The Hidden Cost of Leadership: Why Doing the Right Thing Still Hurts

Today's guest is Mahesh Guruswamy, the Chief Product and Technology Officer at Kickstarter and the author of a powerful new book called how to Deliver Bad News and Get Away with a Manager's Guide. And this is a no nonsense exploration of leadership, authenticity and mastering tough conversations. Mahesh's story is the definition of courage and perspective. He went from earning $40,000 a year in his first tech job to leading teams at one of the biggest companies in the world. And along the way, he learned that real success isn't just climbing higher. It's about gratitude, clarity, and making bold choices when fear tells you to play it safe. In this episode we talk about the mindset that drives great leaders, the immigrant experience that shaped him and his brilliant one way door versus two way door framework. A simple but game changing way to make better decisions in life and business. This conversation will remind you that growth doesn't always come from moving faster. Sometimes it comes from stepping back, taking a breath and rolling the dice on what truly matters. Let's jump in.

So I'm like 40 some years old and I came here as an immigrant and for the last 20 some years I've been in tech and this is the day to day workings of, you know, what you go through. You have all these problems, right? It's like this project is delayed. This conversation was not great. You know, this thing is like painful. But today I like went out for a run and I came back and I, and I told myself I'm like way too blessed to be able to do what I have to do, what I can do, be able to like live the life that I can live. And I think it's just like people should be more grateful for what they, what they have. And it's obviously there's a lot of like hard work like blood, sweat and tears, like associated with it, which, which I'm not a discount because I, because we did work really hard to get to where we are. But you know, just the fact that there is opportunity for me to be a better version of myself in this country, in this sort of segment that I'm in, is, is, is very fulfilling. Is, it's very like, that's where I derive my energy from. Like, yeah, anything is possible. Yes.

Oh, that's powerful. And when it comes to gratitude, I agree with you. I think it is, it's one of life's greatest joys just to be able to feel grateful. And a lot of times it's an issue of focus and perspective. There's always something that we have, even when things are tough that we can find some level of gratitude for, but we don't pay attention for it a lot of times because we're not looking for it or we have the wrong mindset. And is this something for you that you've always done or something that you're starting to come to a little bit more now?

Well, I think I've started to do more of it now because so I'm at Kickstarter. My wife is also in tech, she works at Pinterest. So both of us are very successful. And you know, like, we've been in this like last few weeks. We've been catching ourselves complaining a lot. So about like a lot, like work stuff or you know, this person is not great. Like this project is behind, you know, we're behind on revenue, whatever. And, and, and then, you know, we started talking about how things were before. So we were like, we're making. I was making. My first job was. Well, my very first job was at McDonald's. So let's exclude that. If I exclude that my first like professional job in tech was like $40,000 or something like that. And my wife was like similar and we were like very happy. And you know, we, we always imagined, okay, if we had, our goal was a hundred thousand dollars in like salary. We always imagined what our lives would be when we got to that number each. And then we realized, oh crap, like we were like way happier back then, then we are now. How is that possible? We have more money than we had like 20 years ago. But that's what I was like. You get caught up in the day to day, just the world is crazy. Tech is going through this big shift in the way it operates. I think tech is becoming more and more commoditized like the auto industry did 50, 60 years ago. So this is going through the same, same metamorphosis. We're getting older, so it's like pause and catch ourselves. Okay, what we have, we have to be grateful for it. Not everybody can do what we're able to do. So we just should be just happy with what we have. And so now whenever I get into those modes, I tell myself, life is great. We're just blessed and lucky to be able to do what we do and have what we have, which is, and you know, so it's, it's easy. Your mind loves negative conversations. It just loves it like misery loves company. So, you know, the minute you get into that mode, you just, the brain keeps feeding you negative energy and you just like get caught in a loop. And I tell myself and tell others who get caught into this loop is like, look at us people, right? Like, you know, we're in tech, we're making, like, good money, we're having good life. You know, health is good. There's literally nothing else we can ask for. So just be happy and move forward.

