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Sept. 30, 2021

Trillion Dollar Leadership Secrets of Amazon’s Jeff Bezos & Google’s Eric Schmidt with Ann Hiatt | Partnering Leadership Global Thought Leader

Trillion Dollar Leadership Secrets of Amazon’s Jeff Bezos & Google’s Eric Schmidt with Ann Hiatt | Partnering Leadership Global Thought Leader
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In this episode of Partnering Leadership, Mahan Tavakoli speaks with Ann Hiatt, Leadership Strategist & Consultant and Author of the book Bet on Yourself. Ann Hiatt shared the many lessons she learned while working alongside the world's top tech CEOs—Google's Eric Schmidt, Amazon's Jeff Bezos, Yahoo's Marissa Meyer. In addition to the story of her reinvention, Ann Hiatt shared common practices and approaches of these and other top-performing leaders.  


Some highlights:

- Ann Hiatt on how she ended up working at Amazon and supporting Jeff Bezos

- How Ann Hiatt handled the crisis when the helicopter she booked for Jeff Bezos ended up crashing

- The leadership models, habits, thought processes Ann Hiatt learned from working closely with Jezz Bezos and Eric Schmidt

- Ann Hiatt on how to hire people who are value-aligned and a good culture fit for your company

- Why you should and how you can Bet on Yourself.


 Also mentioned in this episode:

-Jeff Bezos, Founder and Executive Chairman of Amazon

-Eric Schmidt, former CEO of Google

-Andy Jassy, President and CEO of Amazon

-John Doerr, Venture Capitalist at Kleiner Perkins, an early investor in companies including Amazon & Google, and OKR advocate



Book Recommendations:

Bet on Yourself by Ann Hiatt

Measure What Matters by John Doerr


Connect with Ann Hiatt:

Bet on Yourself Website

Ann Hiatt on LinkedIn

Ann Hiatt on Twitter

Ann Hiatt on Instagram

Ann Hiatt on Facebook


Connect with Mahan Tavakoli:



More information and resources available at the Partnering Leadership Podcast website: 




Mahan Tavakoli: 

Welcome to Partnering Leadership. I'm really excited this week to be welcoming Ann Hiatt. Ann after graduating from college, got a chance to get her business training working for more than 15 years first as the executive business partner to Jeff Bezos, CEO and founder of Amazon, and then as chief of staff to Eric Schmidt, CEO, and executive chairman at Google alphabet.

Now, Ann consults with executives and companies across the globe to help them reverse engineer their moonshot goals and get results. She is an international speaker, angel investor, sits on different boards, has recently relocated from Silicon Valley to Europe and is just releasing her first book called Bet on Yourself. I really enjoyed this conversation full of insights of what great leadership is all about and how we can all become more impactful and better leaders ourselves.

Now I also love hearing from you. Keep your comments coming. mahan@mahantavakoli.com. There's a microphone icon on partneringleadership.com. You can leave voice messages for me there.

Don't forget to follow the podcast on your favorite platform of choice. And finally, those of you that enjoy it on Apple, leave a rating and review when you get a chance that will help more people find and benefit from these conversations.

Now here's my conversation with the author of Bet on Yourself, Ann Hiatt.

Mahan Tavakoli: 

Ann Hiatt, welcome to Partnering Leadership. I'm thrilled to have you in this conversation with me.

Ann Hiatt: 

Thanks very much. I've been very much looking forward to our chat today.

Mahan Tavakoli: 

So, Anne would love to know first about your upbringing and how your upbringing impacted the kind of leader and person you've become.

Ann Hiatt: 

I think it's not until we're in adulthood and looking back in retrospect to see how much those early influences shape what is to follow. But for me, it was a huge part of the leader that I've become. 

So when I was young, I was actually born on MacDill Air Force Base in Tampa, Florida. My dad had just finished pilot training and was chosen to be a fighter pilot. So he flew the Four Phantom fighter jet for the first half of my childhood. I was born in Florida, my next two sisters in Alaska, and really we're kind of everywhere in between. And then when I was around 10, my dad decided to go to law school after his military career. And that's how my family ended up in Seattle. 

So I share my dad's career journey a little bit because he really reinvented himself several ways. And I myself have done that as well. So my parents actually were born and raised on farms in Idaho. They met that way. Their families were in the same community.

Actually I'm a first-generation non-farmer in my entire family. So my career in tech is extremely unlikely. But yeah, so he saw that life of farming, saw the multiple heart attacks that his dad had, knew that that would be his future if he continued down that path. And so he did the impossible and made a big bet on himself and tried to be a pilot, not only a pilot, but an elite fighter pilot and accomplish that goal. Then he reinvented himself again, went to law school, put himself through school, even when he had three little daughters and one on the way. He left the military and put himself through school by working part-time as a janitor and really invested again in his big dreams and the lifestyle he wanted for his family.

And the fact that his first big job after law school ended up in Seattle changed the course of my life. Because when we moved to Seattle in 1985, the personal computing revolution was happening within five minutes of my front door. And that is how I ended up in this very unlikely career of tech. I was just raised up among it. And that was the start of my very unexpected career journey.

Mahan Tavakoli: 

It sounds like you didn't necessarily want to pursue tech. You've studied at University of Washington. Now, one other piece I would love to know, you speak Swedish fluently having spent some time in Sweden. Now I've spent time in Sweden, and I think this says a lot about you because anyone who hasn't interacted with Swedes, they speak English better than most Americans. So how were you able to learn Swedish?

Ann Hiatt: 

So my degree in University of Washington was international studies. And within that program, you have to be able to speak to foreign languages, pretty fluently. And during undergrad, I lived in Sweden for a year and a half, almost two years. And it was really important to me while I was there. But absolutely to your point, you do not have to speak Swedish to live in Sweden very comfortably. But I was motivated one by my program requirement to be able to check off that language requirement. And two it's my DNA. It's where my family heritage came from. 

