Finding Mastery with Dr. Michael Gervais - Inside the Mind of a Modern Leader | Micsoroft CMO, Chris Capossela

Episode Date: November 3, 2021

This week’s conversation is with Chris Capossela, Microsoft’s chief marketing officer and executive vice president of worldwide consumer business.As the chief marketing officer, Chris runs marketing across both the consumer and commercial businesses, which includes marketing for all Microsoft services and products, business planning, brand, advertising, events, communications and research. As leader of the worldwide consumer business, Chris oversees the Consumer Channel Sales and Marketing team, Microsoft Advertising Sales and Microsoft Stores. These teams are responsible for driving revenue, growth and share across the consumer business.Chris joined Microsoft in 1991 as a marketing manager for the Windows Seminar Team. In his 30 years at Microsoft, Chris has held a variety of leadership positions and oversaw the creation of new business opportunities and consumer experiences, including the transition of Microsoft Office on-premises products to Office 365.This conversation is important.Chris is a model for the modern leader - he empowers his team and leads with empathy._________________Subscribe to our Youtube Channel for more powerful conversations at the intersection of high performance, leadership, and meaning: https://www.youtube.com/c/FindingMasteryGet exclusive discounts and support our amazing sponsors! Go to: https://findingmastery.com/sponsors/Subscribe to the Finding Mastery newsletter for weekly high performance insights: https://www.findingmastery.com/newsletter Download Dr. Mike's Morning Mindset Routine! https://www.findingmastery.com/morningmindsetFollow us on Instagram, LinkedIn, and X.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

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I'm Michael Gervais. And by trade and training, I'm a sport and performance psychologist. And I'm fortunate to work with some of the most extraordinary thinkers and doers across the planet. And the whole idea behind this podcast, behind these conversations is to learn from people. We want to pull back the curtain to explore how they've committed to mastering both their craft and their minds. Now, our minds, as you know, are our greatest asset. If you don't invest in that asset, the dividends are not what you hope they will be.

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Get a free variety pack, a $25 value and 10% off for life when you head to davidprotein.com slash finding mastery. That's David, D-A-V-I-D, protein, P-R-O-T-E-I-N.com slash Finding Mastery. Now, this week's conversation is with Chris Caposella. He is Microsoft's Chief Marketing Officer and Executive Vice President of Worldwide Consumer Business. So as the CMO, Chris runs marketing across both the consumer and the commercial businesses. This is a big job. And it includes marketing for all of Microsoft's services and products, business planning, brand, advertising, events, communications,

and research. And I don't know if you've heard me talk about the research department, but it is ridiculous what they've done. It is so inspiring, but that's for a later date. Anyway, so as a leader of the worldwide consumer business, he oversees the consumer channel sales and marketing team, and then Microsoft's advertising sales and Microsoft's stores. I mean, talk about a big job. I know I said that earlier, but it's just hard to even imagine how to really get your arms around what an important company Microsoft is to all of us and what it is that he's doing to try to tell those stories to market the company in the right

way, in an authentic way. These teams that he's leading are responsible for driving revenue growth and share across the consumer business. So Chris joined Microsoft in 1991 as a marketing manager for the Windows seminar team. In his 30 years at Microsoft, Chris has held a variety of leadership positions and oversaw the creation of new business opportunities and consumer experiences as well, including the one you're probably most familiar with, the transition of Microsoft Office, the on-premise product that they had,

the thing that you would load into your computer, and then all of those products into that migration over to Office 365. So for me, this conversation is really important. Chris is defining by modeling modern leadership. He's real. He puts others first. He's open. He's honest, empathetic, clear about who he is and what he values. And the way he works from the inside out, it is a natural accelerant to empowerment and autonomy and agency for those he works with.

And those are not light words that I'm mentioning. Helping people feel powerful, have a sense that they can decide how they can best serve their mission in their own life, mapped up against the mission of the company, and to have a sense of agency, which is like a sense of like, I can make a difference in my life. He is modeling and defining what a modern leader looks and feels like. And this conversation, I think, captures it beautifully. There's a really great moment in the conversation and you'll hear a barking dog in the background for a portion of the interview. And of course we could have paused and solved it, but instead we

get a glimpse into how he works from the inside out. Chris has both this unique and rare combination of high awareness and then a command of himself. He does not let the external world dictate his internal experience. Rather, he has clarity of his first principles, and then he has the psychological skills to stay close to them, even when it's challenging. And I think you're going to love this conversation. And hopefully it will be a sharp reminder to bring it in your life, as he likes to put it. So with that, let's jump right into this week's conversation with a true legend, Chris Caposella. Chris, how are you? I'm great. I'm really happy to be with you today. It's a real privilege.

Oh, thank you. And I feel the same way. And so I have really appreciated the way that you lead and the way that you hold an authentic space in how you do it. And so I'm excited to see where this conversation goes and just to get a little bit of the good stuff from Chris Kapp, which is just basically being fully you in conversations that are not necessarily easy. So thank you in advance. Yeah, my pleasure. My pleasure. Okay, so you grew up in the north end of Boston, and you're the son of a restaurant owner. Can you talk about how that has shaped your adult experiences and the 19 and 20, very young. We lived in the apartment on the top floor of the apartment building. And my grandparents, my father's parents, lived right below us. And then the restaurant was on the ground floor. And you come

home from school and you go into the restaurant, you know, you didn't, you didn't go up to the, to the apartment and you had your afterschool snack at the bar. And then you kind of hung out at the restaurant, you did your homework and you went to work to work obviously and so it was a very the restaurant was the center of the family and we all worked there cousins worked there uncles and aunts worked there it was very I guess classic Italian American small business sort of upbringing when I think back on things now it felt like my parents were a lot smarter than I knew. They made us do all the jobs at the restaurant. You know, we, you know, based on your age, you know, you did different things.

