Ann Hiatt shares valuable lessons learned on career development from her 15 years working alongside Silicon Valley’s top CEOs.
- The top three things you can do to develop your career
- How to deal with the pressures of big-impact opportunities
- How to carve out your path to promotion when there is none
Ann Hiatt is a best selling author, executive consultant, speaker, and investor. She is a Silicon Valley veteran with 15 years experience reporting directly to CEOs Jeff Bezos (Amazon) and Eric Schmidt (Google/Alphabet).
She has published articles in publications such as Harvard Business Review, Fast Company and CNBC. She has also contributed to articles in The New York Times, Economic Times, The Financial Times and Forbes. Her first book, Bet On Yourself, was published by HarperCollins in 2021.
- Book: Bet on Yourself: Recognize, Own, and Implement Breakthrough Opportunities
- Website: BetonYourselfBook.com
- LinkedIn: Ann Hiatt
- Book: Mindset: The New Psychology of Success by Carol Dweck
- Book: The Hard Thing About Hard Things: Building a Business When There Are No Easy Answers by Ben Horowitz
- Book: Measure What Matters: How Google, Bono, and the Gates Foundation Rock the World with OKRs by John Doerr
- Previous episode: 396: Insights into Embracing Emotions at Work with Liz Fosslien
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Ann, welcome to How to be Awesome at Your Job.
Thanks very much. I’m excited to be here.
Oh, I’m excited to hear your wisdom. And I’d love it if you could kick us off by sharing a story or two that was particularly instructive for you and career and being awesome at your job working with Jeff Bezos, Eric Schmidt, Marissa Mayer. Give us something that’s inside scoop.
Absolutely it’s been the greatest privilege of my life to have been able to work so intimately and closely with some of the greatest business minds of our generation. I would say that that story actually started a little bit before my very first job working for Jeff Bezos.
So, my very first job at 16 years old, when my friends were working at Burger King and the library, I worked at a five-person startup founded by two brothers who had just graduated from Harvard Business School. So, that was my first taste of entrepreneurism and gave me some of my instincts. I made all of my very novice mistakes with them. And, yeah, my very first job after university was working directly for Jeff Bezos.
And we could talk literally for days and days and I wouldn’t run out of stories of the stories of these entrepreneurs. But I think the foundation really was set there in the beginning. Each of these environments taught me to be a bold risk-taker. Even though my nature is not bold and fearless, I was nurtured into that very much by this entrepreneurial environment that I found myself in.
Okay. Well, yeah, I bet there’s many, many stories but I’m going to put you on the spot for one. Are there words that reverberate in your head frequently as you’re making decisions, navigating your career, wondering which way to go, and you hear Jeff or Marissa or Eric in your mind’s ear, and say, “You know what, okay, yeah, we’ll do this thing”?
That happens constantly, actually. Even though I left Google, let’s see, almost four years ago and Amazon much longer than that, more than a decade ago, but I can still very much hear them in my head. I think from Jeff, if I had to pick a single word, it is relentless. He is relentless in the pursuit of his passions. He’s relentless in his enthusiasm for his vision of where he wants to take the company. And, in fact, this is a little-known fact, if you go to Relentless.com, it redirects to Amazon. That is how much of a core value that is for the way he approaches his work and what he is doing or was doing at Amazon.
From Marissa, I really learned to focus on the people. It’s much more about the who than the what and the how. You need to be laser focused on exactly who your clients or your customers or users are, and understand not only the needs under their feet today but really anticipate the needs of the future. And understanding those needs of the people you’re trying to serve is important, but, equally, if not more important, is the people you have on the team. I really learned to hire the best possible talented team that you can find.
And from Eric, I really learned the value of insatiable curiosity. He is somebody who will ask about a hundred more questions than a normal person would about any given topic. And so that relentless pursuit of curiosity in new information and expanding his knowledge, those are key attributes that I call upon now as an entrepreneur myself and trying to instill in my CEO clients as well.
Okay. That’s beautiful. And so then, I imagine there are times when something seems harder than it should be.