You're so right. And for me, the key thing that I'm hearing is that this is a choice. It's a choice and it takes effort as well, because there's so many forces working against us. First of which is our own psychology. We have a negativity bias. Bad things kill us faster. So evolutionarily speaking, it makes sense for us to dwell on the negative. But now we're at a point where we're doing well. And so my family is. I'm a first generation Caribbean American, so first generation born here. And I think back a lot of times when I'm searching for perspective because I can get really in the dumps a little bit too. And I think about a lot of its competitiveness, too. I'm like, I always want to push to do better. And I say, okay, well, I think about my ancestors. How would they, if they just looked at me, how would they say that I'm doing, going back far enough? You know, we, my ancestors are slaves. I think they'd be pretty happy about my position right now. And sometimes I say to myself, like, man, Kwame, you are insulting your ancestors by daring to feel like this is a hardship. What your experience. You missed a flight for a keynote. That is not a hardship. You know, and it's something for me, it's like I have to just figure out the right reference point in order to, to feel good. We can find a reference point to feel bad. It's like, we, oh, I'm doing well now. Well, you know, Steve Jobs, he, in terms of what he built, he's doing. He did better. Jeff Bezos, in terms of what he accumulated, in terms of wealth, he's doing better. But in terms of what I used to have with, with my wife, like our, our, our dates when we first got married, we would call them Kroger dates. It's like, what are we, what are we going to do today? We're going to buy eggs with. It is going to be amazing. And we loved it, right? And so if I just take, take a different reference point. If I say, okay, I'm not going to compare my wealth to the, like the tech billionaires, I'm going to compare my wealth to where I was coming out of grad school, now I feel good, you know?

That's right.

And so. But it takes a lot of effort now, which is so interesting.

That's right. That's right. I think, like, you also hit upon something very interesting that I've observed in the South Asian community, too, is South Asian immigrants are wired to be competitive, right? So we are all wired to be do the best we can. And I think it's like, even if we, you know, like, decide, like, oh, you want to take a step back, the ghosts of our ancestors will pop up top of our heads and go, wait, why are you slowing down? Like, you got to, like, speed up now, right? And I think that's something you have to, like, consciously teach yourselves that, okay, your lives are different than your ancestors. And then the other dynamic that we South Asians suffer from is we hate to spend money. We just don't like it. We like this, like, save, save, save. And my parents and my wife's parents, too, we asked them, like, why are you so saving now? The kids are all successful. They're fine. They're out of the house. What do you need this for? We can pass it down to you. And we were like, well, we don't really need it, so you can just spend it on whatever you want. And they're like, well, no, we'll just, like, save it. This is a luxury. Like, why do we want to spend it? So that's something. Also, we teach. I mean, I've been teaching ourselves. Is it's okay to pay for a maid. It's all right. You don't have to clean the house yourself. It's just fine. Reclaim your time, back a little bit. Do something else with it. But it is, to your point, it's a choice. You have to consciously make that choice. It is. It is so amazing. Not amazing. It's kind of sad for me to see all these, like, successful people so, you know, like, disappointed with life. It's like, how is that possible? It's just, you know, So I thought we'll be in a golden age where everybody's, like, happy and there's a disposable income everywhere. But it's. It's not always the case.

Well, you think about it, it's really interesting, like, because to your point, we have some people who are doing exceptionally well, who are emotionally and psychologically struggling, and there's such a discrepancy between what they, like their stat sheet says in terms of accomplishments and how they're actually feeling. And I remember One of the, one of the things just giving more historical context to, I was saying to myself, okay, imagine being the richest person in the world in the year 1900. Would you take that? Probably not. That's not a great, not a great existence. And I said to myself, man, with everything that I have right now, if I can't find a way to be happy, that's on me. Like, that's, that's my fault. Because it's either I'm happy now, or I have to accept the fact that there's no version of my, myself at any point in history that ever would have achieved happiness. And that's a scary, that's like, that's an unacceptable outcome.

Right?

And, but what's so funny, though, is that the, it's these competitive mindsets. Because I'm, I'm assuming our, our immigrant parents are very similar. Because I, I, I know it's like, okay, great, I didn't celebrate my undergrad degree because I, oh, he same.