But I did everything from dishwasher to busboy to prep cook to inventory to bookkeeping, like literally sort of everything. And the restaurant was filled with people from all walks of life. A lot of people from Brazil and Portugal, believe it or not. A lot of people from Chile, obviously a lot of people from Italy. And so it was a very rich, sort of loving, very hardworking way to grow up. And, you know, you felt like you were part of something much bigger than you. You know, we're all working hard together. And I've had a weird career at Microsoft, where I've done tons of different jobs. And I often wonder if my dad and mom's design of moving us around, you know, from the kitchen to the front of the restaurant,

et cetera, prepped me for a career of weird multifaceted roles, you know, going from sales to operations, to engineering, to marketing. And so I think it, it prepared me for a lot of things that I didn't understand it was preparing me for um you know and that hard work ethic you know I growing up in a restaurant it's a tough tough business and so um I think of that the way I lead today is typically not with me in the forefront you know it's typically other people giving the stage to other people. The restaurant only works if everybody works together. There's a lot of stuff, Michael, that I think I learned in the restaurant without understanding I was learning. And so that I think

instilled in me a good set of values and a good understanding of it not being about me all the time. I mean, obviously I have incredible privilege in, you know, being at the top of a function at Microsoft. There's a lot of you, but compared to a lot of people I see every day, I think those are things that I thank my dad and my mom in ways that I didn't understand was happening to me when I was 10, you know, or seven or 12 or whatever it was. Needless to say, frugality, you know, understanding the value of money. It was just such a rich, such a rich way to grow up. I always used to be jealous of kids having sleepovers and families going on vacations and stuff. You know, the restaurant was open every day of the year except for two.

And, you know, you just didn't, that wasn't how we were brought up. And now, of course, I'm like, oh my God, how lucky, you know, how incredibly well they served me because of what they did to raise us. I mean, we weren't some perfect family, of course, but it was a gift I didn't understand. What was the name of the restaurant? My dad's name is Dom. So he called it Dom's Restaurant. And restaurants, you know, they come and go, you know, it is like you said, a really tough business. Is it still around? And if not, how many years did it last? Yeah, it had a 46-year run. Wow.

And eventually we sold it and it's closed soon after. But it was an amazing, you know, it's an amazing thing. And restaurants can be a fabric of the community. You know, they can be something that makes the neighborhood special. And so to see people come in on their, you know, get engaged at the restaurant or celebrate a birth or mourn a death or, you know, all those milestones, you get to know people through sort of their life. And it's, it was a powerful lesson in sort of local, you know, the power of local and the power of doing something that's not just about putting food on the table for your family, but there's also this larger thing that it does, you know, to form kind of the soul of, be part of the soul of the neighborhood or the community. That was good. Chris, my heart is pounding right now. That's good. Okay. And the reason being is because I know I'm a nerd, but I love, I recognize changes

internally for me because it's such a calibration moment. My heart's pounding because I'm going, oh, I get it. Like, because like I have watched how you work and you have an empathetic, authentic relationship based approach that is anchored in deep intelligence and competency. And so like it's, it is a, it is a remarkable blend that you have, but you don't lead with intelligence and scare people away. And you don't lead with empathy in a way that becomes soft. And so as you're describing your early experiences, I'm going, Oh my, so my heart's thumping because I'm like, Oh, this is so exciting. Like, okay. Relationships you just talked about, you talked about purpose bigger than you. So this is one of the anchors, as you know, that where empathy and purpose ladder together. And when you get those two, it's call it your adult assets, you know, from a leadership humanity standpoint, all in the, you know, formative years in this restaurant. Totally, completely.

Were your parents intentional? Like, did they say, okay, we're going to get Chris over in this part of the department or, you know, in that department and he's going to clean and he's going to do books and he's going to do greeting. And, or was it more like scrappy where it's like, Hey, we're short in the book department, Chris, you understand number. Yeah. Your math is pretty good. Hey, get over there and try to solve the books. Like were they intentional or was it more scrappy? I always thought it was scrappy. And certainly when the service starts in the night, it's, you know, it just becomes total scrappy. You know, you're just trying to, you're just trying to make the night work. But without a doubt now, I believe my dad in particular was very, was very intentional

about, hey, I want you to do the books now and you're going to learn what it looks like to balance a bank account and to write checks for food. And like, I definitely believe he had in his mind that this was his opportunity to give his children an education and do what he could to prepare us for whatever we wanted to do in, you know, in the rest of our lives. So what felt scrappy to me, I think was far more intentional on his part. And he made the restaurant just the center of our family, for good and for bad. But mostly, it was for good, because it was, you know, he was sort of giving us a life education, as was my mom, although in a much quieter, much quieter way. But he's a great, he's a great teacher.