My family immigrated from Scandinavia in the late 1880s. And there was something about that was really motivating to me. And I also think my dad instilled in our family our love for cultures. He lived abroad. He lived in Austria when he was younger. In fact, every single one of my siblings with one exception has lived abroad and speaks minimum one foreign language. It's just part of our family DNA. That's always been the expectation.

And I think that really enriches your experience. And I like to say it's being able to speak the language of someone's heart. It gives you an opportunity to connect with them in a very different way. And now fast forward, 20 years later, and now I'm living in Spain and married to a Spaniard. And again, I don't have to speak Spanish to function here where I live, but I choose to most importantly, because it's the language of his heart, but because I love languages and I find you connect with people in a very different level of authenticity when you at least make an effort to speak their language.

Mahan Tavakoli: 

What a beautiful way of putting it Ann. And I think it's that same mentality that helped you operate also in very different cultures, which will eventually get to Amazon, Google are not, even though they are in tech, they're very different cultures. So how did someone pursuing international studies speaking Swedish fluently ended up at Amazon?

Ann Hiatt: 

Yeah, it's a very unexpected turn of events. That was definitely not plan A. Plan A was to be a professor to go into academics and study the effects of membership in the European union on social democratic states like Scandinavian countries. 

So I graduated from the University of Washington in 2002. That was just after the.com. And Seattle is a very tech heavy city. And so a lot of the economy and opportunities had disappeared seemingly overnight. Trillions of dollars of investments went up in smoke. And so I, and many of my peers graduating from undergrad did not have very many opportunities for work when we were graduating.

During my last two years I worked at the European union center on campus at UDaB. And the director of my program asked me what I would be doing upon graduation. I said I honestly didn't know, because I think I'd sent out about 50 resumes and hadn't even received a request for a phone interview, just nothing. And his wife was working in recruiting at Amazon at the time and so he just said, "Why don't you apply there?" And honestly, it had not occurred to me because I had no intention of working in tech and that's literally the only reason I applied at all. And that single suggestion changed the course of my life. 

My story of actually getting hired was really long, cause it took about nine months. My first round of interview was with all the assistants in the company. They were just considering me for general admin role, junior most person, intern level stuff at Amazon. But I scored really well. I didn't know that at the time, but it scored well and it qualified me to be considered for some more advanced roles.

Three months later they brought me in for a second round of interviews. And this was with all senior vice presidents of the company. Now this is again is 2002. So Amazon is not the behemoth massive power that it is today, but still I found that very odd. I wasn't sure why they were using executive time to interview someone for their first job after undergrad. But that was because there had been an opening in Jeff Bezos' office and I was being considered to join his support team. Three of those interviewers unbeknownst to me had been assigned to find my breaking point to see if I could handle the stress or the pace that would be in Jeff's office. And they had been challenged to see if they could make me cry. 

I did not cry and I just chalked it up to tech personality awkwardness. It really didn't faze me at all. That's one of the blessings maybe of being raised in Redmond, Washington, surrounded by a lot of very special tech personalities. I just thought, okay, no problem. I've seen this before. 

And then three months later, I came in for a final round of interviews. And that is when they sat me down with Jeff Bezos himself. He just asked me two questions and hired me on the spot. That's my unexpected path into Amazon.

Mahan Tavakoli: 

That is both an unexpected path to Amazon. And also it's incredible, even though Amazon wasn't as big back then still back in 1999, Bezos had been on the cover of time magazine. So Amazon was in the news. Bezos was a personality. As a pretty recent college grad weren't you sort of all struck by this person that all of a sudden you've been put in front of to interview and be working for?

Ann Hiatt: 

Looking back, that's the part that shocks me the most because I was not this big, bold, carefree, whatever you think of me is fine, kind of kid. At 20 year old self, definitely I was not that self-assured. But I do think that's one of the reasons he hired me was because yes, he had been Time magazine's person of the year in 1999. Seattle is a small, big city. So there was an article at minimum about him in the Seattle times, every single day. We were definitely keeping close watch of one of the sole survivors of the.com bust. So I definitely knew who he was when he walked through that door and they hadn't told me my last interview would be with him.

But when he walked through the door, I knew exactly who he was. But I think I can chalk it up to the advantages of naivete, honestly, because I think I massively underestimated what it would be like to work in that kind of innovative environment at that pace and irreplicable visionary mind like Jeff Bezos.

I quickly, like a month or so into the job, realized I had no business having that job and how under-qualified I was for the tasks that I was given. But thankfully in that interview, I was pretty relaxed. I was just able to talk to him like a normal person. We kind of engaged in a very natural back and forth conversation. And I think he really resonated with that because even back then, and he was not the celebrity billionaire CEO that he is today, even back then, he was being treated a little bit differently and he's always sought out people who had challenged his ideas who would be really comfortable sitting across the table from him. And I think a little bit of that naivete gave me that advantage of just talking to him like a normal peer.

Mahan Tavakoli: 

And one of the things I love about your story and your book, Bet on Yourself is that you didn't only bet on yourself you also spent a lot of time to earn the right to be sitting next to Jeff Bezos supporting him.

Ann Hiatt: 

Yeah, my journey didn't start there. That's often where the interviews start and that's the kind of fantastical part of my story. But I did do a lot of training when I was young. I was a very serious kid. I know how to be a good student. My ambitions have always exceeded my natural talents. So from a very early age, I had to learn how to work harder than people around me to make up for what I saw as differences in natural abilities. 

