Interview: Dona Sarkar After One Year on the Job as Chief NinjaCat and Head Windows Insider

This October, the Windows Insider Program will turn three years old. It's been helmed by two people in that time -- Gabe Aul and Dona Sarkar.

Sarkar's had the job for a year, and we wanted to talk about what it's like to take over a program with a constantly-changing product and a tsunami of user feedback.

When you are running a program that has millions of enthusiasts eager for a new build everyday, whom want their favorite features as part of the operating system, and are quite passionate when things do not go according to plan then you certainly have your work cut out for you.

As you will read throughout the interview, Dona takes all of that in stride each day she comes into work and endeavors to give Insiders the best opportunity to excel at what they are best at - being passionate about technology and helping members of the community.

What It Means to Run the Windows Insider Program

Everyone is likely to remember Sarkar's one year anniversary in this position, June 1, 2017, because of the inadvertent builds that were pushed out to some Insiders late that day and wreaked a little havoc for some Insiders.

However, if you are a Windows Insider you know Sarkar's is about more than just a day on the calendar. She is more focused on interacting with Insiders via social media at what seems like all hours of the day where she teases new testing builds plus spends time talking about some of her passions such as fashion, technology, and building Windows.

We reached out to her for an interview to look back on the last year. Here's what she had to say.

There are so many people who knew that it was the one year mark and that it's been you know a pretty extraordinary year. So that's been a really really surprising and you know just wonderful. It was absolutely wonderful. 

I was able to spend some time talking to Sarkar last Friday on Skype about her first year on the job as the Chief #NinjaCat and Head of the Windows Insider Program. As you will see in the interview, it does not take much to prompt Dona to begin talking about her team, Insiders and the impact they are having on the development of Windows and the larger global community.

We had the opportunity to talk about her year on the job, how her team approached the inadvertent-release situation and how she dealt with solving problems while an audience was watching -- and providing feedback via social media. The behind the scenes perspective is quite enlightening:

I think for us the biggest challenge is just balancing between handling the internal stuff and keeping an eye on social. We watch social just across the board in a very deliberate way. We keep an eye on it and if we see like two or three reports of something we immediately send a ping around our team like OK I'm seeing this - anyone else? We consider that to be smoke then we start checking forums and social immediately. So ... that's why we catch these things pretty early because one of us is generally always online. 

Read on for the full interview.

Interview Questions and Answers with Dona Sarkar (Full)

What did you think of the response yesterday (prior to 3PM your time of course) from so many on social media, including your predecessor Gabe Aul, about reaching this milestone?

I thought it was so incredibly flattering. I was very surprised honestly because you know for about a year I've been saying I count the days because every day counts and it turns out a lot of people have been counting the days too. And I was so flattered and pleased by both the insiders as well as my team. There are so many people who knew that it was the one year mark and that it's been you know a pretty extraordinary year. So that's been a really really surprising and you know just wonderful. It was absolutely wonderful. 

What has been your biggest surprise since taking on this job a year ago?

It's how many people want to help others with the tech. I knew that there was a lot of people that we have in our community who help others with technology and this is not just an IT Pro saying I helped my company with technology. Just in general in their life they like to do it and I've noticed that trend come up over and over again this year. A lot of people contact me on Twitter and other social channels to say I support a forum, I support a Facebook page, I support my community, I support the town, I support my city.

They, the Windows Insiders, really are the millions who represent the billions and that is where the phrase came from. Around here everyone was like "What are you talking about? What does that mean?"

My response is that they are the millions who represent the billions. They speak on behalf of Insiders, they speak on behalf of the billions of people. I truly believe that between all of the millions of Insiders there are at least 1 billion people and 1 billion people's voices because it's just logically it makes sense. If everyone helps hundreds of people then just from a scale perspective that is actually true - that's not an aspirational statement. That's been one of the most amazing surprises and I love that. It makes me really happy because with the work we're doing is not just "Hey, let me you know help a bunch of tech enthusiasts play with really new software". No that's not that's not it at all because we're working to build software with a bunch of hardcore tech enthusiasts is not actually a good thing because you can look at passions and they conflict very quickly when you don't have that kind of stuff going on.

Via Twitter (@donasarkar)

So in the last year, what has been your biggest achievement?

