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What’s next for the Windows Insider Program

February 5, 2020

In this episode, we’re looking at what’s coming for the Windows Insider Program. First, we’re talking about the future of the program and our goals for the new year with Ian Todd, who’s helping guide us while we search for new leadership.

Then, we take a look behind the scenes at how the podcast gets made and at what’s next for the program’s marketing content with Allison Shields, our team’s content expert.

Windows Insider Podcast Ep 27: What’s next for the Windows Insider Program


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

This is Episode 27, What's next for the Windows Insider Program.

But first, if you're not yet a Windows Insider, head over to our 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 onto the show.

This month, we'll be talking with our special guests about the future of the Windows Insider Program, as well as getting a sneak peek at how this podcast gets made.

First, we're joined by Ian Todd, the interim lead of the Windows Insider Program. Despite the ongoing search for our new leadership, he's here to talk to us about the future of the program and how we prepare for what's next.

Then we'll be joined by Allison Shields, our trusted podcast producer who handles all things digital for the Windows Insider Program. She’ll be talking to us about how the podcast gets made and what to look forward to next from the marketing side.

Without further ado, let's welcome Ian Todd to the podcast. He's the acting lead of the Windows Insider Program. Welcome Ian. Thank you so much for joining us today.

IAN TODD: Thank you, Jason.

JASON HOWARD: So, I'll say, as my acting lead, I happen to know you pretty well. But for the Insiders out there who haven't had the opportunity to hear from you yet, can you tell us a little bit about yourself and what you do here at Microsoft?

IAN TODD: Absolutely. I'm Ian Todd. I am Jason's acting lead, and what that means is that the Insider program team, that-that leads the program reports up through my organization. And as part of that, I'm here today to share with you a little bit about what goes on in that organization and how we think about the Insider program these days.

So, who am I? I'm a 20-year Microsoft veteran. I'm in product management, formerly program management. My focus has always been on user experience and end user facing experiences, with a more recent focus on how we listened to our customers, which is the segue into this role and the fact that the Insider team is a part of my world.

As far as stuff I've worked on, I've worked on Windows itself since about 2013. I was part of the team that came in to make Windows 10, and previous to that, I had worked on a user experience role in Windows phone, and before that my legacy is Zune media center, and my favorite Encarta.

JASON HOWARD: (Laughter.) That's some serious throwbacks in that sentence.

IAN TODD: Been there.

JASON HOWARD: It's the proof that you've actually been around for 20 plus years at this point.

IAN TODD: It's been awhile.

JASON HOWARD: Wow, yeah. What's interesting is, I didn't realize it until I was having a side conversation this morning. Yesterday was my eight-year anniversary here at Microsoft.


JASON HOWARD: It's not one of the, you know, the big five, 10, 15, 20-year milestones, but it was just like, oh yeah. Another year has kind of ticked by and you know, added to that column. It's like, okay. Two more years to the next big milestone, but you know, the first stage has been pretty cool, so we'll see what happens next, right?


JASON HOWARD: So, as you mentioned earlier when describing your role, the Windows Insider Program is now a part of your universe, even more so while you actively interview for a new program leader.

IAN TODD: Definitely. I mean, first, it has been great to learn so much about the Windows Insider Program and how it operates while filling in, and yes, we are actively interviewing candidates to fill the leader role on a long-term basis, which is super exciting.

JASON HOWARD: Absolutely. And beyond the Insider program even, there’s a lot more that’s on your plate than just this program, so can you tell us a little more about some of the other things that you’re working on and what you help drive within the current space that you own for Windows?

IAN TODD: Sure, yeah. My product management team has a fairly broad charter, it’s how Insider program fits into it. And the word for word of the charter, and of course each word is carefully selected, is that we're here to provide for more users’ needs for more effortless Windows experiences.

You can't get enough of that in a product like the one that we make and with a user base as large and as varied as the user base of Windows. We have so many different types of customers that interact with the experience every day that there ought to be a group of people who are shepherding that experience day to day, making sure we’re hearing from customers and acting on what customers tell us. With an eye on this notion of effortlessness, so that when you use Windows, it's feeling as effortless as possible. It's simple. It's quick. It's satisfying. The idea is to elicit, we use this term internally, to elicit love from our customers. And so that's kind of what motivates us, and everyone on the team, Insider folks included, typically are wired to be customer-oriented folks that feel great when they know they've delighted an end-user.

JASON HOWARD: And that's a big reason that the Insider team ended up in your space when there was the decision to do some reshuffling and moving teams around, which happens a lot here at the company. But given the charter for the area that you own, it seemed like a natural fit to slot this in alongside some of the other things that your team is responsible for.

IAN TODD: It-it both seemed natural and was new. I don't recall in what you now know as my lengthy history, a moment when we've placed the customer listening channels this close to the rest of the user experience. So, there are folks right next door, as Jason already knows, down the hall, who are shepherding the actual UX architecture of Windows, the folks who are the club that works on the Start menu, the taskbar, things like this. This is all happening, Settings, Action Center, this is all happening right down the hall from where we do our customer listening and get our feedback.

It is true that Windows is more than just the tippy top of the end user experience, and there are many, many other teams that are working on Windows, but to have the center of excellence around listening and the center of excellence around end user experience right nearby is really satisfying for me, because you start to see the whole—the whole system working properly.

JASON HOWARD: Yeah, so kind of as a part of this effortless area that, you know, we-we are connected into, one of the things that I think’s worth noting is the concept of the Hassles program. Can you share a little details on that and what all that involves?

IAN TODD: Yes. You might even expect it given the mission statement, but part of what we do as we listen to customers, as we consider the end user experience, is to identify the most frequently occurring, most severe hassles that our customers face. And this is across all audiences, consumer customers, commercial customers, whoever, on where they're finding their experience to be not effortless. And we have that list, and in some cases, these are just bugs which are quicker and easier to fix. But this is so that we can do feature level work as well to improve the experience.

Sometimes, these are just small things. A good, somewhat recent example would have been that we added a slider to control the brightness of your screen to the, what we call the quick actions, at the bottom of the Action Center. Yes, many machines, many laptops already have other ways of doing that. Some customers have other ways of doing that, but there are quite a few use cases for Windows where you may not have access to say a keyboard, and you need to quickly change your brightness the same way you would on a tablet. And so, that's why that slider got added there. It was always in Settings, but bringing it a little closer to the surface was a point of feedback.

