When Keshav Puttaswamy began working at Microsoft, he anticipated two years of trying something novel before finding a more mainstream life outside of Seattle. Twenty years later, he craved the change for different reasons. Find out how feeling years to be long or short is sometimes related to the pace of change and sometimes to how right things feel.
Guest Keshav Puttaswamy was excited to be able to dabble in the full liberal arts curriculum of college and found an interest in computer science. When he had the opportunity to intern at Microsoft in a rather new role of product manager he took it despite not knowing what it would entail. He ended up learning a lot about not only computer science but also how the business worked and had fun doing it. But it felt didn’t feel like a mainstream route for either a computer scientist or a business person so he thought about other roles in each field. Ultimately he decided to take the offer to work at Microsoft, but he figured it would be for only two years and then he’d get into something more “normal” in the business world.
Those two years turned into twenty when it became clear that his skill set was well suited for product management and seeing how the variety of projects he got to work on was vast. But the desire to change came again when he thought about providing his children the opportunity to live abroad, as he had been afforded by his parents.//In this episode, find out from Keshav how feeling years to be long or short is sometimes related to the pace of change and sometimes to how right things feel…on Roads Taken with Leslie Jennings Rowley.
About This Episode’s Guest
Keshav Puttaswamy is a near lifer at Microsoft. He spent the first 20 years there in product management leadership roles and currently leads the collaboration and workplace experiences there, helping to deliver transformational digital experiences for Microsoft employees that serve as a blueprint for customers’ own digital transformation journeys. During his family’s two years in Sydney he led the server and enterprise-focused data center products for Atlassian before boomeranging back to Seattle. In addition to the travel, Keshav also enjoys cricket, cooking, and cocktails. (307)
Executive Producer/Host: Leslie Jennings Rowley
Music: Brian Burrows
Find more episodes at https://roadstakenshow.com
Email the show at RoadsTakenShow@gmail.com
Keshav Puttaswamy: You know, 20 years at Microsoft is a long time, but this little hack somebody shared this was like, if you want time to slow down, obviously time doesn't really slow down. But if you want it to feel like it's slowing down, change things up, you'll remember things a lot more vividly. And I think that was very true for us.
Leslie Jennings Rowley: When Keshav Puttaswamy began working at Microsoft, he anticipated two years of trying something novel before finding a more mainstream life outside of Seattle. Twenty years later, he craved the change for different reasons. Find out how feeling years to be long or short is sometimes related to the pace of change and sometimes to how right things feel…on today’s Roads Taken with me, Leslie Jennings Rowley.
Today, I'm here with Keshav Puttaswamy and we are going to talk about going round the girdled earth and back again, and what we learn from all those experiences combined. So thank you so much for being with us today.
KP: Thank you, Leslie. This is gonna be a lot of fun.
LJR: So you might know that I ask the same questions of all of our guests. And I start off with these when we were in college, Who were you? And when we were getting ready to leave, who did you think you would become?
LJR: Yeah, it's fun to reminisce. When I landed at Dartmouth—Just this context, like I'm from very middle class family in Bangalore—I'd never seen Dartmouth, never done any campus stores. I actually did one right now when I was at the 25th reunion with my daughter, we were like, Hey, let's do a campus tour. But you know, I'd lived sort of vicariously through college brochures. And so when I landed on campus—so first of all, I was incredibly fortunate that I got that opportunity. My family could never afford sending me to Dartmouth. And back then, We did not have sort of need blind admissions for international students. I'm really, really excited that Dartmouth has changed that and is able to afford to extend that to all international students. So back then they had very limited money. And so it was a bit of luck of the draw almost. Nevertheless, I came in very much set on experiencing a true liberal arts education and if I had chosen to stay in India, I would've gone down a very sort of regimented path based on my test scores. There were admission tests and then I would be ranked and that would pretty much decide what major I was gonna do. And so for me, the opportunity to come to Dartmouth and really just explore was what I was looking forward to. My dad was a physicist, so I thought, hmm, maybe I'll do physics. But I really wasn't sure. So for me freshman year was amazing because I got to take things like writing and studio art.
LJR: Wow.
KP: And courses that I had never, never really imagined doing. And so I really didn't know who, who I was gonna be other than this really excited Indian boy coming into the U.S. and just wanting to absorb everything that Dartmouth was gonna offer me. And I had no idea what that was gonna look like. So I was, it was just one of those things. I was living the dream, if you will.
