Brad Johnson: Welcome back to another episode of Do Business, Do Life. We have a special guest, Ann Hiatt, here with us today. Welcome to the show, Ann.
Ann Hiatt: Thanks, Brad.
Brad Johnson: Well, I woke up this morning, I was excited. I didn’t read your book. I listened to it. I’ve got a nice little commute. So, I downloaded on Audible. And such a fun, diverse background you come from. So, we’re going to get into that. I don’t know if you have a sales background, but let’s just say you could, because the hook you open your book with is quite the hook, which is, “Hey, I almost killed Jeff Bezos.” And I’m like, “What?” But how did this come to be? So, let’s just dive right in. I have to hear the story, and I’m sure the listeners will be very intrigued with it.
Ann Hiatt: Yeah. So, my very first job out of undergrad was working directly for Jeff Bezos at Amazon. It’s a long story how I even got that seat. But yeah, just a few months in to working for Jeff, I got one of my first direct project assignments. I was 22 years old, my first big girl job, so I was really excited to have a project assigned to me. And we can get into the long story. But what could have been the end of that story and my career, yes, there was a moment where I thought I had literally killed Jeff Bezos. So, we get into the details of…
Brad Johnson: Let’s do it. Yeah.
Ann Hiatt: Okay. So, Jeff came to my desk one morning and he had a white piece of paper with a long series of numbers on it. And he said, “Ann, I want to visit these properties next week. We’ve got Tuesday, Wednesday, and Thursday to do it.” And off he went. And I thought, maybe this was some kind of like brainteaser or a joke because they were not addresses. But I figured out eventually that they were GPS coordinates, which I thought was strange, but whatever. And this is, again, pre-Google Maps, didn’t yet exist, so I had to figure out using the old-fashioned way where these properties were in the middle of nowhere, West Texas.
But as I plotted them out, these properties were too far apart for him to visit all of them, the amount of time that he’d given me. We’d chartered a jet. It was the first time I’d ever done that. And there’s only one runway. And it was too far to drive to each of these five ranches that he wanted to visit. So, I went to my manager, John, and I told him it’s not possible what Jeff has asked for. And he didn’t even look up. John just said to me, “No is not an answer.”
So, I went back to my desk and thought, “Okay, I can’t bend space and time to make these places closer to each other. We can’t move the jet. The car takes too long. Helicopter?” So, I went to John and said, “Maybe we should hire a helicopter.” He said, “Sure. Do that.” I’m 22. I have no helicopters in my Rolodex, no experience in hiring one. But I went through the charter company and ended up chartering my first helicopter.
Off he went the next week to West Texas to look at his properties and came back excited as a kid on Christmas morning. He had loved what he’d seen. He had narrowed down the properties and he was considering two finalists to decide which one he was going to buy. I and not anyone else on the entire planet knew what he was doing buying property in West Texas.
But at this point, I have a helicopter guy, I have one in my Rolodex. And so, he went back the next week to look at the two finalist properties. At this point in my career, three or so months into my time at Amazon, I really started to appreciate how little business I had having this job. I didn’t understand tech, to be fair to me. Nobody really did. This is 2002. But I had a notebook on my desk where I kept track of all the acronyms I didn’t know, all the people I’d never heard of, the publications that were mentioned, the books, and I just treated it like school.
And so, I came in hours before anyone else at the company. So, it was early one morning. Only I and security were in the building and I was doing my self-imposed homework. And my desk phone rang, and it was the charter pilots. They had never called me before. And they say, “Ann, I don’t want to alarm you.” So, instantly, I’m very alarmed. My hands start shaking so much I can hardly hold a pen to write. And they say, “An emergency beacon has gone off and there’s been a helicopter crash in the area. We don’t know if it’s him. It’s just one of those automated beacons. But with that, you should know.”
And this is the moment where I pause and I think, I have just killed Jeff Bezos. And not only Jeff, but the entire company, because at this time in 2002, Amazon is not yet profitable. All of our investors pretty much have only Amazon standing as one of their last remaining dot-com survivors. And so, I could have singlehandedly taken down the entire organization.
Now, pause for a moment. Think how different the world might be today had he actually died in a helicopter crash that day. But thankfully, we all know that that’s not how the story ends. He did not die. However, it was him. It took me a couple of hours to figure out what was going on. But he did crash, and then the helicopter, the very first helicopter I had ever chartered in the middle of nowhere West, Texas. I have a feeling he likes telling this story because he was truly a superhero. In this moment, I literally still get sweaty palms every time I tell the story, even 18, 19 years later now.
But he saved everyone. He pulled out. So, the helicopter had crashed and cracked open like an egg, and the only water within probably 100 miles of where they were. And the pilot, the ranch owner, and Jeff’s personal assistant were trapped inside. He singlehandedly saved all three, climbed up to the top of the hill next where they crashed and used the satellite phone that I had insisted he take to call for help, which is really one of the only reasons I could tell the story is because he used his real name on that 911 call.
And later, a journalist who was investigating the private space race figured out why Jeff was in West Texas, which was to buy the property, which is now Blue Origin, from which he shot himself into space just last October. So, I tried to think what do you do if you’ve killed Jeff Bezos. And so, I called my manager, John, and I say, “Tell me what’s happening.” And he said, “I think we need to put together an emergency board meeting because at this point, I still didn’t know if it was him, if he was dead, alive, injured, etc.”
And I assembled a board meeting of people who’d never even heard of me before because I’d only been here a couple of months and we had contingency plans for every possible scenario of what was happening. Finally, find him, again, pre-Google Maps, so I have to physically look at a map and think about if he had crashed where I think he was, where would they have taken him? So, I called all the hospitals until I eventually found him, patched him into the board of directors meeting. He told them not to issue a proactive statement and then he asked to talk to me. And I thought, perhaps, I was about to be fired from my very first real job because almost killing your boss maybe is a firable offense, but instead, he said, among the nicest words that have ever been said to me professionally. And he said, “Ann, I hear you’re really good under pressure.”