I would say the biggest achievement is helping people realize that they have this belonging to this community and having these abilities to actually install builds, give feedback, and be a part of this community that is a superpower and people, more than one, has seen me this year and said "I'm so proud to be a member of this community. It's something that I go and actively tell people that I do. I realize I have such a technical superpower because it's not just me and it's not just you know those few people who I interact with on a day to day basis. I'm part of this global movement of people who use technology to make a lasting impact in the world."  I'm very happy that it is something that has been resonating across the community. We actually have data to show it like we did a big survey back in January and I think it was 55 percent of Insiders said they love to help people with technology and out of I think like 91 percent of people responded and said that they're part of Insiders because it gives them the feeling of being a part of this global community of fans who are passionate about technology in general. I love that and it makes me really happy because that's not something that I knew was in the plans.

Around the time I took this thing over I spoke with Jeremiah Marble and asked him what do you think is the biggest opportunity we have and he said "how deep the connections are in the community".

I said what are you even talking about? He said "These people are really good friends with each other. They help each other. There are some of the Insiders will say that my Insider friends are the closest friends I have in the world. We've gotten together at conferences, events, happy hours, and things before and we are so proud to be part of this global community - we're part of this global movement".

He and I decided last May, actually at the end of May, when we started to work together to actually do this on purpose take this idea of the Windows Insider Program and turn it into the Windows Insider Community as well. 

Via Twitter (@donasarkar)

That is where Winsiders4Good came from, right?

Exactly. It came out of our week long hackathon. We were just toying with this idea of what communities do and we had been reading Seth Godin's novel Tribes. So all of us read that on the team and we realized we've definitely got a tribe. You gather the people, you give them a way to communicate with each other, and externally and give them something to do.  Giving feedback on Windows is something to do but that's not an activity you do together. 

So we said you know what let's use our technical superpowers to make a lasting impact in the world. And that has resonated so strongly. When people who've already raised their hand once already then raise their hand and say I want to do more than just live this life that I have. They didn't have to sign up for this so the fact that they've already raised their hands once means they're hungry to do more with this technology. It's amazing to watch and see it happen through either the different events that people get involved with or just the people who reach out and help others on Twitter when they keep up and tweet you about a question and they jump in there and try to help out and stuff like that.

So that's something we want to make easier. Twitter's really a terrible platform of being able to help. We're building out forums just for Insiders and not for us to talk about troubleshooting but for people to help other people. We've just been trying to figure out like the subgrouping for forums because there's so many ways to do this.

Via Twitter (@donasarkar)

How has your job and the work it involves changed over the last 12 months and what prompted those changes - do you all approach your roles on this team with the same kind of agility that is used now in the development of Windows 10?

Oh yeah, things are insane. One of the tenets that we live with is that we move fast, we experiment really hard, and our team is tiny and scrappy. There are seven of us who Insider 100% of the time and all of us have our unique areas that we are very focused and passionate about.

One of the ways the job for me has changed in the last year is removing myself from this idea that I'm their boss because I'm not their boss. Well technically I might be their boss but that's not how we approach things because none of us actually know how to do this because we are inventing a whole new model. Co-creating with a community of millions of people that is not a thing anyone knows how to do.

So for me to say hey I'm the V.P. of this thing and I will tell you how to do this is just dumb. That would be a terrible idea. So that's not my way and that's not the team's way either. They would just say Dona  are you crazy. What are you saying. Instead all of us are very empowered to do things as needed. Some examples - we realized that Insiders have different learning styles and different communication styles. So we need to just be a little more inclusive not to say this is how we're going to do things because this is how we want to do things. Instead we're experimenting with all of these different consumption styles.

So Jason Howard used to run a radio show in college. So we said why don't you just run our Beam Casts. We know we want to do webcast with Insiders and we've known this for years. We just haven't had the right time to actually do it because it takes a committed person to do that every month. And so we just asked Jason why don't you just do it because you're good at it. We want to and you're obviously very passionate about it. So he just runs with it and he's amazing. He has new ideas. He's hit up like eight different teams to come in and be guests. He does everything. We realize when you empower people to just do the thing that they're really good at and like to do they're going to do that really well. Brandon LeBlanc is amazing at wrangling all of these teams to write good content so he helps me with all of this content writing. So he and Jen Gentlemen run around and figure out all the things in the builds and how can we make sure that this is all covered and they'll help me track down all of that like known issues and stuff because you definitely need more than one person to keep an eye on that.