We've seen flighting recently of things like improving the tablet posture, where can we get some of the benefit of the tablet mode without having to enter all the way into the tablet mode? This also came from hassle work.

Again, we make that list, and we knock them out. And that list, the hope is that we can actually knock out so many of those and not churn the user experience so much that Windows becomes a more effortless, less hassle experience, all up. That we’re staying ahead of the hassles.

JASON HOWARD: So, in looking at some of these hassles that you know, Windows users experience along the way, there's many different avenues where we take in the insights from our actual users to say, these are the things that should become priorities. Obviously, through the Insider program, the release of new builds as new features get developed, we take in feedback through the Feedback Hub, and then retail users as well who are on Windows 10, they can also submit feedback through the Feedback Hub, but there’s additional listening channels that we use as well.

Any calls that come into, you know, the Microsoft support centers. We do the Intercept program with some of our partners over on the data side, where we actually host calls with direct customers and listen to their verbatim feedback as we ask them line by line of, hey, how do you feel about this experience? Have you used this feature before? What do you think we should improve or change? What do you like, and what do you not like about it? It seems like all of these things kind of come together, and in essence make this program what it is.

IAN TODD: Yeah, the examples you rattled off are all good ones, and those are very much inputs to the Hassel program. I would add one to the list that's kind of my favorite. If the feedback ends up in this one, it's very easy for us to parse it alongside other feedback and make sure that we're listening to the right pieces of feedback, because so many sentiments come in through this channel. And I'm not sure that Insiders even know about this particular one, ‘cause it doesn't come up for everyone every day.

Occasionally, Windows will ask, I forget the exact wording, but you know, would you recommend a Windows device, basically to other people, and it asks you to rate on a scale from one to five, like whether you would. And then it gives you a chance to enter something into the box about, you know, why the number you picked was the number you picked.

Well, that is actually a very high-fidelity way to get feedback to us that helps us work top-down across the entire audience on what they're feeling, what they're expressing. Because what we can do is, we can look at the numeral rating, and then we can look for, in the cases where it's positive, note the reasons why. We can bucket those reasons why, so that there's a simple list of the most prominent reasons why. And in cases where it's negative, as you might expect now that you know these details, the hassles often will show up there. People will mention a particular reason why they provided a-a more negative, an unfavorable we call it, response to that question. And it gives us kind of the whole ocean of response, and we can rank those and bucket those, and it becomes a little easier to discern.

That being said, we don't only look at that channel, we look at the other channels like the ones you mentioned. I'm not sure you mentioned, account managers for our commercial customers. That's a place where you have large organizations using Windows. Those organizations might not even be set up so that that particular question ever gets asked for their end users. So that's another place where we know, there's one mechanism with a blind spot, so we have another mechanism that helps cover up that blind spot, and then we get input from both places.

And then there is a point where an actual human being looks at the results from all the lists, we apply a rating, we apply a number, and then boom, you have a single top-down list where you can take a team with a finite number of people, set them out on addressing these problems, and they come back with almost every single time, a significant chunk of our population going, “Thank you.” There's even a more recent, for those keeping track on Twitter, we have a hashtag #CloseTheLoop that is, that’s loosely related to the Hassles program. But you know, I think in more and more cases where there's public understanding of a particular hassle that exists and public addressing of it, that's the hashtag we'll be using to let you know that, yep, did that.

JASON HOWARD: That's awesome. Like, and it's interesting to hear some of these, you know, other data sources that, you know, are paid attention to. One of the things that it's interesting to hear from Insiders sometimes is, you know, when that pop up shows up as the, “Hey, would you recommend Windows 10 to a friend?” that kind of thing. There's people who fill it out, you know, routinely. They love it, right? It's a good way for them to give feedback. And there's other folks that are, oh, I don't, you know, I don't know if anybody's paying attention to it. You know, I don't, I just, you know, most of the time I just kind of swipe it out of the way and keep on with what I'm doing. Obviously, there's people who are paying attention, and it's actually a great way to have your voice heard.

IAN TODD: Yeah, I wish all of our touch points with our Insiders and our end users were as easy to respond to and to listen to as that one. And we may come to that in other, later in this discussion.

JASON HOWARD: So, jumping topics a little bit, there was a shift in the leadership of the Insider program, and because of the open role that exists currently, I know that the Insider program has taken a bit more of your time than it did previously, as you kind of guide us along in the day-to-day activities and where our focuses are. Can you tell me a little bit about how it's been, I don't know, maybe the adjustment that you've gone through of getting to know the Insider program maybe a little deeper than you had beforehand?

IAN TODD: Sure, yeah. Even though it's not my intention to play a public facing role, despite this podcast happening right now, I am happy to report both to you and to the listeners that, there is something about this program that has drawn me to want to engage more deeply, to make sure that the program gets the attention it needs from a manager at Microsoft, even as we find someone that is tailored to this exact role. And what I've gotten to do is get a sense of not just what is happening, but why it has been happening, the history, the origin or the-the beginning of the program, how it has evolved, what happened during the phase where Gabe was running it and how things worked and why things were the way they were, and then how things changed under Dona's watch. The introduction of the community or emphasis of the community element is notable there.

And then to try and ask a deeper question around why we even chose those tactics, and what would motivate a group of people, both the folks who coordinate the program itself, the leaders of the program, as well as the participants in the program, to take it to the next level, to do more than just sustain it. And in order to gain that understanding and to even flesh that out from the group of people who know it best, I've had to go hands-on, and it's been delightful getting to know the team, you, Brandon, Vivek, also the marketing team. There's a, our flighting team, that's a team I didn't know as well up to this point. There's partners in Office. It's a fairly big group of people that run the show, often behind the scenes at Microsoft, to make the Windows Insider Program happen.

And regardless of how we portray it publicly, how many different people are in the public view, it should feel inspiring to anyone who gets involved with it that there's an energy there, and that it's an energy that is at a next step on its journey. And defining that next step and helping bring the group along and helping bring the participants in the program along, so that it's better than ever, is something that I hold near and dear.

