come out on the you know, on the other side with.

BRANDON LEBLANC: Yeah, yeah. Well I-I found myself just diving deep into like some of the mechanics of what we're doing. Because in order for me to properly turn that into some sort of customer-facing message, I feel like I have to-to be really in the weeds on like how we're doing stuff.


BRANDON LEBLANC: I used to do that a lot on the marketing and PR side when I was on the Windows blog. You know, I would be given the challenge of communicating things like our strategy for the additions, the SKUs of Windows, and I would spend a lot of time with the people responsible for those-those decisions. And I wouldn't say I would be an expert but, I mean, I’d be fairly-fairly educated on how all that works. And I'm doing the same on the engineering side, which I find fun, but again, like–you know, we hit –I’ve hit misses, but it's all-all part of learning, like, okay, well, we didn't quite explain this element correctly or as clear as possible, so I go back to the team, and like let's work out, let's figure something out. And for the most part, teams are like, okay, we get it, we hear the feedback and–

But I would say that that's been the biggest challenge. You know, there's been pops of challenges, but like the way that we're doing Windows now, it's–

JASON HOWARD: It's definitely different than earlier releases.

BRANDON LEBLANC: Oh yeah. Oh yeah.

JASON HOWARD: Especially if you compare it to, you know, four to five years ago.

BRANDON LEBLANC: Well, I mean, I remember–I remember it feeling like it was a challenge to communicate, like when we introduced the Release Preview ring, and this is nothing compared to a new ring. And so–yeah. So it's-it’s fun.

JASON HOWARD: So, to where we're at now, right, so kind of looking at current day, what is your favorite part of the program?

BRANDON LEBLANC: My favorite part of the program is–well, I mean it's the Insiders. It's seeing them get excited over the engineering work we're doing for the product.

There's two parts to that. There’s that part, and then there's the part of seeing the excitement from the PMs and the engineering teams when I help them communicate something that–some work that their team has done in a build, and then like connecting it with the Insiders, and like seeing their reaction to like, oh my gosh, the Insiders are, you know, liking what we're doing or, you know?

Both those sides, I find really gratifying. I really love helping engineering teams communicate the work that they're doing to Insiders and relaying some of that excitement and comments and feedback back to them and getting their reaction, like, oh wow, the Insiders like this. Or, you know, sometimes it's not all positive, but the teams take it, and they're like, okay, well we need to make these kind of adjustments, and-and whatnot, and I-I like that.

JASON HOWARD: Yeah, I mean, constructive feedback is just as important as getting a "good job" pat on the back, right? It helps us kind of re-tailor things and you know, shift direction to something different.

BRANDON LEBLANC: Yeah, yeah. Well, there's–there’s some PMs who I reach out to who feel like their feature or their work isn't important to note.

JASON HOWARD: Oh, see, that's not right.

BRANDON LEBLANC: And I'm like, no, everything that you're working on is important.

JASON HOWARD: Absolutely.

BRANDON LEBLANC: And you can see that it brings a smile to their face, because like they–for some reason they think that they're working on something relatively, I would quote, "minor." But it doesn't matter, it doesn’t. It's all important. And so, I'm like, we will talk about it. Even if you're moving some icon over here to that, to, you know, one different side of the thing, let's communicate it.

JASON HOWARD: And I will say this, one of the things that never ceases to amaze me, surprise me, whatever, is how even the smallest change, changing the font on an icon, somebody notices it, right?


JASON HOWARD: It's not always the same people that notice everything, but there's always an Insider somewhere who, it happens to be something they use frequently, or it's something that they're really interested in, and somebody always catches it, and it's like, hey, why wasn't this-this font change in the blog notes or why wasn't this icon, you know.


JASON HOWARD: You change the shading of an icon, like. I'm like–and this is one of the interesting things is, because, I mean, you and I both, we're so just buried in taking new builds, using, you know, the machines to do our daily work, that I'll be honest, that unless it's a super-drastic, you know, visual change, there have been small changes made in the OS that I didn't notice until somebody called them out. And it's because, it's either something that I don't frequently, you know, navigate to or use, or it's just something that, you know, I'm just, I'm clicking to get something done and, you know, I miss little details like that, and I'm like–and you know, you just stop and you're like, oh yeah. And you actually take note of it, and it's like, that's kind of cool, right?


JASON HOWARD: And it's good to like give the teams that are making those, even the subtle changes, to give them their call-outs, and be like, hey, this–this may look like a small change, but somebody's, you know, work, effort, and passion went into even making this small change.

BRANDON LEBLANC: Well, my-my favorite is when I notice something before the build goes out that I think we should note, and it's a minor change, and sometimes there are some PMs or some engineering teams that are like, oh, they won't notice. (Laughter.)

JASON HOWARD: Yeah, they will! (Laughter.)

BRANDON LEBLANC: Yeah. And so, then we go out with a build, it's not in the release notes, and they notice. And I throw like the tweets or the comments back at them, like, yeah, yeah, they-they noticed, and this is why we should note it. And they're like, oh, wow, that's crazy. And so, sometimes I get a kick out of that, like, yeah.

JASON HOWARD: So, if you had to look back over the past five years, right, we talked about earlier like what's your favorite part of the program, and you mentioned, you know, connecting teams into the communications process, and then obviously communicating to Insiders and hearing their feedback, and like that–in essence, that communications and feedback loop between the engineering teams and Insiders.

If you had to isolate it down to a specific memory, like one thing that you would say, I know this is going to be hard because even I would have a hard time answering this, but, what would you say is, let's just say one of your favorite memories of anything over the past five years?

BRANDON LEBLANC: That is–that is hard.

JASON HOWARD: I'm telling ya! Like I'm sitting here trying to answer the same question in my head while I–while I ask it to you, and there's just story after story running through my head.

BRANDON LEBLANC: I mean, the whole experience has been great.

JASON HOWARD: The fact that we have an Insider program is pretty fantastic, because it was a monumental shift from the way preview efforts were done in the past.

BRANDON LEBLANC: One of my favorite memories is being able to shift to that weekly Fast ring-like pattern that we try to–we-we aim for. Because when we were doing the monthly, we got a lot of feedback from Insiders who just there was this pent-up desire to want more, quicker.


BRANDON LEBLANC: And, I smiled a lot when we were able to achieve that in a way that was efficient. When we finally found our footing with regards to releasing that way, I remember smiling a lot, because, like, we-we addressed feedback from Insiders, we're getting engineering teams feedback earlier and quicker on their stuff. Like, I felt that that was like an important pivot, with like an important element of a pivot on the program.

But I just, I have so many favorite memories, you know.

JASON HOWARD: You're already laughing, and you haven't even said it yet. This is going to be a good one.

BRANDON LEBLANC: I'm laughing. I haven't said it, and I don't know if this–I remember there was one time, where we had a flight. I was in Gabe's office, because we were still doing the whole like, I would go into his office and that's how we would flight. There was no call or anything like that.

And I remember the team responsible for the flighting, you know, said, hey, we're live, Gabe did the tweet, we posted our blog post. All of a sudden, Insiders were saying, no, we're not getting it, we're not getting it. And Gabe was so passionate about the community and making sure that what he said was correct.

JASON HOWARD: Correct, yeah.

BRANDON LEBLANC: But the flight was not live, and for some reason, there was no one around who could jump in and figure out why. And all I just remember is him running down the hallway yelling, "Where are the people? I need to know what's going on with my flight!" And–

JASON HOWARD: (Laughter.) Gabe is–Gabe is not exactly a small guy.

BRANDON LEBLANC: No, and he's-he's loud.


BRANDON LEBLANC: And I just sat-sat there on his couch. I was just like, in his office, like–


BRANDON LEBLANC: But I mean, like it was great that he had that passion for the community, and he took so seriously that, you know, the accuracy of what he says. That's not to say–like Dona's also the same way. If we say something or we do something and she tweets about it, and then we come back to her to say, oh, that's not right, she hates that.


BRANDON LEBLANC: So, it's that seriousness with regards to like how important communicating and being clear and like what we say is actually what we say, that's just it's-it’s important.

But like that Gabe memory kind of stands out as like, oh wow, I'm going to just sit here and hope for the best.

JASON HOWARD: So, it's funny you telling this, right. So, I'm like, you know, I said I was sitting here kind of think through some of these myself and reaching back in the memory bank here. It reminds me of the origin of the taco hat, right?

So, I've never–I've done a partial job of explaining it on one of the webcasts back in the day, but I don't think I've ever told the entire complete end-to-end story of how the taco hat came to be, so, I don't know. Maybe with the 5th anniversary episode maybe this is the time that I should actually do it, so here we go.

Several years ago, what, 2017, we had just started doing webcasts, right? We had tried one out in, I think it was November of 2016. We did kind of a test run.

BRANDON LEBLANC: I remember that.

JASON HOWARD: And we're like, hey, you know, people are going to show up, you know, is anybody going to, you know, think this is cool, and we had like 20 or 30 people kind of come and go over the couple of hours that we were on air, and it was like, eh, you know, we'll see how this goes.

And then in February, we had a bug bash, so February of 2017, we had a bug bash, and I hosted a full hour and a half. There was a bunch of people in the room. We had I think 100 or 150 Insiders kind of show up over the course of the hour and a half. It was very–it was very structured, kind of rigid, right?

I-I will admit like now you see me on a webcast, and I'm super laid back and just, you know, I like to have fun, but like the original one, like I was kind of formal and rigid, and like-like it didn't have so much of the fun side to it, right? I had to learn how to loosen up, you know? Because I was just like, hey, this is super serious, I need to be super, you know, direct and forthright in this. And there's definitely a note of seriousness, like when we were taking about content and some of the things, like the messages we're trying to convey.

So fast forward a few months and, you know, May rolls around, and we're having a Cinco de Mayo like get-together.

BRANDON LEBLANC: I remember, because I was with you.

JASON HOWARD: Yeah, and that's, hey, trust me, I'm not leaving this out of the story.

BRANDON LEBLANC: We went to lunch.

JASON HOWARD: Yeah. And so, the person who was running flight ops at that time was Stephen, and he was like, hey, you know, can you go to the Party Store and grab us some, you know, some fun stuff to kind of hang up and whatnot, you know, just some decorations or whatever. I was like, okay.

So, you and I ran, we went to lunch, we went had had Fatburger. because it was right next to the Party Store. And we go in the Party Store and we're getting, you got a couple of banners and, you know, some like plates and stuff, you know, because we were having like a potluck type thing.

And you know, as we are approaching the front of the store, Brandon was like, oh, this would be kind of cool, and it's the giant taco hat. And I'm laughing, I'm like, oh my goodness, this is ridiculous and hilarious, and it was like 5 bucks. And I was like, oh yeah, I'm gonna spend the 5 bucks and buy this myself, I don't care. So, of course I–you know, I didn't even–Microsoft didn't even pay for the taco hat, I paid for the taco hat, because I'm like, you know, I'm not going to put this on company budget or whatever. So, I bought the taco hat.

So we had our little get-together, it was fun, you know, and then after it, you know, I set the taco hat in the office up on the bean machine, right, the computer that we ended up having built to do the webcasts with.

And so, we used to do the little teaser announcements where, you know, Dona would hot on a Post-It note or on a whiteboard what the next build number was. Well, completely went way overboard and ridiculous, and we spelled the build number out in granola bars on my office desk. (Laughter.)

And for anybody who's wondering why I had that many granola bars, it was just like there's a–there's a store here in the U.S. called Costco. It's like a warehouse type store that sells everything. Like you go to a store and buy a small box of granola bars, and it has like four or six in it. You know, Costco sells like 30 packs of everything, right? It's just, it's ridiculous. It's a bulk warehouse type thing.

So, I had a bought a giant box of granola bars, and I had them at work. And so, I was like yeah. So, I spelled out the build number in granola bars on the desk. Well, Dona takes the picture and tweets it out, you know, as a teaser for, hey, this is the build that's coming. And, you know, folks are like, oh, hey, there's the build number, ha ha ha, that's hilarious, right, because it got spelled out with food of all things.

And then somebody was like, is that a taco hat in the background? And that was the tip of the iceberg, right, that's what started it. Somebody asked, and I was like, oh yeah, we had like a little fun little get-together here at work, da-da-da-da. And they were like, no, that thing is hilarious, that is awesome. And I was like, are people, like-like really fascinated with the taco hat, like of all things, like the taco hat. And more tweets came in, more people were like, oh my goodness, that's hilarious. And I was like, okay, I'm going to have to bring this to one of the webcasts, you know.

And lo and behold, like the lore of the taco hat was just kind of born completely randomly. I had never had the intention of putting it on a webcast, I never even realized it was going to go on the internet, right? It was just, it was a party favor that was, you know, meant, you know, for a fun get-together. And the next thing you know, it's kind of like almost like my default kind of like personal logo or something. I don't know how to describe it, but it's a thing.

BRANDON LEBLANC: Well, it just comes to show you like how much the community is observing the things we put out, like the pictures. Anything we tweet that's a picture of something, they're going through pixel by pixel, looking at what–is there anything hidden in that?