When it comes to yelling that's mostly my job. "Dear Product Team why did you do this stuff?" or "Dear Product Team can you please check in your stuff." or "Dear Product Team please help us figure out if this is exactly the right message for Insiders or not. So a lot of mine is like yelling.

The other part is finding opportunities for Insiders. I travel a lot and that's by design because the more I've traveled the more I realize there's huge opportunities for Insiders all of the world. Every country I go to I tell everyone I'm never off duty ever. I'm always figuring out opportunities for Insiders because we have then in every country in the world. We have them in every single kind of demographic of age, diversity, job. So whenever I see an opportunity I'm like hey why don't we have Insiders doing this whether it's teaching or starting businesses or working at this company or coming in and doing an event or something. I am always looking for opportunities for Insiders since they already raised their hands to do more.  So that's been really powerful for us to build relationships all across the world with these like entrepreneurship hubs so that we can help Insiders launch their businesses and dreams.

Via Twitter (@donasarkar)

So would it be an accurate description of your small seven member team that they are the voices of the entire Windows development team that is building Windows in the same way that the millions of Insiders are the voices of billions?

Yeah we're the people who represent those thousands to our Insiders community. There's something really, really powerful about working with Insiders because you know a lot of people inside Microsoft are like "oh my team is, this my team is that" and our team is the seven of us but it's also all of the Insiders. People will ask me "Hey Doan, how do the Insiders feel about this or how do the Insiders fel about that? It's just like being a manager of any other team. A manager always has to know the troops are happy or the troops are sad or it's a good day or it's bad day. We have to know that at all times what is the sentiment of the Insider community. So we actually have a ginormous freaking team. It's really the same responsibility. Us as the wranglers and the managers of this giant community of people we are responsible for their care and feeding.

Windows as a Service (WaaS) has really changed the way Windows is built at Microsoft and how quickly it receives feature and maintenance updates - when you were an early software engineer at Microsoft when Windows and services used to get updated every three years or so - could you have ever imagined this pace?

Absolutely not. Operating systems are amazing. I've always loved operating systems. I've never worked on anything else so it's very strange for me to think about working on something else. No one believed that you can build an operating system in less than three years. They were like "That is insane" because it takes three years to build an operating system because the way we thought about it was you have to go soup to nuts; kernel to UI and tear down the whole thing and then build the whole thing up. As people evolved and as technology became for everyone and not businesses we realized that is just not true - no one needs a new kernel of Windows every three years. When it's necessary for whatever reason such as security or  new device families sure it makes sense to do that but that's not a mandatory thing or cadence. So for me the idea that we'd be shipping every week is insane.

Why is WaaS and this development process a better approach for Windows users?

Well first of all it removes the shock of having to upgrade your entire world every three years. Those dramatic changes in operating systems while some consumers really like them and they want their operating system to change completely. We just crave change so much but for businesses and governments they hate that so very much because suddenly people who are not tech enthusiasts, they're all people who use tech to do a job but I wouldn't say they're tech enthusiasts. Other than the IT department for them this may be personally exciting but now I have to teach my VP how to use this. 

It was this like horrific thing where people are like "oh I have to upgrade my company, I have to upgrade the government of Germany. We have to make sure all our apps work, we have to make sure our drivers work. We have these random devices from 20 years ago" and it was just brutal on our customers and honestly that's where we started because the feedback we got from every single customer who was not hardcore tech enthusiasts was it's so disruptive to have a new operating system with all these new things to think about every three years you know it's it's like total downtime for a company for six months to try to transition.

So we realize that we have to help our customers have better and easier lives. The way to do that is to release more often so they don't have to go and do these big upgrades and we've moved away from this model of you have to learn how to do everything new every time,  every three years.

Via Twitter (@donasarkar)

How do you work as a leader of this Insider team to keep your folks from burning out with this pace from the constant flow of feedback and other challenges?

We actually find it really energizing. It's addictive. Flighting is addictive. Insiders love when we flight but we actually love when we flight. On flighting days there is an excitement in the air and everyone's got their fingers crossed all day.  Everybody - every single person is like "Dona, that build is going out right because I want to see what Insiders think of my new feature".

You are talking about the developers who are creating those features right?

