Executive Leadership: Learning Alongside Legends, With Ann Hiatt

Success is not reserved for the chosen few—it’s about finding audacity within and humility to learn. Join us as Ann Hiatt dives into the world of executive leadership and what it’s like to learn alongside legends. She shares her incredible career, from her days as the right hand to Jeff Bezos, the founder and CEO of Amazon, to her pivotal role as Chief of Staff to Eric Schmidt, the former CEO and Chair of Google. In a world where career fulfillment can often feel like a distant dream, Ann inspires individuals to find purpose in their work and redefine their paths. Throughout the episode, she emphasizes the dynamic blend of audacity and humility that drives success at the highest levels. Don’t miss this opportunity to hear what it’s like learning alongside legends. Tune in now!

Check out the full series of “Career Sessions, Career Lessons” podcasts here or visit pathwise.io/podcast/. A full written transcript of this episode is also available at https://pathwise.io/podcast/ann-hiatt

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Executive Leadership: Learning Alongside Legends, With Ann Hiatt

Former Executive Business Partner To Founder/CEO Jeff Bezos At Amazon And Chief Of Staff To CEO/Chair Eric Schmidt At Google

In this episode, my guest is Ann Hiatt. Ann is a Silicon Valley veteran with fifteen years of experience as the executive business partner for Jeff Bezos, Founder and CEO of Amazon, and Chief of Staff for Eric Schmidt, CEO and Executive Chairman of Google. Ann left Google in 2018 after 12 years with the company and has since founded a consulting company with CEO-level clients across the globe where she applies the lessons of innovation, ambition, growth at scale, and forward-thinking leadership that she learned at Amazon and Google to new businesses and the next generation of leaders.

Ann empowers entrepreneurs and executives through practical suggestions of how to develop a corporate culture of relentless ambition and vision while pacing themselves for long-term success. She has a Bachelor’s degree in International Studies from the University of Washington and began a PhD program in Global and International Studies at Berkeley before ultimately leaving the program to accept her role at Google. She resides and works in Spain.

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Ann, thanks for joining me. I appreciate your time.

It’s a pleasure to be here. Thanks for the invitation.

We’re going to do this a little bit differently than the way I have been doing some of my episodes where I have started with the work that the person’s doing. We have to start with your upbringing and career journey because it’s pretty foundational to everything else. You grew up in a military family. What did that teach you watching your dad flying Air Force jets and living the military life?

It did teach me a lot of foundational things that have come into play in my career in seemingly unexpected ways. I was born on MacDill Air Force Base in Tampa, Florida, and spent the first ten years of my life as a military Air Force brat. My next two sisters were born in Anchorage, Alaska. We were everywhere in between.

My dad was a fighter pilot and flew the F-4 Phantom Fighter jet when I was born. He spent most of his career in Alaska. This was during the détente period of the Cold War with Russia. It was a very interesting time for his military service. That’s a whole other episode for so many interesting stories. Even though I’m very timid by nature, especially as a young girl, and I was naturally very shy and introverted, it taught me to be self-sustaining, make friends very quickly, be adaptable to new environments, and rise to challenges.

I saw that modeled by my mom as well. She was an Air Force widow for a lot of his career, running the family solo. That taught me a lot about learning a lot of things fast. My mom had never been outside of Idaho before she married this Air Force guy finishing his pilot training. She was forced to learn very quickly, become adaptable, and be the rock upon which our family was built. All of those skills came in handy during my very unexpected career.

I’m an Air Force veteran. I did not fly. I did engineering work. The people I have talked to who grew up in military families all talk about how they had to learn to adapt. You were moving regularly. You had to learn how to pick up, be in a new environment and sometimes in a new country, make new friends, and deal with a new school. It does teach you to cope with change and learn how to be adaptable. You are echoing what I have heard from others.

I went to three elementary schools by the end of second grade.

Your dad left the Air Force. Your family moved to Redmond, Washington. You were growing up having a firsthand view of the tech boom at Microsoft and other companies. How did that shape your early views of the business world?

My parents had no idea the way in which they were setting me up for this career trajectory. They moved to Redmond, Washington. After my dad retired from the military, he went to law school and got a job in Seattle, his first big job. My parents moved to Redmond because they didn’t want to live in the city. They were both born and raised on farms in Idaho.

We bought a property where our neighbors had horses. We had lots of land and a huge garden, not expecting that less than five minutes from our front door was announced that same year Microsoft headquarters in Redmond. I grew up in junior high and high school. All my friends, their parents were executives at Microsoft. I watched the personal computing revolution happen right outside my front door.

I wasn’t interested in tech for a very long time. It wasn’t until the end of my undergraduate studies that I even considered working in tech but there’s something interesting you pick up in the air, in the environment, and the personalities of the people around you. The energy of the city was very palpable around this tech pace. With the people that moved there, curiosities, and talents, through osmosis, you absorb a lot more than you realize.

You weren’t all that interested in tech and yet you had a teenage job working in tech.

