[CTQ Smartcast] Models for career growth and better decisions, with Aseem Datar
Aseem Datar is Partner, Madrona Venture Group and formerly General Manager, Microsoft Cloud, leading one of the fastest-growing businesses at Microsoft. He is an engineer at heart but has held several roles across product development, management, marketing, sales, and operations functions. He is also a Seattle 40under40 honoree and was the youngest to publish his thesis on digital economy at the IEEE consortium in India. He also serves as an advisor to several early-stage startups, VC funds, and other types of organizations dedicated to accelerating global innovation and technology. What inspires him the most is working with next generation entrepreneurs for bringing breakthrough tech to life. Aseem has been an avid cricketer & a keen follower of sports.
In this conversation with CTQ co-founder Ramanand, Aseem talks about the lucky break that took him to Microsoft, lessons learnt while working on three distinct kinds of businesses within Microsoft, his decision-making principles, mental models for career growth, and the role of collaboration.
Note: this conversation was recorded when Aseem was at Microsoft.
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Some of the things we spoke about
The ‘lucky break’ that got Aseem into Microsoft even before he began his Masters
Managing internal shifts, from one role to another
Three vectors to evaluate job opportunities
What makes someone a successful generalist
Aseem’s decision-making process
What Aseem doesn’t want his team doing in meetings
Lessons from three different kinds of businesses at Microsoft
Spotting trends in the tech world
Why Aseem doesn’t like the term ‘networking’
How teamwork has changed over the years
PLUS
Aseem’s hot-takes on the future relevance of…
AND
Aseem’s productivity routines & habits
What featured in the conversation
How to evaluate an opportunity using the vectors of people, skills, and domain.
Thinking about “two-way doors” and “one-way doors” when making a change.
How to fall forward, instead of falling backwards
Standing on the shoulders of giants and using a personal ‘board of directors’
The 10-10-10 method for decision making
Being the best version of yourself
Spotting patterns
Aseem recommends…
The platform Geek Wire, for tech news
The book “Open” by Andre Agassi
The book “Indian Summers” by John Wright
If you enjoyed this topic, watch the CTQ Smartcast on How Mid-Career Professionals Can Keep Themselves Relevant
READ THE TRANSCRIPT OF THIS EPISODE
[Start of Transcript]
[00:00:00]
Aseem Datar is General Manager at Microsoft Cloud, leading one of the fastest growing businesses there. An engineer at heart, he has held several roles across product development, management and operations functions. He's a Seattle 40under40 honoree, and serves as an advisor to several early stage startups and VC funds because what inspires him the most is working with next generation entrepreneurs to bring breakthrough tech to life. An avid cricketer and keen follower of sports, Aseem says he was lucky when he got into Microsoft, even before he began his Masters. Aseem has made several shifts internally at Microsoft. He uses three vectors to evaluate these job opportunities when they come along. In this conversation, he speaks about his decision-making mental models, what makes someone a successful generalist, the role of your network in helping you grow, what he doesn't want his team doing in meetings, and lessons from cricket and team sports. We hope you enjoy this conversation.
Ramanand: Hi, Aseem. Welcome to the CTQ Smartcast.
Aseem Datar: Hi, thank you for having me. Pleasure to be here.
Ramanand: Great. Aseem, we want to talk about your journey from being an engineering student all the way to getting into Microsoft. I heard a rumour about a very interesting story about how you got into Microsoft. Why don't you tell me that?
Aseem Datar: Yeah, I mean, I like to say right place, right time, and luck had a huge role to play. I'll give you my story in a nutshell. I came here to do my Master's in the University of Washington in Seattle. Like most other grad students, when you come here, you're instantly poor, right? [00:02:00] Because your exchange rate hits you well. I didn't have any assistantship when I went there. I was geared up to take myself through the first semester, but I came here looking for a graduate assistantship, or a tuition waiver or something of that sort. So, I landed 10 days early.
The very first day I went to my college campus, I was supposed to meet my advisor, and I was a little early. I walked into this big ballroom kind of thing where some event was going on. Little did I know that there was a career fair. I walked into the career fair, I saw a booth that said Microsoft. Back in the day, we used to have a black logo with an orange background. So I went there. I started talking to this guy from Microsoft. I told him about what I do, my vocational background learning in India. He was very intrigued by the mini project work I had done in my final year. Then he said, Well, would you like to apply for a job? And I'm like, wait, but I don't even know if I can work. You show up on a visa, that's a student visa, and beyond that you don't know anything. I told him, Look, I don't know if I'm permitted to, he was very kind. He said, Look, in that case, how about applying for an internship because we hire a lot of interns? And I said, Well, I'm not so sure. But sure, why not? He asked me for this thing called my resume. I came to the University, the very first day, I didn't have credentials, I didn't have access, no ID card, nothing. The school was not open. At the scheduled time, I went to meet my advisor, his name was Dr. Radha Trivendran very, very, very nice guy. I'm in touch with him even now. Occasionally, we exchange email. I spent the first 15 minutes introducing myself. He said, Well, I'll see you when school starts. I said, Dr. Trivendran, can ask for a favor. He said, What? I said, Can I get a printout? [00:04:00] He said, What do you want to print? I said, Well, I want to print my resume. There's this thing called Yahoo! Briefcase back in the day that I have a resume on, can I print? And he said, What already looking for a job? I said, No, no, this thing happened. I went to the career fair. At that time, you had to pay ₵25 to get a printout. I didn't even have cash because I was not geared up for it. He was kind enough, he printed me a copy. I gave it to the gentleman at Microsoft.
Within a week's time they called me on the campus, the Microsoft campus, for an interview. I got into a cab and I showed up at the recruiting building, and I went and I sat there and this girl next to me looked at me funnily and said, Why are you so overdressed? And I'm like, What are you talking about? I was wearing a tie and a formal shirt and pants. Everybody was in jeans and T-shirt. Again, the interview happened, they offered me an internship and that was the beginning of my Microsoft journey. Literally, before my courses started, I had an internship in hand and while I was figuring all my ID cards, login, status, etc. at the same point of time, I was trying to answer this question of can I even work in the summer? That's why I call it a very lucky spot to be in.
