Lessons from Silicon Valley's C-Suite • Ann Hiatt

Former right-hand to legendary tech CEOs Jeff Bezos and Eric Schmidt Ann Hiatt  joins Niki remotely to tease out the lessons she learned from her high-powered, high-stakes career spent at some of the world’s most prominent tech companies. Ann is also the author of Bet on Yourself: Recognize, Own, and Implement Breakthrough Opportunities and works as a leadership strategy consultant for entrepreneurs around the world.

"I'm a big believer, especially if you're working at that pace, that your job needs to give as much to you, as you give to it." -Ann Hiatt

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Transcript

Intro: 

[music plays]

Niki: I'm Niki Christoff and welcome to Tech’ed Up. Today's guest is Ann Hiatt, the former right-hand to legendary tech CEOs Jeff Bezos and Eric Schmidt. Ann and I worked together for eight years, during an era I think of as the golden age of Google, when the company was creating magical tools like maps, Android, Google Earth, and voice search. 

Nobody, then, was mad at the internet- ​our conversation is a walk down memory lane that teases out the lessons learned from these high-powered, high-stakes gigs on the front lines.

[music plays]

Transcript: 

Niki: Today on the show, we have a friend of mine, a long-time colleague of mine from Google, Ann Hiatt. She's calling in from Spain. Thank you for coming on Tech’ed Up.

Ann: Thanks for having me, Niki. This is going to be super fun. [chuckles]

Niki: This is going to be fun. I just want to say, for the record, America misses you. I know you've moved to Spain, to the ocean, and married a Spaniard, but you're one of our top people.

Ann: Oh, thank you. I miss the states also, but yes, having the Mediterranean two blocks from where I'm sitting right now is a bit of a solace. 

Niki: Yes, yes. Rub it in! So, I want to start with who you are, how we know each other, and then talk through your career because you've had this absolutely fascinating career in tech. So, high-level, you were the right-hand, your very first job out of college, you worked directly for Jeff Bezos at Amazon. You went on to, ultimately, become the Chief of Staff to Eric Schmidt, who was the CEO and Executive Chairman of Google. [Ann: Correct] So you have been, literally, sitting next to some of the most powerful and wealthiest people in the world, including the people they operate with and see every day.  [Ann: Yeah] And so, this episode is just going to be a conversation about what happened, what you learned. And I think going through, kind of, your career path will pull out some of those stories that people just find really interesting.

Ann: Yeah. It's definitely been a circus. It's been an unexpected career for sure. But I'm just so glad the universe put me on this path because it has been like the most elite business school I ever could have dreamed of. But yeah, I literally sat at, in the desk physically closest to, some of the most powerful CEOs in the world for, like, 15 straight years. Like, basically not going anywhere else.  [chuckles]

Niki: Amazing. I mean, ‘cause these workdays are endless when you're working at that level. [Ann: Yes] And when a mistake is a billion-dollar mistake potentially [Ann: Oh, yeah!] so the team around them is so high intensity.

Ann: I mean, once I calculated the hourly rate of the people we were on average having meetings with, and I was, like, if there's, like, a 15-minute error? And then, I got really terrified by the result of that math [both chuckle]. Like, how much money could be wasted by the smallest mistake, but it was really high stakes, for sure! 

Niki: Okay, so, let's start with your background. So, you grew up in Seattle, you graduated from college. [Ann: mm-hmm] People think about 2008 as the major economic recession of our adult lives, but actually, you and I both graduated during the .com bust. And you were in Seattle. 

Ann: Yeah! Yeah, Seattle is a very tech-heavy city, even was so way back then. My very first job at 16 years old was working at a startup of five people in Redmond, Washington. The founders were brothers who had just graduated from Harvard business school. So, unintentionally, literally, my entire career has been in tech. But yeah, I grew up; I studied nothing technology-related at all in undergrad. I studied international studies focusing on Europe, and in 2002, the year I graduated, the Euro had just launched. That's how old I am. [chuckles] And then, because of the bust, I had sent my resume out to at least 50 companies, y’know, anticipating graduation and wanting to get my big start in the world and got, like, crickets, not a single phone call back.  That ended up being the best thing that ever happened to me and changed the course of my life. At the time, I was working two student jobs while studying full time and one of those student jobs was at the European Union center on campus. And the director of my program is the one who recommended that I submit my resume to Amazon. It had not even occurred to me, even though it was one of the largest employers in Seattle, I just wasn't interested in tech so I hadn't seen that as part of my next step in my journey.  But his wife worked in recruiting and he's like, “Hey, since you're not getting any calls back, might as well try.” And that suggestion literally changed the course of my entire life because- it was a very long hiring story. It took about nine months and 25 plus interviews.