My very first job was at 16. Two weeks later, I got my driver’s license. I was working for 2 brothers who had graduated from Harvard Business School and they were a 5-person startup. I was hired as a receptionist to office manager wearing all the hats. I was in charge of doing whatever needed to be done each day but that was my initial insight into what it’s like to found and ran an early-stage startup. I had no idea how much that was preparing me for my first big job after university.

Even doing what was a lot of relatively mundane work for them, you get a sense of the atmosphere, uncertainty, and ambiguity that comes with being in those situations. I’m sure it prepared you well.

Yes. I was doing a lot of photocopying, answering phones, and things that seemed unglamorous but you don’t realize being in an environment and overhearing the brothers talk about what’s working or what’s not, or closing sales. You get to know the business vocabulary. I was also exposed to literature for the first time.

I didn’t even know that business magazines existed like Fortune and Fast Company. Fast Company was launched that same year that I joined. Those things were around the break room. I started flipping through and getting to know who were the journalists or the movers in the tech world, not expecting me to get to know them on a first-name basis soon thereafter.

You went to the University of Washington. You had designs on being an academic and Scandinavian study. You landed a job at Amazon working directly for Jeff Bezos. You get this question all the time so I will apologize in advance for asking it but I have to. How did you get the job with Jeff Bezos?

It makes no sense. Honestly, I had no business having that job. The short version of it is I graduated in 2002 as an undergrad. As you might remember, that was immediately after the dot-com bust. Seattle was a very tech-heavy city so the entire economy disappeared overnight. I applied to 100 jobs and didn’t get even phone calls back for unpaid internships. I was feeling pretty desperate about it.

It was through a recommendation of the director of a program I was working on at campus that I applied at Amazon. It took me 9 months and 3 rounds of all-day interviews to get that job. I could tell the longer version of the story but the truth is the last interview I did was with Jeff Bezos himself. He was looking for something raw, somebody who was ambitious and unintimidated by him. Even by then, this was the earliest stage of Amazon.

He had been Time Magazine’s Person of the Year in 1999. He was a bit of a local celebrity, not of the stature that he is now but a lot of people were intimidated by him and I was not. I talked to him like a normal person. He found that refreshing and I was excited about what he was building. I got a seat on a rocket ship.

Sometimes people in that situation are looking for somebody who shows a particular spark and upward potential, not somebody who wants to be an admin and do a very narrow definition of the role. He saw that and the broader team there. You interviewed a bunch of the senior people before. You even got to that interview with Jeff. They all saw that in you. Credit to you for landing the job.

Looking back, that is the craziest thing. It’s a sliding door moment. It changed the course of the rest of my life getting that first job with him.

I’m sure you learned many things while you were working there but can you share a few that years later stand out for you?

If I had to pick one, it would be very hard because the three years I sat next to Jeff, I was given the desk physically closest to him in the entire organization. I was at his side quite for 15 to 18 hours a day. I absorbed a lot. He was my business school. He was my mentor. I was his apprentice. If I had to pick one thing, it was about the people, how he hired, retained, and harnessed the power of the people around him. When we were hiring my replacement, he rejected a lot of candidates.

I was very nervous because I was starting a PhD and I couldn’t change the start date of grad school. We didn’t have somebody. I had planned on training someone for a minimum of three months before I left. We didn’t have anyone. I went back to him and said, “Would you reconsider these top three candidates?” He wouldn’t even take the papers out of my hands. He said, “I am only going to hire someone that I have to hold back, not push forward.” I use that as my mantra whenever I’m hiring. I have interviewed hundreds, if not thousands of candidates for both Amazon and Google and my CEO clients. I use that as my bar.

People are constantly like, “Why on earth would he hire someone like you with no experience?” That was it. His bar was he saw someone that he was going to have to hold back rather than waste his time pushing forward, inspiring, incentivizing, and encouraging. He has a lot of systems in the way that he harnessed the intellect, curiosity, grit, and passion of the people who work for him in ways that I appreciate are very rare. Most executives do not approach their teams and systems in the same aggressive way that he did. If I had to pick only one of the many things I learned from him, it was about how to utilize and attract the best world-class talent possible.

I’m sure you have seen it in your time since. A lot of senior people hire people who are unthreatening to them because they have some level of insecurity. Ultimately, he was hiring people who were going to make him and the team better. That story that you told in the book when I was listening to it struck me. It’s the idea of hiring people who you have to hold back rather than push forward. It is pretty rare. From my experience too, the percentage of people that I have seen out there who have the guts to hire somebody who is going to challenge them is a minority of leaders in the scheme of things.

It is, unfortunately. It’s such a shot in your foot. There’s an executive at Google who put it so well. His name is Jonathan Rosenberg. He ran products in the first decade of Google. Jonathan used to say that A people hire A people and B people hire C people. It’s exactly what you were describing. They feel threatened by that but the truth is, people like Jeff, who’s an A person, knew the value of hiring A people around him.

I followed that when I hired my first team and I eventually ended up working for Eric Schmidt the CEO. I was asked to redesign his entire office. I only hired people that I thought were better than me in very specific areas that would fill in for my weaknesses or experience gaps. It can be intimidating. If you do it well, you are at a table full of people who have expertise that far exceeds yours but then each person can be their best self. You should hire A people.