You know, something as simple as you're 12 years old and you're going to wait on your first table, you know, a waiter at 12. And saying, hey, look, this table you're about to go to, you can tell these people are on their first date. Like, look at how nervous he is. And, you know, it's just the two of them. You figure out what they need from you. And that's very different than the party of six who's about to go to the Celtics game. And, you know, they're super psyched and they're all good buddies. And so, you know, your energy with these two tables is

going to be super different because you need to put these two people at ease you need to you know be calm and um and with these folks they want to have fun you know you can joke around with them and commits with them so that's sort of you know that's sort of really cool i don't know what you call it interpersonal reading people and understanding what they need from you so that they're going to have a good time and come back. Yeah, so there's EQ, emotional intelligence in there. There's social intelligence that you're reading a room. And sometimes, this is curious for me, sometimes when people are put into situations where they have to read and react well, and it's, you know, intentional and purposeful, and it requires you to do it to either survive the family dynamics or, or work well in a workplace. If we don't have the anchor

of, of our core principles in place, we find that we start to morph into what they want us to be. They meaning the six, you know, they're going to the Celtics game or, or the date, you know, the couple, like they want us to be a certain way. So I'm going to morph into it. And then if we're obtuse in the other direction where we're just like, no, I'm rigid. Like I'm just going to be me and missing kind of the eloquent dance of what the others are hoping for or asking for, it becomes problematic too. So I'm say all that because who, who are you? How do you, that is a big question, Chris, who are you? And I I'm hoping you'll go to like some core principles of what make you,

you. Yeah, that's a great, that's a great question. You you know growing up the way i grew up i think the notion of family comes first was was very strong and so i do think husband father son brother uh that that feels very much like it runs in my blood um you know you helped you helped the microsoft leadership team our ceo and historic reports with a lot of this you know why are you here what is your purpose and not as a leadership team. Like, Chris, what is your purpose? And how do you want to live every day of your life? And, you know, and I think about those things, obviously the purpose has to work for me, for how I behave as a family, with my family and friends, but it obviously also has to work for how I work with Satya and Amy Hood, our CFO, and Brad Smith, the president,

you know, all of the people. And so, you know, for me, I'm a balance of, I think, kind of weird contradictions. And our work has helped me understand that a big part of me is balance. You know, I try to sort of say, okay, every day I want to try to have the courage to put other people first. And I want to balance things that don't always go together. You know, I try to balance inspiration with accountability.

I try to balance thoughtfulness with joyfulness because often I can miss the joy in every day and I'm a little in my head a lot and it's like no no find the joy every and I would try to balance learning with performing because a lot of my life has been performing it's been you know deliver the specials to that tape you know 15 tables tonight and you know close the restaurant and do well in school and get a good job, like the pressure to perform, at least I've always felt it deeply. And learning, Satya has taught me, is actually more important. And so how do I balance my innate desire to perform and this need to feel like I'm performing with, no, what have you actually learned today? So, you know, those are some of the things I think of

when you say, who are you? And how I try to go to work, show up for my wife, show up for my brothers, et cetera, et cetera. It's sort of this balance of things that don't come naturally to me. Finding Mastery is brought to you by Momentus. When it comes to high performance, whether you're leading a team, raising a family, pushing physical limits, or simply trying to be better today than you were yesterday, what you put in your body matters. And that's why I trust Momentus. From the moment I sat down with Jeff Byers,

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Two questions. Okay. First question. How are you right now, real time managing the barking dog? And managing it by, you know, feeling like this conversation is supposed to be authentic to who I am. And right now, you know, my dog's going a little bit nuts and that's okay. You know, unless you want super high production value and then we'll go ahead and reshoot.

So is this a, is this a quick little conversation in your head where it's like, okay, I've got an external variable and then you're mapping it up against a first principle, which is authenticity. And you go, what am I supposed to do? You know, let me just keep being me. So is, so external world come like variables come in and then you map it up against the first principle. Totally.

Yeah, there you go. Listen, you don't need me to say this, but this is how I've come to learn that the most dynamically powerful, and rather than the external being the reason why we're going to contort into some sort of response. And so I thank you for just kind of shaping that. And then let's go back to the restaurant really quick. You're living above the restaurant, the whole DNA. I mean, the thing is, let's call it the dinner table or wherever the moments are that he invited these big ideas to you? Yeah, he was, he was, and he, I think he was very good at communicating that his job and my mom's job was to get us into a great high school. And then the rest was sort of up to us and he wanted us to go on to college, but he was really clear, like what's college starts, you know, you're sort of now it's up to you on to college, but he was really clear, like, once college starts, you know, you're sort of, now it's up to you, you know, you got to figure out what is going to come next for

you. But his focus was very strong on, you have to get a great education. My job is to set you up so when you apply to college, you have the best shot of getting in. And he was clear that after that, he was sort of done. And not that he wasn't going to love us and all those things. But like, you know, we were we had to grow up and figure out what we kind of wanted to do. And I think he tried a ton of things to figure out what could help and not knowing, you know, neither of them knew what the recipe was. He randomly read an article in the Boston Globe when I was 13, that was about this company across the river in Cambridge called Lotus 1-2, Lotus Corporation. And he read about this thing called Lotus 1-2-3 and thought, oh, you know, technology.

This is interesting. The next day, he went and bought an IBM PC, plugged it in at the restaurant and said, Chris, this is your thing that I want you to figure out how to use and apply. I don't know what the answer is. Apply it to the restaurant. And these spreadsheet things that we're going to buy Lotus 1-2-3 and you're going to start with that. And he enrolled me in a database programming class at a local computer reseller in Boston that of course doesn't exist anymore. And I started to learn how to program

databases, you know, create databases and write, you know, D base three plus this product that doesn't even exist. And I wrote a reservation system for Dom's to track how people were coming to the restaurant. And then a couple of other restaurants hired me to write it for their restaurant. And so like, he didn't know I was going to fall in love with computers, but he just read this article and thought, Hey, maybe we should try this thing. You know what I mean? He literally, I think was seeking education and trial and error for what his kids would latch on to. I don't know why he picked me instead of my older brother. You know, who knows? But that one happened to stick in a pretty huge way, as you know, as you can imagine.