Can I just get a real-time cortisol monitor? Apparently, there is but they’re not commercially available for the public, so I’m going to have to hunt down some people who wrote some papers. So be it. There’s some relentlessness and curiosity at work as opposed to, “Oh, I guess I’ll just wait three years. Maybe it’ll be around them. Okay.”
Well, then let’s hear about your book. What’s the big idea or main message here Bet on Yourself: Recognize, Own, and Implement Breakthrough Opportunities? What’s the core idea here?
So, this book is my attempt at creating a playlist, taking the best practices of these seemingly super performers that I’ve worked for and translating it for us “normal people.” I have felt such a privilege of working with these incredible minds and not only learning their best practices but experiencing things, moments in time that probably will never happen again.
The dawn of the internet will never happen again, Jeff inventing the gold standard of e-commerce will never happen again, the constant innovation cycles of Google. I really saw some things that were very privileged to experience and I felt a responsibility to pay that forward. So, my book Bet on Yourself is my attempt to give you that playbook of best practices that I think are applicable regardless of your growth stage, whether you’re an intrapreneur or an entrepreneur, regardless of industry, these are some of those gold standard best practices that everyone can benefit from.
And I use my career as a case study in the book to show you that anyone with some ambition and clear goals in their mind can engineer serendipity and create opportunities for themselves. So, I kind of walked through some of these crazy moments in time and reverse-engineer a little bit of some of the luck and very, very hard work that went into those moments.
Oh, that’s cool. Well, I’m excited to dig into the particulars. But maybe to inspire the ordinary people like myself, is there a cool story you could share of maybe a client or a reader who took action on a particular principle and saw a pretty amazing breakthrough from it?
I have a client now who’s working in the food tech space, he is incredibly talented. He was doing a PhD in chemistry and material sciences and discovered mycelium-based protein structure and learned to manipulate in a really unique way, so he’s creating this alternative meat product.
So, when I first met him and worked with him, it was a referral from a common friend of ours, and it was a very, very early growth-stage company of about 30 people. And now, today, he’s just close to Series C, and he’s got contracts literally all over the world for this incredible product that he’s invented. I think he is among my star examples of doing some big, bold risk-taking. He’s doing something that no one’s ever done before.
So, when you’re doing that, you don’t even have the dashboards or the metrics, you don’t even know what you should be measuring quite yet. He’d never produced a product like that before but he really has adopted these principles of insatiable curiosity, of humble leadership, of not only tolerating the demanding pushback and peer review from his employees, and he’s really been very focused on not only hiring the best talent he can find but hiring for passion and mission alignment above all else.
If you get really smart people in the door who are driven and determined to see your vision through, you can teach those people to do anything. And so, I think hiring for that value and mission alignment has been essential. I’m just incredibly proud of what he’s doing.
Ooh, I like that there. You can teach them to do anything. I think that resonates. And I guess, there’s just a little bit of what you said in terms of like aptitude and different…I would not be the guy you want to hire to be your contractor even if I’m super fired up about building your dream home, Ann. I was like, “I’ll just learn drywall and plumbing and electrical. No problem, I’ll just learn it.”
I don’t know, I believe you know. I think you can figure it out.
I would need maybe four draft homes before I did the real one. But that said, people generally have strengths with, I don’t know, people or things or, what’s that world of work, or data or ideas. But within that, sure, that totally resonates. Okay. Well, let’s dig in then. So, us ordinary folks, can you lay it on us a few do’s and don’ts in terms of, as we’re kind of maybe in the middle of, say, medium to large organization, not at the top and not at the bottom, we’re just sort of making our way in terms of career, what are the top things you recommend people do and don’t do to really develop and move quickly?
I love this question. I think three things come to mind. If you’re mid in your organization, there can be a really important mindset shift that you can make, and this is the way that you put yourself back in the driver seat of your career. A lot of us feel very disrupted coming out of the pandemic, opportunities might seem to have disappeared, everything got turned upside down, so these steps are particularly relevant for this moment in time.