And I start the book with a teaser on that. And I like that you started the interview here because I think it sets a really important sliding door moment in my life and career, where him acknowledging that I was really good under pressure did two really important things that changed the course of my life and career after. One was he no longer saw me as the 22-year-old who has no business having this job, who is untested, who may or may not be able to hack it. He could trust me. He could give me assignments of things that far outside my skill set, my seniority, my experience, my playbooks, and trust me to figure it out. I could keep a calm head. I knew how to assemble my experts, and I knew how to ask the right questions to get to the right results.
And most importantly, number two is it made me see myself that way, where if I fell unprepared for a situation or a challenge, or if I’d made a huge mistake or embarrassed myself in front of people whose opinions that really mattered to me, it almost became my mantra, I would just be like, “Well, it’s not a helicopter crash.” And I could trust myself to just be brave and do the right thing and make the best of it, learn from it really fast, pivot, and do better next time. And so, that is the fiery start to how I got my beginnings in tech, which was very unexpected career path for me.
Brad Johnson: Yeah, you have quite the story. And that was at 22, right? And were you headhunted? I believe you were headhunted into that job, correct?
Ann Hiatt: Not for this one, but this is the last time I ever interviewed for a job. Since then, it’s always been headhunting. So, I graduated from University of Washington, Seattle, which is my hometown in 2002. So, we had just experienced the dot-com bust. The economy in Seattle, even back then, was very tech-heavy. We had Redmond, Washington, which is where my parents still live to this day is the headquarters of Microsoft. It was just very, very early tech adopters, just like Silicon Valley. So, the entire economy had basically disappeared overnight.
While I was studying in undergrad, I worked two student jobs. One was at Suzzallo Library reshuffling books, and the second was at the European Union Center, which was really close to my heart because I was majoring in international studies, focusing in Europe. The Euro launched in 2002. So, it really woke up my curiosities to global economies and it made the world feel like a much smaller place. And so, yeah, it was kind of in that environment that I was coming out of my undergrad, but I had applied it like a hundred-plus places and didn’t get a single phone call back, even for free internships, just because the economy was turned completely upside down, reminiscent of 2008 or maybe even this moment in time as we’re recovering from the pandemic. Yeah, it’s an interesting ecosystem that reminds me a lot of that original time.
So, the Director of the European Union Center is the person who suggested I apply to Amazon because his wife worked in recruiting there. That one offhanded comment changed quite literally the course of my life. That’s the only reason I applied there. It took me nine months to get that job, but once I got that job, it was like a rocket ship.
Brad Johnson: Actually, one of our team members at Triad actually went through the Amazon interview process and he has shared so many insights that came out of that. I’m curious, back in 2002, what was that interview process like? Was it super hard? Obviously, it took you a while, but what was that like?
Ann Hiatt: It was very hard, regardless of what you were applying for. My interview experience is probably an outlier even back then, but it was really, really rigorous because Jeff is a big believer, especially back then. We were trying to do things that no one had ever done before. You couldn’t hire for the expertise and the experience and the skill set that we needed because literally, no one had ever done this before.
So, what he did was he would hire people who are insanely smart, who had long track records of tenacity and ambition and self-starter, and he was looking for smart people who could teach themselves to do anything because that’s really what he needed. We were inventing the future. We didn’t know what that skill set was. So, it was very rigorous. So, my first round of interviews, I don’t even remember what the role was I applied for. But the first round of interviews was with every assistant of the company. I think there was like 11 at the time. This is back in the day when Amazon was in a single building, like one small…
Brad Johnson: Do you remember what employee number you were, just out of curiosity, back in 2002?
Ann Hiatt: I don’t know what number I was, but I know the total number of active employees was less than 200. And now, there’s literally over 1 million. So, I don’t know how many people had come before me that weren’t still there when I joined. But in 2002, yeah, I would say in the thousands probably was my employee number. But yeah, it was a wild time. So, I did one round of interviews. I loved it but didn’t hear back for three months. Then he brought me in for a second round of interviews where he had me in front of all the senior vice presidents, which I thought was a scheduling mistake. It was like, someone’s going to be really embarrassed when they realize they put me in this room instead of an engineer.
But I didn’t know at the time, I was being stress tested because there had been a vacancy in Jeff’s office and he actually, literally assigned three of his SVPs to find my breaking point and to even see if they could make me cry. Not to be mean, but because that’s kind of, you had to have a really thick skin to survive in Amazon at all, let alone in the C-suite. And he needed somebody who was unflappable, very calm. You saw all kinds of different personalities, just would run really fast and just the stress of it would just roll off your back. So, that’s what they were really looking for. And then the final rounds, three months after that, was with Jeff Bezos himself.
Brad Johnson: That’s cool. Just knowing, reading your book, and hearing some of your background, one of seven kids, your dad grew up on a potato farm in Idaho. You were a military kid that moved all over the place, including Alaska, I’m assuming some of that background really helped during that interview process. Is that fair?
Ann Hiatt: Absolutely fair. I think something about being an Air Force brat just kind of forged something, especially since my nature was very timid and perfectionist to a fault, like all the negative connotations of a perfectionist. I would have been really, really held back by that. But being in the Air Force and watching how my mom managed our family, you just had to learn to be very adaptable, to make friends quickly, to be self-sufficient, to be self-soothing or self-aspirational, and to really set your own adventure, especially in a military family where, where you’re living and how long you’re going to be there isn’t up to you. And so, making the most of every opportunity and kind of cherishing each day in and of itself was really important.
And watching my dad, who had reinvented himself from the beginning of time, you can trace my family back thousands and thousands of years, I am first-generation non-farmer in my family. My dad was the first one that broke that mold. He saw the lifestyle and he thought he wanted something different for his life and his family. His out was the military. He became one of the elite. He was chosen as a fighter pilot, which is less than 1% of people who make it through, through pilot training. And he flew the F-4 Phantom fighter jet. And I was born on MacDill Air Force Base in Tampa, Florida, and then my next two sisters in Anchorage, Alaska.