You start your PhD program and head off to Berkeley. You probably break Jeff’s heart at least a little bit. You get this persistent call from Google about coming out there. Ultimately, they convince you to. You go to work for Marissa Mayer, who was not a CEO at that point but became a CEO later. What did you learn from your experiences in working with her?

That’s a whole other episode in and of itself but Marissa was very good at talent recognition. She made a bet with her boss, Jonathan Rosenberg, that she could train internal leaders faster and better than he could hire external ones. The two of them had a bet about hiring the next generation of leaders for the organization. She, by both accounts, won that bet.

I learned from Marissa how to spot talent in its infancy, how to harness it, and how to train the next generation of leaders. I’m talking unicorn-level leadership. We call them soonicorns. “You are not yet there. You need a little bit more experience, exposure, and fire testing.” She was an incredible identifier of early talent and would go to bat for you. If you weren’t yet at the skillset but she saw the opportunity, she would be there to champion, train, and mentor. She heavily invested in her team.

She also taught me to be unapologetic about my ambitions. In my very first interview with her, she told me that she was going to be CEO one day and she did. After working at Google for more than a decade, she was hired as employee twenty, the first female engineer in the entire organization. She was recruited to become the CEO of Yahoo for very good reasons and took on an enormous challenge there. I learned many things from Marissa but, 1) Was about being unapologetically ambitious, and 2) Surrounding yourself with the best quality people. There’s a theme here.

You ultimately became Eric Schmidt’s Chief of Staff and worked with him during his time as CEO and Chairman of the board. How did the experience working with him build on your prior experience with Jeff and Marissa?

I was recruited from Marissa’s office specifically to work for him. I didn’t fully appreciate at the time why. Everyone knew that I had worked for Jeff. Eric had no question that I had been fire tested and that I could handle the pace and the stress of being in a very fast-paced C-Suite with all the global spotlights that we were under.

More than that, what I didn’t know at the time was he knew that two and a half years later, he was going to transition from being CEO to executive chairman. He was looking for someone to help him in that transition. He brought me on board early to learn his habits and get to that mind-reading stage where I can anticipate his questions about what he’s going to like and hate. When he transitioned out of being CEO and Larry Page, the Cofounder came in as CEO, we had to design a role for him that had never existed before.

A full-time executive chairman had never existed at Google before and he’d never been a full-time executive chairman before. Our task was to first decide what are the major responsibilities of this role. How are we going to measure if we are being successful? What’s the impact we want to have? He told me very unapologetically that he wanted to 10X his output as CEO. It wasn’t going to become semi-retirement, which at the time was what the transition meant for most executives. He wanted to blow the doors off of it so that’s what I was tasked with doing.

At the time, the role of chief of staff did not yet exist anywhere outside of the US military and politics but I had seen it because we did a lot of policy work with lawmakers trying to educate them on emerging technologies and help them legislate to the best of their abilities for their constituents. I was exposed a lot to the policy world and also to the role of chief of staff. I thought, “That’s a lot of what I’m doing and a lot of what I would like to be doing.” I set that task for myself.

It took me three years of making the case and working with HR to make that an official role but I was the very first chief of staff ever at Google. I created the gold standard for the role, which is pervasive across tech and beyond. That was not a job that I inherited. It was one that I invented first and foremost to support Eric Schmidt in the most powerful way possible, and second, as a career progression to take what I had learned catapulted. I call it springboarding. I don’t make any lateral moves. I like to springboard because that’s what my executives do. It was an opportunity to meet what he needed me to be as his right hand in this new role.

You worked for three CEOs ultimately. None of these were handed out. You earned them all. What is it that you brought to the table at a relatively young age to be able to be successful working for the three of them in a few of America’s biggest corporate success stories over the last several years?

I first have to acknowledge some serendipity here. I worked my tail off and there are a lot of things that made me successful but it was also a lot of timing. It’s the fact that I was in Seattle after the dot-com bust. The reason that’s important is that over the years and at the point of growth that I joined both Amazon and Google, there was more opportunity to break the mold of what’s expected of you.

For example, at Amazon when I joined in 2002, that year, 95% of the valuation of the company disappeared overnight. It was all hands on deck. A lot of people were jumping ship. It gave me an incredible opportunity to raise my hand for stuff that was far outside my job description for somebody who had zero actual corporate experience. I was given the opportunity to do that because every single person, SVPs included, was doing things every day they had no idea how to do.

No one had ever done it before. It was an environment where I could be successful and be given the green light on things. If I joined Google as a 22-year-old, those types of opportunities would not come to me. I have to acknowledge that I joined organizations when they were young enough. Someone who is ambitious, bold enough, willing to fail, and learn fast can be rewarded.

It was the right place and right time, and also a whole lot of effort on very long days. If I had to pick a third quality, it was that I was very passionate and aligned with the work that they were doing. I was giving myself homework. I was reading books and articles. I was incredibly curious about what we were doing because I thought it was very important especially when I was at Google. I was there for twelve years. That’s a very long time, especially in the tech years.