Yeah, I didn't, we didn't. I didn't do the, I didn't do the ceremony. I was like, straight. I was on a flight to come to the States to get my master's degree. Like, I didn't even do the, Whatever the kids here do.

Exactly. It's like, Kobe Bryant, job not done. Why am I celebrating? Job's not done. And so it's. Sometimes you can, you can drive so hard in a career that you forget that celebration. Joy, like, that's, that has to be part of the game. And we, we almost struggle to give ourselves permission to enjoy parts of life. Like you said, like, we. Saving can have its place, and it does. But then there's also some joy in spending, donating, whatever it happens to be. That's right. But we. What do you think it is that holds us back from accepting happiness?

Sometimes I think the, for me, specifically, like, I can trace it back to kind of my South Asian lineage, right? Because my parents were, like, middle class. They were not, like, poor by any means, but they were, like, middle class, but their parents were poor. And we grew up not in, like, not in abundance.

Right.

So the vibe has always been you work hard, you study well, get a good job, and then save. Because there's not, you know, we don't have. Abundance is not a thing that we talk about. And my wife and I, we made it a point to live with a mindset of abundance, at least for our son, because we don't want him to get wired the way we are. But it's so this is the weird part. Like, I think some of it is like genetics. It gets passed down to your, to your kids. And my son is, you know, he is also like somewhat wired like us. He's very competitive and he does not, you know, he does not deal with losing the, that well, he was 11 years old. So at some point he'll learn how to deal with that. And then also like money, you know, it's also, he is very thoughtful. You know, obviously he'll like ask for money to spend on roblox or whatever 10 year old dude, right? But he's also like, okay, well this is, you know, way too expensive. Or if I like say stuff like, you know, I just like to mess with him, I'll say stuff like, you know what? I want to buy a G wagon. And he's like, why would you need that? Like, why do you need that? You know, you're not like, not like a rapper, like why do you need it? Right? So only not like a Russian gangster. You're like South Asian dad. Why do you need that? So he's already like wired like that. And you know, like what I, what we try to tell him is, hey, you know, find your own path. Find financial independence and you know, don't be afraid to like, you know, live life. Like I think money can not buy you happiness, but it can buy back time that you can use to do something else with it. So let's see what he does.

You bring up a really good point too. When it comes to the mindset of abundance, it's really, as parents, it's our responsibility to create these money mindsets in them when they're younger because if we don't, they'll just observe what we do. And a lot of times we don't like the parts of us that they observe. It's like, it's like, where'd you get that from?

From you.

It's like, oh, stop, don't look at me, don't look at me. Do that. You know, so we have to do it with intentionality, but it's also teaching them the balance. And, and one thing I started doing with my son is, is telling him a bit more about the business, but not just the wins, but also the things that don't go well, right? Because it's like, okay, hey, this did not go well. This deal didn't work out. As a result, we have to make this change or I have to be on the road a. Whatever it happens to be. But, but explaining him and explaining to him why you make These decisions because I don't want him to be afraid of these decisions. And of course I know I, I don't know about you, I'd be interested to hear your perspective on this. But the weight of decision making, the guilt and shame associated with certain decisions that you might have to make, just the, the heaviness of it, you might not even need to engage in a particular activity when it comes to executing upon the decision. But the ex. The decision be so exhausting sometimes when you're at upper levels of business. How for you, how have you managed that yourself and have you communicated any of that to your, your kids?