And there’s just something, I don’t know, really powerful that comes from those environments. Watching my dad give himself permission to have a dream that no one around him even had let alone knew how to accomplish and my mom also being really resilient and she had never been outside of Idaho in her entire life until she was following my dad around finishing pilot training and to watch her become so strong and adaptable. She was very young and she just really made it her own. She wasn’t going to sit back and kind of be this lonely military wife. She was going to create a life of adventure for herself. And so, she really taught me how to be resourceful and to dream big also. So, I think I’m an interesting combination of my dad’s left brain is and my mom, who’s an artist, like very creative and emotionally intelligent, and somewhere in there created the skill set that ended up working out pretty well in tech.
Brad Johnson: Yeah. Well, our time is so limited, so sorry. I’m just throwing questions at you here.
Ann Hiatt: Let’s go.
Brad Johnson: Your dad’s callsign as a pilot, you have to share that quick story because it’s such a fun one.
Ann Hiatt: It is. So, yeah, when we were stationed in Anchorage, Alaska, on Elmendorf Air Force Base, there were screenwriters who were writing a movie about pilots. And they want a permission to listen to cockpit recordings because they want to get the lingo right. Pilots love to tease each other. They have very shorthand, lots of acronyms. And so, they wanted cockpit recordings to get the script right.
So, Air Force gave the permission for them to listen to my dad’s flight squadron’s recordings. That movie then was returned to the Air Force and they could approve it or reject it. And they didn’t love how the pilots were portrayed, so they pulled their permission to call them Air Force pilots. However, the Navy had no such reservations, so like, “Sure, call them Navy pilots.” And that movie was Top Gun, the original Top Gun.
But as they were listening to the cockpit recordings and getting the lingo down, they also kept all the call signs of that flight squadron. And my dad’s callsign is Goose. And so, the character Goose was based on my dad, who was a good family man. However, he has a couple of objections. He loves that they kept him a good family man. He doesn’t love that they killed him. More than that, he objects that they made him a navigator and not a fighter pilot, which he was. And his third and last objection was he’s not Navy, he’s Air Force. But otherwise, it’s a great claim to fame. So, I am Goose’s daughter, the original.
Brad Johnson: Yeah, you’ve had such an adventure of a life. And it started with your dad. And I’m sure, there’s a lot of other family stories in your history. And by the way, I don’t think I even mention the name of your book. So, Bet on Yourself, which came out two years ago, was it ‘01 when that’s released?
Ann Hiatt: Yeah.
Brad Johnson: So, a lot of these stories, by the way, if you’re listening and you’re like, I need more of this, we’re going to give away a lot of copies of your books to listeners. So, Ann, I appreciate you coming on. So, let’s jump from, are there any other learnings during your time on Amazon? I’m sure we could fill a whole episode if you had to pick one or two things that this is an audience of financial advisors, entrepreneurs, independent business owners out there that could help them. Before we get to the Google season of your life, what would those be?
Ann Hiatt: I mean, you’re right. This could be a 10-part series if we dissect all the things that I learned from Amazon. It was my personal business school. I consider the greatest privilege that the universe has given me, that I got to sit literally at the desk physically closest to Jeff Bezos’ in the entire organization for three of the foundational years. If I had to choose just a couple of lessons, one I teased already, which was, especially when you’re starting out as you’re scaling, prioritize people. I strongly believe that people matter more than perfecting your business plan or a lot of those other core deliverables they teach you to think about in an MBA.
Jeff taught me to prioritize the people and surround yourself with the highest quality people, not only in how smart and resilient they are, but are they honest? Are they passion and mission aligned with you? Jeff really taught me about humble leadership, which usually gets a little bit of a funny look. When I say, because probably not the first word that comes to mind when you think of, at least today’s version of a jack space cowboy version of Jeff Bezos probably isn’t humility, but it is 100% the secret to his success, especially in those early years that I spent by his side. He surrounded himself with people who he not only tolerated but demanded tell him the truth.
He had a full-time role called the shadow, which is now called technical director, where that person’s full-time job was to be at his side, copied on every email, in every meeting, on every flight, literally shadowing him 24/7. And that person’s full-time job was to poke holes in all his favorite ideas and make sure he was looking around blank corners and didn’t get too comfortable and rest on his laurels. He knew he needed someone in that role. And when I look at CEOs now, that’s often a big differentiation. When I consider taking on a new client, I often first want to meet their leadership team because it tells me a lot about the character of the CEO themselves, the team that they’ve chosen to surround themselves with. And then, I could go on and on. Sorry, I was going to quickly choose a third, but it’s so hard. I think it’s like…
Brad Johnson: Yeah, go. If you’ve got one, go for it.
Ann Hiatt: It’s a floodgate. Now, we’ve opened floodgates. I have so many ideas. But if I had to pick one to wrap it up, the top three would be his risk tolerance, which for me was so eye opening. And now, at least looking back, it seems like he had a crystal ball and everything was very obvious and the path forward was there and the money printing machine was going from day one. Incorrect. What I really wish people would understand was how much calculated decision making was going on. We did not know what would work out. There’s a lot of famous results of huge failures that Amazon had.
But the reason why it didn’t break down the whole company and the reason why he was able to be profitable when very few others could after the dot-com bust, was he considered every decision an experiment. He never just made a decision once and they never touched again. He would make a decision. And in that meeting, we would then lay out what I now call the green lights and the red flags. We’ve made a decision today documented based on these premises, this information, this data.
If our decision is correct, we expect to see these following green lights turn on and very, very specifically laid out what we’re looking for. If our decision is incorrect, if there is data we didn’t have a premise upon which, which wasn’t steady, we will see these red flags show up. And that gave us indicators when we need to circle back. Either it’s all green lights, then we need to replicate this decision making across other areas of the organization, or red flag indicators, like time to come back. Let’s see what’s changed in the meantime and let’s pivot and do it better as fast as possible. So, I think that in and of itself taught me probably one of the most important executive lessons for me, which is, yeah, consider every decision and experiment. And I think that’s why Jeff has remained or Amazon has remained very, very, very competitive even several decades into their journey.