And-and also, it's just, again, that-that community element of interacting with us and having fun. It's like, you know, when I would take–show pictures of my desk or in the office, and they would see some of my-my nerdy action figures and things like that. Like I think that's part of why the program is the way it is, is that we're out there on the front lines, but we're authentically showing ourselves–our true selves.

The taco hat, it shows, well, you like tacos–

JASON HOWARD: Oh yeah. (Laughter.)

BRANDON LEBLANC: –but it shows a sense of humor, like it shows elements of you. And so, I think, that's definitely a favorite element of mine, of the program.

JASON HOWARD: Well, it's the same thing with you showing up to webcasts carrying a–I'm going to say this wrong, the bathlet?


JASON HOWARD: Bat'leth. Okay, I got this a little backwards. Every single Star Trek fan out there is going to like, you know.

BRANDON LEBLANC: I make it a point to go to the webcast with some sort of nerdy thing, but I think that–

JASON HOWARD: Yeah. You showed up wearing your X-Box onesie, which was hilarious, and I'm still jealous that I don't have one.

BRANDON LEBLANC: Yeah, but those are elements of-of our personalities that we get to-to exert with the program. And then it feels like they have a connection to us. And so that's the community element of the Windows Insider Program, that I think you don't get from other programs like it.

I mean, like if you look at what Apple and Google are doing, it's just straight up beta program, beta testing. You don't interact with the people who are running those programs. You just send feedback through an app and hope for the best.

And, we have a lot of work to do to improve, like we're not perfect, but I do think our authenticity and genuine ability to put ourselves out there, I think that makes things a huge positive for what our program stands for. And people get to know us. They go–they go to Twitter, and they talk to us about stuff, you know–you know, like–

JASON HOWARD: (Laughter.) Whether they like pineapple on pizza or not.


JASON HOWARD: It's like-like one tweet is somebody saying, I found this bug, here's some feedback, and the next one's like, oh no, they're jumping into the pineapple-on-pizza war. It's hilarious.

BRANDON LEBLANC: But at-that same person, like, I think that there's also like, they feel like they can reach out to us about these issues, and-and they feel comfortable, because they can talk about these issues, and the next minute they're asking us how pizza was or how teriyaki Tuesday was–

JASON HOWARD: I know, right?

BRANDON LEBLANC: You know? And so, we should pride ourselves on-on those elements.

It's something that Dona actually really pushes us to do, is the authenticity. She really embraces our personalities and wants that to be reflected outward. Whereas, you know, Gabe didn't stop it, but wasn't as–like he didn't push it as much. I think that's an important like difference between the two.

JASON HOWARD: Well that's one of the interesting things is even before Satya kind of made it a theme company-wide, right, Dona was like, hey, be yourself, have fun, you kind of know what the appropriate boundaries are of, you know, just-just exercise common sense, right? And then kind of internally and it's-it's spilled over like, I don't think it's ever been formally quoted externally, but the-the gist of what Satya said was, bring your whole authentic self to work, right?

You're-you're more than just the code that you write or a spec document that you've collaborated to put together. You're more than just, you know, a tweet asking somebody, hey, can you file feedback, right? These are individual things that happen, but collectively, like your personality drives how you interact with somebody, or they drive the style in which you work, right? They-they drive your day-to-day activities and how you end up connecting with people.


JASON HOWARD: And I've gotta say that, at no point when this program began, did I ever think that I would be doing, you know, a monthly webcast or be doing a podcast series.

BRANDON LEBLANC: I didn't think–I didn't think we would be doing this either.

JASON HOWARD: It feels like anything I'm gonna say just is an understatement.


JASON HOWARD: I guess I'm having a serious moment here, right, like a true introspection. I'm so thankful for the program in general, as well as kind of how it’s evolved some over the course of time.

You know, we get feedback, "Hey, I like that y'all are doing this now, I've missed some of this, the way you used to do things," but just like with anything else, right, the only constant is change. And while the program may not change as fast as some other things, like the nature of the program has changed over the time, and I think it's for the better. I hope that most people would agree.

BRANDON LEBLANC: The big change has just been the community and the growth of the community. And it's no longer just installing builds, it's doing things, like doing things on those builds.

Like, if you're a photographer and you're using our builds and you're, you know, importing, you know, your photos from your camera, your DSLR, and you're having some issues with the import, like, it's helping the community embrace some of the things that they're doing and tying it back to the program.

I think that's-that’s fantastic, but I mean for me, like the program is my heart and soul. Like, I go home, and I'm installing builds. I don't have a single device that's not running a preview of some sort, unfortunately/fortunately. (Laughter.) You know, my Xbox is on the Xbox Insider program, my Surface Studio is running Fast builds, all my laptops. Like it's, you know, I'm also an Insider, too.

JASON HOWARD: So, you know, since we're having kind of an introspective, like almost serious moment here, what do you think has been probably the most inspirational story you've heard from Insiders over the years? Like-like something that really was like, almost like a wow and a very genuine, like almost heartfelt kind of–kind of moment?

BRANDON LEBLANC: There are many. And I know that-that's kind of like a-a cliché for I can't remember, but it's not. There-there are so many. I remember when you and I went to Texas to do the Microsoft Store.

JASON HOWARD: Yeah, we went to Frisco.

BRANDON LEBLANC: Yeah. And it was amazing that we had two of our Insiders, an older couple. They were there like an hour, two hours before we got there because they were so excited to meet us.

In my heart I felt like, wow, like us getting out of Redmond and going to these small places that Microsoft normally doesn’t hold events and all that stuff, and getting out and talking to customers, like that was a moment where I realized that, like how impactful that is. That-that really stood out. Like that was when I realized that going to events, whether they're big or small, can make a difference.


BRANDON LEBLANC: Whereas I, prior, didn't really understand the importance of going and being at certain things in-person. My takeaway from both the store events that we did, we did one with Frisco, and then we did one in-in Boston, and my takeaway was that, events like that are important.

Which is why I like the Ignite Tour, they're amazing. Because we're going, and we're taking Ignite on a tour. People who can't go to the big Ignite in November in Orlando, we're going to take that on the road and go where people are, and I think that's important.

And I would love to do more store visits, because I think that, whether it's two people or 10 people or 15 people, like, there's always value.

JASON HOWARD: You've hit on something that's bigger than just telling you know, one story right, there's a story I'm going to tell in a moment of something that kind of hit me out of left field that I never expected to happen related to the program.

But like you've definitely touched on a bigger point of connecting with people, right? Like Insiders are Microsoft customers, they're just part of that really passionate fanbase, right, who love to interact with us, love seeing what we're working on. They love, you know, grabbing the preview builds and installing them. They love the banter that, you know, we have in the various channels.

Not everybody comes and connects with us on Twitter and whatnot, but, you know, I'm super thankful for those who do, because they're-they're taking the time to come and do that. Like whether they're at work or they're at home in their personal time, they're literally, you know, devoting a part of their limited time. Everybody on this planet has a limited, fixed amount of time, right?

And you know, I'm eternally grateful for those who come and talk to us, whether or not it's about a bug, or if it's about a taco hat, or if it's pineapple on pizza, like, I don't care. Like I love the conversation, because these are real people who are coming and having conversations with us, and they're people that I would never have the chance to meet otherwise.

BRANDON LEBLANC: And we owe it to them to-to continue. That's how they feel that they're getting value out of the program, is that they're-they're feeling that connection with us, and so like we owe it to them to continue to-to foster that connection.

JASON HOWARD: This is a bit of a serious story, but it's kind of a highlight of something I never would have expected to come from the program.

There was an Insider, I'm not going to name names or anything, and thankfully most of this happened via DM, so there's not like a direct paper trail out on the internet of it. But there was–there was an Insider who was participating in the program, was diligently, you know, sending in feedback and bringing, you know, bugs big and small to my attention.

And I got a message one day that was like, hey, can I talk to you? And I was just like, okay. And I immediately sensed that it was more than just, hey, I found a bug, you know, here's the feedback link. I was like, yeah, you know, send me a DM.

And so, we kind of like stepped into the–you know, a private conversation, and what came kind of pouring forth from this person was, in essence, a thank you for–I'm not going to change the words that were written because they're stuck in my head, and it was a thanks for giving them some purpose. Because they were going through a really just, say, tough spot in life, and like, I'm getting emotional thinking about it because it was just it's-it's-it’s interesting, right, and it's-it's hard to–it's actually hard recollecting this, but–

BRANDON LEBLANC: He's gonna cry. He has a heart, I finally realized. Now I know that Jason Howard has a heart.

JASON HOWARD: Let's just say they were in a really bad spot, right?


JASON HOWARD: I'm not–I don't need to get into all the details, but being able to focus on the program gave them something to distract them from a lot of, what I'll just call like the negative that they were going through, and some of the bad thoughts and other things that they were experiencing.

And to realize that somebody could take a program like this, and how it could impact them in a way that helped them get past something–we'll just say a series of really bad and uncomfortable things–like it's-it's not something I would have ever have expected.

And to know that, you know, even-even having that kind of impact for one person, right? It's not a story that I've ever told, right? Because it's definitely private for that individual, and that's, like I said, that's why I'm not giving out any details, but that's–

And-and I still talk to this person, right? They're still on Twitter, they're still, you know, in the program, they're still active. They're in a very different place in life at this point, something I'm super thankful for. I'm glad things changed, I'm glad they had an outlet and a focus, you know, where they could put attention in a positive way, that kind of brought them past some of what they were going through.

I realize this is like just one example, you know, of something very specific to that individual, but everybody who comes and participates in the program gets a little something different out of it.


JASON HOWARD: Whether they're doing it for, you know, a distraction from life, or they're doing it, because they just want to see what's next. Or, you know, we have some folks that just want to get the news and newsletters and read the blog posts, right? And there's other people that are doing it because they want to know how–what's coming for work, right? They're IT pros, and they want to see, hey, what changes are coming, what features can I implement.

There's developers, you know, what new thing is going to integrate. Oh, fluent expanded, cool, I can integrate that in my apps. And then there's just the really big fans that love getting new builds and tinkering with them and finding the stuff that we've talked about, some of the stuff we haven't talked about, that kind of stuff. Like everybody gets something different out of it.

BRANDON LEBLANC: It's that community aspect of-of the program that I think has just been a big surprise for me as well. Like, it went and it grew that way, and like I've had people interact with me, like when I talk about my anxiety, like, they're like, wow, I feel the same way, like they can relate.

And it's that-that authenticity that we put out there that we're real humans. It fosters that community. I mean, we’ve had kids who have ADHD, who-who had been struggling, who now participate in the program and find their footing and no longer struggle. Like it's-it's rewarding to see and that's why I feel passionate about the program being not just straight up, it’s, you know, it's not just a straight up beta program. It's a community of-of people that are using our products, who are passionate about technology and then also just are real people.

JASON HOWARD: Well, we've done a bunch of looking back, right? And we've even done some, hey, you know, what do you think of the current state of the program, but like although I'll get into this more with, you know, the next guests on the program, what do you think the future holds, right? Like what are you excited for in relation to potential changes or just the state of the program overall, like, what are you looking forward to?

BRANDON LEBLANC: I'm excited about some of the efforts we have in place to grow the program beyond the current audience that we have of the more tech, technical, tech-savvy people. I believe that there is a whole, like treasure trove of feedback from people who are like my mom that can help us make Windows better, and I think that evolving to find ways of engaging with that audience, I think is going to allow us to-to do some amazing things with the product.

JASON HOWARD: Yeah, and that doesn't mean that we're going to stop, you know, anything that we're currently doing, engaging with the more tech-savvy or tech-forward folks that are in the program.

BRANDON LEBLANC: No. It's just going–it's just–it's just

JASON HOWARD: It's adding another layer.

BRANDON LEBLANC: Adding another layer and continuing to evolve the-the community aspect. I want to hear more from how our community is doing things with-with their PC, like what they're doing with their PCs, whether it's–and I'm an IT pro deploying it in a business, or if I'm just a user who is into photography or making movies or–like, all of those stories I think are just, you know, I think all-around making Microsoft a better company, and our products better, and that I think is the most exciting part of the-the future.

JASON HOWARD: Yeah. Well, we're five years down, and this train's still a-runnin', boss. It's going to be fun to see what comes next.

BRANDON LEBLANC: Here's to the next five years.

JASON HOWARD: Alright, one last thing. Any embarrassing Jason stories you want to tell? I'll give you the opportunity.

BRANDON LEBLANC: So, yes, there’s definitely a story that-that sticks out in my mind.

JASON HOWARD: Oh man, okay, here we go.

BRANDON LEBLANC: And that is when we were walking through the airport, I think it was in Texas, and we were having a conversation about making noises, and you ended up making dolphin noises at the airport. (Laughter.) And so, I then decided that from here on out my ringtone for you and text message tone for you is now the noise of a dolphin.

(Laughter.) I remember–I remember I was out with my parents for dinner, and you texted me and my phone just made dolphin noises, and my dad's like, what is that? I'm like, oh, that's just Jason. Jason–I-I’ll get back to him.