And the first is to be very clear with yourself. What do you want out of this next stage in your career? What do you want to learn? What expertise do you want to become known for? What teams do you want to learn how to lead, or projects? What is your specialization? How are people going to recommend you for jobs in the future? And so, first, you have to have that conversation with yourself and be very clear on that.
And then, second is then share that with your mentors and sponsors within work. So, have that conversation with your manager, of, “This is where my skillset lies. My interests, my goals, my talents are here. I would love your idea of ways that I can utilize that or expand my influence on this team.” The way you get a yes to that is, one, expressing your interests and helping them know how you’re trying to evolve. And second is what I call creating a win-win-win.
The first part of that conversation you have with yourself of what you want in exchange for your very hard work every day. Two is look at your manager’s responsibilities and see what she or he has been tasked to do within the team on the big bet of the company. If you can allow her to delegate something to you, that frees her up to have bigger impact and look good in front of her boss, and that gives you an opportunity to grow into that area.
And the third element of that win-win-win is understanding “What are the primary goals and objectives of the company right now? And how can I align myself with where the company, the skillset, the reputation, the energy, the relentlessness that they might need? And how can I exemplify that?” When those three things are in place, you’re going to get yes every time. Even if the project you want to work on is outside your job description or your current seniority, that’s a great way to open the door for yourself.
So, that’s, I think, element number one for my fellow intrapreneurs out there. Number two, I think is seeking out leaders that you not only like but you want to become like. Now, not every manager is worthy of this. I can appreciate it, especially in your career, you might be working for someone whose leadership style you don’t want to emulate in the future. If that’s true, maybe look for an opportunity to have a cross-functional project or work on something outside your team.
Or, if that’s not even available to you within your organization, maybe volunteering in the community and seeking out a leader who is exemplifying the way you want to manage a team, or is really good under pressure, or is able to exemplify some of those habits that you hope to have in the future. So, surrounding yourself with the best people possible, especially among the leaders you’re working for.
And then I would say the third that comes to mind is proactively disrupting yourself. Now, this probably is not something that many people are seeking out right now because we feel like we’ve had enough disruption, and I can definitely sympathize with that feeling. But what I mean by this is create a checklist for yourself where you’re expanding your skills, your expertise, and you’re up-leveling very consistently before the market or your team or your manager can do it for you.
And that goes back to point number one, which is knowing exactly what you want out of this phase in your career, and finding a place where your team, your company’s goals are in aligned with that. If you think of those three things are in place, intrapreneurs can feel extremely empowered rather than passive and reactive to these items I’ve given, and that feels really, really good, especially in this moment in time when we’re all craving that feeling again.
And so, I’d love it if you could give us some example articulations of being precise with what you want because I’m imagining, “I want to kind of be better at Excel,” may not be quite what you’re imagining or suggesting when you say, “Be really clear on what you want.” Can we hear some sample articulations?
So true. So, I actually did this exercise for myself when I left Google after 12 years, and decided to found my own company. I sat down to write my mission, vision, and value statements, as many do, as part of your business planning. And I found that exercise to be a little bit exhausting. In fact, I created a free download on my website, on the book’s website BetonYourselfBook.com, to download it because I found it so hard to do myself. I think it’s a 14-page download but I walk you through how to create meaningful value statements.
I learned this from Jeff Bezos, actually. I started working for Jeff in 2002 in the very early years of the company. He’d officially founded it in 1994 but he was just getting traction right about the time that I started. If you can imagine a time when Amazon was not yet profitable, they had had a single profitable quarter but not yet a profitable year, so that’s the moment in time I’m talking about. I know it feels like a wild money-printing machine right now.
But Jeff really doubled down on creating very clear leadership principles for his entire team because really important decisions were being made in rooms that he no longer could be in. He just had to replicate his thought process across the company as fast as possible. So, I saw him work with three of his SVPs to draft the now-famous Amazon leadership principles. At the time there were 10, then it became 14, and now there are 16 with Andy Jassy as the CEO.