I was there for twelve years because I felt like there was a direct match for what I wanted in return for my very hard work. I believed in the mission of organizing the world’s information and making it universally accessible and useful. We did that in many different iterations and that’s what kept me there for so long. When I realized that my learnings had met the ceiling, that was the time when I knew it was also time to move on.

We will come back to your work. You left Google in 2018 and started a consulting business. Talk about the types of services that you provide and the types of clients that you work with.

I started consulting very unintentionally. I’d love to say this as a grant plan of mine but that’s not how it worked. In 2023 was the sixth anniversary of me leaving Google, which is such a crazy milestone. While I was working for Eric Schmidt at Google, he had a personal VC fund called Innovation Endeavors where he supported entrepreneurs working on important global problems, especially around climate change.

When I left Google looking for my next challenge, several of those portfolio CEOs said, “While you are figuring out what you want to do next, could I bring you on board for this particular challenge I’m having or this project?” Before I knew it, I had a full consulting business with a waiting list. It is a great privilege but I was also figuring out a whole lot of stuff that I had no idea how to do while trying to be very useful to these CEOs.

I focus on CEOs who are experiencing all the challenges that come with rapid scale and growth. I specialize in 2 of the 4 legs of the stool of any startup. We have the legs of funding and revenue, and then also the tech or the product. That’s not what I specialize in. I speak those languages fluently but I specialize in the other two legs, which are the people and operational systems.

The CEOs that I work with who are across four different continents are all in different areas. I don’t take two CEOs in the same industry so I don’t have accidental conflicts of interest. More importantly, I never forget that I’m not there to give them answers. I’m there to ask the right questions and accelerate them into finding the right answers for themselves.

Going into spaces I know nothing about like crypto, FinTech, or health tech prevents me from coming in and being like, “Here’s how we did it at Amazon. Plug-and-play.” It doesn’t work that way but I help them get to their answers faster and see around some of the blank corners that I have been around many times.

I can imagine that there’s a lot that you can bring to bear given your experience. What are some of the things that you learned in your time at Amazon and Google that have been most beneficial to you as you have started doing this consulting work?

I focus on people and systems. When you are rapidly growing, there are a lot of people who have been so instrumental in your garage days. These are people who believed in you before there was any proof point to back them up. When you have this rapid scale of growth, there’s a moment in time where it’s unreasonable to expect a human’s growth curve to match that.

We have this very uncomfortable moment where we need to hire people above those who have been so loyal to us and try to do so in a way that isn’t demotivating or making them feel undervalued. Anticipating that before it happens, identifying what are the skillsets that are missing, and how we can bring in someone with more experience would be an incredible growth opportunity for these people who have been very loyal to you.

That’s a very common inflection point when some CEOs come to seek me out like, “Help me reshape this team without losing the morale or the culture that we have so carefully built.” The second is around those operational systems, especially within the C-Suite. “How do we build systems so that we have the most effective use of executive time?” That’s the most expensive time in the organization.

That’s everything from your senior staff meetings to your offsites and your board meetings. How are we gathering and organizing data? Do we have the right analytics so that the CEO gets the insights before anything breaks where you can see those early success indicators or early red flags that your strategy is or isn’t working out the way you expected?

Those are patterns that I have seen from Amazon and Google that have these universal truths. Regardless of what industry you are in, there are particular systems that work that help you through this incredible growth influx that I have experienced at Amazon and Google that seem to be universal truths regardless of what content you are on or the industry you are in.

You also wrote a book which was published in 2021. That was something that you’d wanted to do for a while. Why so?

Yes and no. Yes, I wanted to write a book because plan A was to be a professor in an academic. We all know academics are publishers. Publishing I always thought would be a part of my life but no. I started speaking at conferences very accidentally, which is a whole other story but when I would get off stage, people would often say to me, “I hope you are writing down these stories or principles, the things you have learned. It’s helpful.”

I thought that was a nice thing you said to someone. I didn’t take it seriously because, in my mind, I thought that if someone wants to learn the best practices of Jeff Bezos, Amazon, Google, or Eric Schmidt, those books exist. It took a very long time before I accepted that I had a perspective that wasn’t represented anywhere else.

My opportunity as an author was to translate the best practices of these seemingly super performers for us normal people, to use my career and my experiences as a case study, and as an example that anybody with ambition and drive can produce extraordinary results. You can’t engineer serendipity for yourself. Bet on Yourself was my attempt to give this playbook that I have had the great privilege of learning from some of the greatest business minds in the world and translating that for us normal people so that anyone of ambition can make their greatest dreams come true as well.

It’s not something that you see covered a whole lot on how to be an exceptional individual contributor. The book aimed very well at that audience. It’s an audience that the vast majority of people who are out there in the work world are individual contributors. They need to feel that there’s hope for them and that there’s somebody who gets where they are coming from.