Ramanand: Yeah, it speaks volumes about talent spotting at Microsoft, I would say, because it's almost, I mean, to use a cricketing analogy. I know you're fond of your cricket, it's almost like John Wright spotting Jasprit Bumrah and saying, Hey, you should be with Mumbai Indians or something like that. So pretty…
Aseem Datar: I don’t know if the guy at Microsoft is going to say that! I've been here 17 years. Maybe they'll say something to the extent of Yeah, I think we'd rely on you to take that single and get off strike. That's what you wanted to do.
Ramanand: Yeah, that's pretty interesting. Tell me what happened to your journey after that. You became an intern and clearly, you've been there for a long time, what sounds like a long time from Yahoo! Briefcase to when Yahoo! briefcase doesn't exist anymore in that fashion. In some sense, you're doing things around the cloud that started from an early promise of those years ago with the cloud. Tell me, can you describe what else has happened to you? From then?
Aseem Datar: I think [00:06:00] a lot has changed, like you mentioned, and a lot has not changed to a certain extent. I interned there, as a dev, I worked on the setup team. The internship lasts through the summer. As soon as I finished summer, Microsoft has this thing, they interview every intern and they want you to come back full time. I was one of the lucky ones to have two choices to pick, either the Windows team or the Xbox team. The Xbox was very new. I was not a gamer and I ended up declining that and people on my team just couldn't believe it. They're like, What? You didn't take the Xbox offer? I'm like, Yeah, I mean, I'm not a gamer. But I met some very interesting, deep, fun, and very knowledgeable people back then, who've been my mentors, my managers through the years. They wanted me to come back right away. They're like, Look, you should come back next month, full-time and join us because we need to ship this product. And we need all hands on deck. My boss at the time was like, Okay, so can you quit? I'm like, Well, I have like five subjects to go. Or seven I think at that time. He's like, Yeah, but we need you. I was like, Nathan, man, like, I'm this close, like, I don't even know if I can...
You need a certain amount of credits to get a baccalaureate or to get a grad degree to then get your work visa. I'm like, Nathan, I don't know if you can apply for a work visa, if I don't finish it. He's like, Well, in that case, we have no choice. Okay, I'll give you a semester. What typically takes two semesters, I had to finish in one to come back in time to get going. There was no concept of a break in between or anything of that sort. These were also days where visas were very hard to come by. Again, I lucked out, joined Microsoft, did the technical dev role, then ran a PM team, then moved over to doing product planning and product management.
One thing that always interested me is going from a function that I was in to a function that almost seemed like a sister function, but I knew very little about. [00:08:00] When you're a software developer, I used to work with a bunch of PMs. I'm like, Wow, that sounds great. Oh you are program managers, what do you do? And so, getting talking to the PM team, I then took on a PM role as a next step. From PM then I used to look at these marketing people. I was like, Wow, you guys must have a really cool job, like, sounds really good. What is that? Then jumped over to doing marketing, moved over to the office team, incubated the Office Web Services business, changed the dynamic on how services are thought of, in the world now.
And then I took on this detour to go to sales, again, similar hypothesis, similar model, I knew very little about it. An old boss went there. He's like, Hey, you want to do sales? I'm like, Sure sign me up, so did that. Then came to the world of cloud when just around the time, Satya took over as CEO and there was some re-shuffling. I've been with cloud ever since. So, I think the common thread there has been taking a role that I know very little about and trying to go learn and net new different skills. That's kept me afloat and tied to Microsoft, it almost feels like a net new company, different job, different role.
Ramanand: Right. So, I want to go into this attitude of yours a little bit deeper. Did you always have this aptitude towards exploring things on the periphery and using that to catapult yourself to a new role? Or is that something that you grew into because you're also in the environment that you found yourself?
Aseem Datar: I think it's more of the latter. Look, I mean, I'd be lying if I said that I designed it that way. When you're in your 20s, the next interesting thing that comes across, you tend to think of it and you're like, Oh, great, I'll do it. I'll learn. I think that learning thing was always with me where I have that penchant I would say for the unknown a little bit. But I certainly can't say that I designed it this way or I always thought about it in my thought deeply.
If I talk to [00:10:00] anybody graduating today, they think 10x more than I did when I was that age. That's just the nature of being exposed to new models, new thinking. Of course, the internet has a huge role to play. Mentors have a huge role to play. I would say that I was lucky to have great mentors and people who could guide me. But at the same point of time, there was that element of I didn't want to do the same thing again. One part of it was also, if I did spend time in Windows, I was actually going to compete with some other folks who have spent 20 years there on compilers. Then I'm picking my career and saying, Look, I want to be a compiler guy, which is fine. There's nothing wrong in having a depth approach. But I always preferred breadth over depth. That has been my thing since the get go.
Ramanand: Let's take a more concrete way of looking at this. So, let's say you made that shift from, say, being an engineer to getting into sales and product management, those kinds of things. Let's say you do that same thing in a few years’ time to something else. What would you do next? Would you go and talk to people? Would you start reading a bunch of books? What are the components of making that successful shift from, say what you're doing today to something that you didn't know you could do?
Aseem Datar: Yeah, I'll share a model that I think I've learned from, of course, people I've deep respect for in the industry. One of my mentors mentioned this to me, saying any job or opportunity you take or evaluate, you look at it from three vectors. The first is the people you work with. The second is the skills you have or are required for the job. The third is the domain or the space that you're going to take the job in. At any given point of time, ideally, you want to keep two of these things constant. Either the people and the skill, and you are entering a new domain, or you pick up new skills, [00:12:00] but your domain and people are constant. Again, this comes down to their risk managing appetite for that jump. When I did the sales role, I followed somebody who was already there. I had somewhat of the 'people' thing constant. I knew the business, it was a different skill. When I took the Azure role, the domain was new, the people were new. The skill set was also new, because now I was going into more of a CEO type of function. But the way I thought about managing those changes, the skill set, although in its entirety weren't new, the things that I had done leading up to that were all required for me to be successful in the job. I could rely on my skill set, yet change things. That's a simplistic model of thinking about any job chain, in my opinion. Now, not to say that there aren't other models. But this is what simply resonates in my brain.
