Somasegar – Part 1

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Chris Williams: I met Somasegar more than 25 years ago at Microsoft. I recall from the start being struck by his quick wit, and raw intelligence. He revealed his deep passion for the products and the people who built them with a disarming quiet confidence.

Soma spent almost 27 years at Microsoft leading some of the largest teams and the most complex products. Today, he’s a managing director at Madrona, a leading Seattle venture capital company. Through it all Soma has been a thoughtful and respected leader.

When I was in human resources, I offered some assistance as Soma pushed to establish Microsoft’s first Development Center in India. We worked together to consider how to compensate the teams, how to handle repatriation, and how to translate the Redmond-based company culture. Today, 10s of thousands of people work in Microsoft development centers around the globe. Decades of experience give Soma a very clear view of the world of remote work we all now face thanks to COVID-19.

We’ll talk about that and his move into the venture capital world in the next episode. But in this first episode, we talk about his fascinating journey from southern India to Redmond, Washington, and his remarkably fresh perspective on leadership. The simplicity and clarity of his approach are a breath of fresh air. And that’s what this is all about.

This is Leading Smart, the show about managing in the brainpower age. It’s a field guide to the joys and challenges of leading and working in the modern workplace.

I’m Chris Williams, your guide to the stories and ideas that I hope will inspire you to be a better leader in the world of knowledge work.

This episode is another of my conversations with leaders, this time with a remarkably thoughtful and worldly leader. This is Episode 223 — Part One of my conversation with Somasegar.

Before we begin, I should note that Somasegar is his last name. I remember asking him what his first name was, with a huge grin and a chuckle he told me, “you couldn’t pronounce it, so I just go by Soma.” I said, “so it’s Soma Somasegar?” He smiled and said, “Sure.”

Somasegar: I grew up in southern part of India. That’s where I did my schooling, high school. And then I did my undergrad in engineering. And then I had come to the United States to pursue my masters. And I landed in Louisiana State University. Got my Master’s in Computer Engineering there. And then I wanted to do a PhD. So I went to State University of New York at Buffalo.

CW: Was leaving India and coming to the US, was that easy? Was that something your family expected you to do?

SS: In hindsight, I feel differently than what I felt at that time. Okay. At that time, I felt it was a no brainer. Because like, you know, back in the late 80s, like, you know, the Indian economy hadn’t opened up. There were a few IT services companies starting to emerge. But really, there wasn’t a whole lot of what I call computer science related innovation that was happening kind of thing, right. And you know, and we I grew up in a with a cohort of people that all thought like, hey, if you finish your engineering in India, go abroad for higher education so that you equip yourself well, and then you decide what to do, kind of thing. So it almost felt like it was a no brainer. It didn’t have to think like ahead do well in college, write your GRE, apply to school here. Come on over here, right, that just felt natural.

I think it was more hard for people around me my parents and my grandparents and my sort of extended family. I remember back then there is no internet. You know, the phone charges were incredibly expensive to make long distance calls or international calls, kind of thing. And the postal mail was the the standard medium of communication, right, you write a letter to three weeks later, it might reach. So for them, I think it was way harder, but none of them ever showed that and they were all supportive of my aspirations. I was right.

Today when I think about, and I wish I had the, I still think I would have done the same thing. So I’m not like regretting or thinking like, change my mind kind of thing. But I don’t think I really understood what it meant to go to a different country and set up roots there. Because it’s not just you, it’s your immediate family that’s going to come together, it’s generations to come kind of thing, right? You’re making a decision, maybe it’s the right decision. But like, you know, the consequences is broader than you getting excited about: let me go get some education and get me look at some opportunities, kind of thing, right? I don’t think I appreciated that. Even if I appreciated that I would still have done this. But that was a thinking that I I evolved later on.

CW: Did you come with family? I mean, did you meet? So you met your wife here?

SS: That’s another funny story. Okay. So I was working at Microsoft here. And we decided to my parents said like, “hey, you know, it’s time to get married.” kind of thing. And so sure, we’ll do that kind of thing. And I was one of those guys who say like, you know, I’m an arranged marriage kind of guy. So I told my parents, like, hey, please start looking. Whenever you find a girl and a family that you like, you know, send me a picture. If I like the picture, then I’ll say yes. Okay. So after a few months of looking around, they send me like, you know, my wife’s pictures. I like the pictures. I said, I told them, like hey, I don’t want to talk to multiple people. If I’m gonna to talk to this person know that I’m going in thinking that like, you know, hey, I want to marry this person. If that person says No, that’s okay. But you can’t come to me later on and say no. So you better make sure that you are ready for this, right? So I talked to Akila and the Akila talked to me. And luckily, both of us, like talk to each other on the phone, and we decided to marry. And so I went to India about 10 days before the marriage. And that’s when I first met her in person.

CW: Wow. Okay.

SS: And it’s been like more than 25 years and we are still happily married.