JASON HOWARD: So it sounds like, not only obviously the-the number of folks involved in kind of making this happen, because as you, as you well mentioned, right, there's a few of us who tend to be more prominently focused on, in the social aspect, you know, around in the community. There are a ton of people behind the scenes that work to do this on the data side, on the technical side of the delivery pipeline, the whole flighting team, so on and so forth.

Outside of that, I want to ask you like, has there been something of a, I don't know, a big revelation, kind of an aha moment of something that you found along the way that you didn't necessarily know before you kind of dug in a little deeper?

IAN TODD: Sure, yeah. My work, if you remember my rattled off list of previous products, skewed a little bit on the consumer side, a little less on the commercial side. Certainly, in the recent years with Windows 10 being for both and other audiences as well, I have more recent experience with commercial, but I had not yet been to Ignite. And Dona invited me, she said, “Ian, please come to Ignite. It's time. You'll love it. It's going to be great.”

And I was there with the Windows Insider team at the booth, on a panel or two, but I think most importantly, meeting customers, and in my mind, viewing the event through their eyes. What goes on at that conference? How does Microsoft tell its own holistic story, and how does that land for someone who's got a job to do and a set of customers who are using Windows products in their organization?

And it got me thinking about how we could simplify that story. It got me thinking about the wide diversity of people who are using Windows technology in their organizations, not just the people themselves, but the organizations, and what those organizations do. I think there's probably an assumption that when you think about Microsoft, and you think about commercial or business use of-of software, that we're talking about, like a company, like a Microsoft perhaps. And yet there are organizations of so many different shapes and sizes. There was one person who I spoke with in particular who ran IT at a university. And sure, the university use case that seems like something you could assume is, okay, that's an institution. It's got an IT administrative staff. It's got end users. And when you have those thoughts, you're probably thinking teachers and—or professors and students, except he mentioned the landscaping crew. He mentioned the folks that work at the cafes around the university.

There are so many different facets to the way Windows gets used across both individual customers and organizations, each trying to do great things, that even having—after having worked at Microsoft for, at that time, almost 20 years, it reminded me that there are use cases that aren't top of mind all the time, that both I and we, who build the product, need to keep in mind. And that was a fantastic moment, and I wouldn't have expected showing up at a big convention hall in Orlando to be where you'd have an epiphany like that, but-but that is where it happened.

JASON HOWARD: That's one of the interesting things, and I know we've talked in a past podcast about the big conferences that Microsoft does every year. So usually sometime in May we have Build, which tends to be developer focused, middle of summer, usually July, we have the partner conference Inspire, and then Ignite, which Ignite kind of jumps from month to month depending on the year. It was just announced today that it'll be in September of-of 2020 this year, where it was in November of last year. So, you know, it feels a little bit like Easter, where it bounces around from month to month. We'll just see where it lands, right?

But the people that you meet and talk to in each of these conferences, they all come from a slightly different perspective. But it's always interesting to hear that, the insights we take from one group of folks who are kind of using Windows in one way, where their focus is, and as we use those insights to develop and guide the product, kind of what that trickledown effect is to users in other groups, right?

So if you take a developer, and they're looking for specific way to interact with the OS, and they're able to redesign some of their apps, which affects end user experience when they come in and use the OS. Or if we do something to make it easier to access something between Settings and Control Panel, right? It doesn't just affect the group who initially gave you the feedback, it ends up affecting everybody's experience all the way through.

And that's-that's one of the things I kind of want to jump in and talk a little bit about is, as you—as you spent the time at Ignite, and you were able to interact with Insiders directly, right? And it was, if I'm—if I remember correctly, this was like the first time you were actually meeting Insiders in person, kind of shaking hands and asking them, you know, what they think about the program, and you know, how they're using Windows. What was it like for you to actually meet, what I would call some of Windows’ biggest fans, it's like the, it's almost like the Insider fan club, if you want to term it that way. Like, these are the folks who are super passionate about Windows and love what we're doing here.

IAN TODD: Yeah, I mean on a, on a somewhat lighthearted note, but it's the first thing that comes to mind when you ask me that is, I had no idea how much people want that swag. (Laughter.) That Windows Insider Program swag, that t-shirt, that-that sticker that we've got, I had no idea that that would be such a hot commodity. And you know, on a slightly more serious note, the idea that that holds so much meaning for our Insiders, to be able to wear that badge on your laptop, or wear that shirt to rep that cause that you have invested in, that you are a subject matter expert in relative to your own colleagues.

It made that much more palpable to me that there's a chain reaction of value, of meaning, of helping other people be productive, that you participate in when you step up, and you say, I'm actually not just a pure consumer of the value of Windows or from Microsoft. I'm actually someone who's going to act as an advocate for its use with other people, so that those folks get the most out of it. And then what happens then is, the-the person builds their own credibility and ability to help others. Other peoples get help, so you get satisfied, relative to the empathy you have for them. And then we, at the kind of beginning of that chain, can look out and say, we did something. We did something meaningful for a larger group of people. That is very exciting.

And the fact that the swag of all things would be the artifact that lets you know that that's happening, that that's desired. (Laughter.) It warms the heart.

JASON HOWARD: It is funny, when I do a webcast, and if I happen to put a new sticker on the back of my laptop, there are those clever folks out there who are super attentive to detail, and I'll get the, oh hey, there's a new sticker on your laptop. Where did you get that? It's usually, you know, it's anything from something from Azure or quantum computing, it's a new ninja cat sticker, something, so on, whatever. And the people with a really sharp eyes are like, oh that's new. And I'm like, oh yeah, they came from, you know, the Ignite conference, like the dolphin one that came up a couple of years.

IAN TODD: Yeah, brainstorm moment right here on the podcast. I wonder if we need another variation on ninja cat, right? I wonder if-if you know, perhaps the listeners have their suggestions for what should happen next in that space, especially given the swag factor from Ignite.

JASON HOWARD: Of course. Yeah, absolutely. So, there you have it. If you have something that you want us to make a sticker out, just let us know. We're always in the business of feedback, right?

IAN TODD: Exactly.

JASON HOWARD: So, a minute ago, you mentioned kind of the interaction you had with somebody who you spoke to that was on behalf of the university, right, in the education space. So, you know, at each of these conferences, we have a booth, we kind of talk about the program, the benefits of the program, introduce it that way. And along the way, we interact with people who have never heard of the program, people who've been Insiders for five plus years, you know, the folks that joined on the first day, and everything in between.