LJR: And so how, and when did you find that thing that, okay, I'm gonna start winnowing down and find a place where I feel most comfortable or most alive or whatever.
KP: Yeah. I mean, from an academic point of view, it was my freshman spring, I believe when I took my introductory computer science class and I just loved it. I'd kind of dabbled around in computer science…first of all, the whole experience at Dartmouth, if you remember, like we all showed up and there was like, This AppleTalk network and we all have to buy Macs, right?
LJR: Yeah everybody carrying the boxes across campus…the Apple.
KP: Exactly. The apple and you know, between classes you'd stop at Collis and check email. Yeah. Remember those lines? It was kind of real. I mean, it was a moment in time. This was obviously 1992, where technology was still kind of in its infancy in some ways. And we were doing things that people weren't really doing at that time, like emailing each other about, Hey, where should we go for lunch? Or, you know, almost real-timeness there. And so that whole idea of technology and how it could transform our lives, combined with just an amazing experience that I had in my introductory computer science class, I just fell in love with computer science.
LJR: Yeah, that was, I, I think I wished somebody had told me at the time, wake up, like this is happening right now> Because I was kind of like, oh, I've never been to college; college must have his technology, like that must just be a thing. But it was really of the moment [KP: Yeah.] Where you were getting in at the kind of leading edge to some degree, at least in the, kind of what we would call modern computing.
KP: Yeah. Yeah.
LJR: So that was something that you pursued and then were you pretty sure early on in that, like, this is how my, my business, my professional life is gonna go?
KP: Not quite, I think I just knew that. Loved computer science. So I thought, Hey, I'll just take that. And it seemed like a good area given through my background. I felt I was pretty good at it. I didn't know where the journey would lead me. But I just kind of pursued it more as a passion through my sort of subsequent years, I was trying to figure out, okay, so what is exactly, what am I gonna do? And so I ended up doing a couple of internships, you know; with the D plan, you do sort of this wacky structure. So I landed up doing two back to back internships. The first was with a consulting company Price Waterhouse at the time. And it was out in Florida, Tampa, Florida, of all places. And in spring it was super hot. And then I did an internship at Microsoft at that time. I remember my interview for Microsoft on campus. It was a Dartmouth alum that they came onto campus to, to talk to folks and, and he said, well, what do you wanna do? We have this, you know, software engineer, which we all understand you know, write code. And I'm very familiar with that. Or there's this other role called program manager. So sounded like a very lofty title for somebody who had never worked. , you know, I'm like
LJR: Yeah 20-year-old
KP: I’m gonna be a manager. He's like, no, no, no, it's not that kind of manager. It's a little bit different. And I'm like, so what is that? He's like, I mean, it's kind of hard to comp explain. It's like you do a bunch of things. You just make sure the right things happen in. And I'm like, okay, what do you think? What should I he's like, give it a go, just do the internship and then, and then see how you feel. So I did that program manager internship, and it was not something that anyone in the industry had at the time that kind of function didn't really exist. And it was a pretty cool experience. So when I came back for senior year, I was in the throes of trying to figure out, okay, what do I do now? I had this really fun experience doing this hard-to-explain program manager role in this technology company, which by the way was Microsoft, which, you know, at the time, Dartmouth was not exactly a Microsoft friendly, you know, university. We were very Mac oriented. And those were the heyday of Apple and Microsoft and, you know, Steve Jobs and Bill Gates. And it, it was, it was really interesting to, to say, even that I worked at Microsoft, you know, in the computer science, I mean, people kind of joked and it was fine.
But I also then got sucked into thinking about, you know, sort of at the more typical Dartmouth tracks, which are consulting and investment banking. And, and so I started going down that path to and exploring what would it mean if I pursued any of those. So I was a bit confused to be honest, my senior year, I was like, what do I actually do? Should I go back to this thing that feels really good. And I enjoyed it or should I do what most of my friends are doing, which is this, you know, frantic kind of interviewing process. You know, it's a bit chaotic. I was, I was flying to New York and Boston and they're putting me in like hotels and you know.
LJR: And how do you enjoyed your price Waterhouse experience of kind of that consulting world?