And I encourage you to do that even as an intrapreneur. You don’t have to be in your garage starting something with your computer or going to Silicon Valley and looking for venture capital funds. I really encourage you to do this for your own life and career. And first, it starts with that mission statement, “What is the reputation or the living legacy I want to be leaving right now?” Now, whenever I propose that to a client, they feel a little overwhelmed, especially if they’re early in their career, thinking about legacy, but I think it’s a nice clarifying question, to be like, “What do I want in exchange for this?”
My career in tech has been intense. I’ve definitely worked really long days. There were periods of time I was working 18 hours a day and every weekend, and I didn’t burn out because one thing was true. I knew exactly what I wanted in exchange for my very hard work. I was willing to have that be a very high bar. I worked incredibly hard but I knew what I wanted in return. So, that’s what I wanted to learn, who I wanted to become, and the stages on which I wanted to stand in the future.
And so, I think, in writing your mission statement, think about that. Who do you want to be serving? Why is that you? What about your background, your talents, your desires, your drive makes you uniquely qualified to get there? And then surround yourself with the very best people who can supplement any weaknesses or lack of experience that you might have. Does that answer it?
Yeah, I hear the importance, like, “Yeah, that makes sense.” If you got that kind of clarity there, then you can have that sense of purpose, that mojo, that motivation, that inspiration to persist in those intense times. So, that totally checks out. I guess, so the articulation then is not merely one sentence but rather pretty detailed in terms of we got a mission, we got a vision, we got some values. Can you give us some examples of what those could sound like?
Sure. So, mine has taken me quite a while to put together, and I am allowing to be a living, breathing thing that will evolve with me and my work. So, at the moment, my mission statement is that I am here to discover and empower underrepresented entrepreneurs through actionable education and mentorship.
Now, the first word in that statement was the last one I added because, at first, it was just to empower underrepresented entrepreneurs through actionable education and mentorship. But I realized that a lot of people were not yet self-identifying as an entrepreneur. They’re like, “Well, I’m early in my career,” or, “I’m a mid-level manager,” and so I really wanted to wake that up in people and help them discover it. I wanted to seek them out where they were right now as someone trying to get that big first promotion or own the dream client. I wanted to wake that up in them.
Now, the reason that mission statement was important for me to evolve, it really took quite a lot of like heads-down work and testing it, but it’s important because it helps me know what projects to say yes to now. It helps me if I have a limited number of time. I know I’m going to prioritize an underrepresented entrepreneur over someone that I feel is already well served. If it’s an opportunity to help someone discover their inner entrepreneur, I’m going to say yes to that, for example. Maybe university that has a lower-speaking fee than somewhere else, I’m going to prioritize that over maybe people who are already in a privileged position as an entrepreneur, for example.
So, what you really want is your mission statement to be specific and time-bound, like, “What do I want to deliver right now?” And I think that’s really helped me show up in the right way. When I first started my company, I had to try on a bunch of things and learned the hard way of what I was and wasn’t good at, what excited me, who I was best suited to serve, what did that look like, what stage in their growth are they. So, it took a lot of experimentation.
So, don’t think that just sitting down for 30 minutes is going to be one and done with this mission statement. But you know you have an effective one when it allows you to make much clearer decisions and show up in the right way that is rewarding and exciting to you rather than draining and diminishing.
So, that’s the mission piece. How about vision?
So, my vision is more about “What am I putting into the world? Am I going to say yes to just the highest-paying project?” For me, I really want to be mission-aligned with you. I want to be working with, for me and my consulting business, I want to work for entrepreneurs who are making a change, I, too, want to see in the world. I’m very attracted to anything around climate change, anything about empowering new generations of entrepreneurs, or expanding education opportunities.
So, that gives me kind of a checklist in my head. There’s just a lot of places you can show up in the world, and I really am value-aligned with that, and I find it if I’m working on a project. For example, I have a friend who started an incredible SaaS company, software-as-a-service company, and I think he’s amazing, and I’ve done a little bit of like helpful advice and coffee chats with him, but it doesn’t wake me up. I’m much more excited to be working on mycelium-based protein alternatives because I think that’s important for the future world that I want to create.