Ramanand: Right. The other thing I realized is that you could easily have been this specialist, like you mentioned, the depth versus the breadth conversation. A lot of people these days, because of the nature of change around us, and also the nature of opportunities unfolding in front of us, they need to make that shift from being a specialist to a generalist. So, how do you compare these two? Because we need both kinds of people in an organization. You need some people who like that depth-first approach. One is, what makes someone a successful generalist. What is it that a specialist can learn from a generalist because some people listening to you today, have been doing one thing steadfastly for the last 20 years. But maybe they've hit a ceiling, or they want to pursue other things, but they're not comfortable with the idea of that exploratory breadth. So, do you also have a recipe for it? [00:14:00] How do you test the waters before you get there? Two things, one is what makes a successful generalist? And how do you test the waters before you make a leap?
Aseem Datar: I'll answer the second one first. How do you manage that risk? Let's just call it risk. Or how do you manage that? Or how do you test the waters? I tend to think of decisions as a two-way door or a one-way door. The simplest way to think of it is, let's assume that you're trying to enter and check out rooms in a castle. Unless you go into the room, you really don't know what's in it. Therein comes the concept of a two-way door, right? You open it, you go there, you spend some time, you check out the room and you come back. There is a way to come back. The good thing about specialists is that they can rely on their core-skill to always come back if it doesn't work out for them. But what I would say is you need to give it a significant amount of time to stay in that room. So, maybe give it a year, 18 months, whatever you feel is right. until you feel that, yeah, it's not working out. Only you can be the judge of that.
Whereas the concept of a one-way door is a little bit more, I would say riskier, because there are some decisions that are irrevocable at times. Those could be things like changing geographies, or completely like going from, let's say, the tech world to health care. Some of these are harder to make the return. Just evaluating with an open mind-set on are you making a revocable or an irrevocable decision, is a good way to think about, am I just testing the waters? And can I come back? Or am I swimming too far from the shore? As far as what makes a successful generalist, I actually think that the biggest thing I would say there is, you have to be able to deal with ambiguity very well.
Generalists typically just get problems thrown at them, and you're trying to, what we call at Microsoft, growth-hack your way out of it. You're going to try something, [00:16:00] you're going to fail, you're going to fail again, you're going to feel again, you're going to go one step forward, and five back. Then you're going to suddenly go seven steps forward, alright? You have to be able to deal with that ambiguity and manage that anxiety, to be honest, that some people have. If that's something that makes you super anxious, and you feel that you're out of control, and you're falling in a spiral, maybe that's something that you want to rethink. Whether you are meant to be a generalist or not.
The other thing that I will say is, and a lot of people can probably resonate with the word called jugaad, right? You've got to be able to have that jugaad mind-set. I think growing up in Bombay, a lot of us have that. I was lucky enough to bring that to bear. I mean, basically, you have to pick yourself up when you have a setback in your life. Oh, shit, okay, now what? I think the 'now what?' is more about you having to fall forward rather than fall backwards. That, to me, I think is the biggest skill set or a mind-set, I would say that generalists should have.The only other thing I would say is nine times out of 10, you have to rely on standing on the shoulders of giants to get that victory and leaning on people who are advisors, who are experts in their field, because generalists don't know it all. They certainly don't have the depth expertise that a depth expert has, but relying on others to extract the information, to connect the two points, to see patterns is the other thing that I would say is probably another important skill.
Ramanand: Right. Aseem, you may have heard of the idea of a board of directors, for individuals, right? Have you over the years assembled a group of people that play different roles in your life and career?
Aseem Datar: You stole the words out of my mouth. Like that's how exactly I would have described my mentor base. They're my board of directors, right? I mean, I get different perspectives, I get support, I get negativity, and which is good, healthy negativity. I get caution. [00:18:00] I get pushed. I get questioned. I get conflicting opinions. The one thing that is consistent with the people that I talk to is they never give you the answer, which I think is a core skill to have in a board, right? You want the board to pose questions, and then you're in the driver's seat, as the product, trying to figure out, which way do you want to go? Or how would you answer that question? I don't think any of my mentors has ever said, go take this or go do that, or go do Y or go do Z or don't do X and don't do Y. I think the biggest question they've posed to me is, okay, great. I understand what you're saying, tell me the why, what and how, and Aseem, how would you describe it?
So, that's a core thing that any mentor plays the role of coach. You will often hear in the cricketing world, people talk about, I want a coach who's guiding me, I don't want a coach who's fixing my elbow height. I mean, you try to tell Virender Sehwag to correct his stance, he's going to say, that's not going to work for me. Or you try to tell Rahul Dravid to play a lofted shot and he's going to say, that's not my strength, I'd rather keep it on the ground.
Ramanand: Yeah, in fact, they are literally sounding boards, or their job is to make you listen to yourself from a different angle. That's how I sometimes see it. Aseem, as one grows in their careers, the big difference between being a fresher or an intern is moving from execution to taking these high value decisions, that is what you ultimately get paid for, in a sense. You mentioned a couple of things around decision-making. Do you have any other principles or mental models around how you make decisions that have served you well?
Aseem Datar: I'm generally big on trying to model everything. It's not that there's a black and white answer. In fact, my wife will tell you that I'm more grey than any person she's seen in the world. Whenever she asks me [00:20:00] a question, she says, don't say ‘depends’, because it doesn't depend, I want an answer. I'll come back and say, no, no, I think context matters. It always depends. And so, she will tell you that I'm a very 'depends' kind of person. But I think in my defence, you can at least have some questions that you might want to ask yourself to get all the data out in front and really ask yourself, what is that model?
To me, the simplest one has been the 10-10-10 model where any decision I take or want to take, however ambiguous situations there are, I tend to rely on data as an input. A lot of people rely on data as the sole input. I look at it as one signal, there's many others. But ultimately, it comes down to how do I feel? If I make this decision, in favour, let's say, how will I feel in 10 days? How will I feel in 10 months? And how will I feel in 10 years about that decision? And I think if the answer to those three things is a resounding affirmation of that decision, then I think it's an easier one to make. But if I have doubts, and I'm like, look, I can, let's say, I'm dissatisfied with somebody on my team. I basically just go and say, hey, that's really bad, you did it the wrong way. I'm not feeling great, because I've given them very harsh feedback. But in 10 months, I'll be like, Yeah, I don't think I should have done that. In 10 years, I certainly will feel about it differently. I'm like, it didn't even matter.