Interestingly enough, each of these, kind of, different groups of audiences, they bring us different types of feedback. Some of it's about the program, some of it's about Windows, and some of it's about just general things related to Microsoft. So, reflecting back to some of the conversations you had, what would you say was a valuable piece of feedback that somebody brought and presented to you during your time at Ignite?

IAN TODD: I think the one that is most memorable, it's less a user experience thing, you know, where I have a lot of my own history, like I know the feedback on the Start menu, and the taskbar, and the Settings, and such. I know those feedbacks, I've seen them for a long time, and we've made progress on them, and I stay up to date on those. But as we've already discussed, Insider program feedback on the program itself, that's going to be newer to me.

So the most memorable one there was, even though we had done talks at the—at the event about how to run your own Insider program in your organization, there was someone who wanted to do so, and wasn't sure they could pull it off, because of the security and size, scope requirements of their particular organization. And there was this moment during the conversation that was like, oh, you know, I was thinking like, it probably will work for you, actually, I don't know, but I know the people who I can connect you with to, you know, check to make sure it’ll work.

And then, it just sorta got said like, oh, it's this organization. Like, and-and I can't, I shouldn't say the exact organization, but let's just say it was a cabinet level agency of the United States government. And that was a major like, oh goodness, that really is a vast, large number of people type of an organization that probably has complexities that are beyond the most frequently used cases of our technology. And to think that the actual in the flesh human being who is in the role that's attempting to do what we suggest for any group of customers who you as an IT administrator are being empathetic toward, would do. And this person's just trying to make it happen as well. That was a beautiful and challenging moment to realize just how big a size and scope the work we're doing here can be. So that, that'd-that'd be the one that I'd say most memorable.

JASON HOWARD: So, having received that type of feedback, right, that actually gives me an interesting segue into the next question that I want to ask you.

So, in your role, you're a big part of helping drive strategy for some of the key areas that this program touches on. And obviously when the lead gets hired, some of that will shift, but at least in the interim while you're working on this, can you tell us a little bit about what Windows, and more specifically the Windows Insider Program, are going to focus on in 2020, and namely some of the things we're hoping to achieve or improve along the way?

IAN TODD: Sure, yeah, there was a moment, also at Ignite, where a journalist, you know, point blank said, hello, good to meet you, by the way, what's your vision, your vision, ha ha ha, for the Windows Insider Program. And you know, I had a thought, and then I said something. The thought I had was the pretty prominent thing we had been doing at the office, Jason knows very much about it, where we were talking through what we wanted the goals of the program to be over the next 12 months.

I had that thought, and then the next thought was, I'm not ready to just blurt it out, particularly to a journalist. So, I'm sorry man, that I didn't say it then, but I do feel that, right here on the podcast, of any question that you've asked, like, yeah, let's-let's-let’s talk about it. Let's talk about where this program is headed. Let's talk about those reasons why we do what we do, and how to advance it over the coming years. And what I would say is, even though I'm gonna rattle them off right now, as Jason well-well knows the whole group of people, the, our leadership of the Windows Insider Program, actually worked together to come up with what this list ought to be. And it's a pretty short list. It's-it's actually just three things.

The first thing that the Insider program is focusing on over the coming months is just growing the-the diversity of the audience that participates in the program. And that could be in terms of where in the world that those people sit. That could be the type of machines those peoples are—those people are running, to make sure that when we're listening to our customers that we're listening to a representative set of customers who are giving us feedback that we're acting on. We want to try and eliminate bias in the feedback that comes in, through a program that-that will always have some built in biases. We want to kind of transcend those biases and get to feedback that's truly representative. And while we're at it, make sure that the—that the product is being used enough that we can get feedback that's like, oh yeah, these larger more diverse group of people are using the product fully. So, whenever they give us feedback on something, we could have high confidence that it's representative.

That's the—that's the first one. And that's-that's been a quest in the past, but making it our top priority is something that is relatively new.

JASON HOWARD: Something-something before you jump to number two that I want to add in here.

IAN TODD: Sure, yeah.

JASON HOWARD: It's-it's interesting, and you're talking about like, kind of some of the, like the bias we get in feedback. Like one easy call out in that space is, we get a ton of feedback relating to deployment, right? So, as the build downloads to a machine, as it does the online preparation, where it unpacks the software that is downloaded, then it boots into offline mode, where it actually, you know, lays down the wim, and actually finishes the install, right? This is very front and center for a user, because it takes them out of their productivity mode, right? So, when something goes awry there, and a build doesn't install, it fails at 62% or something random, right? We get a ton of feedback in that space.

Some of the spaces that we don't get feedback in is, for me, I use inking once in a while, but I'm definitely not a power user of the inking function within Windows. So, I don't provide a lot of feedback in that space. So, it tends to come from a very small number of folks. And so, when we look at the feedback, you know, that comes in from Insiders, you end up with areas that are skewed. So like, deployment is something that affects every user of Windows, and if something's going wrong and affecting a big number of users, we're going to get a ton of feedback on there. If there's some small bug that happens to hit the inking space, we're not as likely to see it.

And so, it's things like that that we have to try to work our way through of, what's the volume of feedback we're seeing in a space? How representative is it of the broader population? How-how well used and well-loved is this particular feature? And then that of course goes into the whole follow on of stack ranking, figuring out which bugs we need to prioritize first, so on and so forth. There's a whole—there's a whole can of worms to unpack there. I realize I’m kind of mixing metaphors, but there's a lot to dig into there. And so, that’s a—that's actually a huge space that we're focusing into.

IAN TODD: Yeah, if you can elicit more usage from more customers who are more representative, it helps with all that coverage, and then Windows becomes a better product, and we've heard from the widest possible set of voices on how to make it a great product. So that was the—that was the first one the group came up with. It felt like something that you'd want to make sure the program was doing as meaningful work as possible.

The second one we came up with was, sure we can do that, but what about putting specific energy into making the program as satisfying and as engaging as possible to folks who are already in the program? So, there are bunch of people who are already in, they’re using the product a lot, they're giving great feedback, and we want to make sure that that audience is—feels celebrated, feels valued, is getting what they need to continue to engage in the great ways they already have been.