KP: Yeah. That, that was kind of a boondoggle internship to it. oh, okay. Okay. In terms I didn't realize it at the time. I mean, I shouldn't say that. I did learn a few things, but it didn't really give me a sense of consulting. Anything. It was actually their training center for consultants. So I just did a bunch of Excel work and I hope I added some value, but I don't know. I didn't really come out with like, oh, I understand what consulting is.
LJR: I see. So that was a really kind of a point where you're like, I don't know. I like this thing that no one else seems to be valuing around here, but then there's this way that, you know, we are seen to be successful in going down this frantic consulting thing. So how did you choose?
KP: Well, first of all, I did a bunch of these interviews with consulting firms and banks. I was a little bit of fish outta water, to be honest. I was doing these interviews. And, you know, I was trying to mold. One of the things that I think I'm good at is, is adjusting. So people that talk to me go, are you from India, really? Like you grew up…I don't sound…you don't sound Indian. I'm like, well, I don't know. I just picked up. This is just how I talk. I didn't really think about it, but I just kind of adapt. And so I was quickly trying to adapt and, and sort of fit the mold of you. Wearing suits and doing like things that I usually hadn’t done. So it was both ways. I think I was struggling. I was doing a lot of first round interviews and even subsequent rounds, but I wasn't actually lending offers. And I couldn't figure out exactly why. And at the same time, I wasn't like enjoying the experience. It was like a little awkward. So it was probably going both ways. They were like, I don't know about this guy. And, and I was like, I'm not so sure about, I don't really understand what I would be doing here and I don't know how to have fun. So I still had a bunch of interviews lined up, but at some point I said, you know what? This thing at Microsoft, it feels right. I have an offer. I'm just gonna take it. And I know it's going to Seattle, which , you know, puts, takes me away from every everyone else, pretty much for the most part. But I thought I'd give it a go.
LJR: And that turned out to be a good decision in hindsight, right?
KP: It was, yeah, I, yeah. You know, my, my plan trying to stick to the mold that Dartmouth had kind of trained me into was like, okay, I'm gonna do two years at Microsoft. And then I'm gonna business school. Because I can still do that, right? I just like my consulting friends and, you know, that seemed like the pattern. And so I went into Microsoft thinking two years, and then I'm going. You know, apply to some business schools and, and then I'll be back to whatever else the kind of the mainstream Dartmouth crowd was gonna do, which, you know, turns out there isn't really a path. But I thought there was some sort of road, I guess, that we all follow.
LJR: Magical road. Yeah. Yeah. But your magical road kept you at Microsoft and in Seattle for 20-something years, right?
KP: It did. Yeah. So my first stint at Microsoft was actually almost exactly 20 years. Moved there in 96 and I was there till 2016. I never imagined I would stick around in Microsoft. At that time, you know, two years felt like a big, like long time, you know. Four years of college felt like a long time. Two years at work felt like a long time. So I'm actually my mind blows every time I'm thinking about. The idea that I would work in a company for 20 years, but it was actually pretty amazing just because Microsoft went through so much. From sort of the early days. I remember when I was an intern, I was there for the windows 95 launch party. [LJR: Wow.] Which was pretty wild. I wasn't working on windows, but you know, there was a big party going on and it was, it was weird traditions. People being tossed into fountains. And, you know, there's this thing called Lake Bill where people got dropped into and, and Bill gates at the time, still a smallish company. I remember when I was an intern, he did this thing where he invited all the interns to his backyard for barbecue. And we'd all like walk around the lawns sort of chatting with Bill , which kind of you know, think about it now. But, and then there's all this kind of growth. And then the antitrust stuff hit and you know, it was a slog for a while, but at the same time, there's always this kind of like, we, we can fix this. We're gonna go figure this out. I do think it was a very rewarding experience being there for 20 years.
LJR: Yeah. And I'm sure. And kind of having that first experience be this hard-to-explain program manager role that just needed to make sure everything worked right, you got to see from a, like somewhat different lens into kind of the scope of everything that was happening at the company. And then in that longevity period, like to be able to see longitudinally how things were changing, that it definitely doesn't sound like a boring 20 year period. But…you had an opportunity to say maybe it's time to do something different. So tell us about this really exciting moment.