Brad Johnson: Yeah, I love that because I think a lot of times people get so stuck, it’s like, “Oh, this is a final decision and it’s irreversible.” And it’s like, “No, this is kind of experiment. And yes or no, I love them. I love that.” Yeah, go ahead. Did you have some thoughts there?
Ann Hiatt: The way you describe that reminds me of Reid Hoffman talks about it as one-way door or two-way doors. And there’s very few decisions that we actually make as business leaders that are a one-way door. It’s like we can never come back from this decision on, less than 1%. Most of them are two-way doors. We can come back, we can revisit, we can go through it in a new way. We can iterate, pivot. And it’s actually, I mean, you want to be decisive. You want to constantly be changing or distracting your teams. But for me, that is very freeing. As somebody who has natural tendencies or perfectionist in nature and I can have perfectionist paralysis, it’s very helpful for me to be like, “No, no, this is an experiment. Let’s just experiment, gather more data, and then go.”
Brad Johnson: Yeah. Well, your story on, he literally called it his shadow was the role?
Ann Hiatt: Yeah. Literally, the official title, shadow.
Brad Johnson: Wow. I read The Daily Stoic by Ryan Holiday, and this was a couple of days back, but there was a story in there about these Roman generals. They would go conquer civilization and then they would throw a big parade when they came back and they would literally have somebody riding behind them in the chariot and they would be whispering in their ear, “Remember, you will die. Remember, you will die,” just to keep them grounded and like you are not some God, even though all these people are singing your praises. Do you have any idea where he came up with that role? Because that’s what it reminded me of immediately when you told that story.
Ann Hiatt: No one’s ever asked me that before. Actually, I don’t know if he modeled this. Having some historical reference, he is a voracious reader, so it’s very possible that those stories were fresh in his mind. But yeah, I don’t know. I don’t know where he got it from.
Brad Johnson: I just think that is such, as a leader, the most dangerous thing that I’ve seen. I’ve seen a lot of very successful financial advisors that they’re hungry students in the early days. There’s no ego. And then, as success starts to come along, now all of a sudden ego creeps up and now all of those ideas they were open to, now it’s like, “Oh no, I’ve got this figured out. I’m kind of pretty good at what I do.” And I just love that role. It’s literally to check his ego, poke holes. And I just think there’s such a lesson in that. That has to be a big piece, an unspoken piece because I’d never heard that story before, one of the reasons Amazon is what it is today.
Ann Hiatt: And that original shadow was Andy Jassy, who 19 years later was tapped to become Jeff’s successor as CEO of Amazon. That’s how long. This is how far in the future Jeff is investing in humans. People ask me all the time, what’s it like to work directly for Jeff Bezos? And my word is relentless. That is a core value of his. He is very successful because he does not give up in the face of adversity or doubt or speculation, or it’s just he knows his vision, he’s very confident in it. But I think you’re right. He must have seen the need to counterbalance that confidence. He’s insanely smart and always has been. Since he was very, very young, people knew how wildly intelligent and fast learning he was.
But him investing in Andy is just one way that he did that. The average tenure of his senior vice president, his direct reports, is more than a decade. And if you are signing up for more than a decade to an environment which everyone unquestionably would agree is relentless, you have to know that you’re getting a lot in return. So, I would say that’s something that he also did as a leader. If you disappointed him or you didn’t do your best, you were definitely going to hear about it. He did not hold any punches.
But he did that in a way that was investing in you. You knew that you were going to be stronger tomorrow, smarter tomorrow, better tomorrow because of this. And so, it didn’t wear you down. We didn’t burn out because it was– my mantra now is that your job should give as much to you as you give to it. And for me, that’s always been a decidedly high bar. And I think that is what I learned from Jeff and the way he thought about talent, developing talent and investing in people in the long run. There’s a lot of people in the early Internet who burnt through their teams and it was kind of like an 18-month in an outdoor because people just couldn’t hang. He did the opposite.
Brad Johnson: All right, before we get to Google, now, I have to ask the question. I just finished Elon Musk’s biography by Walter Isaacson, and I think people would also describe him as relentless. And I think, even the term they used in the book was he would go into demon mode when he was like, “Hey, we’ve got to get people to Mars. We’ve got to build an electric car.” And there’s a lot of similarities in Jeff’s story and Elon’s story, which is they’re changing the world, inventing things that have never existed before. But I see a different parallel track because Elon is known for just steamrolling people, and then they’re gone the next day if they don’t get the job done. So, I’d love your take. Have you ever met Elon, by chance, in person?
Ann Hiatt: Many times, yeah.
Brad Johnson: Many times, okay. So, if you were to say, here’s some strengths they share and maybe here’s some differences, I would just love to just hear your quick take on that.
Ann Hiatt: I’ve been thinking about this a lot recently because I’m writing a presentation. I’ll be giving at South by Southwest in March. And the title of my presentation is The DNA of Unicorn Leaders. And so, I’m really looking at this. One is I want to dispel some myths, and I think this is at the heart of your question is what makes some wildly successful and what makes others inhibited by the exact same character, seemingly exact same character traits. So, I think I’ve come up with five or so characteristics, which I think are universally true. And to break this down, like a unicorn leader, by that I mean, someone who’s doing something disruptive. It doesn’t necessarily have to have that unicorn valuation, although it applies there as well.
Anyone trying to do just something disruptive should be looking to these traits. One of those five traits is disagreeableness. I personally am not that disagreeable. Probably one of the reasons why I’m a very, very good pair and I’m a very good match with my moonshot dreamers is because I’m the one in the room who’s there with my feet on the ground, reverse engineering these crazy dreams of theirs. I am unwilling. Jeff literally said this all the time. He said, “Entrepreneurs have to be willing to be misunderstood for long periods of time.”
And I think that is a characteristic that he and Elon share. They’re both very willing to be misunderstood, to have people doubt them. Jeff had framed in our office all these magazine covers. It was like Fortune or I can’t remember, Forbes or somebody that had the Amazon.Bomb with Jeff’s face on it, like his head in a box, decapitated Jeff’s head inside a box with Amazon.Bomb. He loved it. He had that on the wall. It’s like pure motivation. He was like, “Watch me, watch me. This is not over.”