I think if you put that frame of reference, your outcomes start to be a little bit more consistent. And your outcomes start to be a little bit more, I would say something that you can conform to in the longer run.
Ramanand: Fascinating. I think, a lot of us who are trained as engineers, we are not necessarily trained to recognize these emotions, right? Or the volatility of a lot of these emotions, and the fact that they even out over time. Again, what's this vocabulary of emotions, how important is it for managers, [00:22:00] for leaders to recognize that there is this emotional landscape that you're always dealing with when you're working with humans? It's not all cut-and-dried. You need to have an emotional model of the world as well.
Aseem Datar: I think some of it has to have a no regrets move, right? I mean, I do remember a time when we had our first daughter, and I have two, 7 and 3. One of the entities that I was looking to join wanted me to join right away, and I was like, No, I can't do that. I want at least a month's time off, I want to figure out childcare, etc. This was a very up and coming entity and it would have done wonders for me. I decided no, I think principally, it didn't make sense, because it was a first child and I wanted to spend time, I wanted to be here. I didn't want to miss out on those moments. However small or big it might be. It was a matter of 30 days.
So, I decided to pass on the opportunity, because philosophically, it didn't align with the principles. It would have changed the course of where I would have been, what I could have done, what could have happened. But to me, I think it's still a no regrets move. Like, I don't regret it one day. I would still make the same decision again. And purely because if I put it in the context of fullness of time, 50 years down the line, or 20-40 years down the line, I would still have regretted chasing the opportunity over spending a month where my heart was. That's what I call a no-regrets move. That to me, is still a no-regrets move even after like seven-years or nine-years.
Ramanand: Right. I can't detect any trace of regret in your voice while you are recounting that anecdote? So, are you the reflective kind of person wherein you make time for reflection very systematically? You say, I'm going to schedule some time for it? Or do you just let it happen? Tell me about that.
Aseem Datar: Yeah, I wouldn't say that I'm the kind of person who will sit and have a [0:24:00] schedule, thinking time or whatever. I'm often guilty of not wanting to do too many things in life in general. I try to keep it simple. Driving times are mostly thinking times. I hope it doesn't come across as deadly where my mind is half asleep on the way. But times when I step out to go get my coffee, or, my morning routine has to have some amount of coffee.
Funny story, I used to live right across from my building at Microsoft, but I never walked because I always drove to get my coffee and come back. But I think those mini breaks are what energize me. I think those are thinking times. I hope I don't complicate things too much in my head. Try to keep it simple. But then again, I think I feel that the more data you add, the more cloudy you get your judgment. Keeping your principles and your priority list updated, at least in your head, I think has served me decently.
Ramanand: Are there any other principles that you would like to call out as being very important to you?
Aseem Datar: I do have some that I occasionally revisit. What I would say is I think in general, transparency, high integrity, the usual and a lot of us share those principles. Those are generally top of mind for me. I try to not run towards things faster, meaning that I don't want to be in a race. I think this is something that growing up playing on a sports team teaches you. You're competing with wanting to be the best version of your own self. You're not competing with the world, you're not competing with somebody on grades, or GPA scores, or how fast have you been promoted? Or what are the things that you do, because I think everyone's journey is different. I think the quicker you can recognize, the better at peace, you will be. [00:26:00] That's one principle that I follow.
Look, I don't want to compare myself to anybody. Because, honestly, there's no comparison. For every vice president that you meet, there is a president and for every president you meet, there's a CEO or a CTO or for every CEO and a CTO, you'll meet a billionaire. So, I think there's no sense of trying to compare apples and oranges, because everyone's journey is different.
Ramanand: Since you mentioned things like these important values, once you rise up the so-called corporate ladder, you go into more rarefied kinds of zones. There is a danger that it's hard to get real feedback, the feedback that is not so pleasant, grey. How have you taught yourself to get that part of the radar going in, as you've grown?
Aseem Datar: I want to make sure that I understand your question. Is it more along the lines of how do you extract information from the feedback? Or what do you treat as signal versus noise?
Ramanand: Yes.
Aseem Datar: See, it's a tough one. I don't think that I've made it very clear, or I've gotten a very clear understanding of how to do that. I think the key there is to recognize patterns, right? Like, if you're seeing consistent patterns on people are hesitant to react with you. Or I think I'll give you a simple example. As you grow in your career, when you ask for a meeting with your team. There's a lot of production that goes into it. Right? While it is sometimes necessary to have the level of depth and detail and preparedness, I sometimes feel that I don't want my team to do that, right? I would rather have my team just have an open dialogue and say, Hey, here's a challenge. I don't want you spending time in preparing for it or in rehearsing for it, or spending countless hours preparing for an executive meeting. [00:28:00] It doesn't make sense. Then I think you've got to be very upfront and say, Look, I don't want to create new work. I'd rather have a discussion, and so I think, if you're trying to get some of these patterns out and address those head on, that's probably something that you might want to consider. Now, I've also been guilty of not seeing these patterns that quickly. I think that's something that I constantly am working on and saying, Okay, what is the pattern that I'm seeing? Is there a pattern here?
Ramanand: And, in the last one year or so since so much has been in flux, people have also been in a lot of... you don't run into people in person as much, I'm sure you would have liked to. Especially with people who are newer to your organization, who've probably not seen you in flesh and blood? What has changed in the last one and a half years in terms of how you made that effort to keep those channels open, keep that level of intelligence trickling through to you?
Aseem Datar: I err on the side of less is more here, purely because I think there's a lot of realization at least in the working set of folks that they already have a lot of Zoom meetings, or teams meeting, online engagements. There's fatigue that's crept in. People are managing family and work and young kids and older parents and home activities and kids schooling, and it's just a lot more systemic tax on people more than anything else. I try to have these mini touch-points of course, but again, these are very quick flybys. Mostly these are virtual, they have to be virtual. We are not violating any social distancing norms.