Oh, my goodness. Like coming from living above a restaurant slash bar and then becoming one of the working as a leader in one of the most significant companies in the world and, you know, telling the story of that company and having your arms around the growth arc of it. Like it's remarkable. And so that there's the stitch like, oh, technology is an early bug. Like this is fascinating. And then there you have the duality between, like you talked about, like the range of experiences, the almost competing ideas, right? You've got family, empathy, connection, relationships, and then what some might consider the cold art of zeros and ones in tech. And so you've got that yin and yang that was familiar to you from an early age.

Yeah. No, I think that's exactly right. What did dad stand for? One word. Let's be a reductionist. Can we do it, Chris? Can we be a reductionist for a minute? Yeah.

What did he stand for? One word. God. Experimentation would almost be my word. Oh, my God. Experimentation would almost be my word. Oh my God. Okay. Because you tried all kinds of stuff. My mom, excellence, quality. Oh. Quality for sure. Listen, mom got you to Harvard. Let's not make anything up here. Okay. Mom got you to Harvard.

Okay. Are mom and dad still with you? Mom died three years ago. My dad's doing well. He's I I think, 79 or 80 living in Boston, close to where the restaurant was. Okay. Can I ask how mom passed? Yeah. She died of metastatic breast cancer. So she got breast cancer, beat it, you know, more than five years clear, et cetera. And then it came back.

How did you work through that loss? You said, did you say three or five years? She died three or four years ago. You're still in it probably. Oh, big time. Yeah. Big time. How did I work through it you know we were we had the benefit of knowing that this was

likely what she was going to die from and so myself and my two brothers uh were really able to come together and uh take care of her and be with her and um you, it allowed us to say goodbye to her over a longer period of time, and come to terms with all that she had meant to us. Because you're right, you know, I feel like she's the one who really was the force for choosing Microsoft, the force for aspiring for great education, excellence, not just like going to a great place, but soaking up everything it could, it could offer you. And she was the academic in the family, you know, she was the real insane achiever, but very quietly, you know, not, not, she didn't wear it on her, on her vest, so to speak. So I think think it the journey with my brothers was very powerful

uh to help her in the later stages of her life and it brought us even closer we're a very close family but it definitely brought us closer and I think one of the ways I'm dealing with it is through engagement with the two of them you know we live in they're both in Boston and New York and I'm over here in Seattle, but boy, I've never felt closer. We see each other a lot, et cetera, et cetera. And so that's probably the short answer I give. Chris, as you were explaining the relationship with your mom and the passing of your mom, did you feel, did you have emotions as you were just describing? Oh, of course. You know, you get that warmth. You have that warmth well up in you.

Absolutely. And how does that work for you? I'm asking somebody who is extraordinary in leading with empathy, which is really compassion for others. And then you had a moment of feeling flooded with emotion. Like, how did you process and work from the interior, from the inside out? You know, I think that for me, it feels very natural to have that happen in the middle of a podcast, in the middle of a work thing. It doesn't make me uncomfortable. It doesn't, my parents, we grew up in a very affectionate, highly physically affectionate environment. You know, when we would, brothers would fight,

my dad would make us kiss and make up. I want you to kiss your brother. My family, my mom's side is Geritana. And so the Italian side. And they were both very affectionate with us, particularly myana. And so the Italian side, okay. And they were both very affectionate with us, particularly my dad. And so, you know, emotion and affection is not something I've ever felt uncomfortable with, even at work, like even if an employee gets upset and cries, or if I feel the need to cry, I don't feel those, I don't see those as problems. I think because, you know, Italians, they, you know, they wear it on their sleeves, they feel it, they express it. And I feel very lucky that he, they both sort of

encouraged that affection, that expression of emotion is a better way to say it, I guess. So you had practice, and that practice showed up here. I want to know two things about it. What was the, what was the other thought? So you and I were having thought exchange, and then there was another thought about what you were feeling. And does that thought go to, I'll keep it together? Or does that thought go to, oh, this is interesting. I'm feeling, I wonder where this is going to take me.

Was it more curious or was it more, let's call it containing? Yeah. Yeah. Yeah. Not containing, but also not as sophisticated as curious. Almost familiar, you know. Oh, like there it is again. Yeah. Oh, there it is.

I feel it. Totally. Yeah. And I don't think it's going to overwhelm me. And so, okay, just let it run its course. Oh my gosh. So I wish I was, the curious is a great one. It is fun to get into that curious place.

Not there yet. I'm working on it. The familiarity is really nice. You know, like, oh, I know this. Yeah. Chris, that is the essence of the internal work, is to know, to inspect, maybe that's a dirty word but to really like know how your thoughts and emotions work together and this is where the practice of self-discovery

and mindfulness being one of those practices um pays dividends in moments like this where you're like oh there it is yeah love you mom okay yeah that's really cool. Okay. All right. So let's go to your two brothers really quickly. Reductionist model. It's amazing what a reductionist model will get us to sometimes, right? Forcing functions. So mom stood for excellence. Dad was experimentation. And your experimentation and your two brothers the oldest brother was uh is uh affection and joy um we'll go with affection incredibly affectionate loving person and the middle brother the one who's just two years older than me um intensity i'd say if i had to reduce it to a single word. Intensity. We got a mix now.