My very first job when I was 16 years old, was working at a startup back before that term had even been coined. I think I was working for two brothers who had recently graduated from Harvard business school and it was a five person startup called Music Ware which was a tech music inscription software, very advanced for 1995. But I had cut my teeth there and seen a little bit and learned in a five person startup you have to wear all the hats and learn everything very fast. And there's no one to train you. So at least I had those instincts of how to be a good student, how to ask the right questions that serve me well, when I got this job, that was definitely like being thrown into the deepest end of the pool for sure.

Mahan Tavakoli: 

You were even reading the same magazines, newspapers Jeff was reading before he walked into the office.

Ann Hiatt: 

Yeah, I had noticed. So my nerd academic self was like, how am I going to survive here? I have no idea what I'm doing. I didn't know how to invent e-commerce, let alone the gold standard of e-commerce. And I sat down at that desk. It was literally the closest one in the entire company to Jeff Bezos. And I heard these conversations that felt like a foreign language. Thankfully, I literally could speak another foreign language. So I knew how to dissect that. But I started a notebook where I just kept track of all the tech terms I didn't understand. All the people refer to that I didn't know who they were or what was going on in the world and I would do my homework. 

And that's when I noticed that Jeff came in every morning with three newspapers, fully read, cover to cover under his arm. And then he would reference during the day the books he was reading the newspapers, the magazine articles, and I would just make a homework list every day when he was done with those newspapers around lunchtime, I would steal them and read them during my very short lunch break as much as I could to devour it. 

I would read every briefing document that was submitted to Jeff. I read every single email in his box. I listened to every phone call and I used that as my own personal apprenticeship to not only up-level my understanding enough to understand the assignments that were being given to me, but eventually to be able to then be a proactive thought partner in that environment and help them as they were inventing the future.

Mahan Tavakoli: 

Yeah. So you were following up to bet on yourself with a lot of effort put on that bet. It wasn't just the initial confidence to bet on yourself. Now, almost four months after being hired for this role, you ended up almost killing Jeff.

Ann Hiatt: 

I did just a few months into my very first job after university, I almost killed Jeff Bezos and at the time, so this is barely just at the dawn of 2003. Amazon is not yet profitable. We've had a single profitable quarter, but not yet a profitable year. And my very first assignment Jeff gave me was to help him go and look at properties in Texas. And he had walked up to my desk. I think quite literally, it might've been the first time he addressed me by name after he had hired me. He came straight over to my desk with a piece of paper that had a long series of numbers on it. And he said, “I need to visit these properties next week. I've got Tuesday, Wednesday, and Thursday to do it.”

I thought, is this another brain teaser? Because the only two questions they'd asked me in the hiring process, one was a very complex brain teaser. And the next was just about why do you want to work here? So I thought, oh my gosh, here we go again with the brain teasers, why is he giving me this instead of addresses? But it turns out they were GPS coordinates for very large plots of land that he was considering buying in Texas. I and no one else in the world knew why he was considering buying land in Texas. And I didn't discover that until later. 

So I figured out how to plot it out. This is pre-Google maps that did not yet exist. I didn't have those kinds of resources. So it was actually really difficult to plot it out. But eventually I did and I determined these properties were too far apart to visit in the timeframe that he had given me. So originally I went to my manager, John and said, "Hey, this is impossible if they're too far apart, either we need more time or we need to narrow down these options." And John didn't even look up. He was like, "No is not an answer". And I was like, "Okay", went back to my desk. 

And I was like, well, how am I going to bend space and time to make this possible? It wasn't possible to move the jet that we had chartered for this trip, because there were no other runways that made this more accessible and it was too far to drive. What is in between those two? And I came up with the idea of a helicopter. 

So then I went back to John and said, "Hey, how about a helicopter?" And he just nodded like, okay, do that. But I'm 20 years old. I don't have a helicopter in my Rolodex. I have no idea how to go about doing that.

So I eventually figured out I should reach out to the charter company with the jets. They had a relationship with someone in Texas and I hired my first helicopter and Jeff went off on this trip, came back like a kid on Christmas morning. So excited about this trip to Texas. And he said, "Okay, I want to go back in a couple of weeks. I've narrowed it down to a couple of favorites. I want to see them one last time and I'll choose which one." 

Now I'm feeling very confident. I have a helicopter guy. I know what I'm doing. Everything's fine. But at this point I was doing that self-imposed homework every morning. I would come in hours before anyone else often. It was just me and security in the building. And it was one of those early mornings. I was sitting at my desk and my desk phone rang and it was the charter pilot for the jet. And they said they were filing the return paperwork for the flight home the next day, but they had heard an emergency beacon go off and there had been a helicopter crash in the area. They didn't know if it was him. There was no way to know. It was just one of those automatic beacons that happens when something traumatic like that happens. 

My hands start shaking so bad. I can't even hold a pen. I think to myself, I just killed Jeff Bezos. And then it occurred to me that if I just killed Jeff Bezos, the entire company was going to crumble because at that point, all of our stock value, all of our investors and shareholders were invested in faith, in the visionary mind, unique mind that was Jeff. And that might have just disappeared.

Now to make a long story short, you'd have to read all the details in my book. It was Jeff. He had crashed in that helicopter that I had hired for him, but he turns out he was a superhero. He rescued everyone who had been inside and called for help using the satellite phone I had insisted he take. 

And this is only reason why I can tell that story now, because about nine months later, a reporter who was investigating the private space, tourism race around the X prize, figure it out what none of us knew at the time that Jeff Bezos was buying that property in Texas to found Blue Origin which is the company, which has recently been in the news because he blasted himself off into space from that exact property where all of this happened. And so I'm having this crazy full circle moment, 20 years later. But yeah, that's the story of how I almost killed Jeff Bezos.