The first and second goals go hand in hand. One is about kind of some net new usage from some net new people, and the other one is about keeping the folks who have already arrived and loved the program and get benefit from the program, as-as active and as excited as possible, upping the ante on their engagement year over year. So that's the—that's the second one.

And then the third one is about the program itself evolving in ways that reflect the evolving of Windows itself. So, you know, for this year, you know, things that are new that are already visible in Windows, might include the way we release and the way the Insider builds work relative to the releases that arrive later, and the fact that those two are connected in a different way than they have been in the past. It used to just be, you know, there was a particular release-release was coming, you get the beta basically for that release, and then you get the final version.

And then another factor that we need to think about is Windows 10X. That is another facet of Windows that's a, this year, kind of a thing. And so, making sure that the program evolves in a way that can include that aspect of Windows 10 as well is something that we want to keep in mind. And these are just two examples. We actually rattled off a list of about five of these internally that we're looking at. So, we wanna just make sure the program is fresh and up to date relative to the-the products and the ways Microsoft does Windows in 2020.

JASON HOWARD: Yeah, and to-to highlight for those folks out there listening that, hopefully everybody that's listening has heard this, but just in case they haven't, like one of the things that kind of falls into this bucket was the dissolution of the Skip Ahead ring, as well as a—for some people it’s small, for some people it's notable. I guess it depends on what your perspective, or what you were trying to get out of the Fast ring was.

So, the Fast ring used to be tied to a specific release, right? So, we're working through, say just 20H1 as an example, right? It's going to last for X number of months, you'll work through, and then we'll present you forward to the next release. Well, the Fast ring now, it's in essence this, kind of just ongoing, continuous basis, right? The Fast ring isn't specifically tied to an-any individual release at this point. It's just going to be the continuous bringing forth of new features, bug fixes, changes, security releases, and all of this is just going to happen, kind of this ongoing, this never-ending unpacking and unrolling of what the future of Windows is going to be. And I think that's going to be a shift that, for those who had a, depending on what their perception of the Fast ring was, it’s going to be an interesting change, and I mean it's already in place, so we'll see where it goes.

IAN TODD: Yeah. I-I like the new model because it lets Microsoft and its customers work from merely the set of capabilities that are needed, and it puts the union of all those capabilities into one code base, and how they get packaged up for a particular audience that needs a particular type of package is a separate decision than just the new value that gets added to Windows.

I like to think about it as a, back in the Vista days, there was an addition of Vista called Ultimate, and it just gave you everything. And that's how I optimistically view the fact that you can subscribe and just get everything.

JASON HOWARD: So, as we wrap up here, I'm going to ask you my favorite question that I love asking all of the guests on here on the podcast. And of course you don't have to make any promises, and I don't want you to get yourself in trouble, but do you have anything that you would like to share, kind of more broadly, about what you think, you know, the vision or the future of Windows is, or where the Insider program is going to evolve next like, outside of say, the next year? Like what do you see happening beyond that?

IAN TODD: Sure, yeah. I would take you back to that moment I mentioned, where I was at Ignite, and I was looking across this, you know—for those that have never been to Ignite, there's this giant exhibition hall, and there's all these Microsoft booths with all these signs that are lit up above each one describing what that booth's about. And I would say, they were, you know, in the hundreds of these booths, and then they were divided into sections.

And I thought this is nice. First of all, I see no logos. A long time ago at Microsoft, you'd probably have camps, like a camp for Windows, a camp for Office. And as a company, we've gotten to the point, we can just talk about our offering in one breath with one visual design, so that felt good.

But then the next thought was, oh, but there's 200 of these, and no mortal can actually probably engage with, and you know, know exactly which one's which and who's doing what. And I feel like that's a metaphor for what we have in front of us as Windows, and to maybe to some extent as Microsoft, where we can always make life more effortless for our customers. We can always like, make life simpler for our customers. We can always make sure we've got our stories straight in a way that transmits out to folks who want a story to believe in.

We're passionate about the work that we do, and the more I can and we can do to simplify that, to make it as coherent as possible, to make it as consistent as possible. And when we do say something and we do do something in the product, that that’s as meaningful as possible to helping you be a more productive you, to do great things as it were. That's what inspires me, and that is the future possibility, the vision possibility for where we'd go beyond just rattling off the-the goals for the next 12 months. That's the—that's the thought I would leave with.

JASON HOWARD: There's a lot yet to come.

IAN TODD: Absolutely.

JASON HOWARD: Well Ian, I've got to say like, not only am I trying to impress my boss by having him in the studio nudge, nudge, wink, wink, I gotta say this has been some fascinating conversation, right? Hopefully the Insiders have enjoyed some of what we shared, some of the-the inside things that we've been talking about and working on, things that we hadn't necessarily spoken about externally.

There's a lot to unpack here, but I have to say, it's been fantastic taking the time to speak with you. Hopefully the listeners have enjoyed it as well. And yeah, there's a lot yet to come here.

IAN TODD: Thanks for having me, Jason.


JASON HOWARD: Next up, we have Allison Shields joining us to talk about the podcast and our content for the new year. Welcome to the podcast, Allie. Nice to actually have you in the booth this time, instead of back at the mixing board.

ALLISON SHIELDS: Thank you. Thank you.

JASON HOWARD: So, for those out there listening who don't know who you are, can you please introduce yourself and tell us a little bit about your role here at Microsoft?

ALLISON SHIELDS: Sure. So, I am on the Windows Insider Team as a contractor. I work under engineering, but I actually do a lot of the marketing type of stuff, so I help produce this podcast, help put in the cuts, do the little pieces with that, and then I'm also writing articles on the web, anytime you're on social, sometimes you're talking to me on there, anything sort of digital content could be me.

JASON HOWARD: And some of the really cool stuff that's coming for our website, you're actually taking charge and running with that as well.

ALLISON SHIELDS: Yup. We've got a lot of exciting stuff that we're planning for the next year.

JASON HOWARD: Awesome. So, as I mentioned in the opening right, you're normally behind the scenes here at the studio making each episode of the podcast a reality. And trust me with me being the host, we all know that's a lot of work.

ALLISON SHIELDS: Sometimes. (Laughter.)

JASON HOWARD: In fact, for those who may not have put two and two together quite yet, you know, the outro for the podcast is actually your voice. You're the one who recorded that, but normally that's the only time we hear from you. So, given everything that goes into making the podcast successful, can you tell us a little bit about what actually happens?