But I also rely on my team and my management chain, to then go down to their teams and follow the same thing. I want to create a lot more space actually for people to have maybe [00:30:00] empty slots where they can get the work done, where they can tend to do things at home as well, because this is the new reality of it. I mean, even at home, we struggled with two young kids for the first three months. My wife, and I were literally taking turns on who's watching the younger one, while the other person was on call. Both of us couldn't be on the call at the same time. I think this is a reality of most. I think just recognition of that fact, I try to err on the side of less is more. it works in some cases and in some cases, it backfires because information is not being shared that easily. It's a push and a pull, a yin and a yang.
I don't think I've gotten a model there as yet, but hopefully, I think when people start getting back to work and the hybrid work environment becomes real and operational. Some of these growing pains will go away.
Ramanand: Aseem, I want to move away from the world of management and the office for a brief while and take you to a field, literally a field that you're very passionate about. I know you're very fond of cricket. So, tell me about your cricketing story. Start with telling me what's your preferred role on the cricketing field?
Aseem Datar: I like to say that I was a star player but for Kiran Building, like most people in Bombay are. There's somebody in that building who's really good at it. My journey like most, I'm joking, my journey like most people starts with playing cricket in the building with my friends and after school every day and it was just a fun time. I wish I could go back and play a game again with my friends and that's how it started. Then I moved to Pune for my junior college and my engineering. It just continued. I played for the college, I played for the engineering colleges. We played a lot of interstate tournaments somewhere in the middle. Again, gully cricket [00:32:00] continued.
Then when I moved to Seattle, I was very excited to find the Microsoft cricket team. I played for the Microsoft cricket team until about like two years back, and then as I started to get older and needed a little bit more time and I couldn't justify traveling for work and playing on the weekends. So cricket unfortunately took a backseat. But I'm hoping that this year hopefully I can get to play a little bit more.
Ramanand: Do you still follow international cricket quite closely?
Aseem Datar: Yeah, I mean, whenever I get a chance. I was following the Australia series ball by ball. The IPL not so much. But the Australia series timing worked out really well and it was great to see and honestly I always thought what is cricket going to be after Sachin? Who's going to follow it? But all these guys, like Rishabh Pant, are very exciting cricketers and so much more athletic, so much more sportsperson-like, I would say. And so, it's always fun to watch it.
Ramanand: And are you one of those people who constantly is quoting cricket stories and taking lessons from cricket or you've just compartmentalized the two?
Aseem Datar: I don't know if I draw a whole lot of parallel but I think playing a team sport definitely influences you. It influences how you think about scenarios, how you think about teams, how you manage teams, how you are a part of a team. That certainly had an effect on me. I don't think I quote it as much. The only time I got to talk about cricket was when I travelled to Australia for customer meetings with a broken foot, and in Australia, of course everybody knows cricket and so they asked me what happened? I said yorker, and everybody got it right. In America, you tell them yorker, and they don't really know what that means, ‘I thought cricket is a non-contact sport, like what happened to you? Why was your foot broken?’
Ramanand: Interesting. You mentioned Sachin. Is Sachin your [00:34:00] number one cricketer or have there been other people that you've really enjoyed watching?
Aseem Datar: I enjoyed watching Sachin in person. Meaning that I've gone and seen a lot of Test matches live like five days in Bombay and then I sat ball by ball, I've seen Vinod Kambli's score is double 100 and Sachin scored massive 100s and I mean, those were definitely my cricketers that I looked up to or at least admired growing up. But I think in hindsight, now my allegiances have changed a little bit towards Rahul Dravid. The tenacity, the grit. Frankly, I think even in the retirement state what he's been able to do with the young cricketers, that's just immense respect. I mean, it takes a certain amount of individuals to say look, I'm going to focus on the youth and create the suppliers you might use for Indian cricket and transform it. It takes a whole lot and he's probably my favourite of the lot.
Ramanand: We briefly spoke about this new crop of cricketers. It's unlike the talent pipeline that was there earlier. Now it seems to be a lot more systemic. There are people like Dravid, I think who're contributing a lot to that. I actually wanted to draw a parallel between that or staying relevant through these other means, advisories, mentoring. I know that you advise a lot of tech startups and you're very keen on the next generation of technology, as well. When you wear that hat, what is different? What are you bringing to the table, in your opinion?
Aseem Datar: I've learned that, I've been lucky enough to be a part of three big businesses, right? I mean, Windows was always a flagship business for Microsoft. I came and I learnt the business when it was already well strategised. [00:36:00] There's 90+ percent share in market. I learned a whole lot on how does a well-established business work. I then worked on the incubation for Office Online, which was basically revamping the entire business model of how office was sold. Again, Office had huge amount of share, but we drove Microsoft from licensed software to the web services version. I was lucky enough to see the transformation of that business and lead through some of it. Azure, I joined when we were a 300-people team growing to 1000s, and then our P&L went from millions to billions. That business was just like a startup which has grown 10x and, fire under the belly.
I think I was lucky enough to have been a part of these three big events, or three big businesses. It taught me something as an operator. It taught me about how to grow, how to scale. In working with startups, it's one thing that I'd like to bring to bear, which is to help them scale because that's what they're looking for, right? They're not looking for talking to me as their product person, or build a new product or write code or anything of that sort. They're incredibly smart people. But I think when you think about scale, and what levers do you pull, that's I think something that I could contribute back. Selfishly, I think I can learn something because the next generation of entrepreneurs are the Rishabh Pants of the world, right? No fear, you're going to go do it, because you have immense talent and passion and energy. It's almost like you can learn something from them, which is entirely different.
Like, if I draw the parallel, there's so much sportsman-like capability and athletic ability that these youngsters are bringing to the table. I mean, if you draw the parallels in the startup world, I want to learn that from them. How do they approach a problem with a no regrets, no fear mentality, which some of us probably did not? [00:38:00] So selfishly, I get to reverse mentor myself. I get to learn from these people on how do they think differently? Like, how would they solve the problem? And then I think you have the push and pull or the yin and yang of let's exchange ideas, and then you narrow down on something that might be, a combined effect might be much better than the silo effect.