Mahan Tavakoli: 

You were able to both bounce back from that yourself, but it also says a lot about Jeff Bezos, too. For having confidence in you in the way you handled the crisis. 

So can you talk a little bit about how you handled it yourself? Because this could have been a traumatic setback that you would have reflected on and it would have made you cautious in doing your job from there on out and how Jeff, his confidence in you grew as a result of how you handled this.

Ann Hiatt: 

Oh, you're so right. This was absolutely one of those linchpin moments in my career. I could have let myself crumble and not being up to the task or rise to the occasion. And thankfully I was able to rise to the occasion. 

So after I hung up that phone call with the charter pilots, before I even knew if it was Jeff or not, I thought, what do I do? What do you do when you almost kill Jeff? And so I thought, okay, I need to do two things. 

One, I need to assemble an emergency board of directors meeting. I have only been there a few months. They had no idea who I was making these phone calls. It was an awkward conversation, but I assembled the right team to be able to do the right things.

And we created contingency plans for if it was him and he was dead, if it was him and he was massively injured, if it wasn't him, et cetera, everything in between. And in the meantime, I had to figure out what were the facts, what actually had just happened. And so while they were all getting assembled, some were on a call and hashing out all the contingency plans.

I was calling hospitals in Texas, not using his name. Cause I didn't want to create a press story if there wasn't one or even if there was one. And so I called a couple of hospitals again, pre-Google maps. It was hard to figure out where they might've taken helicopter crash victims. And I just called three, four hospitals who answered the phone like I was crazy when I asked if they had anyone come in from a helicopter crash. And then about the fifth or so they asked me if I was family. So I figured I had found him. It turns out it was Jeff. He called into the office. We patched him immediately into that emergency board of directors meeting. And then when they finished she asked to speak to me.

Now, I thought maybe I was going to be fired, almost killing him, maybe as a firewall offense. But instead he said the kindest words ever said to me professionally, where he said "Ann, I hear you're really good under pressure." 

And he probably said something after that, but I think I blacked out, I don't remember what happened after that. But that was the moment where to your point, that is remarkable that he could see this emergency situation. I'm sure was hyper emotional for him. I mean, he was a young CEO. He had a young family, his boys were very young. His life probably just flashed before his eyes and he had the wherewithal to see the capabilities of his team and to be supportive like that. 

And then second, I think even more importantly, was it changed the way I saw myself. That comment of his changed the way I saw myself. And from that moment forward, I no longer saw myself as 20 year Ann and who had no business having this job. And Jeff didn't see me that way either. And he started giving me projects that were far outside the job description of a very junior member of his team. And that changed the next three years of my life, of the two of us partnering together.

In fact, I did an interview with the financial times recently where he was asking me, he's like, "Clarify for me what was your job description? What was your title there?" And I was like, it's confusing because in no way, does it resemble what I was hired to do, because from that day forward, he gave me just crazy projects, research projects, launch events, cross departmental, things that I need to do as special projects from the office of the CEO. It was better than business school. Honestly, I cannot imagine learning that volume of information any faster or any better, and it really was all thanks to that fateful day.

Mahan Tavakoli: 

And that single experience teaches a lot about leaders. Both with respect to how you were able to bounce back from it and how Jeff handled that entire process. 

I know you also work with a lot of organizations, both startups, and you have clients all across the globe where they want to become more effective leaders, effective organizations. There is a lot, in my view, to learn from that experience that you had with Jeff. There's one other aspect that I find fascinating, you are. And so is Jeff, probably walking into the room, one of the smartest people, if not the smartest person to walk into a room, however, one of the things that is unique is seeking the sense, seeking disagreement when, you know you're the smartest person in the room. How were you able to do that? And how was Jeff able to do that?

Ann Hiatt: 

I absolutely learned this as a masterclass by watching Jeff. So one of my favorite moments, looking back on my career when I was so young, is how I learned this instinct of betting on myself and seeking things outside of my job description or current capabilities. And I really saw that modeled by a role that Jeff Bezos created called the shadow.

The shadow now still exists. That role still exists, but it's now called technical director. But the original shadow was Andy Jassy. And Andy Jassy has been in the news because he just, now 20 years later has become the successor to Jeff as CEO of Amazon. Now I watched Andy be trained in this. 

So Jeff created that role for many reasons. But if I could distill it down to two main purposes, one was as you're describing to be this dissenting voice, to be the person who was at Jeff's side and poked holes in all his favorite ideas. The one to keep them really honest, helping them see around blind corners, making sure he had all the data and all the information, they had examined every premise upon which decisions are being made. 

And then the second reason is the way in which Andy was capable of doing that. And that is because the shadow was literally called the shadow because that person was always at his side, in every meeting, on every flight, on every phone call, copied on every email. And that person learned the instincts of thinking like Jeff Bezos to like what he likes, hate what he hates, have the same kind of visionary mindset. 

And that I have found, I didn't fully appreciate how rare that was because I've worked for such exceptional CEOs until after I left Google 18 years later and started consulting myself and seeing the varying degrees of humility that are amongst CEOs.

It's a tricky balance, honestly, because you have to be a little bit crazy to start your own company and really believe that you can have this enormous ripple effect in the world. So it takes a healthy dose of confidence. But the ones who are truly successful are those who are humble enough to not only tolerate, but demand those kinds of voices, pushing back on them, challenging their ideas and listening to more diverse voices in the room. That is 100% the pattern of success that I've seen. If those two things aren't both present, this visionary confidence and this massive amount of humility and a heavy dose of curiosity in between it doesn't work. You have to have both.