Thank you. It means a lot to me that felt successful as you were listening to it because it is something I feel very passionate about. In addition to my consulting, I also do offsites and leadership training events. The most popular topic has been a course I do on innovation for entrepreneurs. How do you as leaders or individual contributors use the core principles of entrepreneurship within a corporate organization? That’s when you get these rising stars. This is when you can identify early talent or you as an individual contributor can create a path forward in ways that might otherwise feel very limited.

Ann Hiatt: How do you, as leaders or as individual contributors, really use the core principles of entrepreneurship within a corporate organization? And that’s when you get these rising stars.

I was at an event in London and I was talking to a corporate attorney about the book, my career, and stuff. She was like, “I wish I’d read that several years ago.” Within the legal field, my dad and both my brothers are lawyers. I can appreciate it. It feels very like you do this and then this. It feels very scripted and she’s like, “It’s not.” If you have ambition and you can prove your value in unique ways, it will be recognized. Even within some very structured or maybe traditional corporate environments, there’s a lot of opportunity for intrapreneur behaviors to be rewarded.

I have a friend, Danny Warshay, who I went to school with who wrote a book that teaches entrepreneurship at Brown. He wrote a book called See, Solve, Scale. In his view, similar to yours, anybody can be an entrepreneur. You don’t have to be in a startup company to be doing it. He’s been doing certainly a lot of speaking.

I was talking to him and on the back of his book is a very diverse group of organizations including the military. He was talking about doing some work for a couple of different branches of the military. Harnessing that latent talent in an organization is something you would think more companies would want to do, and yet so much of the corporate world, America or otherwise, is focused on keeping people in their box.

It’s about that. I see that a lot, especially with mid-level managers who haven’t been trained on how to harness that. It can feel very threatening. I saw this a lot during the pandemic that it’s easier to manage a team that’s sitting all in front of you and you are there calling out the orders. You are like, “Follow me.” Now, we are seeing to have 10X opportunities when you allow some of these more creative solutions or experimentation within your organization.

I have done a lot of work in Abu Dhabi with some organizations there. They are trying to take a very entrepreneurial approach to their government work and it’s been incredible the results they are getting. Academics call it the golden ratio. The golden ratio is 70% is your core offering. This is the stuff that you are hired. You are earning your paycheck by doing these 70% core things.

Twenty percent should be innovative efforts like using those core skills in new ways, using new technologies, or seeing new opportunities for different offerings to your clients or customers. The 10% is what terrifies traditional organizations, which is transformational. That is scary because the transformational often cannibalizes the 70% and the 20%, the core and the innovative.

It’s called the golden ratio for a reason. Over the next decade or so, that 10% is what becomes your core. If you are not investing that in yourself as an individual contributor or an organization, you miss the opportunity to build the foundation you are going to need in the coming years. With generative AI and this incredible revolution we are going through, that could not be more true.

I want to turn to a different topic, which is chief of staff roles. You have a lot of experience in this space. In different companies, you hear them called executive business partner, business manager, chief of staff, chief administrative officer, or sometimes chief operating officer. They are not all the same but there are some common threads. What’s your take on the various roles?

I’m very happy you asked this question because there is so much confusion around this. Every single one of those job titles you listed has overlap. The Venn diagram is heavy. There’s this heavy overlap in all those descriptions but they are all different and distinct from each other. The challenge is that if you look at the job descriptions in the US compared to Europe for example, it’s wildly different from what we call those people.

Each of those jobs is distinct and different but there’s a lot of confusion. If I were to break it down, the way I look at it is you have executive business partners. Those are people who are very savvy. They have worked with C-Suite leaders for a very long time, 5 or 10 years or so. They speak the language. They are very sophisticated. They understand the business models but they do a lot of the day-to-day.

They are the ones who are translating this priority list of the executive into their day-to-day. How is that represented in their calendar, their logistics, and where they are investing their time or their influence? That’s an executive business partner. They are translating the vision and mission into the day-to-day structure. That would include logistics to executive time agendas kind of thing.

You move on to a first-level chief of staff. You are inserting strategy into this for the first time. A chief of staff is somebody who can represent their executive in a room they are no longer in. The executive is able to delegate a lot of things to that person to be a first filter because they have learned the instincts. They know the questions the executive would be asking if she was in the room herself. They are able to do that first pass. They are sophisticated enough to read briefing documents or proposals or put together agendas, taking all the data points coming in from all of their direct reports and then prioritizing executive time to work on what is most important and what needs to be.

In my opinion, executive time should be focused solely on what needs to be debated, and what needs to be discussed, and decided to live in a room together. Everything else should be a dashboard, an update, or a weather report on email, not executive time. That person is making that level of decision on behalf of their executive.

We move beyond that to much more senior chiefs of staff. This is where we get into a lot of overlap with COOs. The distinction there is a chief of staff traditionally does not own a particular deliverable. They do not own a department. You become a COO, even though there’s a lot of overlap in what a chief of staff does. The COO often owns at least one vertical. They have people who are formally reporting to them. They are deciding their comp and doing their performance evaluations, whereas the chief of staff does not.