Ramanand: All right. I also know that you're very keen on scaling. Do you have any principles, mental models around scaling, that you often bring to these conversations?
Aseem Datar: I could outline one, I think there's many. It almost applies to scenarios differently. But, like any investor or startup founder will tell you, first prove out the concept, make sure that there's value exchange, make sure that you're creating value for your customers. And then, I think it's a matter of putting fuel on fire, right, but you got to light that fire first.
Ramanand: Correct. So, one thing that you must have encountered when you got into the scaling kind of mind-set is trying to institutionalize things like practices, cultures, those kinds of things. So, any observations on how you've seen that unfold? Let me give you one, maybe, prompt to think about: when you yourself or when Microsoft was going from this old, almost old style, on premise legacy kind of software to making that shift to the world of SaaS and subscriptions and so on. What changed in the way you were trying to unlearn certain practices and institutionalize a bunch of new practices?
Aseem Datar: Lot of it was basically seeing that trend that the world is moving towards and latching on to it. If I draw a parallel, today, people don't want cars, they want to use Uber. Why buy a car, why spend the CapEx, right? And a similar mind-set applied in the cloud services world, [00:40:00] where we're looking at from the perspective of saying, like, people don't want to manage their IT, they want to be doing what's core for their business, right?
A transportation or logistics company wants to focus on business logic for transportation or logistics. Conversely, a soda manufacturing company wants to get good at manufacturing soda and creating new products. They don't want to worry about their IT infrastructure. I think we look at it and say, Okay, great, let us do it for you. That's the pattern matching and tech keeping up with where the world is going. You'll see like a lot of these business models for new consumer companies even right, they are evolving with the audience in mind, and it's even different from a geography perspective.
India was always heavy on the... it was in ecommerce, but I call it phone commerce, right, where you would call up the local store, and you would give the guy a list, and he would send someone home and you got your groceries. The West is just coming to adapt that model where we're starting to do this on an app or a phone. There's Instacart, who's got insane valuations doing that. They've got a shopper that gets dedicated to you, and he or she will pick your list and deliver it home.
Conversely, we are getting exposed in India to the mall culture, where you're going inside, you're spending time, you're seeing those things. We always had that, but we are inspired by the West when it comes to that. There's these different business models. Like contactless payments is the other one where people don't want to carry around cash in fat wallets. I mean, India, for the most part has skipped credit cards and gone straight to Paytm and the West is still catching up to that. To cut it short, it's a lot to do with what trends you are seeing in people's natural behaviors. How do you fit your product or your culture to match that?
Ramanand: In fact, this phone commerce has been the backbone of India's economy for the last year or so, given all that had happened around us. [00:42:00] It was fascinating to see that come to play. I'm sure a lot of people have their... everyone from the average kirana guy to all the startups like Dunzo to thank for staying afloat. Do you see this cross pollination across cultures as a source of strength for people like you, who grew up in one culture, now you find yourself immersed in another. Are they all strengths that just pulled together to be much larger than the sum of the parts?
Aseem Datar: No, I don't know if that provides a differentiated capability. But it definitely provides a different outlook. You've grown up in a country that's fast evolving, and you've come to a country that to a certain extent, has infrastructure settled. But then you're looking at the best of both worlds and trying to compare patterns, contrast patterns. I mean, when ride sharing comes up, I always chuckle because we've had ride sharing for a long time. I went to college on my friend's scooty or scooter. That was just a part of life, right? When Starbucks introduces... They call it the turmeric latte. I was like, my grandma used to give it to me when I was four years old. Now, I'm wanting to pay four to six bucks for it. That's insane. But there's definitely goodness in terms of recognition, understanding. And if I use the word if it's not overused, but empathizing with different cultures and backgrounds and what they bring to the table.
Ramanand: Right. So, in the last 5 or 10 years, there have been a lot of Indian origin leaders, making it right up to the top. Currently, Microsoft is headed by one of them. This is no longer a surprise. It is taken pretty much for granted in many cases. Is there [00:44:00] something different in the makeup of these leaders, did it just happen to be a coincidence. I've read books on that topic that say that there is something more to this phenomenon. What are your thoughts on that?
Aseem Datar: I don't know, right? I mean, to compare and contrast, every leader has their strengths. I think, Satya or Sundar or pick your favourite Indian leader, they all have their strengths. Conversely, Bill who was at the helm of Microsoft had his strengths. I personally don't know if I am qualified enough to say with conviction that there's a definite pattern here or not, but I do think that each of them is incredibly humble, incredibly hungry for learning, and incredibly smart. I just feel that there's just a different amount of intellect and horsepower and empathy and recognition of the world, and broader thinking. I don't think that it is got to do anything with origin, maybe there is research that proves otherwise. But from my perspective, I think it's just the individual themselves who's just stellar.
Ramanand: And they also have the advantage of being deeply, to use the word, meritocratic, or performance-oriented culture, right? Is that something that you felt very comfortable being part of? Or did you have to say, wow, this pace of progress changed, what is expected of me is something that I need to get used to?
Aseem Datar: Honestly, I don't think I thought about it that deeply to be honest. It's a little bit like, when you're sent in to bat at over seven to 10, you're facing a situation and you're batting accordingly. If the going gets tough, you take a single, you get off strike, and you try to keep your wicket. [00:46:00] And if it's a flat wicket, and if it's not turning, and it's not swinging, then you may hate it. I tried to draw that parallel from sport, because that is actually how business and careers are generally. You excel at different points of time in your career, you slow down at different points of time in your career. There's nothing wrong or right. No two batsmen are the same, no two bowlers are the same. Sometimes you nick one, and you walk and you come back on to do the next inning. But that's how it goes. I probably have just reacted to the situation more than being proactive.
Of course, everybody has their set of mentors, everybody has guiding principles, and those have in general served me well. But I don't think I've planned it as much as I’d like to believe. In fact, the people who are entering the workforce today, the recent graduates, they are a lot more planful, they're a lot more deliberate, they are a lot more clearer in what they want to do.