Mahan Tavakoli: 

I absolutely love the way you put it and demand that dissent and when Ann Hiatt can do it and Jeff Bezos can do it, the rest of us can do it. So now you spent a few years at Amazon, but you wanted to pursue your PhD. That was in your lifeblood. That's what you left Amazon for. Why didn't you stick then to pursue your PhD at UC Berkeley?

Ann Hiatt: 

My dad still asks me that question actually. He still wonders when am I going back to finish my PhD? 

Honestly, so I moved to California originally to do a PhD. I got into my dream program. That was always plan A. Jeff knew that from the day he interviewed me. That was my original goal. I just wanted to work for a few years in between undergrad and grad school to have some real world experience. I thought that would enrich my perspective as an academic.

When I got into my dream program by surprise, the very first try, I moved to Berkeley sight unseen. I didn't know a soul there. I had no idea how to be a good academic. I was honestly terrible at it in the beginning. Because it's so different from tech. But yeah, it was by the time I kind of figured it out and was getting in the flow and felt like I was starting to contribute something of value to my program. That's right around the time when Google came recruiting.

Back then, and even still now tech is a very small world. So we all know each other and tend to trade between the same companies. And so my reputation has preceded me. The things that I had done with Jeff, a lot of those Amazonians had since become Googlers and we're down in there. 

So the first four phone calls, I thanked the recruiter very much, but didn't even ask for his contact information before I hung up. But after a while, he was very clever. And he asked if I was just at least interested in coming down to see the campus. And he was right. I was curious, I had heard, of course, all the famous things about the free food and you could bring your dogs to work. And, I was just curious how anyone got anything done in this kind of environment?

And it was while I was on campus that I had this moment of realizing that this was my tribe. Like really, these were my people. I was missing the pace of tech and I thought I have this formula now. I didn't realize how I was making decisions back then. But looking back at the common denominator between how I've made some theory, tricky, seemingly unobvious career choices at the time where I was always looking for one of the qualifiers is this an irreplicable opportunity? Will this ever come around again? And the answer to that was no.

The stage of what Google was trying to do. They were not yet the dominant search engine that they are at today. What they were trying to do is so revolutionary and so unique that I thought this moment won't happen again. My PhD will remain and I can go back if this crazy company called Google doesn't work out, but I saw it as an irreplicable moment in time. 

The second thing I look for. Because I look for are these, the people that will level me up. Are these the type of leaders that I not only like and enjoy, but that I want to become like? And the answer to that was absolutely yes. 

And then the third thing I always look for in opportunities is this a disruptive company, team or industry? And obviously that was a home run. Check check, check to all three of those.

So I cried when I left my PhD. I'm not an emotional person. So those who know me, know what an exceptional moment that is. It was really hard for me to let that dream go back to the back burner, to take a chance on this kind of crazy thing that wasn't Plan A. I'm so glad I did, but if you had told me that day that I decided to take a chance on Google, that I would stay for the next 12 years I would tell you you're insane. There's no way. I mean, in tech years, that's like I was there for a thousand years. But I loved it obviously.

Mahan Tavakoli: 

You did have wonderful experiences there, including working very closely with Eric Schmidt, who is also legendary. Now, Eric and Jeff have very different personalities. How were you able to effectively partner with two people with such different personalities and even practices?

Ann Hiatt: 

A friend of mine once described me as a personality chameleon, which I think was a very interesting observation. It doesn't mean I disappear. It just means I know how to speak to you in your own way to make sure that the recipient will process that information the right way. 

So you're absolutely right. Personality wise, Jeff and Eric are very two different humans. But they actually have very similar thought processes. So they're very data-driven decision makers. They're very linear .They're non-emotional decision makers. They're also visionaries. They're not making a decision for what's under their feet right now. They're not playing whack-a-mole with problems of today. They are very firmly fixed on their vision on the horizon line. And what's coming. They're often thinking 10, 20 years from now. 

In fact, my NDA with Jeff is still enforced because things he wrote in his vision notebooks, these most guy notebooks he always kept in his back pocket, he's launching now. That's how far in the future he's constantly thinking. And it just fills me with so much joy every time I see them coming to life now. But Eric is similar. 

So I am a bit of a chameleon and I can match personalities and the new types I read. I think I have high emotional intelligence, and I got that very much from my mother. My mom is very in tune with people. She's very emotive. She's supportive. She creates these beautiful environments that create psychological safety before that was even a thing we talked about. I think I naturally emulate that having watched her model, that in such profound ways in my childhood and growing up, she still does today.

I am able to find those commonalities of how I can pitch something that will help them make the best decision possible. And I also remember my role. I think a lot of times when people have trouble communicating in business settings, it's because there's a little bit of ego getting in the way. You either are trying to prove yourself, and you lose sight of what the team goal is. 

And so being able to be effective with both of these very different CEOs, was because they were always a hundred percent focused on their responsibility as a CEO and where the company needed to go. So I aligned myself with that and we were always in complete harmony.

Mahan Tavakoli: 

And that's why you were so effective while there.

Now I would also love to get some of your perspectives with respect to the organizational cultures of the companies that have John Doerr in common and I love OKRs, Measure What Matters is a book I recommend everyone to read. So both of them have some similar systems and approaches, but they have drastically different cultures.

However, if you were to pick commonalities that made the organizations and cultures successful, what were the commonalities? What are the things that you tell your clients now? These are some things to try to nurture in your own culture, along with the individual elements that each organization has to its own.

Ann Hiatt: 

My immediate thought, is there high tolerance for risk-taking? And that sounds obvious now how dominant those companies are, because now we think of them as like these money printing machines. They can handle multi-million dollar losses without even blinking. But when I worked at these companies early stage, that was not true.