Niki: So, you have just published a book called Bet on Yourself. And in the book, you go through some of the hiring process. And one of the things you talk about is, you had a normal interview. Then you had an interview with the senior leadership at Amazon, and you were, I think the word you use, is stress-tested?

Ann: Yep. Yes. They- I didn't know at the time, I, I thought it was very odd that they were using executive time to interview what would be the junior-most person in the entire company? [chuckle] And so, I thought that was very strange; the executive time was being used for that. But what I didn't know was there had recently been an opening at Jeff Bezos’ office. I had scored well on the first round, and those senior executives were there to stress-test me. Three of them had been specifically assigned to find my breaking point and see if they could make me cry. So [chuckle], and that wasn't to be mean- that was actually a pretty good evaluation of if you could hang and, y’know, keep yourself together in that environment, because it just was very, not unforgiving. It was just intense, [Niki: Intense] It was relentless! 

Niki: Relentless. And you, actually, this, I discovered this in some of your writings and speaking, if you go to relentless.com today, it redirects to Amazon.

Ann: That's exactly right. [chuckles] It's a little Easter egg that not many people know about. So, waaay back in the 2000’s, early 2000’s, Jeff bought relentless.com. And it redirects to Amazon because in a single word that wraps up everything that was my experience sitting next to Jeff Bezos for 18 hours a day for three years.

Niki: So, you go through the stress-test. Did you cry? 

Ann: No! [Niki: Ohh!] No, I'm not much of a crier. So, that's to my advantage. It's just not in my nature, but honestly, I think, maybe because I grew up in Redmond, I just experienced a lot of, you know, tech-type personalities. And I just thought like, okay, y’know, I don't know it didn't really phase me. I didn't think that they were being mean, so I didn't take it personally. I was just like, well, that was awkward, the way he said that. [both chuckle] And the others were just trying to trip me up, they would ask me, like, multi-part questions and then interrupt me and see if I would come back and wrap it up, if I could keep track of, of, complex scenarios and things like that. But, I held it together.

Niki: And you’re thinking this is for a low-level internship, but then, your third interview, space cowboy Jeff Bezos walks in. So-

Ann:  [laughs] Yes, nerd 1.0 version of space cowboy, like, Jeff Bezos. [laughs]

Niki: Before he was just jacked and going to space, this is what he looked like when he was nerdy.

Ann: Yes, yes. He was not yet jacked and he still had some hair at the time. [chuckles]So, they didn't tell me that that third and final round would be just with Jeff Bezos. So when he walked in the door, uh, it took me by surprise, but that was by design because they wanted to see, even back then in the early 2000’s, Jeff had been TIME magazine's person of the year in 1999. Obviously, he was a local celebrity and a lot of people would get flustered in front of him. They couldn't hold it together, or they were a little too deferential, and that was the opposite of what he was looking for in his office. So, he did want that element of surprise, I guess, to see how I would handle it, how I interacted with them. And if I could keep it together in front of a very dominant personality, which he is. 

Niki:  And the first question he asked you was a brain teaser!

Ann: Yeah. That is when I had a moment of fluster, of, of panic. So, his very first question after he introduced himself and he laid out this, now famous, booming laugh that nearly knocked me out of my chair. He asked me to estimate the number of panes of glass in the city of Seattle. And no one had ever asked me a question like that before; I’m like 22 years old, this is the first sort of formal job interview thing. So, I just paused for a second and thought, “Okay, why is he asking me this question? I'm not an engineer.” That's a little bit more normal for engineers. Uh, I was like, “Okay, he just wants to see how my mind works. Can I take a really complex problem and break it down into smaller steps that would lead to a result?” So, I outlined that for him, thinking that would satisfy the question.  And all he did was stand up, uncap a pen and stand at the whiteboard in what turned out to be his personal conference room, and he said, “I'll do the math.” [Niki:  laughs] [both laugh]  And we filled three floor-to-ceiling whiteboards until we got to an answer, which he circled and said, “I think that sounds about right.”  [chuckles]

Niki: Incredible! I, when I was reading about this, I thought, oh yeah, that's right, cars have panes of glass. So wise and it actually fits with your personality. So, people, I can see you right now while we're taping, people can't see you- you're poised. You were always so buttoned up. We know each other; we overlapped for eight years at Google, which is how we know each other,  [Ann: Yeah] and have seen a lot of crazy things together. [chuckles]

But I want to just continue with the Amazon chapter of your life before we get to the Google portion. But one of the things that I didn't realize is, you were there when people didn't know what a TED Talk was and you helped write Jeff Bezos's TED Talk. You helped with product launches. You weren't just an assistant, you were someone running big projects, even right out of college.