Ramanand: I just want to go into a little bit of how you keep yourself abreast of things. What is your approach to learning as an individual? Let me start with the future trends thing, because we spoke briefly about it. You have a very deliberate approach to understanding how things are moving forward. How do you keep that future radar going? Is it primarily through reading? Or do you subscribe to certain things? Or is it participating in a lot of conversations? How do you know what's coming around the corner?
Aseem Datar: Thankfully, working in tech exposes you to work through all of that. All the big tech companies, enterprise companies are my customers. So are new generation startups. I feel lucky enough to be at a spot where these things are naturally coming. I'm meeting people, I'm getting exposed to them and talking to my customers, I'm surrounded by great engineers and product people. [00:48:00] I think naturally, I get a lot of it through work. As far as subscribing to something specific, I don't think that there's one, there's multiple, like, I read the GeekWire in Seattle. There's, of course, the WSJ. What gives me energy is really talking to a lot of people who are doing deep thinking. Again, these are colleagues, these are customers. I wouldn't say that there's a particular technical thing that I read. I try to read a lot, although it's gone down quite a bit.
But, future trend wise, looking at mostly behavioral patterns has been interesting to me. How people are behaving? Where is money being spent? How do you follow the dollar in an economy? What are tech advances and research that's happening that is going to transform the world. I think 5G is one such thing. Hardware getting cheaper is another trend. People having one too many devices is another pattern. In this potentially smart edge as people talk about, that's another one. Distributed computing, of course, is here to stay, there's machine learning, there's robotics, there's AI. I mean, there's so much trending estimates being made. But the way I try to rationalize it in my head is what's that one killer scenario that brings all of these things together. If you can weave that golden thread, then you can see which ones are here to stay and which ones are not. There's some areas that just seem like there's a lot more studying to be done. If I were to talk about it intelligently, I think crypto is one of them. A lot of people do some deep thinking on crypto and unfortunately I've fallen behind.
Ramanand: Would that make you very uncomfortable and would you say I need to get into a course, start following certain kinds of people. What would you do in such a case? [00:50:00]
Aseem Datar: Honestly, it's a little bit of like, I also know that I can't consume it all. But, I have people who work in the FinTech sector, as friends, colleagues and whenever I get a chance socially, I'd love to pick their brain on like, hey, what do you think? And when you talk to someone, you actually don't just get the raw data, but you also get a lot more insight and analysis on what they are thinking? What are the questions that are bothering them? That, to me, is more powerful than any paper that I've read because I'm also having an active dialogue. Well, it's essentially a Q&A session. Right? That's one of the reasons why you folks might be doing a Smartcast, because you're getting unfiltered, what's going on? And how are you thinking about it? Versus somebody writing an article and saying, hey, go read this. I do enjoy the interactivity. If there's one topic that I feel that I need to go read up more or understand more, then I'll go have that conversation.
Ramanand: In a lot of the threads that we spoke about today, we have spoken about the role of other people. They could be mentors; they could be startup folks that you're advising. Did creating a network or so called networking, personal branding, those kinds of things come naturally to you? Or was it just something that you just built along the way, but you're very deliberate about it. Any thoughts on that?
Aseem Datar: I'm an extrovert by nature. I'm very comfortable hanging out alone, I'm equally comfortable being in a crowd, full of 1000-2000 people. Some of it just comes naturally, you strike up conversation. I'm always interested in hearing from people as to what they are doing, what they are thinking, how is their life different from mine. Again, this gives me a lot of energy, I would say. I'm not one who's quiet, I'm seeking, I'm talking. [00:52:00] I don't think I ever liked the term networking. To be honest, I never enjoyed the term. It felt very made up to me. I explain it to people in a way saying, look, if it interests you do it, and do it, because your heart is in it, don't do it, because you want an outcome.
I've been lucky enough to maintain relationships that I have from school, from college, and rely on my peers, my close friends, people I've worked with 10-15-20 years ago, I still keep in touch occasionally. It's not that frequent. But we've maintained those relationships, even if it's a simple little Hi, or Hello. You don't do it because you want something out of it, you do it because you have a connection with the person and you just enjoy hearing from them on perspectives and whatnot.
Ramanand: That makes sense. I also want to ask you about things like reading. Are you a reader or do you consume your information from other sources?
Aseem Datar: I wasn't a voracious reader, I would say, but I do enjoy reading. I'm somewhere in between. If I get time, I'd love to pick up a book and read. But my reading is limited to mostly biographies, or experiential books, or memoirs, or something to do with business models. Sports are a huge component of what I read about. But I don't enjoy fiction. I don't enjoy the moon-shot kind of things. The reason I enjoy biographies is because 200 pages gives me an insight into someone's 50-60-year life. That to me is the best ROI I can ever get by reading something. I just enjoy biographies, because they're easy reads, there's nuggets of information in there. That's what I naturally gravitate towards.
Ramanand: Any favorite [00:54:00] biographies that you can think of off the top of your head?
Aseem Datar: I think my favorite is Andre Agassi's Open. That is definitely right up there on that list. If I were to pick one book and say which one should people read from a sport perspective, it is that. I mean, I would have loved to pick a cricketing one. But, I actually think Andre Agassi's one is right up there. The other one that I really enjoyed, I sometimes keep going back to is John Wright's biography called Indian Summers. That's the other one that is a lot to do about the player versus coach mentality and there's a lot of parallels to be drawn.
Ramanand: Just staying with sports a little bit more, how have you seen teamwork itself change over the years because I'm sure when you started, there was a certain culture of teamwork or how managers were seen, and there's been a greater degree, because of digitization, because of a certain shift in new generations coming in, how has team itself changed?
Aseem Datar: I think it's an interesting pivot. I actually think that definitely, it's got a lot more collaborative. There's a lot more access to technology, access to information that has opened up a lot of shared understanding. Back in the day, there used to be that one engineer that everybody went to, and everything was in his or her head.
Now, the information is available everywhere. I think everybody has a common shared understanding. There is experience, which means it's still going to have its own value. But a lot of it is starting to democratize, if I use that term. That has also given people a fresh new perspective. People are bolder, they speak up a lot more, and rightly so, they should. There's nothing wrong with that. In fact, the differences lead to a better product. That's why I think diversity and inclusion as a concept [00:56:00] is huge, and is important and has its own bearing in society. The more perspectives you get, the better you look at something from multiple angles. Then that just inherently by itself makes it better.