So for me, so there are few things in, in, in business itself, I, I categorize decisions into two buckets. One is, you know, is this a one way door or is this a two way door? So a one way door decision is you walk through the door, it's going to be very hard to walk back out because unwinding the decision is going to be expensive. Like you're changing the name of a company, or changing the brand of your company, or investing in a brand new team in a new geolocation or whatever. What I realize is most decisions in business and maybe in life are two way doors. You walk through it, things don't work out, you walk back out. And what I somebody asked me, this is my first time CTO at a company and I like to mess with people on my first day if people don't know me. So I run into them in the hallways and somebody will ask me, hey, what do you do? And I was like, oh, I'm in engineering. I said, which team? I do, I go everywhere, wherever I'm needed. And then specifically what is your job? And I said, I thought about it for a second. What does an executive do? And in the moment I gave him some non answer. But now I've come to the conclusion that the biggest job of an executive is to underwrite decisions. So whatever decisions your team is making, you underwrite that risk associated with that decision. And if it's a two way door decision, I just rolled the dice, right? It's okay, you know, it's fine, just roll the dice, see what happens. If you win, we win. Otherwise we learn and move on. But if it's a one way door decision, then I really pay attention to, okay, do we have all the facts, do we have all the data and can we confidently make the decision? And even in those moments, I would say if this fails, it's on me. So nobody feels pressured to own that Decision, because in the end, if my teammate made a call is my call in the end. But I think when it comes to my son, I encourage him to. I encourage him to, like, roll the dice, right? And see. See what. What. What comes out of it. He was very much against playing flag football because he's like, I'm not as fast as the other kids, and I'm not, like, strong. So. But the. But the school that he goes to encourages the kids to sort of cycle through all the major sports to see what sticks. And I was like, okay. I was like, okay, you're. First of all, he also does jiu jitsu, So I was like, okay. Clearly, he's not like, you're not strong, so you're strong. Maybe not fast, but not every. Not every wide receiver is the fastest, right? Everybody has, like, different. Different skills. So. So then he auditioned for it. Not auditioned, like, he tried. He went to the tryouts, and he had a lot of fun. So I was like, okay, see, you should try it out and, you know, see what happens. And then conversely, when he fails on something, then, as I said, he takes, like, failure really, really hard. And I think part of it is subconscious, like, pressure coming from me and the mom, right? Because he's looking at us and going like, this guy's executive. This mom is like, a really senior manager at a really big company. And. And so it's like, okay, you know, it's okay. You know, you tried and you didn't get what you wanted, and it's okay. You know, you learn from it, and then you move on. I. I keep pointing out to him that I was not a good student. So I was an average student growing up through and through. Like, through engineering, through my graduate degree. Mom is the opposite. Mom is, like, valedictorian through and through. So I was like, see, you know, I turned out okay, you know, so it's not like you have to, like, get. Have all the answers you had to win every, you know, every challenge. You just do your best, and whatever happens, happens. So. Yes.

And first of all, it seems like we're married to the same person, because the same thing with Whitney. She's not in tech. She's a doctor, but she was. I asked her this question a couple of weeks ago. I was like, whitney, was there ever a time where you, like, between K through 12, where you weren't first in the class? She's like, oh, my gosh. No, there was never a time. I was like. And I was just trying to get by, man.

Same, same.

I Love this roll the dice mentality though, because one of the things that I want to encourage people to do is to make decisions, but also take bigger. My. My mentality is take big swings. Because I realize that for me, when it comes to the success that I've had in my life, a lot of times it came about from me taking a big swing, where if you have the mindset and the mindset and skill set to hit it out of the park, then the only thing that's holding you back is your willingness to take a big, you know, and.

Exactly. 100%. 100%. Like, when I was at Amazon, I was in the Alexa division and Alexa was on fire. It was. Everybody loved the device. I mean, it's kind of sad what has happened to it since then, but, but, but back then it was on fire. We were like firing on all cylinders. I was in a really good team, running one of the most critical teams in Alexa. And I decided to leave Alexa to go work for Smartsheet, which was, which is a sort of project management company. But the opportunity there was to go run, build and run a site from scratch. They're like, we want to expand in Boston. You'll be hired number one. You go build that Boston site for us. So when I decided I'm going to leave like Alexa and go to go to Smartsheet, my boss back then was, why would you leave such a, such a cushy. Not cushy. Amazon is not cushy at all. But why would you leave such a good job? You know, this is. You can like really accelerate your career here. And I told him that, yeah, I can stay here for the next 10 years and get to VP or whatever, but I got like, I got places to be again. I don't have. The only currency we have in life is time. So I just want to be like, very careful about where I want to invest my time in. And Smartsheet ended up going public right after I joined. And so I jumped from. I was hired as a director. By the time I was done in three years, I was a vp. And that opened doors to my first CTO job. So I tell, like sort of mid level careers professionals and even like early career professionals just take chances, right? You never know where you're going to go. You don't have to be like married to the job, you know, it's just fine. Just roll the dice.