CW: So you did get computer science in for undergrad in India?

SS: I did my undergrad in Electronics and Communication Engineering. So back then, at least in our school, in our college or university, we did not have a separate computer science undergrad degree. My year was the first year where they introduced a few computer science or programming related courses as part of the Electronics and Communication batch. And in parallel, we had started like you know, hey, getting a few students in for computer science for the first time around.

So I joined Electronics and Communication. But I chose to do a few elective courses in computer programming. In fact, I wrote that that’s another interesting anecdote. So my very first experience with programming was in Fortran. Okay, for those of you who still remember Fortran kind of thing, right, and it was the IBM 320, sort of a mainframe computer that we had in our university, there’s only one in the whole of university, and you need to run to the Computing Center, there are that used to be punch cards, you sort of input program using the punch card, and then you submit the punch cards. And then a day later, you will get the results. And sometimes it could be as simple as you know, hey, you forgot a semicolon, or you forgot something here. So there is a compilation error, go back and restart the whole process, right. And that’s how I learned programming, or that’s my first introduction to programming kind of thing.

You know, you look at today with the access that I have to computing, whether it is even like on my phone or like, you know, the hundreds of devices that exist in the home. It’s far different world than what it used to be. But just the excitement, to be able to program a machine to do something that you wanted to do. And knowing that it’s going to do it like in a very fast and like, you know, correctly, kind of thing, there was a that was a thrill back then.

CW: Soma was working on his PhD in Buffalo when this little company in Seattle tried to hire him. He originally wasn’t interested, he wanted to continue to work on Unix. And Microsoft’s MS DOS operating system was seen as a toy. But he went there to see it for himself.

SS: After one winter in Buffalo where I came from Chennai. Okay, so South India, I came to LSU. And then I go to Buffalo and I spent a winter there. And I said, like, you know, hey, I think I’m done with the, you know, Buffalo kind of thing. But but but know that like, no, my background is like, you know, from a lower middle class Indian family, where education is a high priority. The notion of discontinuing education, even at a PhD level was oh my god, what the hell are you doing? This is not like, you know what, you should be doing kind of thing, right?

CW: So this would have been in 86? 87?

SS: It was 87, 88. Okay, okay. I had to finish… So like maybe I can sort of brave the winters here and finish my PhD kind of thing. And then I got a call one fine day from a little known company in Seattle called Microsoft And the reason I got the call was because as I was finishing up a master’s in LSU, I had sort of sent a bunch of applications through a bunch of places. And then I went to join my Ph. D. program. And Microsoft, I guess, after a few months decided to call me and they call LSU. They found my roommate, and he routed me somehow I finally got the call, right?

And to be honest with you, back then, Microsoft was not super well known company. It had gone public and all that stuff, but it wasn’t like you know, hey… And and particularly in academic environment, people would tell you, hey, Unix is king. Everything else is a toy. And who’s is Microsoft building some toy systems? Who cares about it? Kind of thing, right? So there wasn’t like, you know, what I would call it a deep appreciation for what Microsoft either was doing, or more importantly, was going to do in the future, right?

And for me, the call from Microsoft meant like, you know, hey, here’s a company who knows that I need a visa sponsorship to get a job. Okay, they are willing to go do that. And I had some friends in Seattle. It’s a free trip. Let me go experience and see what happens. Right? I came here and back then at least you know, even now, I’m sure Microsoft does this. But back then definitely. This was the, you start the interview at eight in the morning, or it goes till 6, 7, 8 at night, and like just boom, boom, boom, write a program, write code and you know talk to me about this project that just like series of right. I finished that interview, and then I walked away. And I did not get an offer that day. Microsoft said like, Hey, we’re now thank you for interviewing with us, we’ll let you know later.

So I was flying back to Buffalo The next day, and I was thinking about my experience. And there were three things that struck me. Okay, One is: I probably met about nine or 10 people during the course of the day of interviews. And I would say like my each and every one of them, some of them are a little quirky. But the one thing that was common across all of them was they were all incredibly bright and smart, and passionate. And I said, like I hey, if this company really is having a collection of such people. Oh my God, what a thriving learning environment, it would be for me.

The second thing that I liked was even back then, like you know Bill, Bill had this simple vision that was like captivating and resonating with pretty much anybody who cared about technology, which was to democratize access to computing, like his famous sort of phrase for Microsoft, put a put a computer on every desk in every home. And this was back in the 80s. Remember that even today, we haven’t accomplished that goal. But like there was like a very, very powerful vision. And I thought like, Oh my God, that’s like, you know, being part of the journey, would be like phenomenal kind of thing.

And the third thing, this is where I was like, you know, I didn’t know whether Microsoft was going to do this for me or not, because even back then, Microsoft was doing some work at the system’s level, some work at the applications level, all across the stack, kind of thing, right. I was really, really keen on doing systems level work. When I left college, or when I left school kind of, thing.