ALLISON SHIELDS: Absolutely. So normally, we actually start with brainstorming up what we want to talk about next. Jason is a big part of that conversation each month. Who do we want to talk to, what cool things are happening next, what cool feature’s coming out next.

And then we're reaching out to those individuals, trying to get people to represent those products, those things on the air for us. We spend a decent amount of time trying to get everybody scheduled and in the studio, so that it works.

JASON HOWARD: That’s always the fun part.

ALLISON SHIELDS: It's so true. The-the busyness of Microsoft meetings, combined with a studio's very set timeframes, are probably the hardest part (laughter) of making the podcast each month, but obviously we make it happen.

From there, we're bringing them into the studio, and we've got some light, scripted questions, and then Jason runs wild with them.

JASON HOWARD: Of course, right. (Laughter.)


JASON HOWARD: Everybody that thinks this thing scripted from end to end, you'd be completely incorrect. There's a few basic suggestions that Allie puts on paper, but I don't always stick to it.

ALLISON SHIELDS: Oh yeah. One day, you'll get a blooper reel from me too, and you'll-you'll have a full view—

JASON HOWARD: I'm not sure that's safe for public consumption.

ALLISON SHIELDS: (Laughter.) Holiday episode or something.

JASON HOWARD: It'll have to be. (Laughter.) Maybe after I don't work here anymore.

ALLISON SHIELDS: (Laughter.) No, never. We can keep it clean.


ALLISON SHIELDS: And then from there, I'm going through the transcript of these interviews, and I'm putting in notes for where those should cut, how we can lift out pieces of information that, you know, we either aren't allowed to tell you yet, and we put our foot in-in our mouths or just retakes, cause it happens to all of us that we need to stop and-and do a second take of something.

And then, we send those off to the studio, who their lovely engineers chop that all together for us and put together what you actually get as the finished product. And then I get to do fun stuff like put it on the website, and tweet it out to you, and taunt Jason on the internet with it.

JASON HOWARD: (Laughter.) I mean it's funny actually hearing it listed out that way, because normally, you know, I, you know, I come up with—help come up with ideas. We, you know, introduce to the guests. I take them through what a recording's like. We come in here and do the recording, but until it goes live, that's kind of the end of it for me, right?

There's obviously a lot of behind the scenes things that you are part of, as well as others. So even for me, it's a bit fascinating to kind of hear it laid out end to end like that. And I'm sure it's more complicated than that even. But you know, it's—there's a lot of work that goes into it

ALLISON SHIELDS: A little bit. You're lucky, my background before I got into digital content for the web was actually journalism, so I have had a weird, trial by fire inside of audio work and video work. And I never expected that I would come to Microsoft to do some audio interviews. I thought that part of my career was done, but, it's fun to actually use some of those skillsets you think you didn't really need.

JASON HOWARD: And I try to have fun in the studio too. I don't—I don't want it to all just be, you know, direct question and answer. And you know, there is some fun behind the scenes stuff that will probably end up on a blooper reel at some point of me singing and doing random craziness. It’s—you know, I’ve got to keep it interesting.

ALLISON SHIELDS: I think there's a SpongeBob theme song out there somewhere for us to share.

JASON HOWARD: (Laughter.) How many times have I sang hip hop in the studio? I'm not even sure at this point. (Laughter.)


JASON HOWARD: So, getting back on track here, what can we expect from the podcast this year?

ALLISON SHIELDS: So, I would be lying if I said that we had a-a real plan in place for each year, but I'm planning on tweeting out, when we're promoting this particular episode, we want to hear some more from you guys, and what else you want to hear about. Especially since we don't have concrete plans for the whole year. What features are you guys excited about? And then we'll also talk about some of the stuff we're excited about.

So, I know that there are some big stuff coming from us on the marketing side that we'll be able to talk about later in the year. I also know that there's some big Windows stuff that'll happen this year. And as always, Jason is always scheming, so I'm sure that we'll have some other people to talk to. Are we looking at privacy soon? Right?

JASON HOWARD: Yeah, that is definitely on the list.


JASON HOWARD: The security episode that we did towards the end of last year, I think it was last October, it was a super well-received episode. Got a lot of great feedback about it. And in asking Insiders, you know, what are some of the things they want to hear about? Of course, new features are always, hey, what's coming next, you know, what's going to be in the builds, things like that.

But actually, one of the things that I was actually surprised to hear about was the request that came in for us to talk about privacy. And that's such a huge space that honestly, we could probably split it and cover it over the course of two, maybe even three episodes. And I don’t mean, you know—you know, the full hour plus episode being privacy for multiple months back to back. But you know, kind of the format we have is, we usually cover two topics each month. So, I'm considering and talking to the privacy team about having them come on one month and you know, discuss—like if you broke privacy into like two major areas, right—come and talk about the first half in one month and cover the second half in the next month. And if there's follow on from that where we get additional questions, or there's other things that Insiders decide they want to hear about that we haven't yet talked about, we can always go back and add some more later on.

ALLISON SHIELDS: For sure, and privacy is just such a big-big area for us to talk about, and as a company, Microsoft takes it very seriously. So, I think we'll have fun with that.

JASON HOWARD: Yeah. So, you know, as you were talking about earlier, the podcast isn't all that you do for the program, right. You mentioned digital content, you talked about your background in journalism. One of the things that's super helpful for me is knowing that, with our website in the state that it is, right, it hasn't changed a whole bunch since we originally launched the program. There's been some how-to content added, of course when—you know there's build content updates that go on there and whatnot, but the general style and format of the website hasn't really changed much. So, can you talk a little bit about some of the changes that you're doing there, and then just some of the other things that Insiders get to see that’s actually done by you behind the scenes?

ALLISON SHIELDS: Sure, so right now, we're mostly looking at trying to make sure everything's consistent. We want to make sure we're really following Microsoft Style Guide regularly. It's hard when you have multiple voices writing for your platform, and we absolutely have multiple voices, not just on marketing, but when you combine us with Jason and with Brandon, you get a lot of different messages through that, and we want to make sure that we sound like a coherent team.