We got a mix. Okay. And then you, if we're a reductionist here? Yeah. Thoughtful, I guess. Thoughtfulness, quiet. Oh, you can't have two. Let's keep it with me.

How about thoughtful? The observer of the chaos in my family oh that is funny okay the youngest no one really pays attention you know you're just you're just kind of there you can just kind of yeah thoughtful so you're an introverted feeler oh big time and an introverted thinker as well yeah i think so okay and then it's part of why the restaurant i think was so good for me, because you have to be an extrovert. You have to present yourself to people.

You have to welcome them in. Thank you so much for coming. It's so great to have you. You have to connect, and it has to happen quick. So it was a great lesson in how to be able to do that, even if it was a little bit not where I live every day. So I'm fascinated by moments of transition and because they it's like there's micro choices that we make every day do I grab the apple or the apple pie so there's a little transition in my health there you know and I'm not saying that one apple pie is going to do anything but like if I

keep making that micro choice we're going to probably have some problems with some blood sugar levels. But I'm interested in transitions at a macro and smaller level. And so you made this transition from this tight knit Italian work ethic, you know, fun, intense, excellent, you know, experimentation type of family where you're all in to crossing town to go to a different world. Yeah. So how did that transition, was there any dark side or was it all upside? All is too big of a word. Like what was some of that transition stuff that we can learn from you that went from family to bigger pool? You know, the transition, excuse me, to sort of the college experience for me was

incredibly exciting and not, there wasn't a lot of darkness that I felt towards it. I think a fascinating transition for me, which was really hard, was, excuse me, I worked at the restaurant my first and second year in college. So two or three nights a week, I was leaving campus, you know, putting on the tuxedo and working at the restaurant. And it was in the summer after the second year when I had to tell my dad I didn't want to work at the restaurant anymore and I wanted to get jobs that would lead to my future job or you know give me new experiences and that for me was a huge transition more than going to college freshman year because I knew I was going to work at the restaurant Tuesday night. You know what I mean?

Friday night, I was leaving campus and I was going to go, you know, work at the restaurant, make my tip money and then go back to campus. And so really the key transition for me, I think that you're getting at maybe was when I had to say, you know, I went with a walk with my dad on a beach on a, you know, in Maine where we took a few days off. And, you know, I had to bring myself to tell him, I, I want to stop working at the place that has been your life's work. This is like a family divorce. Like, you know, that was a big transition for me. Once I got through it and I started getting jobs at school, it was glorious because it was, you know, just a brand new world. And I felt like I was

now a full-fledged college person, not going home and working a couple of days a week. This might seem like it's not directly related to our thought stream here, but did you ever struggle with imposter syndrome and or a fear of other people's opinions? Did you ever struggle with either of those in your life? Yes. But for me, it happened when I became more of an executive at Microsoft. That's what I was thinking. It didn't happen early. Like I was just gung-ho and so excited.

Like, yeah, let me at him. It was once I started getting, you know, recognized and promoted to like a corporate vice president, very, you know, whatever, 15 years into my career. So I've actually suffered from that more recently than I did in college or in high school or in my early days at Microsoft. And is that imposter syndrome or is that, you know, so is that what we're talking about here? I think so. It's, I don't think I'm good enough to be here. I don't think I, you know, I don't, I'm not at the quality of the people who are now my peers. You know what I mean? I don't think I'm going to cut it at this new, at this new level. I think that, I think of that as imposter syndrome. you know, you don't need me to say this to you, but welcome to the club. Welcome to the club and getting over your skis. And I think that the,

those that really want to explore their potential, like really work to the upper limits. This is part of it, you know, cause you go a little bit faster than you think you're capable of. And it's like, Oh my gosh, I'm a little, I'm right on the edge. And so, yeah. Okay. And then a double click on that's like, oh my gosh, I'm a little, I'm right on the edge. And so, yeah. Okay. And then double click on that. It's like, how do you work with that when it pops up? I don't have any brilliant, I don't have any brilliant insight other than to say, one of the things I've sort of told myself is,

hey, at this level, the expectations are really high. Lots of people fail. And the company tells them it's time for them to move on. That might happen to you. In fact, it's going to happen to you. It will happen to you. Because what is the end of anybody's career? You either choose or the company chooses. And so let's just pretend the company is choosing and it's going to happen someday. It to say, well, damn it. I am going to do everything

I can while I have the opportunity to use this platform, to be my best, to bring it for the company, to make Satya, you know, see that I can, I can kick butt on behalf of what he needs me to do. And so I think there's almost a, I know it will end. I know it will end. So what am I going to do in the meantime? Well, I'll tell you what I'm going to do. I'm going to make the most of it. You know, if it ends tomorrow, because I'm not as good as the person to my left or my right, it ends tomorrow. And in the meantime, I'm going to make today, I'm going to do everything I can to just get the most out of today. And that's been sort of a freeing recognition. Do you know what I mean? I am going to die. You know, I'm going to,

my career is going to die. My body is going to die. Like, okay, accept it, man. It's going to happen. Now what? And then now what? Then it's kind of like, oh, okay, well, I'm going to do this and I'm going to try this and I'm going to'm going to do this. And I'm going to try this. And I'm going to experiment with this radio show. And I'm going to, you know what I mean? And it's just like, let's go. Let's give it our best shot. And, you know, that's, I think that's been my single tool to think through, to get over it, you know, to push through it.