CW: Soma had worked in college and postgraduate work in operating systems. Operating systems are the connection between the hardware — the screen, the mouse, the CPU, and so on — and the rest of the world. It’s among the most technical work there is, and it’s where he wanted to stay.

SS: So my thinking was like, you know, hey, if Microsoft ended up offering me something in systems I would consider it because I still had to go through the mental hump of Oh, my God, I’m going to discontinue my education. What is my family going to say? What is what? What does this mean, right? Am I sort of veering away the traditional path.

CW: The interviews for Soma went well, and shortly thereafter, Microsoft called and offered him a job. The good news was that it was in exactly the work he wanted to do — on operating systems. The bad news is that it was on a new operating system called OS/2 an ill fated joint project between IBM and Microsoft. Fortunately, he was soon moved into Windows NT, which would become the long term foundation for Microsoft Windows.

SS: Luckily, a couple of weeks later, Microsoft called me and offered a job in a in a in a product team that I did not know until then called OS/2. Okay, so I said like, what what is this always too, so I quickly read up on that, and oh, yeah, systems level programming, excited about this, right. And then I did a little bit of soul searching.

But to be honest, I’ll tell you that the winter in Buffalo experience was a huge factor in me make the decision to come to Microsoft, right? So I literally ran away from Buffalo as soon as I could, and join Microsoft. And I did harbored this aspiration my head like you know, hey, sure. I’ll go to Microsoft, work for three, four years, and then I will come back to school and finish my PhD, kind of thing. It remained a dream and I’m glad it remained a dream.

CW: So this was 89. Right. So there were, there were What? 4000 employees? So it was it was a little…

SS: it was less than 3000 when I joined…

CW: that just seems like such a big leap of faith. Didn’t it feel risky to to join this little tiny? Or was it just the fascination of the of the work that was the draw?

SS: Let me let me take it a little differently, kind of thing, okay. You talked about risk. I’ve thought about this often. Am I a risk taker? Or am I not a risk taker? And I actually don’t know that I know how to answer the question. Okay. Because like you just said, like, you know, hey, you know, coming from India to US, with literally no money, and relying on the college to give you like an assistantship and tuition waiver and all that stuff, right? Or leaving, like you know, your PhD education halfway through and coming to some of some company here, or like after 27 year career at Microsoft leaving there and saying, like, hey, I want to do something completely different. Because I didn’t want to sit here as much as I told you, like, hey, the worst case I would sit at home, I have no interest in sitting at home, kind of thing, right? I was really looking for what could I do for the next 25 years? Right?

So each of these things you could look at and say like, hey, those are those all seem to be risky things kind of thing, but what I can tell you was as I was making those decisions, I didn’t think about them as a risk at all. To me it just felt natural. Okay. So I don’t know how to think about like, no, so I don’t think about like, Hey, this is a risk, that is a risk kind of thing, right? If you are passionate about something and you want to do that, go do that. There is no risk of what I don’t know what risk it is, right? You know, hey, I might have failed my 12th grade exam. And you know, life would have taken a different turn, or whatever, I don’t know what this risk is all about.

So I get confused about like, you know, hey, I’m a risk taker or not a risk taker. Instead, I sort of focus on like, Hey, I’m really excited about something. I want to give it a shot. And sometimes I may succeed, sometimes I may, I may have that as a great learning opportunity, because I don’t think about it as failure. Everything is sort of learning opportunity in life.

CW: So you come to Microsoft, you’re gonna you’re working on OS/2, you’re an individual contributor, right? You’re slinging code. Do you remember what the first things you worked on were?

SS: I was working on the OS/2 file system? Okay, that was my first project. Okay. I was doing that for like about nine months. And I should tell you, like, the first year was a little rocky for me at Microsoft, right? I’d like no, no clue about like, no working environment, there was my very first job in my life. I didn’t come from a background an environment where like, you know, hey, when I was 18, I started doing some jobs here, some jobs there. So you get a feel for what it means to be in a working environment with other people. I had done nothing. There was my very first job.

So it took me about a year to even get my bearings, right about like, hey, what does it mean to work in a team? What does it mean to work on a project together with people? What does it mean to think about, like, you know, goals and objectives and meet them and know that somebody else is thinking about it, as opposed to, until then it was all what you needed to do what you felt you don’t you go get it done, right. So you know, it was a, it was a different experience for me.

And then towards the end of the first year, I get a call from my, from a guy who was like, two, three levels above me saying like, hey, I need to talk to you. Said okay, you know, good or bad. No idea. But I went in, and he said, like, Hey, we are starting this new project. And I want you to go there. Said okay. At the time, I wasn’t even sure that I had a choice. I’ll go there.