Everything was on the line at the time. And a miscalculation or a misjudgment really could have cost us the future of what they were trying to invent. Even in those environments, we celebrated people who are thinking outside of the box especially when in those failures, we got a lot of learning on the other side.

So there were built into the culture as well, very different from each other, built into both cultures. Is this celebration of the accelerated learning that comes from trying something crazy, seeing what you're learning, pivoting very quickly and reinventing it again and just getting really fast.

And so I think that's the commonality of not only hiring people who think differently, who are unafraid of doing things that they've never done before, but creating that psychological safety and that culture of celebration of how much we learn when we are experimenting. That for me is why they're different.

Honestly, if I had to boil it down, what they put into the world and how they do it is very different, but the who that they hire. That bar is the same and it's very high and has been from day one. You have to really prove yourself to get in the door at either company. And that remains true today.

Once you're in there, like that's it, we've tested you. We trust you. And there's a lot of autonomy in how you're going to get things done. And I think in that environment where you're not micromanaging how people are creative or delivering their results, you get really unexpected things.

Mahan Tavakoli: 

And one of the points that you make Ann, is you also say even convert your values to scorecards for hiring. How can organizations do that? Because it sounds like both Amazon and Google were successful at doing that. The recruiting you were doing, you were using that too.

Ann Hiatt: 

Very much. So I'm really glad you brought that up because this is something that I have gone through with every single one of my consulting CEO clients now. It’s whenever they often people come to me for consulting work, when they have the wonderful problems that grow with scale. All the systems they had in place worked really well when they're in the startup phase, now start breaking because of their rapid growth or because of the need for hiring. And they've just lost their way a little bit. 

Our first few sessions are always coming back to, do you have a defined set of core values and mission? Is that not just words on your lobby wall back when that was a thing. But is this something that's part of your conversations? How you make decisions? How your employees make decisions when you're not in the room? Do you have a very clear playbook for how to choose between good and good? Because choosing between good and bad, any of your employees should be able to do that, but choose between, we could bet on this or can bet on this? That's the art. That's where you get the magic.

So at Amazon, those leadership principles, there are now very famous. If you apply for a job and you go to amazon.com/jobs, it actually takes you to their leadership values first. Now I think there were 16 at the time I was there when they were creating the original team. I can still recite from memory those original 10 leadership principles. Not because anyone asked me to, but because they were cited constantly in daily conversations as we were making decisions. 

And so if you were thinking about, okay, how do I choose between A and B. Your answer was in those values. 

Google is very similar. I can recite for you the mission statements. I know the values. I knew exactly what we were hiring for. 

So yes, then once you have that firmly established, this is what we're doing and why we're doing it. And a lot of CEOs forget to answer the why for their employees, which is more important than the what, I think. Then you need to translate that into hiring practices. And it was really fun. 

I was teaching a course in Barcelona master's course in innovation. And I had the students do this, write down their core values, cause they all want to be startup founders one day when they finish their masters. And so I said, we'd worked, spent a lot of time crafting those missions.

And then I said, okay, translate that into hiring questions and then interview each other and see if your good culture fits for each other's companies. And the end of the exercise. Did you get the data you needed to measure? If they are value aligned and all of them are like, no. 

So I think a lot of execs need to take that and do the exercise themselves. Be like, are we even evaluating for the way that we get things done here? The way we want to debate really hard issues, the way we make challenging decisions, how are we going to get things done? 

So for me, it's, especially in the scale-up stage, you really need to spend some time in making sure you're getting the right people in the right seats, the old cliche, make sure you hire slow, fire fast. So hard to do, but that process gets easier and you have to face that less when you've really hired for value alignment, more than culture fit.

Mahan Tavakoli: 

What a gem of an insight and for all organizations. I had a client a couple of years back and the CEO had a practice of pulling out hundred dollar bills and awarding hundred dollar bills to people that could recite the mission and the values. And I sort of had to try to reduce his blind spot that was meaningless.

So the point that you made is that it's not whether the mission statement or the values are on the walls or are shared on zoom meetings, or people are given a hundred dollar bills for reciting them. People should know it based on the behaviors, based on the interviewing process, the selection process, the decision-making process. So I think that is critical for all kinds of organizations.

Ann Hiatt: 

And it's really important for how you're rewarding your employees going forward once they're there. I knew what they were at Google because of the 12 years I was there. That's how I was assessed every quarter, not just on my capabilities, in my task, that KPIs, that didn't matter. That was a given, I'm smart. I better be getting the KPIs done. 

But the part of my evaluation that mattered the most was how value aligned I was behaving. And the original reason that Amazon spent so much time creating those original 10 leadership attributes was because Jeff realized that very important decisions that were going to be made in rooms, he couldn't be in. There's no way he could be in every room where critical decisions are being made. So he needed to be sure that there was a way for him to be represented in each room and that's how it became. 

And so, yes, it's how you debate things, how you're making decisions, how you're performing and interacting with each other. And that has to be tied to how you're rewarding and celebrating behavior, not just how you get in the door or who you fire, but the in-between as well.

Mahan Tavakoli: 

So now you've spent 12 great years at Google. Why move on from Google?

Ann Hiatt: 

It was so hard. That's another moment. One of the few moments I got very emotional. Honestly, it was because I went back to those first three things. I've loved the people I worked for. I madly respected each and every one of them, they're still my family today. But I wasn't being challenged. I wasn't able to reinvent myself. Everything was at that point semi in my comfort zone. 

Well, Google is a very innovative company, is doing insanely cool things that no one's ever done before. That remains true. I myself, within my skillset, couldn't break through to the next level, in that beautiful nest of a comfort zone that I had built for myself there.