By no means do we want to remove the personality from the situation. You guys know and love Jason and Brandon's voices. We're not going to change that. But we also—sometimes you don't need to know who was writing it. Sometimes the point is to get you through a process as quickly as possible, and we need to keep that in mind depending on what we're delivering to you.

So, content strategy is something that a lot of people don't necessarily think about, particularly with the web. And it's a big piece of planning who you deliver your content to, at the right time. So, social can serve a different purpose. This podcast can serve a different purpose. Answers can serve a different purpose. How do we get the right answer into your hands at exactly the right time, and not repeat ourselves absolutely constantly?

So sometimes you know, ring structure for instance, we talk about everywhere, because it's such an important part of the program.


ALLISON SHIELDS: But sometimes, maybe it would be delivered in a better format. For instance, something we don't have, that I would love for us to get, is a little video explanation of it that works really well for social, almost like an animation. How can we tailor our content to make the most sense for where you're looking at it?

JASON HOWARD: Yeah, and well, it's interesting to hear that, you know, actually vocalized, because for those of you that are listening who've been part of the program for a while, right—whether it's six months, a year, or since the beginning, five plus years ago, right—you're very familiar with the day-to-day operations, how we release flights, what the rings are.

But there's also continuously new people from all around the globe joining the program. Like, I won't give the specific numbers, but I am consistently amazed by the number of people that join the program each and every day. And it's new for them, right? They need to go learn, explore, figure out what we're all about, what are the rings, what are they for, how do they work? You know, what can they expect in each of those places? And having some very clean, ready to go content that's easily digestible, but also easily shared, is super important to make sure they have a smooth transition as they come in.

ALLISON SHIELDS: Exactly. And then besides that, I'm just touching lots of the little things that you guys see all the time. I work on articles, so a lot of the times when we're featuring an Insider who's doing really cool things out in the world, I've helped interview them and written the article about them, using that journalism background again.

And then if you've ever seen us at the conferences, I'm usually there working the booth with everybody, but I also help make the videos and the presentations that we show at those things. I also help out with all kinds of just weird little things that you would even think about, like designing an icon. There's a whole breadth of strange, like little projects when you build a website, and people don't always realize how much goes into that. So, anything writing, design, that's me. You're seeing something I did.

JASON HOWARD: Nobody wants me drawing icons, ‘cause you're either going to get illegible characters or stick figures. (Laughter.) That's your two options with me.

ALLISON SHIELDS: That's so true. (Laughter.)

JASON HOWARD: That’s about all I got. So not that you haven't covered enough yet, but one of the really important aspects of the Insider program is how we connect with people on social. Uh, and that was one of the really fun things that was new almost when the Insider program started off. There wasn't a large Windows focus in the social space, right? If you look at like the-the service and support side of things, yeah, that—you know, user voice had been there, the answers.microsoft.com platform had been there. (And if you didn't know about that, now you do.)

But you know, Twitter gave us this rapid fire, quick question and answer, and you know, just a very fast way to share information. And it was fun how quickly that blossomed out to show us that it was a really good way to connect with people, to intake feedback, to hear suggestions, to talk about bugs, to have some of those real-time type conversations and even some of the longer, you know, ongoing conversations as we did troubleshooting.

But on top of that, which you know, I've been doing that since the inception of the program, and nowadays, you'll see a bunch of Eddie doing that behind the @WindowsInsider handle on Twitter, but you also do some of the, like the marketing-type activities of broadcasting builds and sharing announcements, and when a podcast is available, you know, somebody sending that tweet out, and that's a lot of the stuff that you're working on as well.

ALLISON SHIELDS: Absolutely. So currently, if you're getting on our social media, our Twitter or our Instagram mostly, you are talking to Eddie or me. Jason and Brandon are absolutely still out there engaging. But as you guys probably know, they do a lot of that through their own handles, because they have pretty significant followings as well. So, for us, I'm personally never going to be the full face of this program, which trust me, I'm fine with. (Laughter.)

But I absolutely still want to make sure that we're doing a great job of sharing out all that hard-made content that we've spent time and invested in. So, the podcast is a huge part of that. Sharing info about when Jason's going to go do his webcast is a big part of that.

And we also just want to have fun. I think that people underestimate how much, Twitter especially, but any social media can sort of serve that role of your fun day-to-day interactions with a community like this. And since community is such a huge part of this program, we really need that ongoing engagement all the time.

JASON HOWARD: Yeah, and speaking of engagement, right? You mentioned earlier that you know, you prepped some of the content that we use at Ignite, both like for the booth demos, as well as some of the presentations that we give. And as you have joined us at a few of these events, I got to ask you, what has it been like to meet with Insiders firsthand?

For me personally, I have a very long background in customer-related activities. Whether it was direct end user support, taking phone calls to you know, handle customer frustrations and concerns, all the way up to you know, direct troubleshooting, and you know, everything that I do with the Insider program now. It's been kind of all over the place.

But one of the things that is always eye-opening for people who haven't spent as much time doing that direct one-to-one type, you know, back and forth and having those conversations is, oh no, I have to talk to these people in-person now, how's this going to go? So, can you tell me what it's been like for you?

ALLISON SHIELDS: Sure. So, I was very nervous about this at first, especially my first event was actually just a few months after you guys hired me. In fact, the week I was hired, you all were away at Build, and my boss was like, it would be really great if you could come to this. I wish we could’ve gotten you in a little earlier. (Laughter.) And I'll be honest, I was still nervous a few months out for that, because this program does have some real technical aspects, and it takes some time to actually ramp up to that. And I will say that it wasn't until I started helping out some with the blog that I really got a better handle on what was going on day to day in the program, and that took a lot of time.

Since then, however, for instance, this last year’s Ignite, I've been feeling a lot better about, oh, I actually—I know the ins and outs of why a developer should be in the program and what they're getting. And we had some brand-new marketing people join us at this last Ignite too, and it was kind of satisfying to be able to help them out in, here's why we do this, here's why Insiders do this, and help build connections between more of our staff and those people instead of just trying to build them myself.

But that being said, for me, meeting Insiders is always actually the most satisfying part. You don't always know how your content’s landing or how you're connecting with someone until you've actually met them face to face.