And then I realized that it was a project that we had codenamed NT for new technology back then. Right? It was a it was an attempt by Microsoft, to say, like, Hey, we think as much as we are working with IBM on a joint development project for a 32 bit operating system, we don’t know whether that’s going to be the future. Let’s start incubating and working on our own sort of ground up, portable 32 bit operating system that someday could get to 64 bit and beyond kind of thing. And we had hired Dave Cutler, and a bunch of people from DEC, or Digital Equipment Corporation.

They had locked themselves in a corridor at Microsoft for a year, they did nothing but write documentation. You would think like, hey, you’re having all these high-powered engineers, and they should be writing some code… But no. And and to me, like, you know, that was probably the first and the last, you know, documentation that ever was written by the engineering team, I think.

But jokes aside, like they just come out of that effort with the with a bound book about like, Hey, here’s the spec for NT. And I think in Bill understood, the leadership team approved the project, and they were building an engineering team to start working on that. And I got drafted to that. And I thought that was an amazing, amazing, amazing experience.

CW: But here again, you were slinging code, right? So at what point did you move from slinging code to leading groups of people?

SS: I would say it took about three and a half years after joining Microsoft before like now, and again, like I one of my managers stopped me and said, like, you know, hey, we really, you know, there is a there is a lead opportunity there. It’s a team of six people. So not a large team or anything, right? We think you’d be great at leading the team. Are you interested? Okay, let me let me give it a try. Okay.

And I always felt that like, you know, I’m a guy as much as I like to work very hard. I also like to take the easy way out, as opposed to the hard way out. Okay. And even back then I felt like, you know, that I had a natural passion for leading teams and people, as opposed to writing code. I’m sure if I continued writing code, I would have been an average developer at Microsoft. I’m not like you know, I know enough about myself to tell you that. I’m like, no, not a Peter Spiro or, or, you know, Steve Wood if you remember, Steve was a prolific coder, kind of thing, that I’m like, my average developer. That’s about all I’m right.

But I felt like you know, I had an energy, a passion, a interest and confidence that like, you know, hey, I think I would be good at leading a team as opposed to being an individual contributor. And also, it gave me the chance to say like, you know, Hey, now I’m responsible for the output of so many people, as opposed to just what I can do, no matter how great I am. So there is a there is a feeling of a bigger accomplishment, or a higher level of impact. And I said, like my hey, I want to go take that path. And I think so that started my journey on like, what it meant to be leading a team of people.

CW: Do you remember how you figured out how to do that? Did you? Did you teach yourself? Did you read books did you take classes, I mean, how did you? How did you know how to lead people?

SS: I think back then, if you if you remember, the first thing is, it was a blessing in disguise, in some sense. Microsoft was growing so so so rapidly, that we were all learning in the job. There is no time to go learn, like you know, from somebody else, or go to school, or go to some other thing kind of thing, right?

I’ve always been a fan of reading books, right from my young age. So I did read a bunch of books to sort of get a … at least hear about what others other people’s experiences were, what other people went through what what words of wisdom, they have kind of thing, just to get a different perspective. But it’s, it’s really like, you know, hey, you are learning in the job, you are observing other people around you, whether it’s people that work with you, people who work for you, or people that you work for, you think about like, you know, what is needed for the, for the team for the product for the customer, as we were scaling up so fast. And it’s all like, you know, self learning at that stage.

CW: You had just mentioned that you felt like that leading was going to be the right thing for you. Did it feel comfortable from the beginning? Was it? Or did you struggle with it?

SS: Ah, it felt comfortable. And yet I struggled. I’ll give you some examples, right? You know, here in here, meaning in the US, when kids go through school, public speaking is sort of like, you know, a skill that you learn, right from the school days kind of thing. I had not done a speech in front of a group of people till I came to Microsoft. The only time I spoke in front of like, an I think five or six people at a time, was when I had to defend my master’s thesis.

So I was not a good public even today, I’m not a great public speaker. Okay. But that’s a skill that I did not have. And I would like, you know, I remember like, I would sweat like crazy, just thinking about, like, you know, oh, my God, I need to get up in front of 20 people and give a talk to about… right. So that’s it. So I struggled with that.

You know, earlier, when we were sort of talking about things we were talking about, like you know micromanagement. I’m pretty sure that as a first time manager, I was probably a big micromanager in hindsight, okay, at that time, I don’t know that I even realized that kind of thing, because I felt like in my head, hey, I was an engineer, I knew what to do. Now I’m managing six people, I better make sure that they’re all doing, you know, the way I think it should be done, kind of thing.

So the first year I’m sure I, I sort of struggled. But at the same time, it felt natural for me that like, Hey, this is something I think I can do well. I can do better than a lot of other people. And I think I can contribute more and have a bigger level of impact and influence on the company and by extension, everything that we are doing by being a leader as opposed to by being an individual contributor, that that feeling and that level of confidence I had from day one, but it isn’t like that I was a perfect manager from day one.