But the difference there, if we were to take Jeff’s disagreeableness was Jeff was willing to be misunderstood, very confident in his vision, but he was also willing to be challenged. He demanded to be challenged. If he thought people weren’t holding it to account, you would get in huge trouble for that. And I think therein lies the differentiation.
So, with each of these qualities, I have kind of a Goldilocks methodology with these where there’s definitely too hot and too cold of these character traits, there’s too soft and too hard. And I think, therein lies the the magic. It’s not a formula. Each of that, I’ve worked with hundreds of wildly talented CEOs, some of the most effective in the world, now celebrity CEO status. And I see these five characteristics in all of them, but the ones that really excelled are the ones that get the balance right. So, you can disagree without being disagreeable. You can have very educated debates. You have high tolerance for risks. You’re wildly smart is another one of the five, like your IQ, your tenacity, your willingness to put your head through a brick wall day after day after day are some big things.
But when I look at the cautionary tales like, I don’t know if I can name names, I look at the cautionary tales like Elon or Travis Kalanick at Uber, or Dan, what’s his name, from WeWork? I feel like they exemplify the too hard, too strong, too hot versions of this, whereas those who have been really successful are those who are able to temper themselves. I’m not sure that entirely answered your question.
Brad Johnson: I love that answer. Based on my readings, I think that’s spot on. I wasn’t there firsthand like you were. But that makes a lot of sense. Would you say most days, Jeff was in the Goldilocks range as far as disagreeableness and the other traits?
Ann Hiatt: Most days, not all days. There were definitely some days where he would just get so mad or so upset. I mean, he’s not a perfect human. And this was a long time ago. So, I worked with him from 2002 to 2005. I wouldn’t want someone to make a summary judgment on me based on two decades ago. But that’s what I witnessed. Sitting next to him was most of the time, he kept himself firmly in that just right zone where you are being held to extreme account. But you were understood, you had psychological safety to experiment as long as you were the first one to raise a hand and then say, “I made a mistake and here’s my plan forward,” that’s fine.
But if you heard about the mistake from someone else or you didn’t know how you were going to fix it, that’s not a good day. Yeah, I think that is the art of it. And then as we get into Amazon, this is something that I really learned at an Olympic level from Eric Schmidt, the CEO of Google. I feel like he is almost always in that just right zone.
Brad Johnson: Well, you headed right where I was going. So, let’s do it. So, you move on from Amazon. I think you went back to school for a bit. Did you go back to school somewhere in there? And then…
Ann Hiatt: I did, started a doctoral program. So, I was in a PhD program at University of California, Berkeley. It was my dream program. Yeah, so that’s why I moved to California originally.
Brad Johnson: But then tech came calling again.
Ann Hiatt: It did.
Brad Johnson: And you just had to answer, right? But what’s cool like, before you got to working with Eric Schmidt, Chief of Staff, you actually spent some time with Marissa Mayer, which is another just, I mean, big name in tech, obviously. So, any learnings, this stop with Marissa, before we get to the time with Eric?
Ann Hiatt: I mean, to do Marissa justice, we would also need a 10-part series. I learned so much from her because she is wildly different in personality from all the other execs I worked with and taught me some things I don’t think I could have learned any other way. Her title at the time was VP of Search Product and User Experience, which meant she was in charge of everything that brought in eyeballs onto Google. So, I joined in 2006. Google was not yet the number one search engine, which is unimaginable now, but we were number three at the time, so we were very much in a…
Brad Johnson: Who were the other two? Yahoo!?
Ann Hiatt: Yahoo! And I think it was…
Brad Johnson: Ask Jeeves? Was it Ask Jeeves?
Ann Hiatt: That’s literally what was I going to say. I think so. I think it was Ask Jeeves.
Brad Johnson: Okay, carry on. I was just curious.
Ann Hiatt: We have to look it up. Let’s fact check it. I think that’s accurate. It’s definitely Yahoo! and one other. And so, we just made cool stuff. Other people figured out how to monetize it. We were just making things that would fulfill the mission statement of Google, which is to organize the world’s information and make it universally accessible and useful. So, we were making it accessible and useful through the products that we were designing.
Starting at Google in the product team was just an incredible school, again, of watching something go. Literally, my first day at Google, Marissa was holding an offsite with the entire product team and everyone was there to present the product of the future, like a product that they thought would be core to human lives 10 years from then. Johanna, who’s a very, very talented engineer, who was on the product team at the time, her pitch, it was like the preemptiveness to Google image search. When she presented the idea that computers could recognize an image and be able to search for those characteristics sounded like absolutely insane, like science fiction at the time. But within a couple of years, we had trained some algorithms. And then now, I mean, we all take it for granted that, within my Google photos, I can search for my niece wearing a yellow cowboy hat, and I’ll have it for you in five seconds. So, anyway, that was my first day.
So, I watched things go from like conception to launch to code review to everything in between. And I really saw how the products were made. And my first day at Google was also the first day that we were using Calendar. They had just created a Calendar. We were testing it internally. So, you can imagine the mayhem in the corporate environment when the Calendar had disappeared overnight and we’re using a new system. We launched chats, and that was really funny because on the product team, we would always test things internally first within the product team, then within the company, and then we would launch it outside.
When we were testing chat, they told everyone on the product team, “Add the five people that you ask the most questions of every day and let’s have your conversations this way.” Every single person on the team, I think it was 700 something people at the time, added me in those top five and we broke it within like five minutes. They didn’t expect all that flow to go to me. But Marissa taught me to be the hub of the team, to be that central point to– she called it shark mode. Many people call it swan mode, where it feels very even on the surface, but you’re paddling madly underneath. She calls it shark mode because she never stops. If a shark stops, they suffocate. So, she’s always in go mode.
But I think if I had to pick one thing, one, it was the way she did code reviews because I mean, she has a Masters in Symbolic Systems from Stanford, where she also got her CS degree. So, she has this incredible coding mind, but she’s also very aware of every tiny pixel on the screen, the different gradations in color and how that affects the way you interact with it. She was very much art and science approach, which I hadn’t really been exposed to before.