Outside of that, there's a lot more, I would say, empathy, there's a lot more understanding of different perspectives, and why that perspective can be different. You're not only designing for 80% of the market, you're trying to go all the way and you're saying, look, I want to design it for everybody. It can't be that I'm designing it for the power user. I'm also designing for the person who's going to use the product at a bare minimum experience level, and it should work both ways. I think there's definitely that element of change in how teams have evolved.
Ramanand: Alright. Aseem, we're coming to the end of our conversation. I want to do two final sections before we close. The first section is getting your hot takes on the future relevance of certain areas. I'm going to give you a topic, just tell me what you think is going to be the future relevance of that. Should you want to pass, you can do that. So, let's start with an easy one. The future relevance of cricket?
Aseem Datar: Huge, I mean, global. Short but evolving. I would say high growth. I would like to say high growth.
Ramanand: Okay, from cricket, let's go to another 'C', the cloud.
Aseem Datar: I want to use the word enabler because it starts to become an enabling ground for a lot of innovation that then starts to happen on top of it, right? There's going to be a point where the value that the cloud is going to offer is going to become assumed value, right? Everybody's going to assume that this just works. This is the way the new world is going to be built. So, incredible amount of potential. We're just scratching the surface today. [00:58:00]
Ramanand: All right, let's ask you about the future relevance of a country like India.
Aseem Datar: Filled with opportunity. I think, right for explosive growth is what I would say. A tremendous amount of talent that's getting exposed to the world in meaningful ways. Frankly, it's just a hotbed of innovation.
Ramanand: Okay, that's good to hear. Let's ask you about the future or relevance of Silicon Valley.
Aseem Datar: I would say steady state to a certain extent, because Silicon Valley has proven out a great model that everyone's latching on to. And so, Silicon Valley will always have a special place in people's hearts from a technology standpoint. But worldwide, whether you pick a country like Israel, or whether you pick something like Hyderabad or Bangalore, or you pick places like Austin in the United States. I think they're going to start to give that a run for its money and not in a bad way. But there's going to be healthy competition in people wanting to replicate that model elsewhere.
Ramanand: Okay, with so much changing, what are the one or two things that you think will remain timeless. Even if we dial forward 10 years, there are certain things that you can take for granted as a business, as an entrepreneur, anything that comes to mind?
Aseem Datar: I think tenacity and grit is definitely something that will be timeless. People are going to push boundaries. That's actually for the better of everybody. I don't think that... you can replace tech and tech will always evolve. But I don't think you can replace that wanting to break barriers, wanting to push envelopes, not taking no for an answer. Those things from a humanity standpoint and what humans will do with tech is going to be timeless.
Ramanand: Okay? [01:00:00] So, you're fundamentally an optimist about technology and humans.
Aseem Datar: I think technology is a tool. Technology is a platform, right? But at the end of the day, you want to be able to innovate with that for the betterment of humankind. I think as long as that goal is unwavering in an entrepreneur's mind, you're just going to make better use of tools, and you're going to keep making better tools.
Ramanand: Okay. With that Aseem, let's go to our last section, a few quick takes on your personal habits and productivity practices. The first thing that you do when your workday begins is?
Aseem Datar: Can't function without coffee.
Ramanand: Okay. How do you structure your calendar? Is it full of blocks, pre-planned? Or is there a lot of flexibility to it?
Aseem Datar: Every week is different. It's a combination of meetings and work time. As much as I like to, I try to bring in at least a mini break within the day. It's just something that, even if it's a 10-minute break, that I can step out, and especially in this new world, where you can go out, just breathe a little bit, come back, maybe get another cup of coffee, drive to a small, close location, take a 15-minute break, that just helps me.
Ramanand: Okay, one thing you insist in your meetings to make them very successful?
Aseem Datar: Less production value, more authenticity, more conversations, more brainstorming, not completely finished product all the time. I think this is the whole philosophy of let's iterate versus wait for something perfect.
Ramanand: Okay. One habit that you picked up in the last one and a half years, it could be because of the environment around you, or just something that naturally happened to you.
Aseem Datar: In the last year, you would say?
Ramanand: Yeah.
Aseem Datar: [01:02:00] I wouldn't necessarily say it's a habit, but I was never a go for a walk kind of guy. But, the lack of gym time or playtime or sport time has forced me to take walks occasionally. It's also probably because I'm getting old, but I try to do that as much as I can. I try to socially-distanced walk with my friends, colleagues, if I can. I think that's one that I wouldn't say it's a habit, but it's an occasional habit.
Ramanand: Okay. One thing that you try to keep in mind when you consume news, which could be PR, which could be fake, one thing that you do when you consume news.
Aseem Datar: I try to sift through what is data versus what is opinion. I think in the world of today, it's important to understand what is the actual data versus when somebody is overlaying an opinion, which is trying to sway you one way or the other? I try to get to the bottom of like, hey, what is the actual thing that is being reported here versus people trying to sway me one way or the other?
Ramanand: Okay. One thing, this is our final question, one thing that you want to add to your repertoire in the next decade?
Aseem Datar: I think spotting growth areas. Empowering entrepreneurs and having at least worked with a couple of them who 've been able to transition an entire industry or deliver huge value for changing the way people use technology or people interact with products. That's something that I would like to go to. I don't know when, what, how, but it's just an aspiration to say, Great, you've done all of these things. You've been an operator, like how do you now take something in? I've been lucky enough to do that to cloud. Because when I started with the Azure team, like I said, we were small, but our P&L is in the billions, but [01:04:00] maybe one more for doing something like that.
Ramanand: Okay, Aseem, we started this conversation talking about your lucky break as an intern, and we've come full circle to talking about luck, but I think you've made your luck, more than anything else. So thank you so much for being part of the CTQ Smartcast. It was lovely talking to you.
Aseem Datar: Yeah, thank you. Thanks for having me. It's exciting and I definitely enjoyed all the rapid fires as well.
Ramanand: All right. Thank you so much, Aseem.
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