Ann:  It was, it's astounding to me now, looking back, that he- the projects that he gave me, like looking back I'm like, “That was insane.” I had no business running those types of things, but I had been really stress-tested, not only in the interviews but through some early projects and early crises that we went through together. And that really was an important moment. While I would say that I had some of the most painful professional experiences I've ever had within the first two months of starting an Amazon, it changed something really important. It changed the way that Jeff saw me. Instead of the junior-most person in the company who has no business having this job, which was probably accurate, it shifted it because I'd handled crises really well. I could be trusted and most importantly, it shifted the way I saw myself. So after those early challenges, yeah, he was asked to give a TED Talk. I literally had never heard of that before. Don't judge. It was again 2002, no, 2003. And, yeah, I helped him write it. Honestly, it was, it was in this room of his communication specialists and his marketing people, and they were brainstorming what the theme should be and he decided he wanted to compare the dawn of the electricity era to the dawn of the internet. 

And I raised my hand. He was like, I want to see some original articles. And I raised my hand ‘cause I was the only person in the room who had an active library card and that's how I got on the project in the beginning [both laugh] because I still have university archive access. Because I just graduated, like, less than six months before. And that's how I, like, weaseled my way into that. And then he saw that I performed really well, you know, partnering with SVPs and then I got tapped to, yeah, help with product launches when we launched jewelry with Paris Hilton at the height of her fame and [Niki: blast from the past with jewelry] [crosstalk] Anna Kournikova, seriously… 

Niki: Wait, what did you do with Anna? You remember those days? Honestly, it’s all sort of a fugue state for me- the early 2000’s[crosstalk] [chuckles]

Ann: Oh my gosh- ditto! I mean, if it didn't happen inside the office of Amazon, I have no memory of the 2000’s at all. But yeah, Anna Kournikova was part of our launch into sporting goods. She had just secured a partnership with the- I can't remember what sporting goods brand Nike or something like that- and she was launching a brand, a line, that's we call it, a line of sports bras where the slogan was “Only balls should bounce.” [Niki: laughs] She's a particularly endowed, like, tennis player. [Niki: laughs] Hilarious. So we, we, use that to get, like, extra, like, headlines and stuff when we were launching the sporting goods category. 

But yeah, I was on projects that were far senior to my job description, but it's not only reflective of me; it's reflective of the time because everyone was doing stuff that they had no idea how to do. I remember Jeff Wilke was in charge of putting together the pipeline, like, not only the software predicting where you're going to be and where the fulfillment centers should be for optimizing, because sending things by air is seven times more expensive than sending it by ground, and he was, he was figuring out fulfillment centers that had never existed before. So I saw that modeled around me and it was just, kind of, all hands on deck.

Niki: And it's a good reminder. You know, I'm sitting in Washington, D.C., and everybody is having so much focus on antitrust enforcement and these huge companies, these behemoth companies, and are they too big, [Ann: Yeah] but remembering that when you started, Amazon was a public company, but it only had a thousand employees. [Ann: mm-hmmh] 

Ann: We were in a single building, a single 15 story building, formerly a hospital, which was a little creepy when I was there really late at night, which I often was. [Niki: Yeah] there were less than a thousand of us. I knew most people, literally, by name and now they have, literally, over 1 million employees. So it is a proper behemoth, but back then, it was just a bunch of scrappy nerds trying to figure out as fast as possible. When I joined, Amazon wasn't even profitable yet. They'd had a single profitable quarter, if you can imagine, and that was it. We were fighting for our lives for the first year and a half I was there. 

Niki: Which is a good reminder,  I think, to people that even if we look at the companies operating today, it's not inevitable that the behemoths will stay that way. [Ann: No] Even if the government does nothing, it's not inevitable. And it's certainly the case that there are smaller companies that might even be public already, but that are going to be dominant 20 years from now. 