I also think people are a lot kinder face to face. (Laughter.) So, there's absolutely a part too of people realize, oh, there are humans behind this. Oh, it's okay that you make mistakes. There are real people there. We're trying to be better all the time, but we're not going to get it perfect on the first try every time. And I think the program advertises that that's the case, but once you actually meet the people behind it, it becomes a lot more real that, oh yeah, these are real people trying to work through problems.

And also, it's a great way to actually make friendships. Some of the people that we interact with at every event, some of the journalists we interact with at every event, it is so satisfying to see them this far into my journey, (laughter) almost two years here with you guys. And we actually get to have really great conversations, not just about the program but also life. It is truly amazing how much the community grows, from this technical point of interest, where you all entered, into real relationships.

JASON HOWARD: It's interesting to hear you say that because, you know, in the—in the earlier interview on this episode, we talked with Ian, and you know, he made mention that, you know, Ignite last year was his first time to go to an event that was, you know, related to Insiders and go and do some of this same thing.

And you know, a lot of the experience that he shared was very similar to what you mentioned. It's, you know, it's one thing to hear about their program and to see, you know, the stats, and you know, the-the feedback that we get in the program. And then you start putting kind of faces to the program, and you actually get to shake the hands of the people who are participating and make the program what it is. And it's just—it's one of those very rewarding things.

It's also, you know, and it doesn't just have to be the events we hold here in the U.S., the three big Microsoft conferences, right? So, like Ignite the Tour, right, where we get to actually do a little bit of travel. We don't get to go to as many places as we would like. But for those places we do get to visit, to see folks quite literally around the world, to come up, say hi, introduce yourself, and know that there are people pretty much everywhere that are genuinely invested in the program being successful, Windows being successful, Microsoft being successful, and we're just as-as invested in return for each and every one of them to be successful as well.

ALLISON SHIELDS: Absolutely, and to the extent that like, we have Eddie now. I first met Eddie at last year's Ignite. I know you guys had had a much longer running relationship with him, but it is so satisfying to get to have that sort of relationship with somebody, and it's not over at the end of that week. And sometimes you-you feel like those relationships are going to be over at the end of that week, and now he's somebody that I talk to every day. That's really satisfying, and I know that the Insiders feel the same way. I know that this is part of the value of this program for them.

JASON HOWARD: Absolutely. So earlier in the conversation you made mention of doing some work on the marketing-side of the program. So, let me ask my yet as always, favorite question. Without getting yourself into trouble, can you tell us a little bit about what big pieces we're planning for this year or just anything in the future in general?

ALLISON SHIELDS: Yeah, so we're looking at some improvements on how we do certain things. We absolutely want to sort of clear up some questions that we have ongoing with the website's content and how we organize that sort of stuff.

But honestly, the next huge thing that I'm sort of thinking about with the marketing-side is, the annual survey’s coming up. We're working to get that out the door. And the insights that you guys provide through that annual survey every year really shape what we do next, not just on marketing, but on engineering for that one in particular. And I know that a lot of our goals that Ian talked about in the first half of this episode were born out of answers that we've gotten from the last two years’ annual survey.

JASON HOWARD: Absolutely.

ALLISON SHIELDS: So, that's a huge piece. We can't wait to get that out to you. We really, really appreciate when you guys take that and give us great answers.

And then besides that, I'm really hoping to set a little bit more of a fun tone on social media all the time. The Windows handle has been doing a wonderful job of this, so if I get snarky with you all, you have to promise, you understand it's in good fun. (Laughter.)

JASON HOWARD: (Laughter.) Uh oh, I mean that sounds fun and ominous.

ALLISON SHIELDS: I promise, it won’t be like Wendy’s level snarky, but—

JASON HOWARD: Oh my goodness. For those of you that don't know, Wendy's is a fast food chain here in the U.S., and—

ALLISON SHIELDS: And you should follow them on Twitter.

JASON HOWARD: Yeah, they're hilarious. The-the folks that run their social media account, more specifically their Twitter account, they have redefined the word sarcasm, and they are not afraid to unleash sarcasm on their food, fast food chain competitors, any random person on Twitter, somebody passing by who wasn't even talking to them is going to get—is going to catch some flack from time to time. (Laughter.) It's-it's a lot of fun. Hey, and we won't reach that level, right?


JASON HOWARD: You'll see their Twitter handle and be like, oh my goodness, it's a bit over the top. Yeah, we're not taking it that far, but we do want have fun, right?

ALLISON SHIELDS: No, but we do want to have fun. If you've got, you know, any-any fun comments, jokes that you want to come at us with, we'll certainly—we'll be playing back.

JASON HOWARD: I'm going to make Allie take all of those. (Laughter.)

ALLISON SHIELDS: (Laughter.) Honestly, Jason will be the person poking me the whole time, but—

JASON HOWARD: Yeah, probably. You know, I am the troublemaker on the team, so.

ALLISON SHIELDS: I mean, gotta have at least one, right?

JASON HOWARD: Yeah. Everybody's got a reputation. I own mine. (Laugher.) That's fine, that's totally fine.

Well hey, I gotta say, like this has been—this has been fun. It's been nice having you on this side of the recording glass, and you know, not out behind the mix board for once.

ALLISON SHIELDS: You're never getting rid of me now.

JASON HOWARD: Oh goodness.

ALLISON SHIELDS: I’m gonna be here for everything.

JASON HOWARD: I feel like I’ve opened some sort of Pandora's box here. (Laughter.)

Well hey, you know, it's—I'm-I'm really looking forward to, not only the things that, you know, Ian and I talked about of what's coming next for the program, but just some of the—some of the things that kind of get taken for granted, like, you know, the-the way we interface with people, our digital assets, things of that nature. There's a lot to come in the next few months, you know, and all the way through this year.

So, I've got to say number one, thanks for all you do, right? Thanks for all you do with the podcast. I wouldn't have nearly as much fun doing this without you, nor would it sound nearly as good as it does. I mean, you know, that's subjective. (Laughter.) But, you know, at least with the feedback Insiders have told us, it sounds pretty good, so thanks for that. But you know, just being here, doing everything that you do, it means a lot. And, you know, we'll have to have you back in the studio at some point, on this side of the mic.

ALLISON SHIELDS: Thank you so much for having me.


JASON HOWARD: And with that Windows Insiders, this episode is a wrap. Thank you to our guests for helping us plan and kick off yet another exciting year with the Windows Insider Program.

And 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.