I agree 100% and because I know you've probably had to fight those inner demons when you were rolling the dice in this way. And you've probably seen some incredibly cap friends stay stuck with the golden handcuffs and not take the risk. What is it that you think holds people back the most from. From taking these big swings?

Well, I think it's the. It's a fear of the unknown. And maybe you can relate to this better than anybody else. The. It is hard to give up a W2. Very hard. Right. So when I started my executive coaching business, and maybe at some point I'll like, stop doing corporate jobs and just go do that full time. But. But I, in my mind, I was doing the math of, okay, how much do I need to, like, pull out of this, you know, my own business to, like, pay for all the bills? All the. It's like, it's tough. It's tough to make that, make that decision. So I guess my point is, like, people get used to a way of living and then they're like, okay, if I take a lateral job and there's like a dip in whatever my overall cash flow, then it's going to be tough for me. I've taken jobs just to pursue either a role or an. Or a learning opportunity. And I gave up on 401k, for example. So the company didn't have 401k when I joined, and I still didn't have when I left, but it helped me get my first engineering manager title. That opened up doors to other things that led to other opportunities done in the future. When I joined, when I came to the US I was on a, on a work visa. So now I'm a permanent resident. But I would, I would argue that my permanent residency was delayed by at least five years because I kept moving, moving jobs. And my parents would be like, hey, why are you moving? Because you should stay here and you get your green card and then, you know, you can do other things. And I was like, what other things? So I'm just like, trying to get to the other thing at my own pace. And now, you know, hindsight, they didn't know my equation well, so now they do. So. But I just want to tell people like you, you are in charge of your future. Like, you know, you can't rely on a company to like, decide that for you. You can rely on sort of external situations to kind of figure things out for you. And like, you know, if people get so frustrated when they don't get the promotion they wanted, and I was like, why don't you just leave? Go somewhere else, Right? But I could have worked so hard for this company. Yeah, I get it. But Whatever you learned in your experience, it's not going to go away when you go to a different company. So, you know, it's like just, just go explore, see what happens.

I agree. And I feel as though a lot of times we. There's a softening that comes with success where, where we say, okay, cool. We. I could hustle in my 20s, I could accept a tough situation when I'm in my 20s, but I'm not going back anymore. And sometimes they're acting like it's prison. I ain't going back, never again. It's like, hey, we're just saying downsize for a couple of years. It's not that bad. But it, it can be really scary when you put on those golden handcuffs and you've invested a lot. And I mean, we could use fancy psychological terms and it's sunk, cost, fall.

That's right.

And the fear of change, all of these things. But really it comes down to being human and then recognizing that sometimes we have to find ways to overcome that in that, that base level psychology to take risks, to become the fully actualized version of ourselves. Because one of the things that seems to be shining through in what you do is that. And tell me if I'm off, but it seems like authenticity and curiosity are important to you, and so you want to do things your way, but also figure out what else could be out there, what skills could be acquired, but what other experiences could be acquired. And you don't want to limit yourself.

Yeah, 100%. Like, I think Carl Sagan said this, right? Like, we are all made of star stuff. So if I think about the chances of humanity springing up on this blue rock, it's like, how rare is that event? And I've been given the opportunity to, to be on this planet with, you know, with like, with skills to go make things happen. So my goal in life is to make a dent in the world that I'm here. Again, like, I'm not saying that, you know, I want to go build the next Amazon or whatever, but I don't want to quietly disappear. I just don't want to make. Stay at the same company, make enough money, retire and then go to the beach or whatever. Right? That's not my thing. So when I go, when I leave this plane of existence, I want people to say, ah, that dude, like, yeah, he did good. You know, he put in the effort. He changed lives as well as he could and he made things happen. So that's kind of my goal, and I tell people this too, is you Know it's you, you know, like the. Even though, like there are like whatever 8,9 billion people on the planet, but the chances of us like existing in the same time is just. The odds of that happening are astronomical. So we should all make the best of the limited time we have on this planet. And then the last thing I'll add is the one thing that I didn't mention when I was talking about, like, taking risks is always live beneath your means. So that has, that has kind of helped me and my wife kind of navigate these ups and downs because we never upgraded our lifestyle based on how much we make, you know, now, yes, be comfortable. But, you know, you don't need that million dollar house when your household income is $200,000. Right. So you just have to like, make those choices so you don't feel hamstrung when you know you, you can't take a risk because your financial situation doesn't, doesn't afford you to do that.