Ann: A hundred percent. And I saw that once I got to Google, I joined Google in 2006. And it wasn't until, I think 2008, that it was finally like a top, the top-ranked search engine. Like, which is unfathomable now. But I've seen this pattern disruption over and over again.  At Amazon- eBay was worth, I can't remember, four times what Amazon was at the time? And it seemed, like, impossible that they’d upseed them as, like, this primary online retailer. And now, like, I personally have never used eBay, it’s kind of irrelevant. So- 

Niki: [interrupts] That’s a great point. [Ann: Yeah!]  And eBay's being taken over by Open Sea, the NFT buying, [Ann: mm-hmmh] whatever. We talk a lot about NFTs on the show, which I think people are probably sick of [both laugh]. Okay! So, you're at Amazon for a couple of years, and then you decide, “Oh, I actually want to be a professor. That was my plan. I'm going to go get my PhD in Scandinavian Studies?”

Ann: Yeah. I know! This is the question I get most frequently of people being, like, you did what?! Why did you leave Amazon when it was finally profitable and your stock value was finally going up? Why did you leave? But that was my plan. A) I worked at Amazon because I wanted quote-unquote, real-world experience, before being an academic. That had been my dream for a very long time. I was a very nerdy child. Like, I thought the greatest job in the world would be getting paid to write and read books every day. So, that was my plan. I really worked for Jeff to learn as much as possible, but it did get in my blood. So, while it sounds insane- I, my very last email that I ever sent from my Amazon email address was to Udi Manber, who had moved from corporate Amazon down to run Amazon’s search engine called A9. 

And my last email was, hey, I'm coming to California. His office was in Palo Alto. Let me know if you ever need my Jeff whisperer skills. And he wrote back in five seconds saying, come see me as soon as you settle in the Bay Area, this is my number-

Niki: [interrupts] This is the thing about tech [Ann: Yeah] is, it's like, Hotel California. You can check out anytime you like, but you can never leave.

Ann: You can never leave! So, I think part of that was I anticipated missing the adrenaline of just madness that was that tech environment in the early 2000’s. And so, while I was doing my PhD, every Friday I went down and did special projects for Udi, the president of A9. So I, kind of, kept my toe in the water while I was trying out academics.

Niki: So, you ended up leaving your PhD program because you were recruited to go work at Google. And this was 2006? [Ann: Yep. 2006] So, again, they were a public company, but people forget this, even as a public company, Google calendar, GCal, did not exist when you got there or did it just launch? The week before?

Ann: One week before I joined. I mean, that's how basic it was, like, we didn't yet have street view or, you know, like, driving navigation, all that stuff got invented in the first couple of years that I was on the product team.

Niki: And we didn't have, we didn’t have smartphones! [Ann: Nope] So, tell me, you have a little bit of, I don't want to say PTSD. I don't want to speak for you, [Ann: chuckles] but explain that iGoogle story. 

Ann: Oh, my gosh! So, [laughs] I guess I did still have a Blackberry at the time. So, iGoogle had been something that the product team had attempted to launch several years before I joined. So, iGoogle was a concept.  Back then, it was before the smartphone existed and iGoogle was an idea ‘cause Google wasn't yet the dominant search engine we wanted to teach people to build a habit of coming to the Google homepage every day. And so we thought, okay, we're going to put some widgets- this is how old it is. Kids today have no idea what a widget is. [chuckles] We're going to put widgets on your homepage, which you can customize. So, it's a shortcut to your email, and a shortcut to weather apps, and it's a shortcut to the newspaper you like to read. And that was a really groundbreaking idea, but it hadn't really got the traction that the team had expected.

Back then, the product team, which doesn't exist now, our only job was to make cool things that brought in eyeballs. Other teams figured out how to monetize it; we just made really cool stuff. So fun! It, it, was really, really, a great team to be on and to learn to think innovatively. So, Marissa had this idea; she was the vice president of that team. [Niki: This is Marissa Meyer] She had this idea of like- Marissa Meyer before she left Google to become CEO of Yahoo. And Marissa had this idea of, like, “I think there's value here. Let's reinvest. Let's double down on this.” And so, she had this great idea. She's this beautiful mix of unexpected talents, like, she has a master's degree from Stanford University in artificial systems, or something like that, before AI was literally even a word. And she also has this incredible design aesthetic. So she wears, on a regular day, she would wear, like, Oscar de la Renta, but with no makeup to do a code review. I mean, she's just this incredible mix of talents.