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And so you're going to create great freedom for others to say, I recognize me in that. I recognize the worry about how it's going to end, life and or business phase. And then, okay, this wonderful leader says, so I'm going to bring it. Okay. So some people say that and then anxiety drives them. And that becomes, it works for a little bit, a little bit anxiety for a little bit works fine, but it runs the tread off the tires quickly. And so how do you prepare to bring it?

And then what does bring it mean? And I'd love to hear you just talk for a moment about that. This is where my relationship with my boss is so helpful because I think great leaders are really clear on what they need from their people. And this is certainly true of my boss, Satya. He helps me think through what is the most important thing for me to put my energy behind and my, you know, try to innovate and try to be thoughtful and all those things because there's so many things we could work on and it is helpful, at least in business, there is a hierarchy, and there is somebody who can help me think through, at the end of the day, how do I help the company succeed? How do I is the absolute must have set of things that he needs from me.

And that guides me. That guides me to make the tradeoffs that I need to make. I feel like he's got my back, you know, if I'm doing X, Y and Z instead of A, B and C. I'd say that's probably the most helpful. I've got some amazing peers. One of the things I've learned that might be surprising to you is I've learned to really appreciate the superpowers of my peers that are Satya's direct reports and to get over their idiosyncrasies, you know, get over the goofy thing that this person does that might drive me a little. It's like, get over, you know, like move on. And so they give me a lot of guidance too, and a lot of support in, hey, I see you struggling with this here. Think about about this so i guess the short answer is the

people closest to me at work uh are really helpful in helping me navigate uh how to manage through it there in the is the value of spending meaningful time to build that relationship and yeah and not just up and down right a lot of people, it's easy to go up and it's easy to go down. I've been a slow learner, but the power of left and right is extraordinary. Okay. So I know that you wrote, it's a transition here about left and right, up and down. I know you wrote speeches for Bill Gates. What was that like? And I guess, how did you get that role, which I can kind of maybe put together? It's like you've got great intelligence, great understanding of the big picture.

You've got this capacity for empathy and compassion. It seems like that would be a good mix for being able to write speeches. But how did you get that role? And then what did you learn from Mr. Gates? Yeah, when the person who had the role before me was moving on, Bill decided to reshape the role. And he wanted someone who had a mix of marketing and product experience. And he was looking for someone who had experience presenting because he wanted this person to do a lot of marketing and product experience. And he was looking for someone who had experience presenting and because he wanted this person to do a lot of demos with him. And, you know, presenting specials at the restaurant led to my first job at Microsoft, which is giving seminars,

three and a half hour seminars twice a day to 350 people in ballrooms and like tier three cities in America. So I gave presentation after presentation and then I did an engineering job and then I did a marketing job. So I had this eclectic set of skills and when he wrote what he wanted and sent it to a bunch of executives, he, you know, a couple of people said, oh my God, I know the exact human being who does this and sent it to me and said, you got to put your hat, name in the hat. And that's how I ended up sort of getting the role. I was 26. He gave 300 speeches a year over that two and a half year period that I was with him. So I learned a lot about project management. I learned a lot about what's a tier one piece of work where you're

going to put hours and hours. He had maybe five of those a year. And what's a tier one piece of work where you're going to put hours and hours. He had maybe five of those a year. And what's a tier three where, you know, 45 minutes of time gets him, you know, an A minus, which for most people is like an A plus and, you know, sort of understanding how to manage that. But from him specifically, which might be more of what you're asking, I saw leadership at scale in ways I'd never seen. He's running a big mega company. I saw a focus on people. Do we have the right people in every job in a way that I'd never seen? And I saw crazy curiosity. I mean, the learning capacity of one human being, the books I would carry around, you know, for him to read wherever we were was just mind blowing and so inspiring.

You know, he would go through a bridge phase where he was just reading all about bridge and then a China phase where he's reading all about China, then a cancer phase. And, you know, you have 20 or 30 books that cover all these different topics. And he's standing backstage waiting to get introduced. And he's literally got a book open reading about China. And they say, please welcome the CEO and chairman of Microsoft. He closes the book, hands it to me, and goes on stage. And it's just the curiosity. You know, Satya talks about a growth mindset. Bill, for me, exhibited that incredible learning desire that was just eye opening and made me realize I need to read.

I need to read a lot more because this guy is just a voracious consumer of content. What are you reading now? I'm into books that, gosh, I'll do my best to explain them. I'm into books that I don't think are a genre, but they tell a story of a single human person as the hero and their journey in life. But their journey in life is actually about a broader system in the world that helps me learn more about one of the important systems that exist on the planet. So two of my favorite books, one is this book called Just Mercy by Brian Skynan and Brian Stevenson. And Brian, as a lawyer, it tells the story of

like five or eight of his cases, but it's also telling the story of the criminal justice system in America and how it doesn't serve many of our communities well. And so beautiful story about him and his life's work, small, and then this mega system called the criminal justice system of America. Another book called The Third Plate by a guy named Dan Farber, a chef who tells his story of learning about his role to make the food system in the world better as a chef serving food that I will like and then demand. And that will impact what farmers grow because I'm demanding it. And it's really a story about, you know, the agriculture system, about the food system and the world. And so I love those. I don't know that

there's a genre, but I'm always looking for that next very personal, vulnerable, intimate story that also educates me on, you know, a system. Systems and empathy, you know, those two types of processing sounds like it's part of the intersection yeah that's your dna okay so speaking of systems like what do you imagine is the most dynamic model for leadership in this new hybrid work environment that we're working into you know so what does leadership look like in your mind? For me, I think it's this notion of combining what the company needs, which often in our case is growth, new markets, fast growth, with what role the company can also play in the lives of our neighborhood, our city,