The chief of staff needs to remain Switzerland where they are the conduit through which every executive is much more effective but that person does not have a skin in the game. I heard it best described to me by one of my clients as the chief of staff or the CEO, they have one eye in a telescope, keeping an eye on that long-term moonshot vision, and one eye in a microscope seeing how is that being implemented and making sure that nothing gets off track. That is where I get excited because that’s a skillset that not many people have and it’s one that I find wildly challenging and exciting. I love that responsibility. If I had to oversimplify what can be very confusing, that’s how I would distinguish between those roles.

You brought up one thing I wanted to ask you. What are the table stakes in these roles? What makes you a star? It sounds like one thing you would say makes you a star is the ability to look through the telescope and the microscope. What are the other things that you have to do well? What are the other things that set you apart?

You have to be able to process an enormous amount of information in a very short amount of time. I was responsible for taking entire board books. We are talking like 4-inch binders, a worth of information, and getting that into a single paragraph. What is my recommendation? What do we need to decide in this meeting? What does success look like?

Often, I have a hallway’s worth of time to brief my executive before they are in a room and have to be very effective. That is a skill I honed over fifteen years. That is an art. That’s not something I could do on my first day but I would say that’s a core skill of a chief of staff at a high level. The second thing, as I mentioned Switzerland, it is very important to build up deep levels of trust with every person that you are partnering with that’s internal and external to your organization.

Ann Hiatt: It is very important to build deep levels of trust with every person that you’re partnering with.

A very effective chief of staff needs to have an impeccable reputation within the organization as somebody who is fair, smart, and makes the right decisions but equally important, that reputation needs to extend outside of your organization with the maybe lawmakers, customers, or whoever you are engaging with outside. You also need that level of trust and sophistication.

I remember once I dropped my business card as I was getting onto a plane with Eric. He picked up the card and gave it back to me. He jokingly said, “I thought your business card would say, ‘Says no for a living and makes you feel good about it.’” It stuck with me even though that was forever ago because that’s the perfect encapsulation of what most of my job was about. I did have to know what to say no to because everything that came to us was a fair request.

It was people needing something because they were stuck. My job was to decide which of those many requests needed his time, which is less than 1%, and how could I be most helpful to them by giving them alternative solutions to what was getting in their way. Those are some of the core skills of being effective in being the right hand to a very high-level executive.

You were in these roles for a long time. Some companies view them as rotational roles. I’m curious to get your perspective on which model you think is the better model.

You have hit a landmine of the issue here. If we have any executive business partners or chiefs of staff, they will have immediate visceral responses to this question. I am much more middle-of-the-road in my response. I do think both models can work well. For example, as I described at Google, Marissa had an accelerator program called APM Program, Associate Product Managers, which she was using as a two-year rotational program to discover, train, and deploy the next great leaders of Google.

It’s highly effective. World-class reputation still exists many years later. That was a program of 2 years where she would take the smartest engineering minds in the entire world, bring them in for 2 years, and every 6 months they were forced to rotate to a different area of the organization. At the end of the two years, they not only had a very diverse skillset but a very diverse and deep network within the organization.

People who graduated from the APM program invented and ran Maps and Gmail. Things that are pervasive in our daily habits were invented and run by APM graduates. This also existed at Amazon. Jeff famously had a role that he called The Shadow that he invented the year I joined Amazon in 2002. The shadow’s job was a 1 to 1.5-year-long rotational program where he identified a young talent. That person’s job was to be at his side 24/7. They were in every meeting, copied on every email, and listened to every phone call on every flight, literally on his side at every waking hour.

They learned to think like he did and anticipate what he would ask. At the end of that rotation, they went on to run something that was a big bet in the organization. Shadow number one is Andy Jassy. Andy Jassy was the shadow when I joined. At the end of his year-and-a-half rotation, he went on to run AWS, which at the time seemed like an insane bet.

The board was like, “What are you doing? Why are you building servers?” We are a commerce store but then it’s a multi-billion-dollar subsidiary of Amazon. Jeff looks like a genius. Andy Jassy, your readers will recognize that name because he was named Jeff Bezos’s successor as CEO of Amazon. That’s how long and deep he trains his executives.

Andy was the model that I followed as a 22-year-old nobody in the C-Suite. I watched how Andy approached his work, how he did his homework, and how he leaned into things he didn’t understand. He was willing to ask the stupid question. He understood that sometimes in the room, his greatest contribution could be playing devil’s advocate and poking holes in all of Jeff’s favorite ideas.

I modeled my contributions the way I partnered with my executives and the way that Andy behaved. Honestly how I invented the chief of staff role at Google was based on the way Andy did. All my fellow chiefs of staff out there are very upset that I have described all the pros of having it as a rotation but you know that that’s not what I did.

What I did was I had a very long relationship with my executives. With Jeff and Marissa, it was three years. With Eric, it was nine years. I liked the long-form depth work with them because I was able to contribute in ways that I probably couldn’t have where I rotated. There are pros and cons to each. I was able to get to a level with my executives that it appeared like I had a crystal ball.