So, she had a lot of relationships with these designers and she thought, “What if you could have a customized homepage by, like, Diane Von Furstenberg and Tory Burch and Marc Ecko and all, the, the big designers?” And so, that worked amazingly. So, we did a launch in New York at the Google New York office, outdoors in the Meatpacking District, and we had these special LED projectors brought in and we projected these iGoogle designed homepages made by all these celebrity designers onto these old brick buildings in the Meatpacking District, which is such a beautiful juxtaposition of, like, old and new. And it was a huge success, like, we got incredible engagement, the designers were really, really happy with it. We thought, “oh, we, y’know, we've saved it.” We've got this big bump in daily active users, and then, literally, I think it was three months later, the iPhone launched, and it became overnight irrelevant. So this is, like, four-plus years of work down the drain. 

And one of the greatest lessons I learned from Marissa was she just pivoted. She had put her blood, sweat and tears, every professional relationship, every favor she could call in she had called in to make that work. It didn't work and became irrelevant and she just moved on. 

Niki: Yes! I think, again, this, you know, I keep tying back to this because I'm always sitting in Washington, but she went on to become the CEO of Yahoo. [Ann: Yeah] I was- I had spent my first six years at Google in Silicon Valley, which is how we know each other. And then, I moved out to Washington D.C. and we were looking at an advertising deal with Yahoo, which was blocked by the government. Yahoo doesn't exist anymore, basically. So, I think that there are these, if you sort of let the disruption play out, the people, the companies you think will never be on their back heel, you just never know because they're going to get out-innovated.

Ann: I think that's such an important point because we were looking at Yahoo being- like, ‘cause they were number one at the time and we weren't anticipating the iPhone. Now, the reason why the iPhone disrupted and made iGoogle irrelevant was because you no longer needed widgets. You now had this phone where everything was right there on the first screen. That had not existed before. So we weren't looking at that. We were looking at Yahoo and then we're, like, “What?!” Apple came out of nowhere with this, like, groundbreaking idea. In fact, my team- I was sitting on like the 35th row at, what's it called? Macworld, when Steve Jobs was onstage and, and, launched the iPhone. One of the greatest moments of my life, I knew in the second he was on that stage, we were watching history and I would tell my non-existent kids about it one day. That is how that I was, like, “Oh, no”, I knew it was a shift like forever at the moment.

Niki: And you mentioned how you weren't necessarily interested in tech; you sort of fell into it. And then once you do, there you are.  [Ann: mm-hmmh] And same for me. So, I moved to Palo Alto for personal reasons. I didn't necessarily- I don't think I had any interest in technology [Ann: chuckles] I just lived in Palo Alto. So, I applied for a job at Google, and Google was, at the time, it had just been ranked the number one place to work by Fortune magazine. It was a public company, [Ann: mm-hmmh]  but we did not have Android. We didn't have smartphones. [Ann: Nope] 

I had a Motorola Razr. [Ann: chuckles] Yeah. I was handed a prototype Gphone, which I put in a drawer, my desk drawer. I'm like, I don't know what I'm going to do with this thing. [both laugh] I can't, I can't, imagine a use case for it. [still chuckling] And it was this- it was right before the financial crisis of 2008. So that's another thing people don't think about, when I started the stock was really high, so my stock options were not worth anything. [Ann: Immediately underwater] Right! [Ann: Yup!] Completely underwater! They were not worth anything for years. And so, these are the chances and risks you take when you go to these companies; but this is how we met each other. [Ann: chuckles] Because over at these companies, you tend to, it's staying somewhere for 12 years, which is how long you were at Google, I was there for eight.  You have to reinvent your role to stay [Ann: Yeah] because it just moves so fast. [Ann: Yeah] And I, I'd love to hear you talk about your path at Google because you ultimately ended up as Eric Schmidt’s, the executive chairman, Chief of Staff.

Ann: Mm-hmm. Yeah, I did reinvent myself several times over those 12 years, which is the only way- I mean, it’s like dinosaur years, right? That’s like being there for a thousand years, in, in tech. But I did, I really, looking back, I can see four very distinct different periods of my career evolution, and nobody did that for me. This is the one thing that you have to- while tech is very open to, like, self-starters, ambitious people, people you have to hold back, it's kind of up to you to see the opportunities and to raise your hand. So the first three years, I worked for Marissa on the product team, which I loved. Incredible lessons, I could go on and on about what I learned about how to motivate teams and how to keep them at a sprint pace when it's really a marathon and how to, y’know, hire, really, for ambitious, talented people. I learned a lot about team building from her. But then, there was an opening in Eric's office. He was still CEO at the time, and I got recruited based on my reputation from Google, but also because I had been able to handle Jeff Bezos. He really, literally, in my interview with him, he was like, “Well, I don't have to ask you about any core competencies because if you could handle Jeff. Yeah. I'm sure you can handle me.” [chuckles] And, he was right! 