So, it’s often the decisions choosing between good and good are, I think, a lot harder than the good and bad, and having a really clear purpose statement helps me show up in ways that are most meaningful to me.
Okay. And let’s hear some values.
So, my values are who I want to be and who I want to surround myself with. So, for me, especially coming out of Silicon Valley, I really drank the Kool-Aid. I am excited by people who are big thinkers and big dreamers. My values are people who want to live up to what is now a cliché of Silicon Valley, of making the world a better place.
I value being around people who are insatiably curious and smart and collaborative and kind, who aren’t competitive in the negative sense but showing up in a very resilient passionate way. And so, my values really come around…circle around the types of people I want to surround myself with through my work and through my consulting.
You said the word resilient, and I did want to zoom in on this a little bit. I had a podcast guest, I love it, Liz Fosslien is her name. She had a few great posts about “Just be resilient.” It’s really a cop-out when organizations throw that your way. But I guess, as I’m imagining a world in which you are zeroing in on sort of big-impact opportunities and going after them, there’s a lot of fun and excitement associated with that but then there’s also going to be a lot of pressure and expectation that comes with that, and potentially long hours and some exhaustion.
So, tell us, is there anything in the realm of resilience or self-care or support systems that you recommend that can make all the difference when you’re playing a bigger game with bigger set of pressures on you?
I’m going to answer that in two different ways but I promise they’re connected. So, in order for me, as a, by nature, a timid, cautious, perfectionist person, that is the nature with which I was born, I am a perfectionist, all the negative definitions of that. Like, I’m afraid of starting something without being 100% sure that I can do it perfectly. That would’ve led to a very small life had I not been nurtured out of that by this crazy environment I found myself in in tech.
One of the most pivotal moments in my life, a sliding door moment for me was discovering Carol Dweck’s book called Mindset, and even if you only read the introduction, I think it could change a lot of people’s lives. In the introduction, she introduces the premise that there are two different mindsets. There’s the learning mindset and there’s the performance mindset.
As a perfectionist, I was in the performance mindset. I was not consciously thinking this but I was assuming that I was born with a certain set of skills and abilities, and anything that went beyond that would just discover and out me for all my imperfections. That’s a performance mindset. You want to know you can get a 100% on everything you tried.
Now, if you’re in a learning mindset, you have the mindset that you, with extra effort and time and practice, can increase your abilities, that if you try something, the first time you get 80 out of a 100, then the next time you’ll be better informed and learned from your mistakes, you’ll get 85 and progressively can increase your skills.
I don’t know, that was such a lightbulb moment for me, to be like, “Oh, if I am uncovered…” this is where impostor syndrome comes from, and you hold yourself back if you’re aware that, “If they discovered that I can’t yet do this, that means I never can and they won’t trust me anymore.” So, being nurtured out of that, really helped me with that resilience of, because I failed now, I am equipped with tools that I did not have in my toolbelt before and I want to be able to show up smarter, stronger, and better for it after that.
And so, I think resilience is much more is first about your internal mindset. And then the second way I’m going to answer this is in seeking out those teams. I was very privileged to work in companies that not only rewarded that behavior; they demanded it. So, I want to acknowledge that not all families, not all communities, not all companies are embracing of this. But if you can seek out a community of like-minded people where you have that psychological safety to experiment and to try some things and learn to trust yourself, that’s when work gets really, really fun.
In fact, I’m training for a half marathon right now. I’ve ran a few before but that was pre-pandemic and I’m not the same person I was then. So, I’ve got this Peloton trainer I listen to while I’m running, and she just said on my run yesterday something that super resonates around this resilience. She said, “You can’t push yourself until you trust yourself.”
So, start with that internal work first and know, like, “I can do that one more step. I will be stronger tomorrow than I was today because I showed up in this way.” And so, I think those two elements need to be there. Trusting yourself and then being in an environment that rewards, supports, and encourages that.