JASON HOWARD: Oh, my goodness, man.

BRANDON LEBLANC: But there is another airport story relating to that.

JASON HOWARD: Oh, goodness.

BRANDON LEBLANC: We were in Boston, and I had done the dolphin stuff on my phone. And I was walking, and you had texted me, because I went out to do something and, you’re like get back to your gate. And my phone started making dolphin noises. I remember walking past a little girl and her mom, and the little girl was like, "Mommy, I heard dolphins!" (Laughter.) And I’m like, you know, yup, that's me!

JASON HOWARD: Scary. Oh my goodness, oh wow. I just like I will say one more thing as we wrap up here. You know, every time we do a webcast, the day before or two days before, I fire up the B machine, make sure all the software is up to date, the broadcasting software. You know, I'll actually livestream on Mixer on a different channel that's just kind of like a, you know, like a prep channel, and you know, some of the crazy stuff that we have done, because like–

So\, for those who don't know, Brandon and I up until a couple of months ago, we shared an office, for-for many years, right? It was good because we got to collaborate together very well. We had lots of random singing contests, name song contests, like we're just working away on content or whatever, and you know we're playing like Name that Song, Name that Tune type stuff.

And you know, I gotta say, you know, you rewind five years and I never had a–I would never have had a clue that, you know, things would have gone the way that they have. I gotta say, man, it's been a blast working with you. I know it's, you know five years down and you know, whatever the future holds, like this is, it's been good times.


JASON HOWARD: I gotta say like –

BRANDON LEBLANC: It's been the-the-the most fun I've had yet, and hopefully it'll be more fun, you know. Also, going back to the–to the–to the office story real quick.

JASON HOWARD: Uh oh. (Laughter.)

BRANDON LEBLANC: I remember, Jason was told he had to share an office with someone, and they were going to have him paired up with someone from a completely weird, different team, we didn't even know, and it was like, okay, that doesn't make any sense.

And so, I actually volunteered. I went to Dona, and I'm like, look, you know, if he has to share an office, he should just–I mean, we work closely already–he just should just move into my office. Let's not make this into a big thing. And I remember you ended up just, like we didn't even do office–official office move.

JASON HOWARD: I just literally like I heaved my desk up.

BRANDON LEBLANC: Yeah, and just dragged your stuff into my office, and we're like, we're problem solvers, we fixed this. (Laughter.)

You know, and I've been thankful for that, because I mean like I like to watch out for my colleagues, and I was like, I'm not–he doesn't need to be in some weird office with some person that you're-you’re not familiar with. Like, I mean, because if I were in that position, I wouldn't–that wouldn't be cool, and so–

JASON HOWARD: Yeah, I just remember, like, our team admin, she-she gave me a lecture. She was like, you're not supposed to do your own office moves, they get coordinated for a reason, you could have hurt yourself. All very valid points, but I was like, hey look, I didn't want this to be some drug-out two-week process, like I just wanted it done so I could get back to work. And literally I moved my whole office in under 30 minutes.

BRANDON LEBLANC: Yeah, it was a quick thing, so yeah. (Laughter.)

JASON HOWARD: Hey, well Brandon, again, thank you for making the time to come hang out today. Thanks for not telling the more embarrassing stories that you could have told for me, there are plenty more but, yeah, we just don't need to permanently record them on a podcast for the internet to hear.

BRANDON LEBLANC: I have some video too.

JASON HOWARD: Anyway, five years down, we'll see what the future holds.


JASON HOWARD: It’s been fun, and there is definitely more to come.


JASON HOWARD: Thanks man.


JASON HOWARD: Next up, we have Amanda Langowski serving as the ghost of the Windows Insider Program's present, to talk to us more about the current state of the program and preview builds.

JASON HOWARD: Welcome to the podcast, Amanda. Thank you so much for joining us.

AMANDA LANGOWSKI: Hi Jason. How's it going?

JASON HOWARD: Fantastic. It's a pretty good weekend and, you know, today's a Monday, at least while we're recording. And it's raining outside. It's prototypical Seattle, you know.

AMANDA LANGOWSKI: Let's bring on fall, it's okay.

JASON HOWARD: Yeah, it's that time of year.

So, for the listeners out there, can you introduce yourself and tell us a little bit about what you do here at Microsoft?

AMANDA LANGOWSKI: Sure. Like you said, I'm Amanda Langowski. I've been at Microsoft for a couple of years now. I think pushing close to 20 years.

JASON HOWARD: I was going to say, it's been more than just a couple.
AMANDA LANGOWSKI: I started when I was a baby but I'm currently–lead our flighting program. So, I own the technology behind how we flight, how we target, and then my team also makes some of the flighting decisions as to what builds we provide out there for the Insiders to take, you know, each week.

JASON HOWARD: Yeah. So, Insiders are used to seeing our team, so me, Dona, and Brandon, kind of as being the external face for the program, doing some of the engagement and troubleshooting, and talking to Insiders as we go to conferences or whatnot.


JASON HOWARD: But, as for the technology, it kind of drives a lot of the systems behind promoting the builds, the data streams that we use to analyze the builds, things like that.


JASON HOWARD: That's where your team comes in.

AMANDA LANGOWSKI: Yeah. Like, we like to hide in the background a little bit and make sure that we're the ones pushing all the buttons and interfacing really closely with your team. Obviously, you know, physical proximity. We're also in the hallways next to each other.

But yeah, my team is like, considered the flight commanders, where we make some of these decisions but also there's a lot of technology, like you mentioned, that actually goes into putting a build out there and making sure it gets–lands successfully where we want it to go.

JASON HOWARD: Yeah. So, while our team pushes the ceremonial red–big red button, so to speak, it's usually somebody on your team who's actually pushing the button on the page that actually lines things up.

AMANDA LANGOWSKI: Yeah, it's not pretty or red though. It's kind of a bummer.

JASON HOWARD: You should–you should actually change it, right? It's just–it's just a standard button on-on a webpage but you should actually make a big, red button.

AMANDA LANGOWSKI: We should make it the big, red button. Yeah.

JASON HOWARD: At least name it that because it's kind of fun that way.

AMANDA LANGOWSKI: Yeah, why not?


AMANDA LANGOWSKI: It's planning season. We can–we can work that in.

JASON HOWARD: So, tell us a little bit about what's happening in the program right now. Like, I know that–I mean, obviously the program's been around for, you know, as of release of this podcast, five years. Right? We just passed the anniversary.

So, obviously a lot has changed over the course of time. From how we initially released builds, you know, five years ago when we first got this thing started, to how Insiders were giving feedback, right? There was the–there was the feedback app and the Insider hub, and eventually those things got combined together. And then just the concept of flighting and how we review information and, you know, what we lovingly call mission control where, you know, where we see the builds that are available, and how to flight, and all that.

All that has changed a great deal over the course of time to, kind of, where we sit now, right? And I would assume from your perspective, you think we're moving in the right direction, or we have moved in the right direction. Can you elaborate a little bit about some of the changes that have occurred and like, what we're doing at this point and like, how that–how that makes things a little easier than they were five years ago?

AMANDA LANGOWSKI: Yeah. You know, I think–when I think of the Insider program, I was kind of there for some of those early years too, in different sort of roles. In our engineering system, we were producing builds, and then when I came over, I did flighting. And it's been really cool to see us grow, and mature, and get smarter about some things. And a lot of that is about listening to the Insiders to see like, how often they want to get flights and kind of, adjusting the criteria as we go along.

As I think about what we're flighting in the future, it's about how we can kind of, really get those clear signals for what we're working on and start to think about how we can preview and process multiple different projects at one time. So, I think we're seeing now is, we are releasing the latest builds of Vibranium, but we're also having Insiders look at 19H2. And so, we're going to see more of those things kind of, happen in the future, and how we can kind of, build a way to make that more seamless, more clear, and have more options for Insiders to kind of, pick and choose what they want to do.

JASON HOWARD: And that was–I mean, that's something that we're doing right now is, the difference between the string of builds or development builds that the Fast ring is on, versus what the Slow ring is on, even versus what Release Preview is doing. And as of now, you know, of course of this recording, Release Preview is just now in seeker mode to take the 19H2 builds that were, you know, being done in a preview state in-in the Slow ring. So actually, I do want to ask a little bit about that. So, 19H2 in the Slow ring.


JASON HOWARD: This is the first time that we've intentionally had a completely different series of builds in the Fast ring versus the Slow ring, right? Usually once a development cycle starts, Skip Ahead would get a build, Fast ring would catch up, they would be rolling in parallel, build quality comes up, we meet that bar for Slow, and then Slow kind of jumps on that wagon, and they would move from the previous retail series of builds up to the next development branch. But what we've been doing for the past–I think it's, what, five, six months? I don't even–I couldn't even tell you how long it's been to just–it feels like it's second nature, right? It's like–


JASON HOWARD: You do this so long you lose track of things. Why did we make the decision to have 19H2 be something separate?

AMANDA LANGOWSKI: Well, I'm not sure what we thought about 19H2 being something separate but like, how our team is thinking of it is how we can kind of manage our audiences better and smarter. When we first had flighting, we had these rings, and the idea is that one build would go get validated and then go to a different set of people to get validated, and so on, and so forth. But really what we started to look at is, our project cycle has this normal kind of, arch to it where it's kind of, unstable in the beginning as we're starting to do a lot of heavy platform development and feature development. And then it kind of gets a little bit more, you know, as it plateaus up, it gets more and more higher quality and-and then it kind of gets, you know, somewhat less exciting in terms of new features that might be coming out and less stability.

So, what we thought about is, with 19H2 is, it was a fairly stable product, right? We're just making a couple of tweaks on it, and so, it some–it seemed very appropriate to go provide it to that Slow audience and get that validation. And so, that was kind of where we started thinking about where–when we started creating internally 19H2, what would be a good place to validate? That's when we started to think about maybe, the Insider Slow audience would be a good audience to validate that against. And we're–we're looking to think of how we want to take that and things like Skip Ahead, and formalize it a little more going forward to the future.

JASON HOWARD: So, do you think the experiment–I guess that might be the right way to call it and might not be the right way to call it. I-I know Dona talks a lot about doing experiments where we try all these crazy, random things.


JASON HOWARD: See if they work or don't work. So, just using that terminology for a moment. Thinking of what we've done with 19H2 as a bit of an experiment. Do you think it's worked out well? Like, do you think it's something we should continue into the future? Obviously, there's-there's nothing set. Even internally we haven't said, there will be a 20H2 or anything like that, right? None of that is guaranteed, like this was something we were trying separately.


JASON HOWARD: But do you think it's paid the dividends that we were looking for?

AMANDA LANGOWSKI: You know, I think–I think of it–I think of 19H2 kind of like, Skip Ahead, right? I see Skip-Skip Ahead was kind of, this experiment that we wanted to do of, when we're doing like, we're focusing on one specific stabilization of one product, how can we start to look at what's even earlier, before that. And so, Skip Ahead was kind of the early experiment of like, can we take some–can we take a set of Insiders who want to go validate that really early and do that? And I think we found some success in that. And then the same thing with 19H2, how we kind of split that off.

I think that, you know, when we think about Windows, more and more we'll kind of look to doing something like that, similar to 19H2. But I'm definitely not the expert, I would say on 19H2. My focus tends to be a little bit more on the active development builds, but–

JASON HOWARD: So, from a technology perspective, right? Given that is one of the things that your team obviously owns.


JASON HOWARD: There have definitely been changes over the course of time, right?


JASON HOWARD: So, to where things sit at now, do you think they're in a good spot? And I know looking forward, hey, there's always things we want to do. Like I know that, you know, even just conversations you and I have had with, you know, some other folks on your team and whatnot, there's things that you're cooking up looking forward.


JASON HOWARD: But where they sit now, does it feel like you're in a good place? Like, have-have the changes that you've made over the past, you know, two, three, four years, you know, as a team, you know, as people have come and gone like, has it–has it put you in a spot where you're like, hey yeah, I am proud of where we're sitting right now?

AMANDA LANGOWSKI: Yeah, you know, I am really proud of where our team has been evolving. When I first joined flighting, my team's role was really focused on just making flighting decisions. So, looking at the build, looking at the quality signals to determine if we should flight going forward. And I saw the opportunities that we can push the technology as well to make some of those decisions easier and better, so then we took on some of the technology aspects of it. And I've-I've been pretty proud of how we've handled it as a team and how we've been able to listen and respond to Insiders. I think we can always get better about that, and so that's kind of where I'm looking forward to doing more in the future, is listening to what people want and you know, engaging more on that side.

And I think of, what are the other different ways that we can start to get builds to people with less intervention, less you know, worry about things like reboots and heavy download times. There's a lot of collaboration we're doing right now with the deployment team, and-and what we think about is velocity. In terms of, specific feature enablement, that there are other things we're looking forward to doing in the future, and I think that kind of sums up that 19H2 touched on, how can we formalize that a little bit more to give more clarity into what's happening.

JASON HOWARD: It's interesting that you talk about like, the speed at which builds go out, because I'm going to get very, very specific here for a moment. You know, to use the terminology like, back in the day, right?