Niki: I started at Google doing public relations, which I had no background in, but at the time Google didn't hire for core competencies, [Ann: Nope!] they hired for utility players. Can you figure out how to do this? Are you smart? Can you figure it out? Do you work hard? [Ann: Yep] Do you have tenacity? Are you someone who doesn't get rattled if things, y’know, there's so much ambiguity and change and the pace is so high. So I started in public relations, I worked for the legal team, I did corporate communications, and then when I moved to the east coast, I became Eric's PR person. 

So, I have a theory and I- you will know better than anyone if this is true.  [Ann: Okay] I've worked for, we’re talking about billionaire wrangling. I've worked, I've never worked directly for a billionaire, I've always had a speed bump between me and the principal. [Ann: chuckles] You've worked directly for them, but I worked at Uber for Travis Kalanick. I worked for Eric Schmidt, as, doing communications for him. [Ann: Yep] And then, I worked at Salesforce with Marc Benioff, and I have a theory. 

There's a difference between a founder CEO and a professional executive CEO. And I think founders are the kind of people where if you say, “If you touch that stove, you're going to get burned.” They'll- they have to touch the stove. They cannot help themselves. They have to do it. And professional executives will hear the people around them and say, “I'm not going to touch the stove”, or at least they'll take in that piece of information. And it's the difference, I think, between Steve Jobs and Tim Cook, and between Bill Gates and Satya Nadella,. This is my theory, but you actually have worked more closely with founders and professional CEOs, including in your new role [Ann: Yeah], which is as a consultant to CEOs. Do you think that this is, this is, accurate, or not? 

Ann: I am nodding like a bobblehead right now, like, a hundred percent accurate. There is a beautifully articulated distinction between the two. And they both have something very special. Like, there's something about a founder that you can't generate any other way and there's something equivalent. I mean, there's a reason why Larry and Sergey brought in Eric as his parental supervision, as his professional CEO, because they were touching all the stoves and they knew that that was not sustainable. And he would just ask the smart questions instead.

Niki: So, I have seen the genius of that. This is my observation: one of the things I liked working for Eric Schmidt is he would, he would ask, he wanted the truth. He wanted to be told the truth. And I remember saying to him, after a speech, he said, “How did it go?” And I said, “I think you should stop saying that one day we're going to take our password like a vitamin in the morning. It'll be different every day. You'll just swallow your password.” I was, like, “I don't want that. I don't think anybody wants that.” And he's like, “Why wouldn't you want that?” [chuckles] I said, “I just think it creeps people out [Ann: chuckles] and you should stop saying it.”  But he was the kind of CEO you could say that to. And he actually would listen to you. He wanted you to get- he continued to say it, by the way. [Ann: Oh, yeah] He, it wasn't that he always heeded my advice, but I felt comfortable telling him my advice. And sometimes with founders, I think it's, it's harder to do that for the staff around them [Ann: mm-hmm]. 

But I want to end with lessons learned. So, whether it's from Jeff Bezos or from Eric Schmidt or at these big companies, what do you think, whether it's hiring or how to manage a team, if you had to do, like, the three big takeaways, what would they be?

Ann: If I had to pick just one thing that I learned from Jeff, it was on hiring.  Hiring, especially back then, it's exactly what you described in tech. Especially back then. It wasn't about core competencies because we were just inventing futures and no one had those competencies. So, he wanted to hire the team that, as he described it, he would have to hold back not push forward. I learned that lesson from him directly when we were trying to find my replacement. My PhD was starting, couldn't change the start date of grad school. He had rejected every candidate, like a hundred. And, um, that's how he defended himself. He was, like, “I will wait. I will wait for the right person. I want people that I have to hold back and not push forward.” 

From Marissa, I learned something that she called “finding your rhythm.” She would go to her direct reports, especially since we were really sprinting a marathon for a very long time, and she was worried about burning out her highly skilled and valuable engineers. She went to each of them and asked them “What do they need?” So they wouldn't resent their jobs.  For one engineer, she needed to be home for-she had two young kids and she needed to be home for a bath time and bed, but she didn't mind being on video conferences with Bangalore, which we were launching that year. We were just expanding into India that year.  