They are excited - it's addictive. That's why we got into this industry in the first place. The first time we wrote something and we saw someone use it. Their eyes lit up and we're like this is why we're in this industry. It's that feeling. They have the opportunity to have users try their stuff every week versus like waiting three years for anyone to even know what I do for a living. It's incredibly powerful.

We actually love when devs come to us and say "I want to know what insiders are saying".

There's all these studies that show when a person knows the exact human that they're creating for they are a lot more motivated to do a good job instead of just someone out in the cloud or something like that. You know we don't use the word customers. We actually say  humans all the time. Customers are like you know some nameless faceless people on the other side of the world who may or may not consume your product but they are humans. We say that all the time. We are building these things for humans so do you want to go talk to some humans today. Do you want to come hang out while we webcast with our humans. You want to look at the words that humans are saying and people love it. They think that's incredibly powerful and the number of devs who are very very human focused is very high. People think "oh devs are these nerds and they just live in their office and we leave them to their own devices" but actually devs aren't like that at all. Most devs are like me - we love engaging with people and that's why we're in this industry and we love being able to share that with you know the thousands of people who work on Windows and our our partners across the company as well.

What does an event like yesterday's inadvertent release of internal builds do to the team - how do they approach things like that when they happen?

I think for us the biggest challenge is just balancing between handling the internal stuff and keeping an eye on social. We watch social just across the board in a very deliberate way. We keep an eye on it and if we see like two or three reports of something we immediately send a ping around our team like OK I'm seeing this - anyone else? We consider that to be smoke then we start checking forums and social immediately.

So yesterday that's why we catch these things pretty early because one of us is generally always online. We're all like crazy insomniacs. So yesterday was interesting because that affected audience was actually really small and it's exactly what you're saying because we were about to launch an actual build. Everyone was on alert and it seemed like a lot of people were affected.

We've been looking at how many people were actually impacted and it's like very low double digits. Definitely people's devices were impacted but it wasn't like every single Insider was impacted. What  was really interesting about yesterday was it was really cool to see everybody like my team, flight ops, all of the community champs just immediately drop what they're doing and bond together to go identify the problem and solve it. There's no discussion, no finger pointing, no blaming. It's like we must all solve this problem at once and that is it. No one even had to say anything, none of our VPs had to get involved they were like "Wow, this team is like a well oiled machine and everyone knew exactly what to do". Everyone just knew what to do.

Via Twitter (@donasarkar)

If you were in front of a room full of future software engineers and developers what would you tell them that they need to do so they, as the Dona of the future, can replace you one day at this job or one like it?

I would tell them that they absolutely should be focusing on building up expertise in future tech. One of the things that is endlessly frustrating for me is when people focus on the tech that was like 10 years ago. Like why is everyone doing mobile development still? Like stop doing it right. We don't need more mobile apps. They're just are not that many apps that we need more of. It's endlessly annoying for me when people are like "Oh, I want to be a software developer and write apps for phones". I'm like, really? Because there's no one who's like - "I wish we had all these apps for phones - my phone is missing so many apps". They all exist. In fact there's too many and they're not written particularly well and not maintained. That's the other thing. Like every month you know you're "Oh this is the latest chat app" or whatever. There's just so many and none of them actually solve all the problems that they need to be solving especially across the world. So I encourage people like don't just do what you think is going to make you money because that's not going to make you money for very long. It's not going to make you a very good software developer who has a lot of customers for very long. So I encourage people l- here are some things that you absolutely should focus on and this is not just for coders - this is for anyone who wants to work in technology because I think coder's is like 25 percent of the people. We need program managers being managers. We need people like our team, the Insiders team, to engage with community. I actually think people who focus on customer happiness is this huge super power that no one knows that they need to build because this human to human contact is going to be incredibly important in the future.

It's going to become incredibly important to be able to resonate with human beings for customer success. Customer happiness teams I think will show up in every single company in the world and if a startup is you know just getting funding and stuff right now they should think about who is leading your customer success and happiness. Because just getting customers is nothing. Retaining them and working with them to collaborate and build new things is where the future is - super important.

To wrap I asked Dona a series of either/or questions to find out just a little more about her...

Books or Movies?

Books

Early Bird or Night Owl?

Both

Coffee or Tea?

Coffee

Sausage or Bacon?

Bacon

Call or Text?

Call

Think before you talk or talk before you think?

Talk before I think.

Via Twitter (@donasarkar)