JASON HOWARD: Three, four years ago like, on one hand it seems like it's a long time ago, and on the other hand it's like, it doesn't feel like it's that long ago. I don't know. Maybe I'm getting old. The-the actual process for releasing a flight has actually changed significantly.


JASON HOWARD: And I don't just mean in the technology side of things. Like, some of the actions that we go through as we're kind of, you know, I don't know, nudging a build out the door, like, the last hour or so before it goes live. Like I can remember, you know, back in the day, there's that terminology again, of us going through a long checklist. Where there was, you know, 10 or 15 different items, and was this there, is this available. You know, it's like this–some of the-the build pieces and some of the, you know, the lips and fads, and all this kind of stuff. It was like, literally a–almost like a manual checklist. Did this light up? Is this ready to go? Is this ready to go?


JASON HOWARD: And you know, if there was a scenario where some of that stuff wasn't ready, that led us to append communications literally like, 10 or 15 minutes before we were releasing a flight.


JASON HOWARD: To say, oh hey, you know, some users in X, Y, Z countries, you know, your stuff is still publishing, or you may notice that your language pack is missing in this build. Things like that. But because of a lot of the technology work that's been done, and it's behind the scenes like, actual Insiders externally don't see it.


JASON HOWARD: Like, that checklist really is, hey, is everybody on the call that, you know, needs to participate in making sure that we're going live appropriately. And you know, we'll have a bridge that starts like, five minutes, maybe ten minutes before we go live. And it's just, literally a chance to catch up, see how things go, make sure that you know, we see some of the real-time signals of, you know, downloads starting, people's machines scanning for builds. And then, we actually use one of those indicators of, hey, have people actually started downloading the builds? Yes. Okay. And that's the trigger for us actually publishing the blog posts because we often get questions. Okay, the build's been live for two minutes, or five minutes, or ten minutes, you know, why isn't the blog post there?


JASON HOWARD: We do want to make sure that it actually is, you know, going out the door appropriately before we say, okay, here you go. Even though some people are like, hey, I already got it. Right? Because there's always those folks that are clicking the thing.

AMANDA LANGOWSKI: Yeah, yeah. I love it. I love it when they beat you. I love it when they beat you to finding, ever since the blog post goes up.

JASON HOWARD: That's totally true. But I have to say, you know, from-from looking back, and you know, and having this 30 or 45 minute process with a long checklist to it just being a few people on the bridge just to go through the mechanics of publishing comms and reviewing some real-time data to make sure that we're seeing a good signal of, you know, the builds rolling out like, just that in and of itself has been simplified tremendously.

AMANDA LANGOWSKI: Yeah, no. Absolutely. I have a lot of confidence in how our flighting systems themselves, have matured. There's very few nights where I'm up–up late, stressed out if it's going to go live at the right times. And I feel pretty good about that.

And so, whenever you kind of reach a maturity in the systems, I think the next thing you want to do is how we can go even further, right? So, like, as we start to take a checklist down from, you know, 45 minutes and honestly, a day's worth of work just to make sure all the appropriate flighting collateral is there, is it targeted correctly, all that stuff. And like you mentioned, it's whittled down to like, hey, you know, hey social, how's it going? Hey, you know, and chatting back and forth. Really the thing is, what else can we enhance? How else can we make this experience better for the Insiders to-to check out the build and to give us their feedback? So, yeah.

I'm pretty–it is pretty amazing when you think back to like, the mega–frankly, the mega conference rooms we used to have–where we would have you know, 40, 50 people in a room, you know, stressing out over certain things, and having a lot more confidence in the signals that we do have. And being able to make, you know, more confidence in our release decisions, as well as the systems that support it.

We can always do better so, you know, I'm not–I'm always thinking about how we can improve that process. But yeah, we've definitely made huge strides as to when we were first starting off, like a startup almost in a–in a way.

JASON HOWARD: So, given that you've been here for a little while, you know, on the flighting side of things. Like, you mentioned earlier you were originally in what we call, the ES, Engineering Systems side of things.


JASON HOWARD: So, the builds. So, having been in flighting for what, three years now? Almost four years?

AMANDA LANGOWSKI: I don't know. Sure. That feels–it feels a lot longer than that, yeah.

JASON HOWARD: (Laughter.) We'll just–we'll just go with that and-and pretend that I got it right. It feels like it's been that long, I guess.

AMANDA LANGOWSKI: It feels like it's been that long.

JASON HOWARD: What is something–I don't know. What is–what is the thing that you feel most proud of? Whether it's something you've accomplished, something your team has accomplished? You know, you can give us, you know, folks on the Insider team a pat on the back if you want. You know, not that I'm fishing for compliments here but, you know.

AMANDA LANGOWSKI: Sure. I don't know. I think–I just, I still think it's amazing that in a matter of days, that we can take a build, do some initial testing internally and flight out to Insiders within days. Right? So, like, the build that goes out to the Fast audience today, really it was built just by like two days before, right? I love how fast that we can take code, create it, and then share it with our Insiders. I love how fast that can go.

And I–and I-I like to see the-the Insider audience growing and to me, that tells me we haven't done things too badly. So, I guess I'm pretty proud of that.

And you know, I think I-I love the collaboration, frankly. This is a process that's not just done by one team, like you mentioned. It's–we have, you know, what we call vertical owners, from across all the different major areas of technology for the product, looking at these builds, evaluating them, giving them thumbs up or thumbs down. And all that collaboration with that, plus the Insider team together is–it works really, really well. And I think that people stay on teams for a while because they know they can trust and have a great collaboration with people. And I think that's a–internally, that's something I'm really proud about with the team.

JASON HOWARD: Yeah, this–it's the whole, one Microsoft mentality.


JASON HOWARD: It was interesting to see–right, and this is some personal reflection, I guess–of how quickly, especially in the flighting space, that each of the teams that were involved there, kind of adopted that and started running forward with it. I think part of it was the nature of what we were doing together was, we were so heavily reliant upon one another. Each team was a domino that had to, you know, kind of, fall in succession to make sure that the next team had the right information and was fully informed. Okay, now that I have this, I can make this next decision, right? My decision's going to affect somebody else, right? And all of these, kind of, fall in place to actually get a flight out the door.

And then, of course, the Insider team were kind of like-like, it feels like we're the last domino, but we're actually not. Because even though we publish the blog post, we come out and we, you know, talk about bugs on social, we do some real-time troubleshooting, we do that engagement, really, it's almost like our domino kind of goes back to the beginning to trigger some of the next process.

Because some of those bugs that show up that we didn't necessarily catch in the internal testing that, you know, in the–you know, once the preview build was released and folks externally are kind of, you know, they've downloaded it, installed it, and they're, you know, going through the process of, you know, whatever they were doing in the previous space. You know, we catch that feedback. Oh goodness, hey, here's something that's interesting or potentially significant that, you know, we didn't catch in our internal validation. We should review this. Is this something that we can, you know, live with for the, you know, a week or two? Is this something that we absolutely must fix before next week's build goes out? If we're going to have another build, do we need to not flight the next build?


JASON HOWARD: Things like that. And it's just this big, continuous loop.

AMANDA LANGOWSKI: Yeah and I don't know if people know about it, but we have a weekly–I drive a weekly meeting after each flight where we have, you know, frankly the directors of engineering for each of these areas, a different set of people, and our, you know, VPs of engineering too within core that look at the data signals for each of the flights and the feedback that we're getting to-to make sure that we're catching everything and listening. It's a really, like–it's a really huge, important part of it. Like, do they like what we're flighting, and-and those do really shape the product. Like, it's not just lip service.


AMANDA LANGOWSKI: Like, I spend a lot of time looking at feedback stuff and figuring that out, of like, is this the right thing? And making sure those things–those-those flags, are raised appropriately. And so, it's a big part of what we do. And you know, and we have–we have fun with it too, right? Though, it can be a stressful space at times.

JASON HOWARD: Especially if your team's the one that's got the bad bug, right?

AMANDA LANGOWSKI: Right, yeah. And you know, I'm definitely glad I'm in the background, and we let you kind of, deal with that, with the external stuff that's not my forte. But I-I think it's a really cool space to kind of be in, where you can kind of hear a little bit from internal and from externally to make some decisions. So, it's pretty cool.

JASON HOWARD: Yeah. And I have to say, you know, having been in a few of those meetings along the way as the need has arisen, it's interesting seeing–I guess for lack of a better way of calling it–like the giant report card that gets reviewed.


JASON HOWARD: And knowing how much effort that each team has put into looking at the measures, right? And the measures being, you know, like–here's an example. Like, so, start menu, right? There's a bunch of measures surrounding start menu, that hey, when I click start, does it actually pop up? Does it actually open, right?


JASON HOWARD: How long–when after I clicked it, how long did it take before it popped open, right? There's things like that that you're like, why would–why would you care how long it takes to open start menu, right?

So, imagine being an end user. Especially as somebody who's not super tech forward, right? So, somebody who's just counting on their computer to work, day-in and day-out, and they don't expect many bugs. So, somebody who's in Release Preview or Slow, right? They click start, and if it takes ten seconds for start to open, you're going to wonder, what's wrong with my computer, right?


JASON HOWARD: As opposed to, hey, you click start, and you know, a quarter or half a second later it's-it's up, it's available. Like, the action has completed as you would have expected, right?

Some of those user experiences are important to actually kind of like, take a look into to say, are we doing the right thing? Have we made a regression? Does Windows still feel smooth and usable? Did we introduce a new bug? Things like that. And so, knowing how many teams have–in essence, all the teams–have created their measures and things that they're looking at.


JASON HOWARD: But knowing that there's these larger meetings where these things get reviewed all up, so that each individual team isn't caught in a silo, where they feel like they have to just, you know, struggle through it alone. If there's something, you know, significant that they've introduced, and they're trying to work and root cause. It's obviously, the impact of one team making a change where it can potentially funnel downfield, right? It's a good avenue for teams to kind of, have some of those conversations with one another.

AMANDA LANGOWSKI: Yeah, no. It's-it's amazing to see the collaboration, right? So, diversity is a huge, important element of that as well, right? So, we know internally at Microsoft, and we do our internal testing, and we're-we're looking at builds and flighting builds even internally. We know we're not all representative of our customers. And so, when we get–when we do flight to Insiders, and we can kind of, hear how it's working for them, and making sure that like you said, some of these–some of these areas that like, is Narrator working correctly?

You know, some of these things are really important to our customer base. Games, right? So, as much as I love–you know, we–I have a lot of, obviously, PCs at home. I have a family that plays a lot of online gaming. I don't have a lot of time to play gaming at work. You know, that would be bad if I had a lot of time with my role. But like, I love, you know, kind of when we put that out there, getting that diversity of-of Insiders testing it out in the ways that are really important to them. And then looking, you know, looking back at that to say, hey are we doing things in the right way? Where do we need to kind of, catch up to kind of, meet needs and meet expectations, is really important.

JASON HOWARD: Yeah. And that's-that's one of the other things that I did want to make mention of. And from time to time, Insiders have seen historically where we've said, hey, if you have an extra laptop, you know, even if it's five years old kind of hanging out in the closet not doing much, you know, boot that thing up and throw an Insider build on it.

And, you know, a lot of that comes from internally, like if you're doing like, population comparisons, right? So where, how does the average Microsoft employee who's, you know, running Preview builds internally compared to the broader retail audience, right? And then you look at the folks in the Fast ring, folks in the Slow ring, so on and so forth.

And obviously one of the big goals of the Insider program all up, is to try and, as accurately and as broadly as possible, represent you know, the whole retail user base that kind of, is out there globally. Now, that's–it's a near impossible task, because you know, when you have over 800 million Windows 10 installations, right, and there's you know, 17 plus million registered Insiders, there's-there’s a big gap there.


JASON HOWARD: And a lot of the folks in the Insider program tend to be tech forward, more enthusiasts, right? So like, their hardware, you know, a lot of folks tend to like, buy Surface devices or build their own home machines, things like that. So, it's–one of the ongoing things that we keep looking for is hey, how can we better represent even more of that external population? So–

AMANDA LANGOWSKI: Yeah, totally.

JASON HOWARD: And so, it's like, so you know, when Insiders hear us say, hey you know, fire up that old machine, or hey talk to your neighbor. Oh hey, would your parents be interested in it, right? It sounds–it sounds kind of funny, right? But like, I got my mom to start taking preview builds.


JASON HOWARD: My mom and I do not compute in the same ways.


JASON HOWARD: Like, she does not work in technology. Right? And so, you know, her use of the–of a computer tends to be like, a little bit of like, online gaming, interestingly enough.


JASON HOWARD: You know, she keeps all her recipes in Word and stuff. So, she uses the Office Suite but a lot of it's just web browsing and you know, basic activities. Wherein, I would definitely consider myself more of a power user, so–




JASON HOWARD: Compared to some of the Insiders, I question that at times, right? Because, you know, I get–I get it wrapped up in some of these discussions, and I'm like, I've got something new to learn here. And I've got to say like, I realize I'm kind of monologuing a bit, but one of the really fun things about this program, you know, historically, now, and you know, even as far into the future as-as we go, is the fact that you get to keep learning things.