Oh, this is good. There's so much to explore here too, because you're. It sounds like your mentality around how you live, living beneath your means, that probably is a good, a really strong foundation for you when you are rolling the dice because you.

100%.

Yeah. Dig into that because I feel like that is one of the things that holds people back a lot.

So I'll give a. Again, like, my wife is the smarter one in the family. So I remember this incident. This is when I made VP at Smartsheet and I think I got a bon. I got a good bonus that year. Sounds like, you know, I really like to buy a new car. And, and I was like, I like the, you know, I like this like, Porsche 911. And I was like, okay, I want to go put this bonus as a down payment for that car. And my wife is like, she mentioned that back then, and to this day she mentions it consistently is if you want to invest disposable income in anything, invest in yourself. So. And then I was like, really upset that you blocked that purchase. But I think in the end it was a good call because I brought it up again when I, when I was about. I was getting ready to publish my book. So then I was like, I want to spend money on marketing this thing. And my wife is like, yeah, go for it. This is probably the same amount of dollars I would have spent on like the down payment on that expensive card which would have depreciated in the last, whatever, six years or so. Right? And she was like, yeah, you know, you Want to spend these dollars on, you know, finding a good editor, copy copywriter, or like marketing it, go for it, because you're investing in yourself and it's going to create doors for you that don't exist right now. And that's what I tell people is, you know, live beneath your means. And, you know, you don't have to, you don't get carried away with the, with the way the world around you shows up. Right. I tell people, you know, actors and actresses wearing expensive watches, you know what, there's like, brand placements. They're not like, really owning those. Sometimes they do, but. But a fancy watch or a fancy car is not going to make you look better or be better in any measurable sense of that word. Right. So invest in yourself, meaning learn new things, explore new professions, and you have start a side hustle or start a side gig. And that will open doors that a car wouldn't. Right. And that's kind of my philosophy for the longest, and it'll continue to be my philosophy, too.

I love this. And you have a good wife, as a very good wife. And I think also too, there's, there's power in partnership, finding 100%, finding the right partner can really make, or I was going to say break a career. I mean, a life really, that's, that's key. And let's talk about the book. Because when it comes to rolling the dice, the. When it comes to your resume using air quotes here, you know, you're beyond resumes at this point, but when it comes to your accolades, you didn't need to write a book, but you, you, you did. What really drove you to, to take that step?