our society, and the lives of our employees. Because, you know, your average employee doesn't really care if the company grows 19% or 20%. That won't, that's not something that's meaningful to them. But if we can market something like Xbox and tell a story of a human being who uses Xbox to connect to other people in ways that they wouldn't connect with them if they saw what they looked like. That's a moving piece of work for that employee to be able to work on. And it matters. Like those stories matter to people in society. And those people don't care that we're going to grow 20%, not 19%. And I think marrying what's important to the corporation and how the corporation can better serve the world and our employees specifically, I think is a real leadership challenge that people can lean into, but may not feel like they have the freedom to.

And my boss says, you have to use Microsoft as your platform to do what matters to you. I never heard anyone say that before. No one's ever said that. Dude, what are you talking about? Like we're supposed to make the company grow. Like that's what we do. Like we're a for-profit company.

Our job is to grow. And he's like, no, no, no. Yes, but you can also use this incredible platform to find fulfillment in your life and boy is that like I think that's quite I think that's quite elevated I think that's quite sophisticated and so as I've worked on that for the past seven years he said it seven years ago for the first time it's like oh I think I get it you know I think being a leader is that, but it's not just doing it for you. You got to do it, you know, you got to awaken it in your team

and then you got to align it because, you know, people can, oh, I've discovered I love X. And I'm like, yeah, I don't, that's good. I like that's aligned to what we do. And so that's one of the leadership. I think that's what leadership is all about. Does that make sense to you? It does. And so if I were to double click just a little bit here and I say, what do you see as the primary role of a leader? How do you answer that? I think it's aligning the company's goals with what society needs, with what employees crave. And otherwise, they're going to go somewhere else that is going to satisfy that need in them.

So I think of those three dimensions. There's sort of the company, there's broader society, and there are the employees themselves. And if you could bring those three things together, that's leadership. Super dynamic. And then let's throw a spanner in there. Let's say you've got somebody that is really sophisticated in being an exceptional earner. They bring home the bacon, if you will. I don't know where that phrase came from, but they are earning at a high level. They're producing. However, they are antagonists to the culture. They create problems with relationships.

They are strong personalities and there's a mismatch in fit. How do you, by coming from a place of empathy, having these three variables that you're managing as a leader, how do you work with that type of scenario? Yeah. I mean, it's easy to say you get rid of all the talented jerks. And, you know, people say that all the time and that's fine. The tricky part is people are complex and, you know, I don't think people are only jerks. You know what I mean? They have good days, they have bad days. And so I do think there's an element here of trying to work with an employee to be direct about what's holding them back from doing better and give them time and support to see if they can change.

And if they can knock off the sharp edges, the sharp elbows, some people believe you can only change 5%, 10%. Sometimes that's a lot. And sometimes it's not enough. And so there is an element of just being super honest with somebody and saying, hey, the culture is different now. And what got you here isn't going to get you there. And so we have to really work on how you behave at work, how you show up, how you treat people, how you make people feel. It's great that you can make it rain money for the company. But this is now your top priority. And you try to work with that for four months, five months, six months, and you have to stay on it. Otherwise, you know,

you're doing a disservice to everybody else at the company. But it's too easy to just say, oh, yeah, you fire all the talented jerks. Well, guess what? You know, someone was a jerk on Monday. They were amazing to another human being on Tuesday and Wednesday. What do you do then? Right. I think that's more of what really happens is it's, it's far more sophisticated in one of the sport franchises has spent time with. They say, we would say, we will coach all of you until you say you don't want to be coached.

And so that is working with somebody with said principles, both from a performance standpoint and an interpersonal standpoint, like we're going to work with you until you say you don't want to be coached. And people say that by choosing not to change or not applying the effort towards it. And so once that happens, it's kind of like, Oh, okay. Gotcha. Yeah. I, I see where you're coming from. I love that. Yeah. All right. So I would love to, I know we're kind of running up on time and I just

want to say thank you. Do you have a moment for a couple more questions? Absolutely. Okay. What are you excited about when it comes to the hybrid work model? And most people are really concerned about it. So I'm choosing that word purposefully, but what are you excited about with the hybrid work model? Well, I think the best thing is that companies have been forced to look at other ways to work. And I think Microsoft has realized we can actually be quite effective with people working in a variety of locations.

And we had a huge bias since I've been at the company to everybody being in one spot and everybody being physically together. The hallway conversations are powerful. The whiteboarding sessions are powerful, et cetera, et cetera, et cetera. And that's great for companies of a certain size, but boy, do we miss out on talent

if we make everybody move to Redmond, Washington. You know, when I told my dad, I was thinking of a job in Seattle, he was like, don't go there. You know what I mean? Like it's Boston or New York and that's it. And you know, like not everybody wants to move. And so I actually am most excited

that companies are going to have to go through the super painful growing pains of figuring out how to provide flexibility that employees demand now. Because, you know, there are one team's call away from flipping to another company without without moving their house they can stay exactly where they are and someone else will be happy to have them and i just think it's going to be such a net positive at the end that we're going to have so much more flexible work options to cater to people who will be better

if they stay in Atlanta, will be better if they work from home. Doesn't work for every job, don't get me wrong. Doesn't work for every person, doesn't work for every team. But if you're 99% one way, Michael, and we get to 75% that same way. You know, we got 24% of our population. We just hit the jackpot in finding new talent, you know, encouraging new diverse ways of working. Teams is going to be a better product, right? Because we're going to have features that make this stuff better.