JASON HOWARD: Every time we release a build, somebody brings me something new and unique that, maybe it was filed in feedback, and you know, it was–it was one item that I didn't see. Or it's a brand new something that just popped up in a new build. I always get to learn things, because somebody's always challenging me in a way or bringing an issue to me in a way that I haven't thought about it before.

AMANDA LANGOWSKI: Yeah. No, it's-it's crazy important. Right? I mean, I-I love–like, I think, you know, diversity and inclusion's a big, you know, buzzword phrase right now. But it really is critical to kind of get coverage from just, hardware diversity, and how people use it, right? You know, I think that's-that's the, kind of the key thing for flighting for me is, you know, getting-getting that coverage outside of Microsoft's walls is always a-a really important thing for me.

JASON HOWARD: Yep. So, I don't want to break you into jail–I love that phrase, by the way.


JASON HOWARD: You don't want to break yourself into jail.

AMANDA LANGOWSKI: You can't break me into jail. I can only break myself into jail. You can just throw me in jail. It's a little–

JASON HOWARD: I will–I will hand you the key and allow you to open the door for yourself. (Laughter.) So, you know, we've talked a lot about how things are a current state, a little bit about how things have changed from the past. But let's look forward just a little bit, right? Obviously, you know, you go far enough in the past, Release Preview didn't exist when we first started, right?

AMANDA LANGOWSKI: Oh yeah. I forgot, yeah. We did pop that in, didn't we?

JASON HOWARD: Yeah. That was–that was an added-on ring that didn't originally exist.


JASON HOWARD: Right? And I probably just blew somebody's mind saying that. They're like, wait, what? Really, Release Preview wasn't always there? No.


JASON HOWARD: Release Preview was not always there. And even Skip Ahead, right? You–

AMANDA LANGOWSKI: Yeah. I do remember Skip Ahead.

JASON HOWARD: Yeah. I mean, that was kind of–that was–that was your fault. I get to–I get to blame you for that. (Laughter.)

AMANDA LANGOWSKI: Yeah, that's–that's not–yeah, it's my–it's a good way to test it. It's about me evolving. It's evolving the flighting system. It's great.

JASON HOWARD: So, knowing that there have been changes in the past, what can Insiders expect in the flighting space moving forward? Like, got any tricks up your sleeve?

AMANDA LANGOWSKI: Well, I'll tell you one thing. I-I don't like the ring names that much. I don't like referring to Fast Insiders and Slow Insiders, right?


AMANDA LANGOWSKI: As an example, right? No one's slow, and no one's necessarily, fast. And-and so, that's one thing that ever since I've got involved with flighting that I kind of–it's my own pet peeve of like, I really don't like Fast and Slow.


AMANDA LANGOWSKI: I think so, we're looking at really about how to manage audience–like, manage the flighting audiences better into, you know, what is like, a quality level that people are really okay with and thinking about that like, opting in in that respect. So, there's–we've got some tricks up our sleeve in terms of how we want to go and evolve that.


AMANDA LANGOWSKI: Certainly, and we're getting really close to-to talking about that here soon. But really, the ideas behind Skip Ahead and audience management, we're-we're seeing that we're kind of, outgrowing our rings, right? We need to–we need to think about future. Skip Ahead was cool in terms of giving people a sneak peek into what's next. But it–but it was also a really small segment of people.


AMANDA LANGOWSKI: And so, that, you know, I want to allow anyone to pick whatever is what they want to go look at in a way that makes sense. And so, we're-we're evolving that right now.

JASON HOWARD: Yeah, and–

AMANDA LANGOWSKI: That’s about all I can say.

JASON HOWARD: It's interesting, because you know, as we've gone to conferences and you know, done like, the-the Build tour, and Ignite the Tour, and things like that, you know, some of the questions that I get asked is like, you know, oh how fast is Fast? How slow is Slow, right?


JASON HOWARD: And the–kind of, the implication behind the name of the rings is the speed at which you're going to get builds. And you know, traditionally, provided there wasn't some, you know, big blocking bug.


JASON HOWARD: That would prevent us from dropping a build in any given week, right? We've been fairly consistent in a speed perspective, right?


JASON HOWARD: But like you just mentioned, it's-it's–even with that being the name, it's really, there's still been an overarching quality lens that gets laid down on top of that. And you're right about the names where I don't think that's what is reflected–


JASON HOWARD: In what people select, right?

AMANDA LANGOWSKI: And that's not reflective of how we think about builds either.


AMANDA LANGOWSKI: Right? So like, when we-we have these kind of, labels associated with it, but it's really about the quality. Is the quality good enough to go to this set of Insiders?


AMANDA LANGOWSKI: And we do–we have a lot of, you know, psychology around, you know, people who select the Slow ring, and they want this level of quality. And we, you know, we have all these great user personas that we spend PM time thinking about and trying to guess. And frankly, we spend a lot of time looking at the Insider survey. A lot of time, pouring over that. What is, you know, what are people motivated by? What do they want? You know, do they want faster builds? Do they want higher quality? What do they–?

And so, we've been doing a lot–a lot of work around that. And I think that, we want to use the folks who have selected the Slow ring more regularly with higher quality builds. And so, we did some work. I think people will notice that like, in RS5 and 19H1, where we would offer more builds to Slow using, you know, more traditional servicing methods, right?


AMANDA LANGOWSKI: So, that was something we called internally, and we called it, “flight like we service, service like we flight,” right?


AMANDA LANGOWSKI: How we can kind of, join these two concepts together. So, I think we're going to take that to the next level too, of right, like, what is a–instead of having to rely necessarily on servicing, how we can provide a more regular validation experience for people within that ring or that flight; however, we want to talk about it.


AMANDA LANGOWSKI: But I think that's a key thing for-for my team right now is, we are going to go out there a little more with–we're going to tag along with you guys more in terms of, some of these Insider events and listening as well as, the survey to offer something better coming up here in the next couple months.

JASON HOWARD: Yeah. I'm-I'm actually glad that you brought up the survey thing because, you know, again. Historically when the program first came out, we didn't do surveys, right?


JASON HOWARD: The program grew a lot organically. We listened to feedback. I mean, we still listen to feedback of course but like, there was, you know, like, a lot of feedback directly coming in. And so, we kind of just made adjustments on the fly that we kind of, anecdotally thought, hey, this will probably be the right thing, or this is something cool and new that we need to add. There was a lot of new growth in how we do things, and we're still making changes, but there are kind of, core foundations that have become just an intrinsic part of the program and the way that it operates. And so, like, the surveys that we have now where we do a weekly survey on Twitter.


JASON HOWARD: And then we have the larger annual survey that gets done in January of each year, and tons of Insiders respond to that. And that, you know, them giving us that direct–it's like, our, you know, as a team, our report card.

Hey, how did we do this last year, right? Was it–did we provide enough builds? Did you think the quality of the builds was correct? Did you receive, you know, presuming you're in any given ring, or if some Insiders, you know, flight multiple machines and multiple machines, right? Did you get the experience you were looking for and frequency of builds, quality of builds, right? Why did you select the ring that you're in? There's-there's tons of stuff that goes into this.


JASON HOWARD: And you know, all of this information feeds back into changes that we have made in the past, that we're currently considering, and it's going to directly influence things that we do in the future.

AMANDA LANGOWSKI: Yeah. Absolutely. It's–I can't tell you like, how often I've looked at that data for different parts of it, right? Like, what do Insiders really want in terms of like, you mentioned build frequency, but also, can I partner with other people within Microsoft to maybe offer something new and special to Insiders, to go along with these, you know, builds that we're flighting?

And so, I can't stress enough how I want everyone to, you know, provide info on those surveys because it really does shape our planning significantly. And we're constantly planning, right? I mentioned–


AMANDA LANGOWSKI: It's planning season now. It's always planning season, but right now is–is a–in a special planning season where, you know, as things start to get faster and faster in one product, they kind of slow down in another. And so, we’re looking about how we can kind of, always take good opportunities within these transitional points to make changes. And I think that's where we're at right now.

JASON HOWARD: Yeah. So, I'm going to make you uncomfortable for a minute. All right?

AMANDA LANGOWSKI: It's hard to do.

JASON HOWARD: I know, right? I–I have to ask to say, that's absolutely true.

AMANDA LANGOWSKI: I’ve got a thick skin.

JASON HOWARD: I've worked with Amanda long enough, and it doesn't matter how badly I've tried to embarrass her, she always takes it in stride and just keeps on rolling, so.

AMANDA LANGOWSKI: And flipping it back to you, sure.

JASON HOWARD: Yeah, of–well, yeah. Of course. That like–that's expected. If I didn't get it, I'd wonder if you like, got mad at me or something. It's not actually embarrassing. But I will say this. Like, there's something I-I kind of–in the–in the–in the fun of this episode, flighting doesn't always go as planned.


JASON HOWARD: (Laughter.) I mean, I'm-I'm sure, you know, me just saying that, you know, the Insiders are listening. They're like, oh yeah, there was that one time.


JASON HOWARD: You know, there's some story they're probably immediately thinking of. So, you know, at the risk of being candid, and you know, having fun with our own, you know, mistakes. Like, what's-what's–come on. You know.

AMANDA LANGOWSKI: Oh yeah. No, I've–we've made some for sure.

JASON HOWARD: Give me–give me a little something here. What’s-what's a good one that you want to talk about?

AMANDA LANGOWSKI: Oh, you know, I think my first week of taking over flighting, and I don't even remember what it was, something went wrong with the flight, where it went live in the middle of the evening, and it wasn't planned. And I just–I just remember getting back to my house, and I think it was around, I don't know, like eight o'clock at night or something. And-and someone calling and saying, yeah, the flight's live, what happened? And I immediately was like, you know, back then in those days, we used to have a manual time set.


AMANDA LANGOWSKI: Like, hey, like, you would say, flight goes live to this audience, at this time. And you know, I would look at it, and make someone else look at it and say, yeah, this–this does say 10:00 a.m., right? It doesn't say 10:00 p.m., right? I'm not going crazy? And-and there was–honestly, there was just some bug that happened where for some reason even though it wasn't set to it, it went live at a different time.


AMANDA LANGOWSKI: And you know, those things happen. It's–they–they're actually pretty rare, given how often we flight.

JASON HOWARD: Yeah. Given how many–yeah, how many builds we've pushed out. Yeah.

AMANDA LANGOWSKI: You know, when you go on a plane, you don't want the flight to go at a different time than scheduled.


AMANDA LANGOWSKI: You know, I think that was kind of, a stressful first flight, and I got a lot of revving from people, and-and I was on that RCA. Which, you know, we-we do root cause analysis. I'm like, pointing out that this was not user error. I did not mess up on this one.

JASON HOWARD: It's Amanda.


JASON HOWARD: It's your first flight, and you can't even get it right. You sure this is what you want to be doing?

AMANDA LANGOWSKI: That's right. And, you know, we have a lot of fun with it, right? Like, we call–like, we call the position of, you know, I used to do it like, almost, you know, regularly. Just being the flight commander, right? Because it is kind of funny, right? And we make jokes about funny flighting hats and all sorts of different stuff. And you know, so, yeah. We definitely have some fun. But again like, mistakes, they-they are–we take them very seriously.

JASON HOWARD: Yeah, I mean–

AMANDA LANGOWSKI: So, when we have them, there's a lot of stress afterwards.

JASON HOWARD: Yeah. They're not fun when they happen.

AMANDA LANGOWSKI: We have a flight bridge. We have a great actually, response if things do happen.


AMANDA LANGOWSKI: If like, where we can kind of like, snap the fingers and say, yep, let's all look at this now and–but yeah. There's been some, you know.

JASON HOWARD: A few hiccups.

AMANDA LANGOWSKI: A few hiccups every now and again. And that's software for you, right? You know, software development at its finest. You-you find out what those things are then you know what? We develop great things for alerts. And so now, there's extra things in place, if when things go live externally, you know, things happen. People are notified. Even if it's planned, we just say, okay, double checks are there.


AMANDA LANGOWSKI: Like you mentioned, making that flight bridge from 45 minutes to like, ten minutes of chatting, you know. It goes well. But man, when mistakes happen you do go, oh my gosh.

JASON HOWARD: Yeah. (Laughter.)

AMANDA LANGOWSKI: You know, things go wrong sometimes. For sure.

JASON HOWARD: I-I-I want to say that it's fun, right? Because I-I'm–I-I work well under pressure.


JASON HOWARD: Like, I can think back to high school and college and I'm, you know, waiting until the night before to do my homework. And my dad used to yell at me like, why are you waiting until right now?


JASON HOWARD: Because he was–you know, if he had a week to do it, he did it the first day and then he would be like, six days ahead of time. Yep, I'm good, I'm done. I'm like, this is due in 15 minutes, and I'm finishing it, right?