I knew what was going to happen in the future because I’d seen these patterns before. I got very good at identifying the patterns, seeing them in their infancy, and being like, “It is the time to attack. We have seen this. This was an incredible opportunity. Let’s go,” or, “This is a red flag. We have seen this before. Let’s not do that.” That takes time and you can’t do that in short amounts of time. That pattern recognition and that ability to have the longevity of relationships and levels of trust that take a long time to build up is a pro for having it not be a springboard into something else. There are pros and cons to each.

What each executive needs to do if we have CEOs reading is be very thoughtful and purposeful in what is this person here to solve for me. In answering that question, you will know which of these models is the best fit. We could talk about that for hours and I do with my CEO clients but that’s the distinction. Be very thoughtful about, “What is this person? What do I want this right-hand person to be solving for me?” That helps inform how you structure the role, their delegated responsibilities, their level of delegated authority, and what you want them to be doing on your behalf.

You made some great points there. It also affects the time commitment that you have to put in. If you are putting somebody in a rotational program, you are developing them for some future role with a stated timeline. That person and you as the senior leader have to work a lot harder at that learning process because there’s a time limit.

It also affects who you are going to put into it. You are describing Jeff’s shadow program. He was thinking about people who he felt could be seriously successful line leaders at a senior level of the organization and not necessarily somebody who would be in a staff role. He was looking for that talent in that program it sounds like.

That’s the perfect distinction. He knew that investing that amount of time in Andy would pay dividends because Andy was on an accelerated track. He was wildly smart and very different from Jeff, which I also think is important. He chose someone who personality-wise was received differently in the room that he was in. Those are all things to consider.

There’s a reason I wasn’t the shadow at 22. There was a reason I was on the staff. I didn’t have the instincts. I didn’t know I could not have gone on to run AWS. It’s understanding of what is the trajectory of this person. You are right. It is an enormous time commitment to train people. I would say of even very sophisticated chiefs of staff, having 20-plus years’ experience in executive partnership, it takes me a minimum of 1 year to get up to speed because by then you have seen everything once and start recognizing patterns.

You can make systems improvements because you can use the data that you have gathered in the first year to make better decisions. In year three, you get to a crystal ball. That’s a lot of investment in a person and that’s minimum. That’s a very high-level person. If you have expectations that you can get somebody to crystal ball level within six months, which a lot of my CEOs are originally delusional to think is possible, you are going to be disappointed. We have to be very realistic about what problems we are here to solve and then design a system and a role around that.

Ann Hiatt: A lot of CEOs are originally delusional. You’re going to be disappointed, so we have to be very realistic about what problems we’re here to solve and then design a system and a role around that.

Thinking about what you were saying about the leaders that you worked with, you say that you are drawn to leaders with humility. You worked for three CEOs. CEOs are not normally known for being humble. What did you observe in your time working with them about how they balanced the audacity and how they thought about their firm’s growth potential while also being humble?

I appreciate this question because you have highlighted a misunderstanding that is very pervasive. Probably the most commonly asked question I get is what are the commonalities between these three world-changing CEOs that I have worked for? People are always shocked that my number one quality is humility.

When you think of Jeff Bezos, especially with the jacked space cowboy version of Jeff Bezos, humility is not the first word that comes to mind. However, I will fight to the death to say that is the number one reason he was successful. The confusion or misunderstanding is that people think that humility cannot be paired with extreme confidence and 100% almost delusional belief in your idea before there’s enough data to back you up.

Jeff never questioned that he was going to be successful in creating the Everything Store. Even when we lost 95% of our stock value, even when the board thought AWS was an insane distraction, and even when they fought him on Prime because they thought it would bankrupt the company, he was confident in his vision.

It was supreme and almost delusional levels of confidence because he could do the math. He knew what the factors were that were controlled and the factors that no one else had ever solved. He had a plan for solving those. It’s supreme confidence. However, I still make the case that he was successful because of his humility and the way he went about proving himself. He designed an entire job, the shadow’s job, to be that devil’s advocate, poke holes in all his favorite ideas, keep him very accountable, and point out when some of his bets weren’t working.

For example, Amazon Fire. They attempted a phone. It was a massive failure. The shadow’s job is to be on top of those failures. You cannot be a CEO who isn’t humble and make that someone’s full-time job is to be at your side 24/7 telling you what’s not working. That is an example of humility. There’s a reason why the average tenure of his executives was more than fifteen years.

Most executives spent more than fifteen years reporting directly to him. There’s a reason why people stick around for that. It comes down to that humility. You are at that table for a reason. Yes, he will call you to task if you are not showing up as your whole self. If you phone something in or you aren’t rigorous in your thoughts about something, you are going to know it because he demands that of you. He doesn’t tolerate people challenging him. He demands it.

Jeff has a very famous saying that he started back in the early 2000s, which is called Day One. He always wanted working at Amazon to feel like day one. They have over one million employees. Every single person reading this surely has put money in Jeff Bezos’s pocket. He wants to feel like day one. We are still inventing the wheel. We cannot rest on our loyalty. He wants to be challenged on a daily basis. That is the two sides of the same coin, which is extreme confidence and humility in the way you are going to get that seemingly unlikely result. I get fired up about it.