I'm a big believer, especially if you're working at that pace, that your job needs to give as much to you, as you give to it. And that the d- for me, that was a decidedly high bar. I knew what I wanted in exchange and I didn't mind showing up because it was giving me exposure to people who I really admired and wanted to become like. I was learning really, really fast. I was in a disruptive industry and that filled me back up at the same time that I was expending a lot of energy. And Marissa did that for me, extraordinarily well.

Niki: It’s a good observation. I felt this way, especially at Google, where a big part of what I ended up doing was crisis communication. [Ann: chuckle] So, if we got hacked by, y’know, our joint venture partners in China, if we had an issue with the U.S. government, if we had a huge acquisition that was closing in the middle of the night, y’know, and the helicopters landing on the building and we're closing it. It was so fascinating. It was so interesting. And you would wake up, especially when I moved to the east coast, I remember there was a day where I was- I turned on the Today show, and Google engineers had these robot dogs, which they still have, they bought from Boston Dynamics, and they were kicking them to show that they could rebalance themselves. And I remember, calling, I just picked up the phone,  I said, like,”You guys can't kick these dogs. [Ann: chuckle] It's not nice.” [both laugh] And they said, a head engineer said “They have metal exoskeletons. Like, they don't, they're not feeling this.” I'm like, “Right, but it's not nice. Like, people don't like it, it doesn't look nice.” [Ann: laughs] 

And those experiences were classic Google. [Ann: laughs] I'd get a phone call from a reporter saying, “I heard you guys are making an investment in asteroid mining.” And I was like, “Oh, that might be a leaked April Fool's joke” Nope! [Ann: Nope] We are, we're making an investment in mining asteroids, and it just- you couldn't make up the stories and it was, it drew you in, it was, the pace was amazing. And I think that's why people still continue to be interested in working at these companies. It's you, just it's so different than other industries [Ann: yep], because, because the founders and the people at the top are so creative.  So then, your last lesson from Eric Schmidt, what was the big takeaway? 

Ann: Eric is a hard one because he's nine and a half years of my career. So, there's so much gold in there, but if I had to pick just one, it would be something- he literally had a plaque on his desk, in his office at Google, that read:  “If at all possible, say Yes.” And that isn't about, y’know, overloading yourself or not delegating or being a micromanager. In fact, the opposite of that, it's keeping yourself consciously available for serendipity, for new opportunities and for sitting at tables where you're not the smartest person, which for him is a very high bar.

So, that is about proactively seeking out disruptive ideas or people with expertise you don't have or things you don't understand. I mean, it was everything from him learning to not only be a certified jet pilot on five different aircraft, but then becoming a helicopter pilot. Or, literally, he got an invitation to go to do some incredible things with technology in Brazil, and then went to a Shakira concert because some random person invited him to it. Like, can you imagine Eric at a Shakira concert? It was very funny. [Niki: I actually can, but only ‘cause I know him, but yes] You know exactly what he was doing and it was probably very cute. [both chuckle] 

But I think that is what I learned the most from him, is he would go to places he would seek places where he would be a little bit uncomfortable because it's a new environment, he didn't know how to behave or expect, or he wasn't the leading expert in the room. And not only did he tolerate that, but he'd sought it out. So, I use that as a little bit of a mantra to myself, as well, as like, if at all possible, I'm going to say yes to things that scare me. 

Niki: And I think maybe we should end with this before we talk about the work that you're doing, but I- listen, listen, am I an apologist for the tech sector? [chuckles] Probably, probably am an apologist for millionaires [Ann: laughs], for sure. But, I have seen these people as humans up close, including moments where they've failed [Ann: Yeah] that have been devastating to them, including moments where they made the wrong call, including, y’know, things go wrong for them. And they do, ultimately you see sort of the Jeff Bezos 2.0, but that's not what he was like when he was struggling to get investments. [Ann: No] When the firm he left did not invest in his company, when you're just scratching it out. And I remember here in Washington, there was a moment, Eric was invited to give an address at a small event at the Supreme Court and Ruth Bader Ginsburg was invited, [Ann: mm-hmm] was, was doing his introduction. And he and I wrote it, it was nighttime, and we were walking up the steps of the Supreme Court and we stopped and he was in awe of the building. And it was such an interesting moment. This man who's seen absolutely everything, met the Pope, who's done absolutely everything, felt this sense of awe and respect for this institution. And it really stuck with me. 