JASON HOWARD: You know, he and I were very different in that regard. But it's-it's-it's interesting when things don't go according to plan. You know, you were–talked a lot about collaboration earlier. The number of teams that come together, work on it, address it immediately.


JASON HOWARD: You know, figure out what exactly happened, how do we prevent it in the future, what do we need to put as a safeguard or a check that's in place? You know.

AMANDA LANGOWSKI: Yeah. You know, and again, my past life was as you know, like in Windows running ship rooms, as we used to call it. And-and you know, having that let's, you know, manage the, you know, the-the deck kind of thing is-is something that comes pretty naturally. You know, like firefighting. But I'd much rather be checklist clean and no problems. (Laughter.)

But the thing is like, we–I think because we have great listening when do–when things do happen. You know, I think Insiders, you know, raise their hand and say, hey. And I hopefully, they-they see that when, you know, mistakes happen, we-we jump on it, and we take it super seriously.

JASON HOWARD: Yeah. Well, hey. This has been a fascinating conversation, right?


JASON HOWARD: Not-not only, you know, we talked about some of the cool stuff that we're doing now but, you know, it's been a fun trip down memory lane. You know, every time we, you know, start talking about some of the things that have evolved over the course of time.


JASON HOWARD: It's a great reminder of where we've gotten to and just how much things have changed. And something I know the Insiders are appreciative of. I am super appreciative of it and, you know, a lot of that has come from, you know, the PMs on your team, the devs that you work with. You know, and then every other team that kind of, fills in and ladders up to make this process what it is. So, I mean, you know, just a heartfelt thanks from me for being, you know, a good business partner over the years. But you know, you happen to be a pretty cool person, too, so.

AMANDA LANGOWSKI: You're welcome.

JASON HOWARD: You know. Did I just pay you a compliment?

AMANDA LANGOWSKI: No, I won't really take it as such. Don't worry.

JASON HOWARD: Okay, good. Okay. All right. Well, hey. Thanks again for being on this episode.

AMANDA LANGOWSKI: You're welcome.

JASON HOWARD: Hopefully have you back again in the future.

AMANDA LANGOWSKI: Thanks. Bye, Jason.


JASON HOWARD: And finally, we're joined by Jeremy Sinclair, one of our Windows Insiders, who will be serving as our ghost of the Windows Insiders Program's future as we wrap up this journey. We're excited to hear how he makes the most of the program and to talk about where WIP is headed next.

Thank you so much for joining us, Jeremy. Can you please introduce yourself and tell us a little bit about what you do?

JEREMY SINCLAIR: Absolutely. Hi, everyone, I'm Jeremy Sinclair, a.k.a. snickler and @sinclairinator, if you've seen me on social media. I live in Wheeling, West Virginia, and what I typically do throughout the day is develop enterprise .net solutions, but I also develop mobile applications outside of work.

JASON HOWARD: And how long have you been a Windows Insider?

JEREMY SINCLAIR: I've been a Windows Insider since late 2014.

JASON HOWARD: So, pretty much the whole five years.

JEREMY SINCLAIR: Absolutely. I've been there since the beginning of the Windows 10 and Windows 10 mobile preview builds.

JASON HOWARD: Yeah, that's–I mean, if you were around for mobile, that's definitely old-school. I can guarantee you that. So, I got to ask you, you know, reaching way back into the memory banks because I mean, I don't know what I had for breakfast last week much less what I was doing five years ago, other than being on this Insider team, what made you want to join the program?

JEREMY SINCLAIR: Well, it really was the Windows 10 and Windows 10 mobile. I-I saw the email and a few things on Twitter that said, hey we have this new program, you can join it and help test out these new preview builds and give feedback. And I thought it was awesome, because I felt like, I was a part of some secret society, and I was getting access to the new hotness.

JASON HOWARD: The new hotness. I like that. I'm going to have to–I'm going to have to use that going forward. I'm going to–you're going to catch me sending a tweet some time, be like, we're dropping a new build. Build blah, blah, blah, blah, blah. Welcome to the new hotness, Insiders.

JEREMY SINCLAIR: Well, you have my permission. (Laughter.)

JASON HOWARD: Fantastic. So, I've got to ask you, obviously you've been doing this for a little while. How has the Insider program made a difference for you, right? What has it meant for you personally, in your work, your community, as a tech user? Like, you know, like, obviously, you know, you can take this program, and see hopefully how it's touched in different ways, and I'm-I'm-I'm excited to hear kind of, what it's done for you.

JEREMY SINCLAIR: Well, what it's done for me personally, it's-it's helped me to be a better tester. So, there's so many things that a normal user does on the computer, on the phone, et cetera, and they don't–it's kind of autonomous. They don't really pay attention to what they're doing. But seeing the-the quests, knowing everything in the-the roadmaps, and the release notes, saying hey, we have this new feature, go test this.

What it's done especially for work–back, I think it was in Redstone, I was testing the build on my work computer and I was able to find out that we were going to run into an issue in the future with one of our third party softwares. So, I was able to get down to the bottom of it, put in a few of feedbacks, and got it fixed before the–my company actually rolled out that build. I was like, hey, you're going to run into this, here's how you get around it. So, I felt like, I directly fixed something because of being able to test the preview build.

JASON HOWARD: Kind of helped your life at work a little bit there.

JEREMY SINCLAIR: Yeah, it really did.

JASON HOWARD: I mean, that's what the whole WIP for business aspect of the program is designed to help with, right? Is get those preview builds out there, and then–I mean, I know that I test it on my personal machine at home, I've got it on my work machine here at work. Obviously, right? I mean, I think I would get mocked if I didn't actually have preview builds on my work machine, especially given what I do for a living. (Laughter.)

JEREMY SINCLAIR: Absolutely. I've got an Insider Fast on every single machine I have.

JASON HOWARD: So, I've gotta ask, what is your favorite part of the program?

JEREMY SINCLAIR: I think my favorite part of the program is, being able to reach out on Twitter with a feedback link and get a reply back and see other people interact with that tweet and see, oh yeah, I have this issue, I have this issue too. And just, kind of see that community interaction between, you know, everyone on the Insider team and random users.

JASON HOWARD: Yeah. I think that's one of the aspects of the program that, while it was–I think there may have been an assumption that something like that would happen when the program was originally created, to see what it has changed and what it's become over the past five years. It has definitely like, blossomed from where it was in the beginning, right? Because just like you mentioned, like, oh here's feedback, you know, here's a link, whatever. In the very beginning, we didn't actually have links that you could share, right? You had to tell somebody, hey, here's the feedback and they would have to like, try to search by the title and things like that.

The-the little aka.ms links that you can actually grab off a feedback, that was something that came later on based upon Insider feedback, and I think that's been one of the significant changes to number one, the Feedback Hub, but number two, in helping Insiders, you know, kind of try to look through and correlate issues and, hey, is it the exact same thing, or you know, is it potentially the same type of device or is it, oh you're on one build, I'm on a different build, maybe it's something different. But it's a good way to like, have that breadcrumb trail so people can actually kind of, follow along with one another.

So, obviously with the Insider program, it's afforded you a few other opportunities. I know that I had the chance to speak with you at Build earlier this year. Can you tell me a little bit about what you were doing there?

JEREMY SINCLAIR: Yes. At Build this year, I was the developer MC, along with my buddy, Daniel, who is the creator of Nightingale, the REST client. We were dev MC's for Native.


JEREMY SINCLAIR: What the dev MC program–what we did was we went around Build. We took the courses that a mobile/desktop developer would typically go to if they were attending Build. But we kind of gave that experience to someone who wasn't able to be there. So, it was a very fun experience. I was actually shocked that I was chosen for it. But it-it really was an eye-opener.

JASON HOWARD: Was it your first chance to attend Build?

JEREMY SINCLAIR: No, this is actually the second chance. I–the-the first chance was in 2018, and I was shocked I was able to go, because I've been complaining to management that they need to send me to Build, and I wanted to go so bad. So, I'm usually on Twitter, just screen-capping and sending tweets about everything that I can see from my screen. So, essentially, being a hype man for Build when I'm not there. So, it was cool actually being able to attend there and do the same thing live.

JASON HOWARD: That does sound like a lot of fun.


JASON HOWARD: Oh, well, you know–I mean, I say it sounds like a lot of fun, but I mean, I've had the privilege of being at Build, I mean, for obvious reasons, right? I don't even have to travel. I just get to drive there instead of driving to the office. But–

JEREMY SINCLAIR: Oh, look at that. Lucky you.

JASON HOWARD: I know. I–like I say, it's one of the perks of the job. But it-it really is–I mean, for those who haven't attended, right? Because we have folks who listen to this podcast all over the globe, it really is a fascinating opportunity to get in and speak with the product teams, speak with people quite literally, from all around the globe who have come there to, you know, engage in some of the sessions, hear the keynotes, the core notes, you know, the breakout sessions, the theater sessions, everything that's available. There's a lot of information that gets shared.

But the good thing is-is, you know, it ends up getting published to the Build site, so you can actually listen to the content remotely, kind of, after the fact. But there is definitely something to being there in person.


JASON HOWARD: So, one more question kind of, looking back a little bit before we jump into the kind of, ghost of the program's future, right? So, obviously with–you know, at this point, five years of the program kind of, having passed–which, it's still weird saying that. It doesn't feel like we've been doing this for five years. I don't know. Maybe I'm just getting old and I don't realize it yet but–or maybe I'm just not wanting to admit it.

JEREMY SINCLAIR: Oh, you're still young.

JASON HOWARD: Well, you know, young at heart. I'll say that. Physically, that's a different story. I've got to ask you, what has been one of the most inspirational stories or things that you've seen across the years? Like, I-I, you know, in-in the previous interview with-with Brandon, there was something very specific that I had mentioned, right? That the listeners have-have heard about. But I'm curious just to something of you, because it's different from me where, you know, it's partly of my job to, you know, be connected, be paying attention, you know, do things like that. But it'd be interesting to hear something from somebody who's on the opposite side from me.

JEREMY SINCLAIR: Well, mostly–interestingly enough, the most inspirational story actually happened at Build 2019. So, I met this guy from South Africa. His name was Gomolemo.

JASON HOWARD: Gomo, yeah. I know Gomo.

JEREMY SINCLAIR: Yeah. He–and he told me, we-we were talking, and it was actually right before I went to interview Dona. (Shout out to Dona Sarkar.) Before we went to interview her, and he told me about what he did, where he noticed that some of his class–classmates, were struggling with programming, so he decided to make his own guides for them, and they worked better than the, you know, the books. And I thought that was just so brilliant that he took that time, he saw that there was an issue, and he found a way to help others get into programming, stay in there, and more importantly, it's like he brought more people to the .NET ecosystem.


JEREMY SINCLAIR: That's pretty important for me, because I'm a .NET foundation member, and I-I really want more people getting into programming and getting into this field, so they can help build future technologies. So, that-that really excited me.

JASON HOWARD: And of course, you know, the Insider program's kind of how the dots got connected, right? It's-it's how–there was actually several folks from Africa that had the opportunity to come to Build this year and it was–it was fantastic getting to meet them and hear their stories, the things that they're doing in their community, and how they're trying to make an impact–not even trying, how they are making an impact, right? I hear their stories and I'm like, what am I doing? Right? It makes-makes me feel like I'm not doing enough with my life, you know? It's a–it's a bit inspirational and it's a–it's a good way to kind of, challenge and reframe some of the perspectives that I have at times, where I'm like, you know what? There is something more that I can bite off here. There's something new that I can do. And it's-it's-it's motivating, and it's inspirational, right?

And so, seeing how the program at large has, you know, you-you-you mentioned Twitter a few times. Obviously, I'm on Twitter a ton just because of the role, and you know, connecting with people on troubleshooting, and announcing builds, and all that fun stuff. The number of people that I've gotten to talk to, right, and they-they span the entire spectrum that you can imagine, right? The quiet and shy people who use the internet, because it's a way where they don't have to be in front of people and do something they're uncomfortable with, but it's a way they get to communicate to the people that are on there every day, begging us for builds. Hey, what are you doing today? You know, people that are asking us like, what do we have for lunch? You know, it's fun stuff like that.

And then there's aspects like this where different members of the program have found out that there are other members of the program in their community, and that starts off as the thing that kind of brings them together. It's like, oh hey, you're an Insider? Oh hey, I'm an Insider. Maybe we should do a meetup together. And there are regular routine group meetups of Insiders in various countries and cities around the world, where they come together and have those conversations, and they talk about the builds and the bugs they're hitting. But it goes beyond that, right?

You know, I've mentioned the community a few times, but it's-it's actually spawned friendships amongst people where, hey, every time we get together we don't have to talk about builds every time. They usually end up doing, right, because tech's kind of what brought them together. It's that passion that got it started. But hey, let's, you know, let's go back and have dinner and talk about a build or talk about family life, talk about careers. How can we help one another? And then just to see it kind of, you know, snowball from there, where it kind of builds steam, and then one person helps somebody else, and they go and help somebody else. And it's this like, this never-ending waterfall effect.