The last question is a different topic. You have a bucket list. You have checked some things off like scuba diving and going on an African safari, both of which are still on my lists. What’s next for you in terms of crossing more items off your bucket list?

I do like to do things that scare me. I have been skydiving. Being around these crazy moonshot people, I have been ruined. I could never have a “normal job” again. My adrenaline threshold is very high. It’s a great question. Next for me is working to solve. The reason why I like going on the shows is because what I’m looking to do next is solve the one-to-many.

I feel like this work experience and this apprenticeship of sorts that the universe has given me is also an incredible responsibility. I have been trained by some of the greatest minds in the world. If the lessons they taught me sat in my little head, it would be an incredible disservice. The next challenge that I’m giving to myself is finding ways to get this into as many minds as possible, especially underrepresented entrepreneurs and intrapreneurs who might not otherwise self-identify as someone who could do something exceptional in the world.

I want to find her in her dorm room and inspire her to take a chance and do something that no one looks like her or comes from where she comes from, has ever done before. My next challenge is to find a way to do one-to-many. My new idea I’m playing with is maybe doing some documentary filmmaking format where I break down the history of these wild days of the founding of the internet and try to glean the lessons, all the stuff we got wrong, all the things we got right, and pay that forward to the next generation of entrepreneurs and technologists so they don’t have to reinvent the wheel. They can learn from our mistakes and best practices, and then make the world very purposeful in the way we use technology going forward.

You talk on your website and in your book about democratizing success. That phrase resonated with me. For me, PathWise is a side project in its fledgling early days. The genesis of it was to find a way to help more people be successful in their careers because most people are not getting the high-touch leadership development programs that people in the senior levels of the company get. Only 30% of people are engaged at work.

They trot out whatever favorite statistic you want but you feel the same way from what I understand. It’s horrible that people don’t like their jobs or that they are underwhelmed by their jobs. You spend so much time working on how can you go through life that way. I have set out on a mission to do something very similar, which is to try and help as many people as possible do a better job of managing their careers starting with the fact that you got to own it for yourself.

We are on the same mission here. That resonates with me. It does hurt me to my core when I hear people who don’t enjoy their work. My motto and I truly believe in this, is that your work should give as much to you as you give to it. For me, that’s a decidedly high bar. I am willing to outwork and outcare everyone around me. That’s the way I approach my work.

Everyone deserves for their hard work to be returned. It’s about being very purposeful. What do I want in return so I can ask for it? What learning or expertise am I developing? What network am I being exposed to? What projects or possibilities am I getting myself one step closer to? Often, it comes down to having that conversation first with yourself so you can recognize opportunities and even in their glimmer of infancy as they are floating by and raise your hand for them.

Second, you can go to your manager and say, “Here’s a skill I’m trying to learn. Here’s a network I’d like to be exposed to. This is why I would like to try X, Y, or Z.” Recognize where your organization is going. Is it aligned with where you are going? Not everyone has the privilege of working in organizations that are solving the world’s problems as they want to.

If you need to look outside your day-to-day, look for opportunities in your community to volunteer for those causes and be exposed to that type of leader. I believe the thing that changed my life the most was working for leaders that I not only liked but that I wanted to become like. That’s what I want for more people.

That makes a huge difference when you find yourself in that situation. I appreciate that you didn’t say no to this request, given that you had a rep for that when you were working for Eric.

No. This is an obvious overlap. We are on the same mission. If I could contribute in a small way to the big ripple effect you are having, that is an easy ask for me.

I appreciate that and certainly appreciate your time. It’s been a fun conversation with getting a little bit more color on some of the things that you talk about in your book and the work that you are doing. Thank you.

Thank you very much. I enjoyed it.

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I want to thank Ann for joining me to discuss her very unique career journey. Her work, the chief of staff role, is a smattering of other career and leadership topics. If you are ready to take control of your career, visit PathWise.io. If you’d like more regular career insights, you can become a PathWise member. It’s free. You can also sign up on the website for the PathWise newsletter and follow us on LinkedIn, Twitter, Facebook, YouTube, Instagram, and TikTok. Thanks. Have a great day.

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About Ann Hiatt

Ann is a Silicon Valley veteran with 15 years of experience as the Executive Business Partner for Jeff Bezos, Founder and CEO of Amazon, and Chief of Staff for Eric Schmidt, CEO/Executive Chairman of Google.

Ann Hiatt left Google in 2018, after 12 years at the company, and has since founded a consulting company with CEO clients across the globe where she applies the lessons of innovation, ambition, growth-at-scale, and forward-thinking leadership that she learned at Amazon and Google to new businesses and the next generation of leaders. Ann empowers entrepreneurs and executives through practical suggestions of how to develop a corporate culture of relentless ambition and vision while pacing themselves for long-term success.

Ann has a Bachelors’ Degree in International Studies from the University of Washington and began a PhD in Global/International Studies from Berkeley before accepting a role at Google. She now resides in and works from Spain.