KP: Yeah, it was, it was one of those things, you know, if I were to think back of how it came together…first of all, you know, once I got past the 10-year mark, I was thinking, okay, I might just gonna live in Seattle and what else am I gonna do? And at that time, Microsoft didn't really have international kind of opportunities, not in my field. We were very kind of Redman-centric. So I would have to leave the company, which I wasn't really keen on at the time.
LJR: And at this point, what's going on in your like family life, world?
KP: Right. So I, I met my wife now. We met in 1998 and then…she was in Utah. She was going to university there. I met her because…so when I was a bachelor, we got, we were four or us four guys. We got like a house and he happened to have studied at BYU. He was not Mormon, but he just happened to go there. So the interesting thing was all the non-Mormons formed a very tight knit group. [LJR: Ah] And so when he came to Microsoft, we were roomies and he was like, Hey, why don't you come? And, you know, we're all doing this thing. We're gonna go offroading or whatever. I'm like, sure, I'll join. And, and that's where I met my wife who was going to University of Utah at the time. Anyway, we did the long distance thing. She moved to Seattle. We've been together. I guess it's been, you know, we'll we'll I guess be approaching well, I can't do my math now. It's over 20. So 22ish, 23 years. So we, and then we had two kids: the first, 2006, and then the second one in 2010. So all of this was happening that kind of kept me going as far as, you know, the first wave between when we were married—we didn't have kids for quite a while—we spent a lot of time traveling. We just, we had this thing going where we never wanted to visit the same country. Soo pretty much every visit would be a new country, a new continent sometimes. And, and I was very fortunate that my job allowed me to do that. It wasn't work, travel. It was like literally, you know, us vacationing, which is phenomenal. And we had this thing up until, up until the pandemic hit, where I was trying to keep the number of countries to be equal to or more than my age.
LJR: Oh, there you go.
Okay. So I was, I was there and then it kind of got stuck at 44. I gotta work on getting, kinda building on that, but we traveled a lot and then we had our kids and we continued to travel with our kids. They loved trips and doing all this stuff. But one of the things for me personally—so even though I grew up in Bangalore, I was really fortunate that I got to do kindergarten and first grade in Germany and seventh grade in the U.S. So my dad he's a professor or he was teaching and he was a visiting scientist. He got to do these things. So that kind of gave me, it was a big part of who I became and this whole idea of living in a different country, going to school in a, I mean, imagine this Indian kid being dropped into a little village in Germany in kindergarten, first grade. Everyone spoke German. I had no idea what was going on, but you know, within a month I was speaking German. [LJR: Yeah.] And, and my mom says that I spoke like a German kid. If you talk to me on the phone, you would think I'd be German. That's a whole other story. I came back to do an LSA in Dartmouth. And I thought, I thought I would have, you know, it'd all come back, but it, it did not right.
LJR: Not so much
KP: Not so much. Still great experience. I loved my LSA. So this was all happening. And I told myself, geez, my kids are growing up and they've never lived elsewhere. I had this opportunity. I think it'd be really good if they got to do something different as well. That was sort of sitting in the back of my mind, but I just didn't know how to, to go about it. And then I got pinked by this company in Australia called Atlassian, which is, you know, really phenomenal story. These two Aussies, you know, taking a $10,000 credit card loan to start a company because they didn't want a real job. And, and they created this company and you know, in a country that really is not known for like tech or startups. That company pinged me once. And at that time, my mind just couldn't make the connections. I was like, this is complicated. I mean, Australia, like, I don't know what, how to even think about it.
But then we made a trip to New Zealand, a vacation. We went to New Zealand for two weeks and we came back and Atlassian pinged me again for a different role. And suddenly, like everything started clicking. I'm like, wait a minute. We just came back. New Zealand was amazing. We know Australia and Sydney may not be New Zealand, but you know, you kind of get the feel of it. And so I kind of said, why not? Like, let me talk to the, you know, and then, so I started having the conversations and it was a great opportunity at a phenomenal company. It aligned very much with who I was, the kinds of things I was passionate about. And it gave us as a family, an opportunity to just pack our bags and leave.
And, you know, it was a bit scary. I'll be honest. Like I was okay with it because I was used to kind of this whole idea of studying in a different country and living elsewhere, but truth be told my wife was quite uncomfortable. She's like, what if, what happens? I mean, what if it doesn't work? And what if you don't like it?