But more than that, she really taught me how to motivate teams. We were sprinting marathons at the time. I mean, the pace at which we were launching things is just unfathomable to me now, looking back on it. But she made it sustainable for us. She added in celebrations and acknowledgments and she made it a safe place to experiment, to fail. And sometimes, we were working on things for years at a time, but we would launch it, and then some kind of new tech came out, like the iPhone, for example, that made what we had just built, put our blood, sweat, and tears into a completely irrelevant overnight. And she was able to keep the team engaged and motivated despite these kind of challenges and setbacks, and I think was an enormous part to Google becoming the number one search engine before she left and became CEO of Yahoo!
Brad Johnson: Yeah. Wow. You should write another book. I know you are. But these stories are awesome. So, one of the things that Triad and, obviously, our clientele, our financial advisors all over the country, we built some cool products. And I won’t put them on Google level yet, but I’m curious as to, if you look at the methodology of which you went from ideation to actually like it’s real world, I mean, exists, I’ve heard a term from Microsoft where they say, “You are not your idea.” Like, throw the idea out, don’t attach your identity to it. I’ve seen oftentimes, when somebody dreams something up, you’re an artist, you build something, and then somebody is like, “Ah, that kind of sucks. Do it this way so that there’s resistance.” Was there anything in your learnings there that allowed because you said you’re just getting products out the door so quickly that decreased that resistance and allowed people to work together better?
Ann Hiatt: I think it does go back to that, what I mentioned at Amazon of learning that decisions are just experiments, not a final touchpoint. So, there was definitely that same culture there where, whenever we launch something, and I think this is a differentiator even still today between, for example, Google and Apple. Google, we were very open with the fact that we were going to launch this before they were finished purposely. We will get them between 70% and 80% of where we thought they needed to be, and then we put it out in the wild because we were often surprised the way in which our users would choose to use it or integrate it into their lives. And so, then we could do that final 20% tweaking to what they were telling us they wanted it to do.
Clayton Christensen, the late, amazing Harvard business professor, he says, he frames it like, “Don’t lose focus on what your customer client is hiring you to solve.” He puts it much more eloquently in his book, The Innovator’s Dilemma, but we think of that all the time. So, Marissa really taught me to love that iterative cycle, to let something go out into the world in an imperfect state, to listen to your users rather than it being a closed feedback loop.
Obviously, Apple is one of the top three most valuable brands in the world, so it’s working for them. But I see this as a differentiator. Apple polishes it, perfects it, seals the back. You can’t tweak it. You can’t take it apart like a toaster, like you can with Android phones, for example. And then they tell you how to use it, works great for them, the products are amazing. But Google does the opposite of that. We want you to feel part of the development process. And so, I think that expectation, that constant iterative cycle was really helpful in it.
And to go reflect back on what you said at the top of that question, at Google, especially on the product team, we would often say to fall in love with the problem, not the solution, because as time goes or tech emerges, that right solution changes over time. But the problem probably stays pretty consistent, the problem that your clients or customers have hired you to solve. So, don’t fall in love with the solution. Fall in love with the problem and constantly look at your experiments again and say, “Given where we’re at now, what we know now, more data, new technologies that have emerged, how could we solve this problem in a better, iterative, faster, whatever way?” And I think that’s what keeps them constantly innovating, even now. Google’s 25 years old now, which is crazy, 25-year birthday in September, and this is how they’re staying on the forefront. I don’t know. I think, generally, I was going to turn all of tech upside down in the next year ago, but they’re still very, very, very relevant 25 years in, which is not a small task.
Brad Johnson: Yeah. My first corporate job, I was sitting at my computer buying Google IPOs, which at the time I was in IT, that’s probably why I’m in finance now. But that’s crazy. That dates me a little bit when you say that. I still like to think I’m nice and young, but…
Ann Hiatt: Me too, but I’m not.
Brad Johnson: I love that phrase. Fall in love with the problem, not the solution. I’m borrowing that, I’m taking that one back, so…
Ann Hiatt: Take it.
Brad Johnson: Okay, cool. So, there’s your time with Marissa for about three years at Google when she was there and then you spent almost a decade. Was the whole decade with Eric Schmidt, was that as his Chief of Staff the entire time?
Ann Hiatt: I invented it mid partnership. So, when I was first recruited by Eric into his office, he was CEO. He had been CEO for about seven years. At that point, I didn’t know, but he had three years left on that. When he was hired by our founders, I still say our, even though I left Google six years ago, still say we, it’s a hard habit to break.
Brad Johnson: That’s okay. You help do a lot while you were there. I think that’s okay. You earned it.
Ann Hiatt: I hope so. I don’t think they mind. Yeah, he was still CEO and he hired me to come on to his team because it takes a long time to build a deep partnership with a CEO. You had to get to that mindreading stage where you seemingly have a crystal ball and you can predict every question they’re going to ask and like what they like and hate what they hate. That’s years of work to become that mind double. So, he wisely brought me in three years before he needed me to be at that level. So, I joined his existing team, got to know all the SVPs, built very deep relationships of trust with our board of directors, with our investors, etc. And then he became executive chairman.
Now, Google had never had a full-time executive chairman before. He’d never been one before. So, we really needed to design his role from the ground up. We spent, Eric and I, almost a full year deciding what those metrics were going to be, what his role should be, what do Google need most, what our users need from him in return. And then I designed his role, his deliverables around that. At the same time, I clearly need to redesign my role because my job is just to make him the most effective CEO he can possibly be. To say, it’s very high bar. But that was my job.
And so, because his role had changed so dramatically from CEO, which was very internally strategy focused to now chairman, which was almost 100% fully externally focused, I had to redesign my job. So, we’d been doing a lot of work around external communications and policy because a big part of his job was really kind of the statesman of tech where we were translating emerging technologies for everyday users, but also very importantly for dignitaries, heads of state, legislators, educating them on these technologies so that they could legislate according to the value of their constituents coming from a place of understanding rather than fear. That was a big part of our job. So, while we were working with so many policymakers, I saw this job called Chief of Staff, especially when we were partnering in the White House and working a lot with the Obama administration in early 2008, right? Forgetting my years, anyway, the very earliest years…
Brad Johnson: Sounds right.