So the whole process started about 10 years ago. I'm a, I'm an introvert by nature. And back then I would shy away from conflicts and I would shy away from tough conversations. I was like a people pleaser. I think I still am to a certain extent. And when I would have to tackle a tough situation at work, I would go home and process it by writing it down. So I would write in my journal and go, crap. I had to deal with this. And it was not a good conversation. And this is how I would have done it better next time around. So those little notes for myself eventually became essays that I wrote for my team. So I started sharing it with my managers who report to me. And so, okay, here's how you diffuse a stakeholder, tough stakeholder conversation. Here's how you diffuse a customer conversation. And then when I look back two years ago, there was enough for a book and I always wanted to write one because I do like writing and I write quite a bit just for, just for fun too. So I was like, okay, is it crazy to think that I can like write a book? So I started like shopping it around and see if, if people would be interested in publishing it. I ended up not taking the traditional publishing route because that felt like a black hole of bureaucracy and giving up your rights. So I went with a hybrid publisher where I get like retained my, my rights to the book, but I end up like paying for certain things like marketing and whatnot. So. And then when I, before I actually closed the deal with the, with the publisher, I sent like copies of the just a PDF to a few friends and few colleagues and say, what do you think about this? Would you buy this book? And everybody is like, yeah, this is the stuff that nobody talks about. And the way I written it is also fairly casual and somewhat self deprecating. And so I was like, okay, it's not a stuffy business book. It's a fun, engaging, conversational book. It'll be easy for anybody to read. And yeah, after like all signs pointed to okay, there's a need for this book, I was like, okay, I'm gonna pull the trigger and get this book out. And again, my goal was not to make money out of this book because if anybody knows publishing in any even a little bit, everybody knows you don't make money out of selling books unless you are like Stephen King or whatever. But, but it does open other doors. Right. So my executive coaching business, that took off because to your point that the book becomes my calling card, my resume, people Google me, the book shows up, it's like, oh, this guy knows what he's talking about. That became the, that became a conversation starter and that started sort of helped me just like formally start my side business. And it all kind of the talks that I gave about this book in like universities and in, in companies, the feedback is always very positive. So I was like, okay, it's not, it's not a terrible. There's, there's one three star review and I don't want, I don't want to go find that person. I'm curious, like what did you not find good about the book? I'm not like to get them to turn their review, but I'm curious on what they didn't like because everything else is like a five star review.

That's good.

That's kind of the backstory.

Yeah, listen, you are officially an author because you Know all your reviews, you ignore the five stars. It's like, who. Who are you, sir? What was that? Yes, I feel you. And I love this. And did the. The content is. It's so important. The topic is so important. And if you were to go back, let's say, to the earliest parts of your career, let's say going back to your time at Amazon, if you could have given yourself this book at that stage in your career, what do you think would have changed?

The single biggest thing that would have changed is I wouldn't delay tough conversations. So there's a part of my brain that goes, you have to have this tough conversation with this person. But today is like a Friday, tomorrow's a Saturday, is a weekend just to have the conversation on Monday. But now I know that the longer you sit on it, the harder it'll become for you to deliver that message. And over time, the content also dissipates from your brain. Right. So now I don't, like, delay conflicts. Not that I relish, like, dealing with conflict, but it's like, okay, I have to deal with this. I'm going to deal it today. Deal with it today. Like, I'm not going to delay it. Like, that is the biggest thing that I would have learned if I, like, I read my book from, like, six years later.

Yep. Oh, that's powerful. And I agree. It's for so many reasons. I think fear feeds on time. So the more you wait, the scarier the conversation becomes. And then the. Also the more awkward it becomes because the person will most likely say, why didn't you bring this up weeks ago when it was actually relevant? And when it comes to this, because this is something we can. We can understand on a cognitive, intellectual level. We can say, okay, I can see how putting time between this makes it more difficult for me to perform, even just from a memory perspective. Like you said, we will start to forget important details, but emotionally, our emotions can understand all of that and then just say, you know what? Still, I feel scared, so I'm not going to do it. So what was it for you that allowed yourself to not just accept the intellectual reality that we should have the conversations, but overcome it emotionally so you can actually do it?

There was this. There's this moment in time. This is back at Smartsheet, where I think I learned a lot of these tough lessons of leadership. Back at Smartsheet, I had to let go of a really senior person who reported to me, and everybody loved them. I love them, too. But there's always you kind of mature out of the company at some point. So I had to, like, let them go. And the week later, week after, I was talking to my CEO back then, and I was like, mark, this is. He was asking me, how do you feel about it? And I was like, this is very tough. You know, they were a really good employee, really good leader, but it was the right move. But it was emotionally very tough. So Mark said, this is the cost of leadership. And if you don't feel bad after these conversations, and if you don't feel like part of your soul has died, something is wrong with you. So it's okay to feel bad. It's okay to feel like a normal person. You don't have to convince yourself that you're some sort of sociopath who relishes, you know, dishing out, like, tough feedback to people. And that changed the perspective for me because I. Then I went, okay, I have to do the right thing for the business, which is having this conversation. But it's okay to feel bad. It's okay to feel bad about the human cost of your decisions. And as long as the decision was fair and just and for the done for the right reasons for the company and for the team, I'm okay with that.