And I know that we don't get to hear all the stories from everybody who has participated in the program or what they've gone on to do at work, or home life, or helping others and whatnot. But those stories exist, and I mean, that's part of the reason that, you know, we wanted to have a chance to talk to you today–was to hear some of that because I–to put it–put it bluntly, it's awesome, right?

It's inspiring for me because it kind of, reinforces some of the work that I'm doing. And I'm not going to–I'm not going to say it's a bad thing that, you know, our team gets to exist because of folks like yourself. But just, you know, and me as an individual, right? Watching other people do the things that they're passionate about, helps keep the fire going for me on the things that I'm passionate about.

So, you know, and I guess all that said in a roundabout wait, I'm trying to say thanks. Not only to you, I mean, obviously. But to kind of, everyone out there who's part of the program, because you know, we wouldn't have made it to five years, you know, and who knows how–you know, what the future's going to hold if it wasn't, you know, as successful as y'all have made it. Because it's, you know, we could sit here and be on Twitter and release builds, but you know, if there's–if there's nobody out there who wants to see what we're working on, you know, the program doesn't have the same flare to it at that point.

JEREMY SINCLAIR: Right. And it's-it's been such a–a wonderful five years. Like, I would have never guessed that my favorite keyboard shortcuts would be Windows + . and Windows + Shift + S. Never would have thought that I would use those keyboard shortcuts so much, and just, all of the things that have been created within this past five years have just–all the feedback, everyone just taking their part, and being an-an Insider. And there's all that communication, and it’s just wonderful.

JASON HOWARD: So, I've got to say, right–obviously we've done a bit of looking back. But let's–let's–let's hit the ghost of the future now, right? So, let's-let's take a–let's take a gander into what's coming.

So, here's some interesting questions for you. We'll start off with this one first. Why does tech matter to the future? It's a very vague question.


JASON HOWARD: But I-I'm super curious to hear your answer.

JEREMY SINCLAIR: Well, I think tech does matter to the future because if-if we go back–yeah, if we go back (laughter) and think about all of the technological advancements that have happened, even over the past ten years, in regards to the advent of social media, connections across the world, even medical. I think we're going to see that-that rate in which the technological advancements happen at a much faster rate. And we're going to start to see many things that weren't, you know, involved primarily with technology become like, a little subset of it. So, we're going to start to see a lot of–more things merging with technology at the forefront.

JASON HOWARD: I've got to say, like, I never thought that I would see an LED or an LCD screen built into the front of a refrigerator.


JASON HOWARD: But here we are.


JASON HOWARD: It's like, you pull it up, you can run apps on it. You know, you've got a family calendar on that. It's just like, I-I-I think about, you know, some of the places that I've lived in the past as I've moved around and you know, all that, and I'm like, what? Like, it's-it's-it's kind of funny, right?

And then you know, it's like, you know, the doorbells, where instead of just, you know, you push the button, and it rings in the house, and somebody comes and answers the door. Now there's like–there's like, video camera doorbells, where you push the button, and it sends video to somebody's phone, and you're like, oh who's at the front door? And they're like, nope, I'm taking a nap, I'm not answering that or, you know, it's like–


JASON HOWARD: (Laughter.) That neighbor that you don't want to talk to. You kind of get to screen the people coming to your door as opposed to using caller ID, right?

JEREMY SINCLAIR: Yeah, that–it's-it's insane to-to even think about all this stuff existing. For instance, my dad, he's-he's a geek. He's a big tech geek. He has everything in the house. He has the whole home automation aspect. He's more kind of, built into, hey, let me use like, Alexa for instance, and control the lights, control this, control that. I'm just like, I never would have thought I would see the day where like, I see my parents just talking to a-a voice assistant, and it does everything for you.

JASON HOWARD: Mm-hm. Like, technology just keeps growing by leaps and bounds. And you know, there's-there's going to be–I'm-I'm-I'm waiting for my dining room table to have an IP address. I don't know why it would, right? I can't imagine the scenario that would enable that, but at some point it probably will, and you know, it'll be curious to see. (Laughter.) You know, I mean, I know it sounds ridiculous, right? That's why I'm chuckling after having said that.

But you know, you-you think about how much like, the IoT, so the Internet of Things, right, where it's, you know, random stuff that you never would have thought was internet connected. Like, being able to turn your lights on and off. Things like that. Things that you mentioned. We've come a long way and obviously, you know, to the point that I think you originally were making is like, this transformation isn't going to slow down anytime soon and it's-it's gonna–it's going to be an interesting change as we keep going forward.


JASON HOWARD: So, knowing how important this is, right, knowing that this technological transformation–nobody's going to tap the brakes on it, because there's way too much cool stuff coming from it. What do you think people should do to get more involved? How should they get involved? Where should they start?

JEREMY SINCLAIR: Well, I think people should likely get started with learning more about the technology, because many of the times, they–we're just consumers. But I think gain-gaining a deeper understanding about how the individual technologies that exist–that exist out there, which everyone uses, they–like their cell phones, social media–getting more involved in the other projects, the-the new projects that are out there coming up. So, there's a lot of open source projects, where you start to see like, hey, I implemented this cool thing that's this new encryption algorithm, this cool thing with AI. Starting to really think about a lot of the ethical implications of things.


JEREMY SINCLAIR: Saying, hey, how–what can I do to reduce anything bad happening? On the other hand, there's the–there's the aspect of medical. So, I remember seeing a video, I think it was from Build 2017, where the-the woman had the–multiple sclerosis, and you saw the researcher build a device to help control that and control the tics. And it was just mind-blowing. Just someone seeing that–seeing that issue and taking that time and building a device to help someone else out. I think that's where, you know, we need to start paying more attention to that, because there's only so-so much that, if we rely on, I guess, individual companies to do.

It's to the point now with, as you brought up the IoT, it's-it's to the point where we have the-the hardware out there. The hardware's cheap. It just takes all of us, you know, taking the time to address the individual issues out there. If there's no solution current, we can all work together, get, you know, some sort of funding from somewhere, and just come together, and put everything on the table, and just address it one by one. Like, what can we do within our power? What can we do with the knowledge of programming? With hardware? What-what can we do in order to make these individual issues eventually go away?

JASON HOWARD: Well, that's the interesting thing–is for every bit of technological advancement that we've made, right? Whether it's, you know, something that Microsoft has done, something that, you know, other tech companies are doing, or something that, you know, individuals who are tinkering in their garage, right? Who-who knows where the next big startup is going to come from? It's all because somebody saw something they wanted to change in the world, right? Whether it was medical or personal, something for a family member, some big idea they had that were–hey, we're going to try to figure out a way to make people's lives easier in general, right?

I mean, you-you scroll back, you know, 30 years, and the concept of, you know, web-based email. It's like, wait, what? You know, it–there's things that people have done that you go far enough back in time and it was a–it was conceptually something that had never been thought of. And every step that people take to push it forward opens one more door, and then somebody's like, oh hey, somebody had this idea, and there's this thing that exists now, I know a way I can go and improve it, right? And so, people start building off of one another, and it just kind of, you know, continues rolling from there. And you know, the next thing you know, you've got a, you know, a billion-dollar company, right?

Not everybody's going to become a billionaire startup, but if you find the right thing to focus your energy on, if you find something that you're passionate about, turning that passion into something practical or some, you know, some way to use technology to make it better. Like, I think that's where a lot of people have kind of, kicked off their interest in technology, besides just being exposed to, hey, you know, you can start with the basics of, here's a computer, here's how you use a computer.

I can think back to, you know, obviously back in the–in the 90s, when my parents had never used a computer before, I remember, you know, my dad bringing one home, and I just start ripping apart the boxes, because I know which cable goes where, and, you know, this is back when there was PS2 ports on computers. And the purple cable goes here, and the teal cable goes here, and all that kind of stuff. And my dad's like, he's getting frustrated, because he doesn't know what I'm doing, but he also doesn't realize that I know what I'm doing, right? And so, there's been a journey with, you know, family, and friends, and relatives, and stuff. And so, you know, of course being at Microsoft now, I'm the–I'm the on-call tech support for, you know, my family and friends.

But, you know, kind of circling back to the point, right? It all starts somewhere for each person who wants to engage, right? And I have to say that when I first, you know, started in this role, when the Insider team was created, there was a lot of things that I didn't know that I needed to know. And I didn't know that I needed to know them. And that sounds kind of funny, but it's true.

And I have to say, near daily, but absolutely every single week, there is something new that I learn because of Insiders. They teach me that there's some piece of the OS that I have never touched before. Hey, I'm having a bug, I'm having an issue, you know, trying to pull up this, or run this command, or work with this software. And I'm like, I didn't even know that existed, right? So, then it enables me to go and learn something new, and then hopefully by, you know, having that conversation with them, somebody else sees it, and then it kind of waterfalls from there. Somebody else can learn about it. Somebody else can go and investigate and explore. You keep opening those doors, and together as a community, we keep teaching one another.

JEREMY SINCLAIR: Exactly. And that's-that's really what it's about. Kind of, paying it forward. Making sure that the next generation is going to enjoy it. And if we set that foundation and just keep things flowing, that's-that's what it's all about.

JASON HOWARD: So, looking forward to the future of the Insider program–this is where I get to ask the really–the really fun question, and kind of, put you on the spot. What do you think the future of the Insider program looks like? What should we do as a team, as–with Microsoft as a company, Windows as an organization? What should we do to-to take this program into the future?

JEREMY SINCLAIR: So, and I think this is something that I've always wanted. This might even be a personal thing.


JEREMY SINCLAIR: I would love to see just even, hardware testing. Hardware with versions of Windows being able to-to be tested. Because honestly, with my ARM64 device, which I'm glad I have, I always wanted to test Windows on ARM, but I didn't have a-a device until I won one.


JEREMY SINCLAIR: And I think, if there's a way to kind of, reach-reach out with the Windows Insider Program, where it's–there's like, a subset or some extension where it's like, okay, we have Windows Insiders hardware testers where you could kind of, demo individual, you know, hardware configurations. Something like that.


JEREMY SINCLAIR: Because I think also–because I-I know there's the Insider program for the Windows Server, but I think that's kind of like, the next thing beyond that. Because if you have all of that together at that kind of, next tier, that may get more people involved. I don't know how that could work, but–

JASON HOWARD: Mm-hm. Yeah, there's definitely some logistical questions about that, especially in trying to share hardware broadly across the globe.


JASON HOWARD: I will tell you this. Like, I have–I have–I have sent some swag overseas and even just a–a bag of swag going to Europe–whew. Those shipping costs. Those things add up quick–


JASON HOWARD: But, you know, it's-it's an idea that I like. It's–it'll-it'll be interesting to see if we ever end up doing something like that. But, you know, it's good actually getting-getting you to actually–you know, and obviously this isn't scripted, right? I'm not telling you what to say. It's kind of fun. It's fun hearing it on, you know, this program because the folks inside Microsoft that listen to these podcasts, you never know who's going to hear it. So, you know, maybe-maybe you're–maybe you're reaching the right person. (Laughter.)


JASON HOWARD: So, for the–I guess, to the–to the software side of things, is there anything that you see that we're doing now that you would change, you would improve? Is there something cool and fun that we should start doing?

JEREMY SINCLAIR: I do see maybe a need–well, actually, I don't even know if this need could even be fulfilled. I know a lot of people either joke about that or actually may be serious about having some sort of–is more kind of, alpha testing level. Maybe-maybe like, up to the point of like, a canary build testers.


JEREMY SINCLAIR: Because I know a lot of people would just be like, hey, it'd be cool if I could have helped catch this back then.


JEREMY SINCLAIR: Because it made it this far, and there was something that–it–obviously, the testers aren't going to catch everything.


JEREMY SINCLAIR: Because I-I know what development, you know, fraud. Things, you know, there’s still a bug that you did not know about. But I think even having like, an upper tier Windows Insiders that gives us that-that kind of, level back before Skip Ahead. I think that would actually be something pretty cool.

JASON HOWARD: Interesting. I–that is definitely not the first time that I've heard that request. I'm sure there's probably other people out there listening be like, I have made that exact request, and they haven't done it. Maybe now that Jeremy's talking about it on air, maybe they'll do something about it.

JEREMY SINCLAIR: I think that–one nice disclaimer is like, it would be at your own-own risk. I know many people, they hop into the program just expecting things to just flow. Knowing that, hey, you're in Insider Fast, et cetera, et cetera.


JEREMY SINCLAIR: There was a disclaimer. You know, there's a possibility of things going wrong.



JASON HOWARD: We-we do our best to try to avoid it but–



JEREMY SINCLAIR: There's-there's only so much that can be done.

JASON HOWARD: Yeah. I-I love dropping this famous line. On occasion, something happened.

JEREMY SINCLAIR: Yeah, that's why I have multiple machines. In case something goes wrong, I have–I have a backup.

JASON HOWARD: So, I know we talked a little bit earlier about like, why does tech matter to the future, right? And you know, we discussed, you know, enabling people to-to do more with their lives and, you know, getting people exposed to it, you know, how it–how it has affected people's daily lives, right? What do you want to see next? Like, if you got to create the next awesome piece of technology that was going to help transform the world or even just transform something in your individual life, what would you like to see?