CW: That is something you have always projected confidence. And I believe that that that’s obviously also an important part of being a leader is that your team has got to feel confident in you and you have to feel confident in your team. Do you know where you got that confidence? Is that genetic? Did you can you look at your parents or whatever and see that or was that something that that you…

SS: I look at my parents, my parents like, to sort of diverge for a second, my parents, neither of them have a college degree. Okay. My mom actually didn’t finish high school. My dad finished high school. And he got sort of a 12th grade moral equivalent and, you know, certificate or degree or program, diploma, kind of thing, okay. But he worked for the Government of India. And for his little domain that he was in, he aspired to be a team leader, and he became a team leader, and for the rest of his life. He was managing, he was leading a team of about seven or eight other people, right. And he was always focused on that. Did that rub off on me, maybe I don’t know, that kind of thing.

My mom is a very, very strong woman, though she isn’t educated and she has never worked in her life, meaning outside the home kind of thing. She’s, she’s very good at math. She’s strong. And she manages the household really, really, really effectively. Did that rub off on me? Could be.

So I don’t know, where I got it. Or I can’t tell you that like, no, hey, this person was my aspiration. And so like, and I just followed what they were doing, kind of thing. It just seemed natural. It may be just like, you know, my personality? Because I’m also not a, you know, and from Microsoft, you know, this, right? You know, there’s a lot of what I call A+ type personality people. You can be a A type personality, and still be what I call not a table pounder. Or you could be a table pounder a lot of people around Microsoft at least back then, were like, hey pounding the table, kind of guy, right? But I’m more like, you know, behind the scenes kind of thing, guy.

And I and I strongly, strongly strongly believed right from day one, in both empowerment and accountability. As much as I probably struggled that first year with micromanagement, I think I had the balance of like, Hey, you want to have a trusted relationship with your team, you want to be there to provide enough clarity on like, you know, the direction and strategy and stuff like that. But beyond that, you sort of empower your people and you hold them accountable. Right. So that I think, you know, was something that you know, it, it felt intuitive to me, as I said, like, I can’t tell you that like, you know, hey, I studied A, B, and C and boom, like, I become a great manager, kind of thing. I’m sure I sort of learned I stumbled I made mistakes. But the core theory about like, you know, hey, how can you work with a group of people and get them to row in the same direction, and try to get the best out of them seem just natural for me to be a part of and to be an accelerant, as opposed to otherwise?

CW: Microsoft in the 1990s was filled with exceptionally smart people who were deeply passionate about what they were doing. The culture featured lots of vigorous discussion, even confrontation. The systems area, or Soma worked was legendary for what could be politely called table pounding meetings, where discussion often made way for arguments.

Yet that’s now Soma at all. I recall many times in which he would let the argument go on without saying a word. Only after the dust had settled, would he speak up, and yet often his comments would change the entire course of the conversation. I asked him if he was intimidated by the atmosphere, or was this a planned strategy?

SS: It wasn’t intimidation, and it wasn’t like, No, I don’t think it was a planned strategy. It is just my behavioral type, right? I sort of believe in like, you know, hey, if they have something meaningful to say, I should say something. And I don’t need to say something just because I have to say something. That’s number one kind of thing, right? Number two, is, there is some merit in listening to different perspectives, before you decide what you want to say, right? You know, I may be a smart guy, I may think I know the answer. But like, often times, you know, hearing other people’s perspectives, makes you a better decision maker in the process kind of thing.

So I sort of not, I always believed in like, hey, let everybody you know, give their opinions talk about it kind of thing. And if you have something that is value add, say it, otherwise, it’s okay. It’s okay not to have to say something, right? If you don’t have value to add, so that’s, that was my mentality. That’s what my that was my mindset. And that’s how I sort of behaved. Even today, I’m like that I’m not like not very, in your face kind of… as much as I’m talking here today with you. I’m not in your face kind of guy, I’m not gonna hey, you know, we have a group of people like take Madrona, for example, we have a group of people, everybody is got their opinions, their points of view. And if I, if I have something to say that is going to be value add or I feel something is wrong, and we ever change direction, or if I have a strong point of view, or if I have a different perspective, absolutely. I should speak up. But if I don’t have that, I don’t need to speak up just for filling time or you know, hearing my own voice kind of thing.

CW: So let’s say you’re in a situation in which you’re absolutely convinced that they are wrong. What tools do you use? Do you rely on the strength of your argument to win?

SS: I think there are a couple of things. One is you have to show demonstrate to the other person that you are listening to what they’re saying. Not necessarily agreeing, but listening.

The second thing is, and I found this like, and this definitely, like came to me with experience over time, kind of thing, the more I can put myself in your shoes, and try to understand where you’re coming from on what is the basis for your arguments or why do you think a particular way, when I obviously disagree with that kind of thing, the more I understand that, the more I can help you understand my point of view. Otherwise it becomes like, hey, who’s got the loudest voice, and anyway, nothing is gonna happen. Because in the meeting, like the loudest voice may prevail, but people will go and they’ll do what they want to they don’t want to listen to you. And Microsoft is, is particularly a) either famous or notorious depending on you want to look at it, for that kind of thing, right.