Yeah. Oh, that's powerful. I think that's something that people really struggle with. Just the reality that all decisions, even good decisions, come with collateral damage. There's going to be some negative associated with the positivity of the decision or the rightness of the decision. And I think it's really. It's really empowering to just recognize that you feeling that weight is not an indication of the fact that you're not ready for leadership. It's an indication that you have still been able to retain your humanity as a leader, which is even more impressive. That's right, because that can be. It can be really heavy. Really heavy. I remember every time I had to let somebody go, I felt like I murdered somebody. I felt me too horrible. But I stand by the decisions. But it. It doesn't make it any easier to make those decisions.

That's right. Yeah.

Oh, this is great. And let me make sure I get Simone in here, because we're coming up on time. I got the time up in the right hand corner of my screen, so I can actually see it now. Simone, what are your thoughts? What's coming to mind?

This question is for both of you.

Because you've been in the same process.

I'm a newcomer.

So if you could.

Set, like, stages of an immigrant, how things start, how things Develop. And when you start feeling that this country is actually your, your country, I'll start. I think I, I kind of figured out the moment aligned in the States primarily because I'm from India. That's where I migrated from. And there's a lot of like, kind of social norms and kind of pressures that I didn't really identify with. Because you're, you're expected to, you know, follow a certain path, right? So if you're like South Asian kid, you're like engineer, doctor, whatever, like, that's your path, right? And America, for me, it's like, I can do whatever I want. I can be successful in whatever path I choose. And there's this country will, there's an opportunity for me to make it happen. And, and then the, there's. The other big cultural difference was, you know, back home, if somebody's older than you, you're expected to like, give them automatically, give them respect, right? And in America, it's not like that you give people respect when they earn it, which I really, really identified with because, you know, you're not automatically. I get to like, I have to like, listen to you because you're older than me. I listened to you because you have advice to give and that I respect you. But ultimately came down to. I immediately knew that this was the place for me because I felt strongly that I can create a path for myself here without needing outside help much.

And I'll put an asterisk here too, because I'm first generation American, so I had the privilege of being born here. So the transition wasn't as hard. But I remember for my parents, they were, they came from the Caribbean, so my dad's from Dominica, mom's from Guyana. And I think it was just the understanding the new world that they found themselves in, you know, because my mom, she was, her father was the first permanent secretary of Guyana, so senior statesman in the Guyanese government. And she went from that to Auburn, Alabama. So that I don't need to go into much detail about Guyana to Auburn, Alabama in the 70s, you know, that that wasn't an easy transition. And then the same with dad. He was in Georgia and he was brought over by missionaries actually. You know, so I think the transition for dad actually might have been easier simply because he didn't come from much. I think the transition from mom was harder because she came from privilege and then had to kind started in grad school in Auburn. And so there was, I think it was the, the transition from. They had different challenges in that regard and Then when they came together, dad was. Dad's a Surgeon, mom's a PhD in nutrition. It was finding a community that. Where they could, like, settle down, but they were never close to relatives. That was always a challenge too. But once they started to. To like, get root and got to stay in a place for an extended period of time, I think that was hu. Them because they were always bouncing around, like three or four years for school here, residency here, and that type of stuff. But once they were able to, like, settle down and get community roots, I think that's when they started to feel more American. Yeah, this was fun. This was a fun one.

I.

Because I wanted. I love the path we took because. And we still got to your book, man. We still got to the book. But it's so fascinating to see the commonality of, like, what the. The through line with everything that you did. Because there was so much intentionality. And I think from the outside looking at. If somebody just looks at where you. Where you went, what you did, people would say, what is this? There's so much movement and now a book and coaching. But then when you hear you. When we can hear you explain it, it makes so much sense because it's so you. It's so unapologetically authentic. And that's what is so. That. That's what resonates with me the most. That's. It's just so powerful, your willingness to. To step into your own authenticity and make these moves, even if people around you don't fully understand it.