I'm like, look, here's the deal: Two years. We'll go. We'll spend two years. We're not like making life decisions, permanent decisions.
LJR: But she knows your two years turns into 20 years.
KP: It could.
LJR: So I dunno.
KP: It could, it could, but that was the deal I made. I'm like we'll, I promise at the end of two years, if we want to come back, we can. I didn't know how, but you know, there was…
LJR: Yeah. Okay. So this, that story that you tell about how it makes sense, and it makes sense in kind of your thoughts about what your family life would be like and what you afford to your children to experience. But let me just take it from, I don't know, maybe your parents' perspective, or other people's perspective where they're like, yeah, so you're leaving this blue chip, ridiculously stable, amazingly successful company, a role that has morphed over a 20 year career there, not just a job, and you're leaving it for virtually a startup on the other side of the world. How does that part play into your thinking? Is it just like great. I've had that run and now I wanna try something exciting and different? Or is there, was there another kind of story you could drill down on that?
KP: Yeah, I think, you know, I will say Atlassian….They were a little bit past the startup at the point that I made this shift. [LJR: Okay.] There, it was six months since they'd gone IPO. They were still very much growing as they were still a very small company, but they were established, ike they were well known. Yeah. If you're a software team, then you use JIRA, you use Confluence. It's like Google for search. So they were very strong in some areas. So it wasn't like I was taking this crazy risk from a professional career. I mean, there was a risk because I had kind of established myself at Microsoft and I was leaving something that felt obviously very known quantity to, you know, halfway around the globe company that, I mean, I felt it felt right.
LJR: Yeah. Yeah.
KP: It, it really did. Like when I talked to throughout my conversations, that was the thing, it just clicked right away. Like from the very first conversation that I had, I met the CEO, one of the CEOs anyway, and every single conversation just confirmed that their values were so aligned. So I just felt. You know what, and they were very generous in the way they structured their, they said, look, we know you don't know if you wanna permanently move, but if, if you choose to, you will be happy to kind of figure it out after that point. But if you, after two years, if you feel like you need to come back, then we'll see. We're not gonna hold it against you. So it was, it was kind of a, I, and maybe I sold this a little bit as well to my wife. I'm like, look, it's gonna be okay. We're in software. There's plenty of technology jobs. And if after a couple years in Sydney, you know, we want to come back, there's gotta be a job somewhere. We we'll find something in Seattle. It's not going away.
LJR: Yeah. That's right. That's right. So you were able to put your kids in this new experience, your younger one, probably about the same age that you were when you were in Germany, right?
KP: Yes. Yeah. That's right.
LJR: And so how did it work out? Did it kind of align with your hopes and dreams for that?
KP: Yeah, it did. I think it. Flew away all our expectations. As far as the kids go, they absolutely loved it. I mean, I think we got very lucky in terms of the timing. So it wasn't disruptive to their education. Not too disruptive anyway, both for the younger one and the older one. And I was the younger one, you know, it's starting to fade a little bit, but she remembers. She remembers quite a bit. I think with all the social tools that we have, it's easier to stay connected and remember things. So she actually remembers. The older one remembers very well. In fact, I was talking to her the other day and she still says that that is her favorite experience from a school perspective throughout, like, she, she loves it so much. In fact, they joke that they're gonna, you know, once they graduate and they want to go live there. But it was, it was phenomenal for them. It was a great experience. I would say for, for me, I loved the opportunity, the, the excitement, the learning of being a small company, I mean, Sydney and you know, it's like one of those things that somebody told me, you know, 20 years at Microsoft is a long time, but it didn't feel like 20 years for some reason. It just kind of flew by. And part of it was because things weren't changing as much, but. This little hack, somebody shared. This was like, if you want time to slow down—obviously time doesn't really slow down—but if you want it to feel like it's slowing down, change things up, you'll remember things a lot more vividly. And I think that was very true for us. I remember like the, that two and a half year period in Sydney, a lot more than I remember say 10 years in Seattle because the 10 years in Seattle felt like, you know, routine, same thing.
LJR: One big year. Yeah. Yeah, exactly. So what happens at the end of two years?