Now I did reinvent myself several times. Looking back, I can see that my reinvention while at Google had three-year phases. My first three years, I was on the product team and I was working for Marissa Meyer, who was the VP of search products and user experience which is a long title, meaning we just made really cool stuff to bring in eyeballs and other people figured out how to monetize it. 

Then yes, for the next nine and a half years, I worked for Eric Schmidt, which was an enormous privilege. But the first three years he was CEO, which meant our tasks were one type. Internal strategy, mergers and acquisitions. Those kinds of things were our focus. 

Then he transitioned to becoming an executive chairman and we had to invent what that even meant. He'd never been a full-time chairman before. Google never had a full-time chairman before. So we had to invent what our contribution to the company and society was going to be.

And so I can see these three-year chunks of how I reinvented myself. Then after that third round within Eric's office, I just realized that that next reinvention wasn't capable there. I explored lots of opportunities. It just felt like the right move to terrify myself a little bit.

In fact, I even went back to the Google IPO letter and in the Google IPO letter, Larry, our co-founder wrote that he wants to remain uncomfortably excited about what he's working on. And I realized that was the challenge to me. I needed to be uncomfortably excited. 

So I decided to completely uproot every element of my entire life. I moved from Silicon Valley. I sold, donated every single physical thing I own that didn't fit into two suitcases and moved to Europe and was very much a nomad for about 18 months in the London office. I was in New York. I was kind of everywhere. And then I settled in Spain. 

And now I've had to become constantly uncomfortably excited about what I'm doing as a consultant, because I've had to distill these best practices, these secrets of Silicon valley and see ways in which it does and doesn't apply to companies in different continents of different growth scales. And I've really had to figure out what is the core element? How do I boil this down to its root true principles self that are universally applicable to all these leaders who are trying to do innovative things across the world.

 And that has been an enormous, terrifying challenge that has taught me so much about myself and given me irreplicable opportunities. 

So, yeah, it's been really scary and I did not know that, less than a year after that the pandemic would happen. So that was an additional challenge I didn't expect, but honestly, it's been the biggest accelerant of my learning by far over the last decade.

Mahan Tavakoli: 

And you've taken on a real challenge Ann because part of the challenge I find, I'm in Greater Washington DC region. Most of my clients are in this area. A lot of times when they hear things about practices of Silicon Valley companies, it's almost as if that we're talking about Mars or Neptune. What are some of the principles that you believe transfer beyond just the isolated Silicon valley bubble?

Ann Hiatt: 

I think we've touched on some of the most important ones already. Being very, very clear on your mission and values that's beyond your business plan. So many people get distracted with the details of the business plan or distracted by pivot tables with investors. That's not where the magic happens ever. It's about who you're serving, why you're serving them. 

And again, it always comes back to the who, for me. Knowing exactly your avatar of who you're trying to serve and then surrounding yourself with the best quality talent possible to be at your side to invent this reality, is the magic. 

So if that foundation isn't yet set, there's nothing I can do to help you. We have to solve that. That's your bedrock upon which you can build.

Then it's about, yes, we look at product market fit and we look at what's changing and we kind of anticipate pivots that are happening in industry and opportunities to be the disruptor rather than the disrupted. But really for me, it's about that.

Yes. There are different challenges for European founders than there are for Americans. There tends to be less runway because your investments that you're able to get is much smaller, there's a higher burden of proof of concept. In the states you can get a lot more money just based on a really good idea than you can in Europe, you absolutely have to have some kind of proof of traction. So the burden is higher. European CEOs have to think globally much earlier which is both an advantage and a disadvantage because when you're thinking globally, you're able to scale smoother than my American counterpoints, but it also gives you a big challenge of having to design for multiple languages right away, GDPR thoughtfulness.

You have to be very aware of different cultural tolerances for the changes you're trying to instill. So again, I think there's more advantages to that than disadvantages. But it can be a big burden for a very small team to have the enormity of that right away. 

So there's these things, there's pros and cons to each, but I try and be very mindful of, if I have a founder in Germany, the tolerance for failure is much lower or especially in Asia, absolutely unacceptable, to do that. To even attempt to be an Entrepreneurial at all is very exceptional. 

And so there's things that I need to be mindful as I take clients from different regions. What I love to see is honestly, there's more commonalities than differences in what we're trying to do. This was the major motivation for me writing my book Bet on Yourself because when I was approached about writing a book, I said no, no, no, no. If people want to learn the best practices of Eric Schmidt and Jeff Bezos. They should just go read the books written by Jeff Bezos and Eric Schmidt. But what I found was a lot of people, as you were saying, opt out and they think, well, that would work for Jeff or that works at Amazon or Google, but that would never work here.

And my goal in writing this book was to show you no, no, no, these best practices and habits of super performers apply to us normal people. And so my book, I use my career as a case study to show you that anybody can accomplish these big things by taking this playbook of best practices, because there was nothing exceptional about my opportunities or my job titles or my education or background. I just learned to recognize opportunities and do what I call engineering serendipity, creating your own luck. When otherwise, if you're unaware of it, your options might appear limited. But when you know what to look for or what to bet on, you can get extraordinary results out of seemingly ordinary opportunities.

Mahan Tavakoli: 

I love the way you put it Ann. Bet on yourself by creating your own luck rather than waiting for the luck to happen. So as you do that, I also wonder, Ann has this always been a part of you, the betting on yourself, or is it something that you grew into? Because I also learned that you were not much of a runner. All of a sudden signed up for a half marathon and went for it. So is it something that was always there in Ann, or is it something that was nurtured based on what you saw in the environment around you?

Ann Hiatt: 

Yeah, 100% not my nature. It was all thank you universe for nurturing me towards this tenancy, because I think had I not been thrown into the deep end of these very challenging environments, I wouldn't have learned to trust myself so early. Hopefully eventually over the course of my life, I would have got there, but what a blessing that I was not given the opportunity to stay in my comfort zone because that didn't exist. If I was going to survive at Amazon, even past day one, I had to learn to just swim rather than sink. 

