Headshot Ann Hiatt

Ann Hiatt has worked as an Executive Assistant to three of the world’s top tech giants: Jeff Bezos, Marissa Mayer, and Eric Schmidt. She has just published her first book, Bet on Yourself

This article is based on excerpts from the interview between Lucy Brazier OBE and Ann Hiatt which took place at ES Tech 2021. The full interview is available as an #adminchat here: https://www.youtube.com/watch?v=MwKGH99oKBo


You didn’t start off working as an Assistant, did you? I know that you really wanted a career in academia. Tell me a bit about that.


I come from a family that really prioritises education. My dad and his brothers were farmers, but unusually, they all had at least master’s degrees. From my early childhood, our family didn’t talk about if I went to university; it was when, and what I was going to study.

I did well in school, but I was very shy. I was a perfectionist. I had these goals that felt like they exceeded my natural abilities, but my parents modelled that behaviour of being unintimidated by the enormity of the task in front of me and just taking it step by step.

My plan was to be a professor. I set that goal for myself really young. I was a very strange child! But that’s what I wanted to do with myself. My first job was working for a start-up before that term had even been coined. I worked for a five-person start-up in Redmond, Washington, and just wore all the hats learning what a start-up was. That was while I was still in high school, before I went to university. I did all these little bits and pieces which I didn’t know were preparing me for that first big job, which was with Jeff Bezos after graduating from undergrad.


So, you’re 20, you landed the job at Amazon, working for Jeff Bezos – a CEO who had been on the front cover of Time. Looking at his desk on day one, you saw he had reading material – a couple of magazines and a book – and decided to go and buy copies of all three of them. And then you continued to read everything he did. I think it is such an amazing way of getting into someone’s head.


Jeff was a voracious reader, minimum of a book a day. How he did that, I don’t know because we were working 18-hour days pretty regularly, but every morning he would come in with three completely read newspapers under his arm: the Wall Street Journal, the New York Times, and the Seattle Times. He would put them down on his desk and then I would take them, and I would devour them during my lunch break, read all of them cover to cover. And any book he was reading at the moment, I would then take. Literally everything, briefing documents, every email in his inbox. I would listen to every phone call and take notes on what I understood or what I wanted to dive into more.

When you are trying to support someone, you really need to become their brain double; you need to be able to mind read, and I knew that I was so far removed from being able to do that in the beginning that I just had to consume as much of the information that he had as was possible, so I had that foundational context. Then I could strive to become more proactive, to make recommendations and see around blind corners, but first I just had to build up a very firm foundation of the industry knowledge that I did not have when I started.


What do you think is the most important thing that you learned from working with Marissa Mayer?


So many things. The first two things that come to mind are that Marissa really modelled and demanded that people do things before they felt ready. Before working for Marissa, I thought being ready to take on a new challenge meant being ready to do it perfectly. Marissa taught me that being ready for a new challenge is just being willing to raise your hand. She created a safe space where it was OK for you to just do your best and run really fast and learn. As long as you were learning – pivot, iterate, try it again, over and over again. She had no expectation that we should do it perfectly.

In fact, in my very first performance evaluation, her major critique of me (which at the time really hurt my feelings and is one of the greatest business lessons anyone has ever given me) was that she told me I was playing it way too safe. I was hitting all my targets; I was accomplishing all my goals, and to her that was more of a failure than setting enormous goals that I was barely scratching the surface of. She allowed me to set goals for myself that terrified me. And I was allowed to learn. When you shoot for the stars and hit the moon, that’s success. That’s the kind of environment that she built.

The second biggest lesson that I took away, and I still think about today, is the way she built teams. She was so talented in identifying early rough stages of talent and investing in those people, polishing them, giving them huge challenges to accelerate their learnings. The people that she hired back in 2006, 2007, 2008 now run the major tech companies. Either they are major executives within Google or they have gone on to run tech companies that you and I use every day. She was just a spectacular identifier of talent and invested heavily in that. She was our greatest champion.


Then you pivot again, and you join Eric Schmidt, Google CEO, as his EA. He was obviously different again to working with Jeff or Marissa. What were the main differences?


Eric is an incredibly unique individual. There are many common denominators between those three, but Eric is more of an academic. He has a PhD. The other two have master’s degrees, but Eric is a PhD graduate. He also went to Berkeley, same as I did. He is just more thoughtful, contemplative and laidback.