KP: Well, at the end of two years, we had to make some big decisions, mostly forced I guess by our older one and then the second, the younger one too. Because the older one was gonna enter high school in Australia. So Australia, it goes January through December. So school year is a little bit different and then they basically have primary school, which ends in sixth grade. And then high school goes seventh through 12th. So she was gonna now enter seventh grade. So we had to kind of decide, okay, does she go to high school in which case we kind of have to commit a little bit in how many years that's like a five year period and then the younger one, it'll be her time. And so we're thinking about a decade now in Sydney. And I don't think we were ready for that big a change. I mean, we liked it. But I mean, we didn't like it, we loved our time in Sydney, but Seattle still felt like home to us. So we actually came back and I was very fortunate that Microsoft was willing to take me back after I left. They're like, okay, why don't you come back and, and share some of your experiences and help us continue to grow, I guess.
LJR: That's great. Yeah. And sometimes two years is 20 and sometimes two years is two. And you kind of know when it feels right, right?
KP: Yeah. Yeah. I think you just go with your gut and I guess the one thing that I've learned is, at least so far, things work their way out. There's no wrong choice. I'm sure if I'd done the opposite, something else would've worked out just fine, but you know, honestly, like everything that..Things feel a lot more, it felt like a bigger deal at the moment then when you zoom out and think back, you're like, oh yeah, that, that didn't feel like that big a deal. It worked itself out, you know?
LJR: Exactly. And I would sometimes ask people to think back to their 20 something year old self. And, but you kind of told me at that point, you were still so interested in just exploring everything that, that feels like a pretty good and authentic outcome for your life, but is there any piece of the way your life has turned out that that young person would've said, wow, I didn't see that coming?
KP: Well for sure. I think that 20 years at Microsoft, I don't think I would've seen that one coming at all. I would've been shocked if somebody told me that. But I think that the parts that I didn't realize, so the amount that we got to travel, I wasn't imagining out of travel to 44 countries that kind of picked up from, I think, a passion for my wife, to be honest, she had the travel bug and I kind of picked it up from her. I don't think I would've expected that. The other thing that I ended up doing at Microsoft in my first five to 10 years, which I had never dreamt was playing a lot of cricket, [LJR: Ah] which is kind of a crazy story because, you know, you grow up in India and it's a cricket, crazy country, but I had never really played much cricket. I was too busy studying. It wasn't a luxury I had to go and, and play cricket and then see what happens with my, with the rest of my life. So I kind of focused on studies, but then when I came to Dartmouth, I actually ended up, you know, we got together a core group of people and we'd play cricket. We had a Dartmouth cricket team and we'd do little road trips to like Middlebury and Columbia and you know, different schools. And we, we, once we had to practice at Leverone in like the indoor [LJR: Really?] It's a little hit and miss, because we were playing with hard cricket ball and yeah, you didn't wanna break some lights or, or do anything crazy. We had nets and we figured it out. But, you know, I came to, to Microsoft and that was actually a thing that I got really into for the first 10 years. I actually helped create two cricket fields in this area., and we created a whole Northwest cricket league, which has blossomed into a full blown, like, I think there's like now major league cricket, like countrywide with Seattle having a team and there's like little kids coming through the pipeline, playing cricket, like it's, it's gone out of control. It's awesome. But, yeah. So I wouldn't have imagined that would've happened either.
LJR: Well, that one's a tough one to have prognosticated. But it sounds like you've had a full life regardless of what continent you've been on. And I just really thank you for kind of taking us through this story and we can't wait to see where your next adventure might take you.
LJR: Yeah. It's exciting. We'll kind of take it one day at a time, I guess. I guess for me, the biggest thing is whenever some opportunity comes knocking, I think, you know, I tell myself lean in and maybe say yes. Because it could open up some new doors and adventures.
LJR: I'm sure it will. Thanks so much.
KP: All right. Thanks, Leslie.
LJR: That was Keshav Puttaswamy, a near lifer at Microsoft. He spent the first 20 years there in product management leadership roles and currently leads the collaboration and workplace experiences there, helping to deliver transformational digital experiences for Microsoft employees that serve as a blueprint for customers’ own digital transformation journeys. During his family’s two years in Sydney he led the server and enterprise-focused data center products for Atlassian before boomeranging back to Seattle. In addition to the travel, Keshav also enjoys cricket, cooking, and cocktails.
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