So, no, my nature is very timid. When I was small I knew the answers in class, but I never raised my hand. I wanted to be a hundred percent sure that I could get a 10 out of 10 and do everything perfectly before I was willing to even attempt it, because I thought like that .Even a nine out of 10 would be a crippling failure. But what I realized from this beautiful unexpected career path was you just dust yourself off. You just get to try again. 

So I love the example you brought out from the book. Yeah, I did sign up for my first half marathon. Having never even run a 5k. In fact, I'm a terrible runner. And when I was young, we had to do the presidential fitness challenge in PE at school. And I remember not being able to complete the mile. I am just not naturally endurance. I was really good at sprints and hurdles. I think my muscles are just naturally built for that, but like the long distance. And this is now I'm saying it out loud, such an obvious analogy for my career, but that was a skill I had to learn.

I'm really good in these short bursts. I'm built for that. I'm comfortable for that. I can conceptualize getting from here to that a hundred meter dash finish line, but the longevity of it often was paralyzing and I'm so glad. And this is an exercise I go through in the book several times as a core framework of the book is how do you break down these big goals you might have for yourself, your moonshot ideas that bring you the most happiness and meaning in her life and make it less intimidating through these sprint challenges. And really getting that in return in investment in your efforts. I was an apprentice to the best and I learned it absolutely by watching these super performers and honestly, anyone can do it too.

Mahan Tavakoli: 

And that's why your book is a contribution to all of us, because it teaches us how we can also bet on ourselves. It's not something we're born with. It's something we can nurture in ourselves with the frameworks and exercises you also share. So in addition to your book, Ann, are there any leadership resources you find yourself typically recommending? To whether it's a CEO you're guiding or for leadership perspectives.

Ann Hiatt: 

There's so many resources. I continue that habit that I learned from all three CEO's that I've worked for. It being insatiably curious, like constantly consuming a lot of information. So I protect an hour of my time every morning where I'm just fueling myself with knowledge. 

So I'm reading , I quote Harvard business review minimum once a day, often 10 times a day. So I subscribed to that and I read that a lot. I listened to so many podcasts. I'm always looking for best practices. I read voraciously minimum, two or three books a week. I want to continue that habit of making sure I'm on the forefront of best practices and being inspired by different practices, different experiences that don't resemble my own.

I know I come from this weird, yes, Mars world of Silicon valley. I don't want that to limit the way I approach problem solving or entrepreneurship. So I try and make sure I'm listening to as diverse of voices as I possibly can. And I really encourage my CEO clients to do that as well. Have this part of your daily practice, because as CEOs it's so easy to just give, and try and be in problem solving mode and you really have to fuel yourself, give yourself that foundation. Again, so that you can give so much to your company. 

And I highly recommend doing, Thinking Retreats. That was something modeled for me by all my CEOs, as well as prioritizing, stepping away from your day-to-day routine and giving yourself time for reflection, because that's your number one job as an entrepreneur, whether you're an entrepreneur of self ,of your own career, that's really important.

Or if an organization literally as a founder or CEO, Equally important. And I find us individual contributors if you're just being an entrepreneur within your role that you've had for awhile, even more critically important to step out of the day-to-day flow, reflect on how mission, vision, and value aligned to mine, because that's really how you future-proof your career and your company making sure you're picking your head up.

When I did triathlon training once.Honestly also not a natural forte of mine, the swimming coach, when I was training for the one mile water swim taught me about sighting. She was like, you have to get into this pattern of a couple of cycles of stroke and then pick your head up and make sure you haven't been blown off course by wind or waves, or someone's swimming next to you.

Such a beautiful analogy for our careers as well. If you don't pick your head up, you can find yourself way off course and not knowing where you went wrong. So those are some of the best practices I recommend.

Mahan Tavakoli: 

That is a great analogy. And in helping us do that Ann. Bet On Yourself is a great book. So how would you recommend for the audience to find out about you, connect with you and find out more about your book too?

Ann Hiatt: 

Thank you. There's a single source, it would be the website for the book which betonyourselfbook.com From there, there's links to everywhere. You could buy it everywhere. You can sign up. I've got newsletters, I've got a podcast by the exact same name, Bet On Yourself. And most importantly to me, I have an accompanying workbook. Especially, if you buy the book and pre-sale, you get free access to these worksheets where you can literally download a guide for how to have a promotion conversation with your manager, how to get that big client account. All of these different things, these milestones that we faced in our careers, I've created some guides and some literal heads down worksheets to help you organize your thoughts and really make your big dreams come true.

So, yes, I hope you all visit me at betonyourselfbook.com and I'm also very active on social media. Find me on LinkedIn, Twitter, Instagram, all the things, @AnnHiatt. 

Mahan Tavakoli: 

Ann, I love the fact and I'm glad that you took the challenge and took the time to write the book, to contribute back to people so they can bet on themselves so you can improve even more lives. I also love your podcast and I was listening to one of the episodes where you said, what if we become known as the generation that lived life to the fullest, you were talking about degeneration. We talk about the greatest generation or the generation of the depression. How about this generation we become known for that. And your book Bet On Yourself is a way for us to have a framework, to be able to bet on ourselves and live our lives to the fullest. So I really appreciate all of your thoughts and joining this conversation and sharing it with a partnering leadership community.

Thank you so much, Ann Hiatt.

Ann Hiatt: 

Thank you so much. And it means so much to me that that was the message that resonated with you. That means a lot. Thank you so much for having me on today. It was incredible to connect with your audience. I look forward to a continued conversation.