Ann: Like, I do feel, like, I always have to preface everything I say with an asterisk of saying, please don't interpret this as hero worship.  As well as we know them, we know their flaws as well as we know their strengths. Right? So there's two sides to this coin, but they are remarkable because of what you just described. They are still able to capture moments of awe when they've met- literally, I mean, I arranged that meeting with the Pope. [Niki: laughs] I arranged- I've, I've, I've literally connected him to the international space station. There's nothing the man couldn't have. He could dream it up and I could make it happen. [Niki: laughs] But he has these moments of pause where he appreciates that.

I remember my version of that story, which I think is so beautiful is, he had a one-on-one lunch with Obama during his last year at the White House. And he invited me to come, not because I was necessary, but because he's a very thoughtful boss who thought this is a moment that will never come around again. So he invited me, and I was there in the Oval Office. And as someone, an Air Force brat, literally born on an Air Force base in Tampa, Florida to a fighter pilot dad, that for me, was the greatest moment of- as an American citizen, to touch that desk and to be in Obama's Oval Office. We did the same thing as we left, we kind of looked at each other being, like, I can't believe that just happened. And, I love that about him. 

They are humans. They, they, when they fail, even though Silicon Valley loves to talk about “We're all about failure and we celebrate them”, they still hurt when they make mistakes. They're devastated, and that's the essential element of this passion that keeps them going. Like, none of them need more money. They all do it for the passion of what they're trying to do, put into the world. 

Niki: Yeah. They're doing hard things. Okay. So we'll end- we're not hero-worshiping except here we are doing it. [Ann: laughs] No, we're not! You are now a strategy consultant. You consult globally. You're sitting in Spain, but your clients are everywhere. They're CEOs of [Ann: yeah], I've heard you say, startups and scale-ups [Ann: yeah], but people who are growing these businesses really fast, and you're a woman who can arrange a call with this international space station, if necessary [Ann: chuckles], but can also help them sort of figure out their mission their goals and bring all of this expertise that you have to them. So you have a book Bet on Yourself, you have a podcast, you have a consulting firm, you do paid speaking. [chuckles] You're doing the most, Ann Hiatt. [Ann: Awww] What do you want to leave people with? 

Ann: Oh, thank you! Yes. I felt this, as I was thinking about what I could possibly do after this first half of my career? First two-thirds; I have a third of my career working life left. What did I want that to be? And I, I started to feel this enormous responsibility to pay forward this elite business education that I'd had as basically an apprentice, a right-hand consigliere to the most powerful people in the world. So, my mission now, my personal mission statement, is to discover and empower underrepresented entrepreneurs through actual education and mentorship. That's my, my personal motto. So, I'm trying to show up in multiple ways. The book is, is, one way with just 20 bucks. I think on Amazon now [chuckles] it's down to 13 or something. You can get these best practices, you can hear these stories of the foundation of the internet. I've translated these best practices of some of the most effective people in the world for us normal people and use my career as a case study.

So, I hope entrepreneurs out there will see this as an invitation and start to self-identify as an entrepreneur, even if you're an intrapreneur. And yeah, in my consulting work, I really love to show up and help scale-ups and leadership teams. My, my, secret superpower, my zone of genius, is C-suite optimization. 

So, yeah, a great place to find me, the book’s website, is betonyourself.book.com. There's links to everything there, my social, where to buy the book and everything and then my personal website is annhiatt.co. 

Niki: Thank you so much for taking the time. You've been very generous with me too. I made a huge career shift after leaving Salesforce, where I had this big in-house job. And, y’know, I was sort of breathing into a paper bag [both chuckle], deciding if I can handle, handle, [chuckles] starting my own firm. And you were the first person I called because you had done it successfully and I just really needed a pep talk. So, you've been so generous with your time. This is such an interesting conversation and I'm so glad we know each other. [Ann: Me too! I wish you all the best with your professional endeavors] Thank you, Ann.

Ann: Thank you. I feel like we're sharing that paper bag. [both laugh] We'll just continue to support each other. Whoever’s hyperventilating [crosstalk] [both laugh]

Thank you, Niki. It's, it's, really a pleasure to be on here, and any chat, any chance to chat with you, I welcome. 

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Outro: 

Niki:  Next week, I'll be joined in the studio by reporter Ashley Gold, who covers technology policy issues for Axios, based here in Washington. Be sure to follow Tech’ed Up wherever you get your podcasts.