“Professor mode” is his usual stance in a meeting, where he encourages and pulls out the unique voices in the room. He is very data driven in his decision making. And then when he speaks, you can see everyone in the room lean in. He waits until he has got all the data he needs, and he has called on the quietest voices in the room (which is a terrifying thing the first time you are in a room with Eric – you are not expecting that).

And then he is a statesman. That was a really important quality for the difficult job he was hired to do. I do not know of any other company that had co-founders that hired a professional CEO to come in and implement their vision. Eric never forgot that Google was not his company, and I point that out because that really shaped the way he performed his role as a CEO: it was Larry and Sergey’s company – he was there to maximise their vision, to hone it and to break it down into manageable steps because of his background and expertise, but he made their vision come to light. And I think that is why this trifecta leadership worked so beautifully. They challenged each other, they were very aggressive and honest with each other. But Eric always leaned back and made sure it was their vision that was being implemented, and I have never seen anyone else be able to do that in the way that he did.


You very famously created the role of Chief of Staff at Google for yourself. It was not something that existed, and now Chief of Staff is the term that so many companies are using for that level. Talk about how you created that role and why.


I wish I could have expanded that story in the book; what I wrote in the book is just the tip of the iceberg.

It took years of kicking and kicking against the glass ceiling that was in front of me. Google is amazing. They were the industry leaders in developing the admin and support structure of the company, recognising that’s the skeleton of the company, that what holds everything up is this administrative support, so we were respected. I think at the time, every single one of us had minimum master’s degree education. We were considered thought partners to our executives. We had to be brain-double-level worthy, so all of us were performing at extremely high levels, but I saw an opportunity to expand it beyond that.

I saw the Chief of Staff role from my friends in government. I was doing a lot of collaborative projects with people in policymaking, and Chief of Staff is something that exists within the politics world in the United States and comes from a military influence. But I saw the way in which they were anticipating, they were leaning into the strategy work, they were representing their policymakers in rooms when they were not there. I saw an opportunity to really 10x Eric’s output by behaving in the same way. So, I went to HR (Human Resources), and I advocated for this role. I wrote the description, I did case studies, I modelled it. I took on that role before they officially gave me permission to do so. And I came back and gave them the data: the results we were getting because of this behaviour shift, what I was able to do, the 10x results that we had got. I asked, “Why don’t we create an additional layer on this ladder to recreate and recognise that?” I got “Nos” for years – years of everything from “That’s not necessary”, “That’s really outside the scope of where we want to build this to”, “No, that actually belongs on the PM (project management) ladder” or “That belongs on the strategy ladder.”

They basically told me I was unqualified to do what I was already doing. And I just found that infuriating, but super motivating. So, after three years of kicking against that glass ceiling, they finally relented. And what I also don’t share in the book is I shared that very first title with a man. Paul was advocating for the exact same role but coming at it from the PM ladder, and they realised that Paul and I were pitching the same job description, and it was because both of us were coming at it that they actually opened their eyes and had that “aha” moment of what this could give the company. Now it is pervasive throughout the company.

Anyone who has been an executive, who has been challenged to do something disruptive, has that right-hand partner that is the Chief of Staff. It was revolutionary within the company and quickly became standard practice within tech like wildfire after that. Now we are seeing other companies that want to do innovative things also recognising and adopting this as a key part of being innovative and challenging the status quo.


Finally, for all the Assistants out there that really want to take that step up and bet on themselves, what would your final words of advice be?


Start today. I find a lot of us pause and we wait until we have this perfect playbook plan where we are sure we are not going to fail and we know where we are going. I don’t think that is how any of this ever works; it certainly has not been for me.

Take a micro-bet on yourself right now. Write down your goals. Start with your mission, vision, and values for yourself, for your life, and realise the decisions you are making today are your living legacy. I think if the pandemic has taught us anything, it is that we cannot take for granted this one single precious life that we have. Don’t wait for tomorrow. Don’t wait for someone else to give you permission to do something outside of how people currently define you or, more importantly, how you define yourself. Write down your mission, vision and values and do things that are aligned with them. And start. Take a small sprint, a little bet that you can accomplish today, and allow that to give you the courage and the bravery to expand beyond that. But start today.

Kathleen Drum’s mission is to bring thought-provoking, timely and inspiring content to administrative professionals worldwide, empowering them to succeed in their roles and excel in their careers. As the Senior Editor at Executive Support Media, she works ... (Read More)

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