Ann Hiatt: I think so. I saw this role in government called Chief of Staff, where it was this right-hand thought partner, business partner to the executive who had all the contacts, who was the sounding board. And I remembered, I talked back to Andy Jassy, and I thought, “That’s what Eric needs now. He needs someone who can play that role, who can challenge his ideas to spitball reactions, to take massive amounts of information and synthesize it down to a single action item or course of actions.” And so, I designed my role.
No one at tech at all had ever been Chief of Staff, it didn’t exist. So, it took me a couple of years. It took me almost three full years to convince HR internally at Google that this was a real career path to design the job ladder, the metrics, how I would be measured. So, I was the very first one at Google ever and in tech. And now, it’s pervasive throughout the tech industry, this role of Chief of Staff that I designed based on the inspirations from government and from what I’d seen at Amazon. Yeah, I worked for Eric for a decade and more than half of that, I would say, like probably nine years of the 10 years I worked for him, I was Chief of Staff. How long I officially had the title is slightly shorter.
Brad Johnson: Well, let’s hit on that, because one of the things I see in the world of finance and we’re fortunate we work with some very successful independent financial advisors, but oftentimes, how they get in the business, kind of a solo entrepreneur. We call it the advisor in charge model, where they’re the constraint, everything comes through them. Then we help them move to phase two, which we call a business owner, actually, true divisions and structure, phase three as CEO. But I will say in all three of those stages, even some very, very successful, like multi, multimillion revenue firms, there’s no executive assistant, there’s no Chief of Staff on the org chart. So, I’m curious your take, if you said here’s an EA role, here’s a Chief of Staff role, here’s the difference. Because I think it’s an education thing in finance, just like you kind of invented the role at Google, they’re like, “Wait, what is it? Why does it need to exist?” So, what would be your take on that, Ann?
Ann Hiatt: This is probably one of the most in-demand questions I’ve been getting over the last couple of years, because this is now seeping out of tech and then everyone’s kind of heard of this. And it’s a very, very misunderstood role for very good reasons. So, the reason why it’s really hard for people to understand what is the Chief of Staff and how would I even start to have one in my office is because every single Chief of Staff is bespoke to the executive that they’re partnered with. So, what Jeff Bezos needed was dramatically different than what Marissa needed and light years different than what Eric Schmidt needed from me, the same person with really the same skill set. Obviously, I evolved over time. But each of them needed a different thing from their right-hand partner.
So, to answer your question, I look at assistance, there are about five levels. So, there is the first couple of levels are administrative assistance. This is when they’re learning the business talk, learning the industry. Their tasks are very reactionary. This is kind of core skills, like calendaring and basic logistics, that kind of thing.
Once you get to a senior executive assistant, this is somebody who is anticipating. They’re not reactionary. They’re very much spending almost all their time in proactive mode where this is, when you get to that crystal ball stage where you can be a sounding board for your executives direct reports because you know what your executives are going to ask, what they’re going to want, what they’re going to like, what they’re not going to like. So, people can use you as a resource and a sounding board that’s more accessible than the executive because they’re not. One single human isn’t scalable.
So, I think of a very sophisticated, skilled EA, somebody who can anticipate, who’s thinking very firmly about the logistics of things, not only conference rooms and flights and things, but how is this conversation going to build upon each other? How do we get to the end goal? They understand the business goals of each meeting. How are we defining success here? In a way that most, even executives don’t really think of it that way, how do we build line upon line to make sure we get this result?
Then, the difference between a very senior EA and a Chief of Staff, I think, comes in strategy. So, I think of an EA as somebody who has very high levels of know, like, and trust factor within your internal teams, but also within the company at large. They know how to connect the dots. They’re the cohesive glue between the different silos of your organization. They are cross-functional, they’re able to cross-pollinate all your ideas. And an EA is making sure that that breaks down into your day-to-day calendars, how you’re spending your time.
Your Chief of Staff is thinking about it from an industry perspective. They are able to make very long-term strategy recommendations because they understand where the industry is moving, how emerging technologies are changing that playing field, and most importantly, they’re building up relationships for you outside of your organization, outside of your company walls. So, they’re known in the industry. They know your equivalents at all your competitors. They have deep networks, and so they’re able to bring insights internally and externally for where you need to be showing up your relationships, you need to be building what skill sets you need to double down on, what talent is suddenly becoming available that you need to bring in-house. They sit at a much higher level where they’re part of your C-suite, although not compensated in the same way normally, but they have that level of sophistication of understanding in the industry.
So, it’s very difficult to give a broad stroke definition of the differences because, as I mentioned, each Chief of Staff, some are there who have extremely deep analytical skills and are sitting there and managing all your dashboards. Others are there to help you really with executive communications. There’s lots of different kind of niches you can have for a Chief of Staff, but I would say that’s a broad stroke.
Brad Johnson: Thank you for that breakdown. I think you have the credentials to give us the breakdown there. So, we kind of coach, it goes from tasks to responsibilities to thinking. And what’s interesting is your description there kind of as you went up the assistant, the org chart there that actually kind of really aligns. So, okay, the clock is ticking here. So, let’s get to what you’re doing today, unless there’s any parting thoughts on your time with Google before we go to the book, we go to the leadership strategist, and your work with fast scaling startups today. Any last thoughts on Google?
Ann Hiatt: I mean, Google will always be home. So, I could talk for, I mean, literally hours about the things I learned there. But I think it feels like home because it was very much a place that kept up to that promise I made to myself that my job will give as much to me as I gave to it. It did that in spades. And so, I’m just very grateful for what I learned. We made a whole lot of mistakes. Every day was not fun. Any days were painful, but it was always worth it. So, yeah, I had a blast there. We should do episodes Part 112 or something to really dig into all that.
Brad Johnson: Hey, I’m game. Question, are iPhones allowed at Google?