So, to me, like, you know, what is more important is not whether you have the loudest voice or not, to me, more important is like a hey, if you have a point of view, can you influence people that need to be influenced, so that like, you know, hey, we start moving in the direction, as opposed to be shouting at each other in a meeting, yelling at each other and pounding the table, and think we have won, when really nothing has happened, because passive aggressive behavior sets in later on.

CW: So you moved from being an individual contributor to being a lead, the next change that people make, and it’s, it’s often very difficult for managers, you can get away with being a micromanager as a lead, you know, in some dimensions, but the next change is that change where you have to manage managers and, and that’s when I think it’s really interesting, I was talking to somebody about the difference, the times that that are inflection points in, in leaders’ careers, and, and very often people focus on that first one, where you have to figure out you know, what it what it means to lead people and how to influence them. And but for me, the real change in leadership is that next one, where you have to manage managers, because you can’t physically micromanage. It’s very difficult to micromanage through someone, right? It’s, so you end up having to work the levers in a completely different way. Do you remember the first time you ended up having to do that?

SS: Yeah, I don’t… I still remember, like the career steps really well. And I think it happened about two years after I became a lead, when like, you know, somebody tapped me and said, like, Hey, we want you to take a management role now, where you’re going to manage a team of leads, or managers kind of thing, right.

And the one thing that I sort of decided earlier on, as I was thinking about, like, you know, what does it mean to lead a team of people, if I had decided earlier on the like, whether I’m managing, you know, six people, or 60 people, or 600 people, or 6000 people, I get to work with my set of direct reports. Okay, what I need to focus on is, what is the relationship I want to have with my direct reports? What is the expectation of each of my direct reports that I have of them? And likewise, what do they have of me? And how do we manage through that effectively. The fact that they may be an individual contributor, or they may manage, you know, thousand people is almost irrelevant to me, okay. As long as I keep that lens, because like, hey, you know, till the very end at Microsoft, at least, right?

Though I used to manage larger organizations, and I like to work mostly with my direct reports and sort of work through them, I would sort of go deeper into organizations, there was a particular thing I was interested in knowing more, I had a deep passion for I want to get something out, or I wanted to participate in that kind of thing, right? So I had no problems doing that. But the key to remember is like, you know, hey, my responsibility primarily, is to hire the right people, for my, who are going to be my direct reports, and empower them and hold them accountable, and give them clarity and help them with strategy. If I do that, well, then I can scale, and it doesn’t matter how many people are there in my organization. So whether I’m managing, you know, a bunch of lead leads, whether I’m managing managers, whether managing, managing a bunch of executives, it really doesn’t matter. Because it’s a formula that just scales almost infinitely.

And, and I felt you know, and this is what I call intuitive because like, No, nobody sat down for me and said, like, Hey, this is what it means for you when you go from managing a team of individual contributors to a team of leads. Nobody said that. You go in with like, you know, hey, what do you think is right? You sort of know, look around and see if there is something to glean from other people who are doing something similar or who’ve gone through that recently kind of thing. And then you apply what you have with the people that you have, and you see what works. And if something doesn’t, I am sure that are like, you know, 200 things that I’ve done that I was wrong, that I realized the minute I was doing, or maybe a little bit into it that I said, Okay, I should not do it, kind of thing, right?

So, so it’s not about like, hey, as I said, it’s not about everything being perfect. But the core principle of saying that like, you know, hey, you’re gonna work with us a finite number of people that are around you, and you’re going to use the same principles of, you know, empowering them, you know, being clear with them on what your expectations are, you know, be willing to listen to them, and they have a different point of view than what you have. Because like, sometimes they may be right, wrong, like, I’m always right, because I’m the manager, right? One of my people may absolutely, you know, have a different point of view. And I need to have the wherewithal to be able to listen to them, and internalize that and decide and be okay, saying, like, Hey, you know, what, I told you, this is what we should do. I’ve heard your perspective, I know that I think what I said was wrong. Let’s go with what you’re saying. Having that level of trusted relationship, empowering people and holding them accountable. Those are the fundamental things that I think, you know, I sort of kept in mind, right from the early days. And that helped me scale through pretty reasonably well at Microsoft.

CW: Sometimes, you get to hire your direct reports, and sometimes you get your direct reports thrust upon you. What what are the kinds of things that you you feel are important to have, in somebody that you hire? Do they have to share your leadership style? Are there things that are stoppers that that no, I don’t, I never want that kind of a person to work for me?

SS: I never believed in like not any one leadership style. I think like no leadership styles are a dime a dozen. In other words, like, and I had different people have different styles. And there are different ways of making work. There are obviously some styles that are probably, you know, doesn’t go well with how I think about things. But that doesn’t mean that that I need people that have that like or that have only my leadership style. In fact, I think that is wrong, I would I would rather have a diversity of leadership styles, because like, hey, different for different people, or different styles may be more effective kind of thing.