JEREMY SINCLAIR: I would like to see–oh man, I can't believe I'm saying this. I would like to see something kind of, like, a cyborg body. So, kind of like-like, an exoskeleton.

JASON HOWARD: Are you trying to create The Terminator, here?

JEREMY SINCLAIR: It sounds like it. But I-I think about–I think about like, some people with–that-that may have like, individual like, ailments that are, you know, kind of like, bone related, et cetera.


JEREMY SINCLAIR: Or some-some sort of way that you have some tech that could kind of, mold to you, learn about you, learn about your, you know, your body health and just be able to help and account for that. Like, nano machines. I'm getting pretty sci-fi with this but that's-that's what I want to see next.

JASON HOWARD: I mean, sci-fi is what's kind of, drives the future, right? Like –

JEREMY SINCLAIR: Yeah. I-I want to see that. And I would say I-I want to see more–I want to see more AI, but it-it needs to get to the point of all the–all the ethics hashed out, and no Skynet happening.

JASON HOWARD: Don't actually want a Terminator popping up.

JEREMY SINCLAIR: I decided to go there.

JASON HOWARD: So, that-that's actually an interesting point that you've made. Right? So, obviously with the future of tech being wide open, what's something–I don't want to say scared. Scared's not the right word. But I guess along the vein of something you're concerned about. Do you think–do you think like, the-the ethics of AI, is that something that kind of, rings true for you or is there something that's more top of mind for you?

JEREMY SINCLAIR: I think the ethics of AI is more or less a–like, a subset of my worry.


JEREMY SINCLAIR: My worry is with people using technology in a weaponizing fashion.


JEREMY SINCLAIR: So, if you have like, the battle of the technology giants, and you get so much off from technology that someone decides, hey, I'm going to use this to restrict, you know, restrict functions, restrict–hey, we have all-all these cars linked up, you have the energy grid, you have everything that's relying on being interconnected. Just, I'd be a little worried about the–too much of that interdependence on it. To the point where we forget our humanity. We forget how to function without technology. That's-that's kind of like, my-my biggest worry. But I want all this technology though.

JASON HOWARD: I know, right? It's–

JEREMY SINCLAIR: I need this future, too. Like, I want–I want the world to progress to the point where someone's sick. They just inject like, a nano machine. Going back to that. Goes through. You're fixed.

JASON HOWARD: Yeah. And it's-it's really the kind of the-the ethical development of technology and making sure that whatever comes forward is used for the benefit, you know, whether it's helping one person, ten people, you know, the entire global scale of humanity.

Rather than the kind of, the darker side of tech that, you know, I mean, there's hacking and malware and everything out there. And so, any new tech that comes out, right, there's always somebody who's like, oh what's the opposite side of this benefit, right? And it–that-that relies a lot on the people side of things. So, you know, we can use technology to make, you know, lives simpler, or easier, or you know, help us live longer and be more healthy, and things like that.

It comes with the string attached to it that we're still human, and it's still humans developing the technology. Because it's not like we're ever going to–I don't know. I-I say it's not like we're going to ever–maybe at someday we'll have your non-Terminator cyborgs programming code to run the world, and we're just like, sitting back, taking advantage of it. Wouldn't that be a trip?

JEREMY SINCLAIR: Yeah, that would be pretty interesting.

JASON HOWARD: We're definitely getting out into the sci-fi realm now.

JEREMY SINCLAIR: I-I think also, I'm-I'm really hoping for a-a future where you're not kind of, seen like an outlier for enjoying technology. Because I knew with me growing up, I was always, you know, oh you're the–you're the geek. Blah, blah, blah, blah, blah. I just liked technology. I liked computers. I liked tinkering. I learned by accidentally running fdisk on my dad's computer, and he–


JEREMY SINCLAIR: And seeing the outcome of that.

JASON HOWARD: Oh my, goodness.


JASON HOWARD: Yeah, for-for anybody that doesn't know what that means, do an internet search, but please, do not actually do it.

JEREMY SINCLAIR: Do not do that. But I-I just wish that we can see the prevalence of the creators use technology. I want everyone to never feel like they're an outcast for liking technology and wanting to pursue a career in it or even a hobby. That's what I-I really want to see happen in the future because I know it's still–like, we're getting better. We're really getting better–


JEREMY SINCLAIR: I know social media, and you know, memes are kind of helping out with making it a little better for others to not get, you know, jokes done about them. But it needs to be something where it's not, you know, like, oh, you're kind of like, the outcast or not cool because you like to program.

JASON HOWARD: Yeah. I have to say that has changed a lot. I mean, even if you look on social media right now, I’d say kind of, one of the–one of the trending areas that's growing, right, obviously machine learning, artificial intelligence, things like that. But one of the areas that I see a lot on social media is information security. You know, abbreviated to InfoSec. There are a ton of people in that space, and it seems that kind of, as that group grows, right, the way that they are including new people into that space and enabling them with, you know, enabling one another with information, and tips, and tricks, and help, and you know, partnering together–there's a lot less of that, oh, you're kind of a computer nerd thing that you know, hopefully, you know, especially compared to, you know, 15, 20, 30 years ago, you know, hopefully the–kind of, what you're describing the–the stigma of being a "computer nerd"–I-I think that's quickly becoming a thing of the past.

And I think as technology continues to progress forward and people realize just how integral tech is going to become in their life that, you know, I think–I think we'll see the flipside of that. Where it's the folks that are doing the programming and creating the new technology–I can't say they'll necessarily become heroes. I mean, if somebody invests a nanobot that goes in and cures cancer, yeah, they're going to be a hero, right?

But there's going to be technological strides that are made on a daily basis that people will appreciate and care about. And there's-there's no reason to, you know, poke at somebody or, you know, to kind of, you know take cheap shots at them, when they're the ones that are working to try to make things better for everybody combined. Even, you know, at the personal level, community level, global, what-whatever scale they're working at. Anybody who's taking the time to try and do something beneficial shouldn't-shouldn't be derided for that. They should be given a pat on the back and encouraged to continue moving forward.

JEREMY SINCLAIR: I completely agree with that.

JASON HOWARD: So, I've got one more question for you. What's next for you?

JEREMY SINCLAIR: Let's see. What's next for me? I am learning more technologies. I haven't given up on the Azure side of our–


JEREMY SINCLAIR: You know, our little challenge of–to learn things in Azure.


JEREMY SINCLAIR: Not given up. With that said, I've had the great honor of presenting in November at Visual Studio Live Orlando. My first time presenting at the one conference I was first introduced to ten years ago.


JEREMY SINCLAIR: Yeah. So, I'm pretty excited about that. I do have a few plans to try to get more people into using .NET. It's–so that's my-my thing. I love .NET. I-I'm a–I go crazy over it.

JASON HOWARD: I think as the kids call it these days, that's your jam. (Laughter.)

JEREMY SINCLAIR: Yeah. I-I really expect for myself to do a lot more community related, because I've built a lot of stuff for myself and for the company I work for. I want to get a lot more people involved and hopefully can help them solve an issue that they may have, or as what seems to happen, every day I go online and someone presents an issue that I didn't know I had and has a fix for it.

JASON HOWARD: Everybody learns from one another, man.


JASON HOWARD: And you're a piece of that puzzle. I mean, that's why, you know, I–well, obviously like I mentioned earlier, I'm super glad to have you here. But you know, having seen some of the way you've participated in the community–obviously, you've been around the program for a while. It was–it was part of why I wanted to have you on today, because I knew you'd have a different perspective than you know, the internal Microsoft side of things, right? I love having our guests on, but it's always interesting to talk to somebody who's on the opposite side. Somebody who uses technology on a daily basis. Somebody who's using what we've created in a way that's different from the way that many of us internal to the company are.

And you've done a–I-I mean, I don't know if you've done a podcast before but I've got to say, it's-it's been fascinating hearing some of the things that you've talked about and hopefully some of the listeners out there have-have found this interesting as well. And you know, looking forward at the Insider program, right, like, I know that–you know, we had the Windows Insider Program, we have the Office Insider Program, there's the Edge Insider Program. You know, you can participate in Server. You know, it's tied to Windows. But that's there. I-I can't even sit here and name all of them, right? So, there's insider.microsoft.com for anybody who doesn't know that. You can go to the website and see the full list of everything we have there.

And one of the things that I'll say, I was always curious about from day one was, what is the program going to evolve into? And I will say that five years ago, when this program started, October 1, 2014, I could not have guessed the opportunities that have been created by this program. For those of us inside the company that are working, you know, on the program or adjunct to the program. The people that we would have met from around the world, your-yourself included, right? But not just from the U.S., but literally from around the world. And the connections that we've made. The community that has grown.

And so, having seen what's developed in five years, and knowing that, you know, it's-it's felt kind of, like a startup inside of Microsoft, which is kind of a fun place to operate. Knowing that you know, we've got our feet underneath us and you know, we're not, you know, doing those baby steps anymore, we've made some big progress. Trying to predict where we're going to be five years from now or ten years from now, like, I can only imagine what's going to change. It's pretty exciting, and I will say, you know, I'm happy to have been here for the first five years. It's been fantastic. I'm looking forward to seeing what's coming next. And to you, you know, for having been here kind of, since the beginning, and then for everybody out there listening, whether they joined on day one, they joined last week, or you know, hey, if there's somebody who's just listening to this podcast that isn't actually participating in this program, you know, obviously I welcome them to come, you know, jump in and see what it's all about.

But you know, just a-a heartfelt thanks from me, because, you know, we couldn't do this without each and every one of you. So, you know, on behalf of all the Insiders out there, I'm saying thanks. But you know, I'll say thanks to you, and you can help share the thanks for me.

JEREMY SINCLAIR: Oh, I really appreciate it, and I know everyone else in the program will appreciate it also, because this program's just–it's given us a new outlet. Instead of waiting for, you know, hey, all the bugs are done, here's something farther down the line, we get to see, hey, here's the upcoming version of this. Here's the next thing. You get to participate in testing it for us. You get to see the-the sneak peek of the new technology. The new features of–especially like, Windows Sandbox, WSL, Windows Subsystem for Linux. That–things like that. Seeing that in Preview and being able to use that before it goes live to everyone. I'm sure that a lot of people really appreciate this–that honor of being a part of it, because I know I sure do.

JASON HOWARD: No, and it's our honor to be able to, you know, have each and every person out there who participates, involved with the program and helping us make, not only Windows, but all of the products and services that we preview out, you know, to Insiders. You know, wherever they may be, to help make all those better. And so, really, the thanks comes from our side. Like, it's-it's huge. And you know, I'll throw a little personal note in there. Thanks for helping keeping me employed. (Laughter.)

JEREMY SINCLAIR: No problem to us.

JASON HOWARD: Well, Jeremy, I-I know we've talked about a lot here, right? You know, just kind of on a personal note with you, we covered some of the past of how you got started and you know, the things that you're doing currently. But thanks once again for being the ghost of the Insiders future, right? You know, we've talked a lot–we've talked a lot over the course of this episode about things that we're-we've done, where we are currently, you know, where we hope to go. And I've got to say, it's been an absolute pleasure having you on the show. Thanks for making the time. I know there's a few time zone differences between us, so you know, I-I know you're kind of hanging out at work, so thanks for staying late. Thanks for hanging out with us and no doubt we'll be in touch again soon.

JEREMY SINCLAIR: Hey, it's no problem to me. Thank you so much for having me on here. It's–like I said, it's a big honor, and I just can't wait to see what happens next.

JASON HOWARD: Yeah. And I'll be glad to see you being part of that.

JEREMY SINCLAIR: Oh, I definitely will.

JASON HOWARD: All right. Thank you again.

JEREMY SINCLAIR: All right, thank you.

JASON HOWARD: Cheers, man.



JASON HOWARD: And with that, Windows Insiders, this episode and the first five years of the program are a wrap. We hope you enjoyed this special episode as we've taken a journey throughout the years. Thank you again to Brandon, Amanda, and Jeremy for joining us for this special, super long episode and for celebrating the program we've worked so hard on. And thank you to all of our team that's helped make the past five years possible.

And of course, a huge thank you to all the Windows Insiders who have joined us these past five years. It is remarkable to see the amazing things you have and continue to accomplish with technology in both your personal lives and communities from around the world. We couldn't have done it without you.

Thank you once again for tuning into the Windows Insider Podcast. Join us for a new episode each month, and don't forget to subscribe to the podcast on your favorite app. Until next time.


NARRATION: The Windows Insider Podcast is hosted by Jason Howard and produced by Microsoft Production Studios and the Windows Insider team, which includes Allison Shields, that's me, and Michelle Paison.

Listen to our previous podcasts and visit us on the web at insider.windows.com. Follow us @windowsinsider on Instagram and Twitter.

Support for the Windows Insider Podcast comes from Microsoft, empowering every person and every organization on the planet to achieve more.

Join us next month for another fascinating inside look into Microsoft, tech, innovations, careers, and the evolution of Windows.