So I'm actually just incredibly excited to blow up the traditional model of how companies work, even though I know it's going to be super hard work. You don't just say, oh, great. The pandemic's over. We're all used to working from home. Anyone can just work wherever they want. It doesn't, come on, it's not going to work. You got to do the hard work. But that is what I'm excited about. Because it's a net positive for the workforce of the world you know what i mean so you are on the path of wisdom you are you know there's a couple paths people get on you've heard this analogy there's the the path of the bitter old fool which is like i'm hey listen i'm

chasing all the external things and it didn't work out there's the path of the fool which is I'm chasing the external things and it's kind of working. It's a path of the fool. And it's a path of the wise human, which is like, I am working to understand the deeper parts of life and to do well with my time here. So you're on the path of wisdom. And if you look back and you say, okay, hey, Chris, you little 15-year-old whippersnapper, and then let's talk to the 25-year-old Chris. Let's go 15, 25, and 35. What do you say at those different markers? At 15, I would say go see the rest of the world.

I hadn't traveled much. And when I say much, I mean much. And boy, is the world amazing. And you know, now I've been to over a hundred countries. I mean, go see the world would be what I would say to the 15 year olds who didn't, hadn't taken a flight across the Mississippi river yet. You know, like I go, go to more places, I guess would be the advice I give. 25-year-old, stop looking left and right and stop comparing how fast you're moving because you're not moving very fast

and your roommates are and your coworkers are. It's long, you know? So just get out of your head. Enjoy what you're doing. The only thing you control is what you bring to work every day. It's a lot of luck. There's a lot of other things that have to light up. So stop comparing, you know, to your peer group. And the 35 year old, I would say, get to know people who are more different than you get to know people who, you know, are super different.

It's one thing to travel to a bunch of countries, you know, but who, you know, who do you spend your time with? Who do you, in my case, you know, watch tennis with like get to know, get to know people who are, who aren't you, that would be, that would be the 35 year old. I was too late to that one. That's cool. There you go. And then, you know, I do want to, I've got a light question and a heavy question. Let's go heavy first and we'll end on light, you know, which is Microsoft's mission. By the way, it's so beautifully big and bold. I love it, which is to, you know,

empower every person, every organization on the planet to achieve more. How do you hold yourself accountable to that mission? Yeah. You know, two ways. This is my answer. I don't know if that's the right answer. One way is how do I treat the people in my life every day? Am I doing things that empower them?

Am I using my platform, my power, my privilege to do that? And two is, what systems am I reinventing? What policies am I tearing down and recrafting? Because they were built a while ago and aren't what we need going forward. So there's the personal, you keep, you keep covering, we keep coming back to this, right? There's the personal, how am I today with the 15 people I work with, whatever the number is. And then there's the, when you're gone, what will you have put in place that will serve the company in that way? And that's the systems, the policies piece.

Seems like you're working from the outside in and the inside out. And it's that hybrid between those two that when I think about the hybrid work model, I go there. There's a change there. I know that it is what you and I were talking about. I was thinking the same way you were, which is like, you know, on campus versus working at home. That's how most people, but this hybrid, I think is starting to also shift that new leadership is going to be required to bring the most out of people. You know, moving from this extraction factory industrial model of pulling the most, pulling people, you know, to work longer, harder hours,

because people right now are saying, no, no, no, no, no. And I think leadership is being called to say, how can I help unlock the potential, the dormant potential that lies within people? And so that's where I get really excited about the co-hybrid model, you know, the two functions, if you will, by it. So I love that. Yeah. Chris, like, this is awesome. And I've also heard as a last little moment here that you're pretty good with the tennis racket. I'm a huge tennis fan. I was a good junior player. When I turned 17, Boris Becker also turned 17, and he won Wimbledon that year. I did not win Wimbledon that year. A year later, we turned 18, and he won it again.

Wait, wait, hold on. Were you really competing with Boris? Like, were you in that? We were the same age. You were the same age. You know, like anything that human beings do, there's a spectrum. And I have a point on the spectrum, but the humility at which I play tennis is high. Okay.

And so what has sport or tennis, like what has it taught you? Where has that been a fertile ground for you to become the man that you are now? rigorous season you know it goes forever and so uh i think the work ethic and the self the self-improvement and the mental toughness in that sport is is maybe there are other sports like it i don't know but it's so different than a team sport and i think that that mental that mental acuity and rigor uh probably the thing I learned the most. And, you know, it's lonely. And so you learn how to find yourself through that almost loneliness.

And I think that would be a couple of things I've taken away from the junior tennis I played. So for me, sport is purely a way to learn more about who you are. That would be a couple of things I've taken away from the junior tennis I played. So for me, sport is purely a way to learn more about who you are. Yeah. And so it sounds like we're on the same page. Yeah, totally. There you go.

Hey, Chris, thank you. What a treat to spend time with you in this way. And so I want to say thank you. And I'm wishing you the flat out best. And the way that you're leading is significantly important. It is radically important because of how important, what an important time we're at and what an importance to lead from the heart and to also match up to the larger shared vision that we call this thing called business and work. So listen, Chris, thank you. Thank you so much. And obviously thank you for all the work you've done with Microsoft to help us to help us get better. Yeah. It's been an honor. Yeah. Okay. All the best to you, Chris.

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