Ann Hiatt: Yeah, all of our engineers can choose if you want an iPhone or an Android. And most of our engineers designing products are required to have both because you need to make sure it’s working as well on the iPhone as it is on the Android.
Brad Johnson: Are you shunned a little bit if you carry an iPhone around?
Ann Hiatt: 100% no, in fact, Eric probably had quite literally three or four phones at all times. He was the last person to give up his BlackBerry. It’s the truth, yeah.
Brad Johnson: It’s been a while since I’ve heard that.
Ann Hiatt: We’d been prying it out of his hands, but he loves…
Brad Johnson: He loved the clicking, the clicking of the keyboard apparently.
Ann Hiatt: The keyboard is hard to give up. Have you ever used Swype, the Swype keyboard? I look like a magician. I have to show it.
Brad Johnson: Oh, that. That you just kind of reminds me of a…
Ann Hiatt: I literally can do this without looking at my keyboard and type a whole message while keeping an eye contact with you all the time, yeah. It’s magic. I don’t understand how people can type like this on a phone.
Brad Johnson: I have to check that out. We only have time for a short version. So, we’ll let catch us up. What are you doing today? Obviously, we’ve got the book. We’re going to give a lot of copies away, I’m sure, after this conversation. Catch us up. What are you up to today?
Ann Hiatt: Yeah. I very unintentionally ended up doing what I’m doing right now, which is maybe not the inspiring journey that I want it to be. So, when I decided to leave Google, I decided to leave because I felt too comfortable. My career always tends to go in three-year cycles where I take on a really big new challenge. I try and conquer it, and then once I kind of feel like I’ve heard all these questions before or I kind of solid lead the expert in the room at all times, I always look for something else. I get itchy for a new challenge.
So after 12 years at Google, I got really itchy and it just didn’t seem, I couldn’t find it within the organization. Something would challenge me in the way I want it to be or the skill sets I wanted to. So, I decided to do what is kind of a Silicon Valley cliché, which was I want to take six months off and just sit, just let my thoughts follow my curiosities and discover like what excited me most. Because I’ve been working for Eric for a decade, he had connected me with his personal VC firm called Innovation Endeavors. So, a lot of his portfolio CEOs were used to coming to me and asking gut checks on things or getting my help. So, while I was figuring out what I wanted to do next, they looked me in and they said, “Could I get your thoughts on this project or this hire? Or could I bring you on board for three months to help me through this particular growth curve?” And before I knew it, I had a long consulting list with a waiting list.
So, now, I’m five years in and not a single day have I been bored, which is exactly what I was looking for. So, now, I help scaling CEOs tackle some of the problems or challenges that come with growth, specifically around people in operational systems. Those are the specialties that I grew in my past life at Amazon and Google and are very applicable, regardless of what their industry is, what continent they find themselves on.
I’ve kind of learned to pull the silver thread between these things that I experienced in the first half of my career. What are the universal truths that are applicable to CEOs of ambition in whatever industry they find themselves in? So, now, I don’t have two clients who are in the same industry by role. I don’t want accidental conflict of interest. And also, it keeps me on my toes. It reminds me every day that I’m not there to give them the right answers. I’m there to ask the smart questions, suggest some playbooks and best practices that can accelerate their success in decision making. That’s my job in the room, which I think is wildly fun. So, every day, I’m learning.
Brad Johnson: Every day has to be a new day. That would be a lot of fun.
Ann Hiatt: Yeah.
Brad Johnson: And you can do it from Spain. So, that works perfectly, right?
Ann Hiatt: It does, it does. Yeah, I spend all day saying good morning. I wake up, with Singapore and Tokyo, saying good morning, then Dubai, then London, then Germany, then the East Coast of US, West Coast of US. All day, I’m saying good morning.
Brad Johnson: I love it. Well, one final question for you. And this has been an awesome conversation. So, thank you so much for carving out some time to share with me and all the listeners and viewers out there. This is the Do Business, Do Life podcast and one of the things we talk a lot about is work/life integration versus balance, which is, by nature, a tradeoff. I know that’s probably not a normal tech thing. It’s a lot more do business, I think, sometimes than do life, but I’m curious as to what that definition would be for you, Ann.
Ann Hiatt: I really appreciate this is a final question, because I would feel remiss to have suggested, like volunteer for all the things and constantly get out of your comfort zone and stuff without touching on the balance part. There is a reason why I haven’t burned out on tech despite long periods of times of literally 18-hour days. And it goes back to what I mentioned before, which was I’m trying to think of where this came from, but from the very, very beginning of my career, I was very clear with myself what I wanted in return. What did I want to learn? What networks did I want to experience? What rooms did I want to be in? What tables did I want to sit at?
And so, while I was working those very, very long hours and sometimes, like fighting to the death to launch something that then became irrelevant the next day, I didn’t feel depleted by that because I got those expertise, though I met those people, I was in those rooms, I sat at those tables, and that was really meaningful to me. And as I’m pondering this, I think, definitely, this was modeled for me by my CEOs. They also made sure that they were being replenished. Because to be a CEO is a very, very heavy burden and it is lonely at the top. It really is. There’s not a lot of room for feeling supported. And so, all the CEOs I’ve worked with have been very purposeful in making sure that they have ways of rejuvenating themselves in that energy and I try to mirror that back. I could go through their death, and each of those three CEOs that we’ve talked about already have had their own ways of doing that, but they were very purposeful in protecting it and making it non-negotiable.
So, that would be my advice to the listeners is if you find yourself on the verge of burnout, find something that’s rejuvenating that fills you back up and ideally through your work that you’re getting in return for your very hard work, the things that matter to you the most, whether that’s skill set, network, people, impact, purpose, mission, ideally, all of the above. That’s how you prevent burnout in very, very demanding environments.
Brad Johnson: Love that. Well, Ann, thank you so much for your time. This was an incredible conversation. Can’t wait to get it out to the world and until next time, which I hope is sooner rather than later.
Ann Hiatt: Me too. Thank you, Brad. This is a really fun conversation.
Brad Johnson: All right, We’ll see you.