So for me, like, you know, what is more important is are they smart? And when I say smart, it is not necessarily do they have the highest IQ or anything like that? It’s really like, you know, hey, are they smart enough to learn, whatever comes your way, and be able to get a quick be a quick study and get a good grasp of things, and be able to drive forward? Because technology, particularly the world of technology, the one thing that we all know, is, it is so fast changing so rapidly changing? What I thought like, you know, was state of the art yesterday is irrelevant today. Okay, so so I want people who have a curiosity to learn, and who have the ability to learn. That’s what I meant when I said like, you know, smart, okay, that I think is important.

You know, teamwork is important. You know, you can have the occasional sort of individual contributor, superpower engineer, who can lock themselves in or in a room, not talk to anybody. And like, no, be a prolific, amazing, you know, developer, I’m sure you can have some of those people. But when you have people in leadership roles, you really want people who, who appreciate and who you know, who are excited about teamwork, as opposed to like, you know, my way or the highway. Okay? So if I have a choice, when I get to hire, I look for that and say, like, you know, Hey, is this person like teamwork?

The third thing I look for is like, work ethic, okay? Or passion. In a Hey, are you passionate about what you’re doing? are you passionate about a customer? are you passionate about the technology we’re building? Are you passionate about the people that work for you? If these things are there, then I’m usually excited about like, you know, wanting to work with that person.

CW: Do you try to coach the people who are working for you? And if you do, I’m curious to know, for example, have you ever walked out of a meeting with one of your direct reports and said, you know, maybe you should shut up a little more, or…

SS: I’m sure I have, I’m sure I have. But here’s the thing, like, you know, my view is, I’m not here to change your behavior. Okay, that I don’t I don’t expect to suddenly say like, hey, Chris, you and I are working together, I expect a different Chris tomorrow. That’s now what it is, right? It’s true. It’s true, from my vantage point, it’s to be able to give you some some guidance, some coaching, occasionally, some directives. Okay. And I hope that the the time were I have to give a directive is far and few between kind of thing, but it’s more like a, hey, you you’re thinking this way or you’re doing this? Why don’t you do it this way? Or because you’re doing it this way. Here is the consequence. Have you thought about it? What do you want to do differently? Here’s how I would do it. But you don’t need to necessarily do what I’m doing or how I’m doing it kind of thing, right? But here is the feedback or here is observation or here is a consequence. Go Think about it. Right? So and it’s one of those things like anything as, right you know, people usually, listen, people usually do things. And occasionally you find a direct report or you find somebody who’s like not not doing that. And you give them like, enough time enough opportunity, enough rope at some point, and you’re to make decisions.

CW: So you joined Microsoft, you had to be among the first South Asians there. Was that hard, easy…? Did it matter?

SS: I don’t think it mattered only because like, and I will tell you, like in a hey, there’s all kinds of talk about, like, you know, diversity and inclusion and all that stuff. It, I had always felt that like, no, Microsoft was an environment that was inclusive, that that, you know, sort of both celebrated and welcomed diversity. Diversity in the form of thinking in the form of thought processes, in the form of styles, in the form of where you come from, how you look, what your color is, what your gender is all that stuff, right?

So I never felt, you know, out of place, Microsoft, I never thought like, you know, oh, my God, like, you know, how do I survive in this, you know, in this world where I’m looking different, or I’m thinking different than other people kind of thing, right? I don’t know whether it is because I it just wasn’t my psyche to think about it. Or maybe I was, you know, fortunate enough to work with a collection of people that all seem to be, you know, behaving right. I don’t know what it is. But I didn’t, I can’t tell you that like no, hey, there was this one instance, I felt.

At the same time, I should tell you that there were a lot of other people who tell me like, you know, particularly if you remember, like, you know, back in, was it 2000 or so when a number of us became execs or VPS, in the company kind of thing, until then, there wasn’t a South Asian who had become a VP kind of thing, right? So some people will be telling, like, hey, Microsoft is not this, Microsoft is not that kind of thing. And my view always was, we just haven’t found somebody who was operating at that level or who deserved that. So it’s not about like, No, I don’t want like, you know, this class of people to become a VP or anything, kind of thing. So I never felt that. But I know, even back then there was some little bit of rumbling and talks about that, kind of thing. My own view was I thought the system was reasonably fair. I never had any issues with the system. But I am also not have thought about all these issues deeply back then.

CW: Organizations in many ways reflect their leader, their leadership style, their their approach to conflicts, their, their… hiring, I mean, you know, in many ways, organizations tend to reflect their leaders. Did you feel like people would say Soma’s organization looks like… you know, is like Soma.

SS: I don’t think I’m that strong a leader, okay, to have my organization reflect my personality, period. Okay. And I personally think 9 out of 10 times, that’s a wrong trait to have. That’s my belief.

CW: Okay.

SS: I always believed in as I said, like, my, I believe in like, hey, here is my style. I’m the first to tell you that this is not the only style that works. And I want you guys to do what do you think is appropriate. Within sort of reasonable parameters or constraints, kind of thing, right? So I actually would be unhappy, If somebody tells me like, you know, hey, Soma’s organization of 5000 people, thinks and behaves just like Soma. That I feel is like now a colossal waste of creative people and talent and, and, you know, and all the good things that go with that, right. So I never want to be in that position.

And I can actually like without naming names, think about some of our contemporaries. Okay, at least one or two of them who were like that, right. And to their credit, they were incredibly accomplished. They, they added a lot of value to Microsoft. But it had a leadership style, a style that I would never, I can never sort of resonate with. And I think in the process, they probably didn’t, didn’t realize the full potential that they had otherwise, not just for themselves, but for what their organizations could do.

CW: But at the very large scale, for example, I mean, Bill had a style of leadership that, that, you know, people tried to emulate even subconsciously. It’s just natural for people to look up in an organization and see the leader and feel, you know, that’s what it takes to get ahead, or that’s what it looks like to lead, or that’s what management is. Bill was incredibly technically visionary. He was capable of having deep technical conversations with anybody on any subject at any time, incredibly, well read and thoughtful. And he also though, the stupidest effing thing I’ve ever heard, and, and people emulated that. Do you feel like you pushed against that? Do you feel like you just sort of did what you were gonna do? Or…?

SS: So I’ve always believed in sort of emulating when there is something good to emulate.

CW: Yeah.

SS: Not emulate just because somebody else is doing it. And like hey feels like, you know, maybe that maybe like, you know, that’s what is required for you to get ahead. I never believed in that. Right. So if Bill did something that I think was like, you know, positive, I would say, like, Hey, there is something to learn here. How can I learn that? And what does it mean for me to be able to do something like that? Maybe in the same way that Bill does or maybe in my own style, because my style is different than Bill’s style, right.

On the other hand, if Bill had a sort of what I call a not so good, you know, attribute, right? I would say like, hey, that’s his problem, I don’t I have no interest in emulating some like you know bad behavior, right? I never use the f-word for example, and I’m not saying they’re good or bad. They’re just my my sort of behavior, what I believe in, so I don’t need to emulate like in other people, because that’s, you know, what seems to be at the top kind of thing, right?

The second thing I would say is even like a guy like Bill, who’s who’s incredibly talented, smart, passionate, bright, whatever you want to call it kind of thing. He never expected his people to be like him. Okay, some people might think that that’s what is required to get there, but I don’t think Bill ever even like had iota of thinking that like, Oh, my God, I need people who are mini-bills, around me, right. So I think it is a fallacy to think that like, Hey, you have to like emulate, you know, your leader, and everything that they do kind of thing. In fact, I would say, if you do that, and particularly if it is against your style, sooner or later, you will stumble and stumble very badly. And I don’t think it is a it is a good idea for anybody.

At the same time, okay, you want to look up, you want to see what is there to learn, but have the discriminatory capabilities to decide what is right and what is wrong. And more importantly, think about what it means for your own style. Because as I said before, this notion of like, Hey, take my example, right? I worked for under three different, you know, completely different CEOs kind of thing, that doesn’t mean the like you know Soma goes from being a mini-Bill, to a mini-Steve, to a mini-Satya one day, right? I am who I am. Maybe some things I learned from Satya, there’s some things I learned from Steve, some things I learned from Bill. And I like to think about what those things mean, internalize those things and think about how do I sort of inculcate those good attributes or good habits, or good practices in how I lead organizations in how I manage people, and how I build products and deliver products to my customers, kind of thing, right?

So it goes back to like the curiosity to learn, I want to be a person who’s always learning because you know, hey, no matter what I’ve done, or where I am, I feel the people around me are constantly teaching me something every day. And if I if I allow myself if I open up myself to learn, to at least understand what people are doing what people are saying, and have the capability to reflect upon that to internalize and decide which one makes sense for me, and which ones doesn’t make sense for me, every day I’m becoming better.

CW: Soma may not want people to emulate his style, but there’s a lot to learn from his approach. His core tenant of simply empowering his team and holding them accountable without a lot of micromanagement is well worth emulating.

Next time we’ll discuss how some have pushed Microsoft to embrace remote work long before remote work was cool, or now required. And we’ll discuss his decision to leave Microsoft and join Madrona, the Seattle VC firm. Please be sure to subscribe so you’ll get this episode the second it comes out.

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That’s it for this episode. The next episode we’ll wrap up the conversation with Soma. We’ll talk about leading remotely and his decision to enter the world of venture capitalism. I hope you’ll listen. Until then, please remember that each of the several dozen decisions you make today are part of Leading Smart.