All right. And then, it sounds like a lot of the work is kind of just foundational in establishing, okay, the mission, the vision, the values, what strengths, what am I good at, what am I going for, what specifically do I want in this role. And then, thinking about some of like the daily habits and practices, what do you recommend when we zoom in at that level to be some key do’s and don’ts for professionals?
I think my first thought is around this element of curiosity. So, all of the incredible super performing CEOs I worked for displayed this in kind of Olympic levels of curiosity. For Jeff Bezos, he did a quarterly thinking retreat. Not all of us have the freedom to do what I’m about to describe but I will translate this for us normal people.
But what he did was, for one week every single quarter, he would lock himself into a hotel room away from his family, from work, from everything, and removed all external stimulus – no newspapers, no phone, no conversations, no nothing – and he would just starve himself of external influences. And then the second half of the week, the only thing he brought with him was a blank Moleskine notebook, and those notebooks are full of ideas. I literally see them launching today. That’s how forward-thinking he was in those moments.
Now, most of us don’t have the freedom to take an entire week off just to think and sit in a room and dream of the future. So, the way that I’ve tried to adapt that for myself is, in the middle of my career, when I was already working very, very long days, I realized that I needed to take good care of my mental and my physical health, to be able to not only survive. But thrive in those very intense environments, it was important to prioritize that.
So, I started having non-negotiables with my teams or with my boss. And so, for example, I started working out with a trainer for the first time in my whole life. It was so hard in the beginning but I had this protected hour from 7:00 to 8:00 a.m. every single day, my phone was not with me. Now, I was working at Google at the time so my gym was literally in the first floor of the building that I worked in.
And so, I said, “Okay, if you actually need me, send my assistant down to get me.” And in the nine years that I kept that practice of taking care of my physical health first before I got to my desk, there were only three times when my assistant had to come down and ask me to come up. So, that really showed me that I can give myself permission to do this hour. The world is not going to fall apart if I take care of myself first.
And I think building in that type of resilience and prioritizing, and especially now, as an entrepreneur, I’m really trying to focus also on my mental health, of giving myself that space to think. And that’s another way I’ve translated what Jeff’s practice of this thinking retreats and being really curious, is now I have these protected hours every day where I’m just reading, reflecting, writing, consuming, because so much of consulting is give, give, giving and I need to replenish my expertise and my knowledge, and just give my brain that space to be creative and to be a connector. So, that’s one of many, many, like Olympic practices that I’ve tried to translate into my work and life.
And so, whether we are spending an hour or a week in this rampant ideation – this sounds like a blast to me, I like it – creative zone, well, one practice is blocking out stuff, although it sounds like, in your world, you are letting in particular things. So, maybe zoom in a little bit, like what are we doing? Are we just sort of sitting there, like, “Hmm” write, write, write? Are there any key question prompts or initial fodder or reading materials that get things going here?
I think your instinct is right. This absolutely needs to be dialed in for each individual. So, the way in which you kind of fill yourself back up in order to give, give, and give, what’s required at home and like your family and at work, I think that’s unique to the individual. So, for me, because my work is in giving advice, and also having this international breadth of understanding of where tech is moving in the world right now, my clients really need me to have that kind of global perspective.
I can’t do that without having time to consume all the information. So, one for me is just, personally, I love to read, I love to listen to podcasts, I love hearing and being exposed to some of the greatest thinkers in the world. So, in and of itself, even if that wasn’t directly demanded of me for my job, I would be doing that anyway.
So, that’s something that fills me up. Even if I’m not reading something for work, I just know that makes me happy. The second thing is I know I need sunshine.
I grew up in Seattle. Most of my life, I did not have that daily dose of sunshine. The second I moved to California for grad school, and now I live in Spain, I know that it’s just like instant happiness for me. So, if I get outside in fresh air and get some sunshine on my face, that’s an instant mood boost for me. Each person is going to be a little bit different. I know I’ll have a good day if I’ve moved my body, if I filled my mind, and if I go outside in nature.
For each person, that’s different. Like, maybe it’s playing with your kids or your dog. Maybe it is in a creative pursuit. You need to paint or create something with your hands. So, ask yourself, “What, for me, even when I am working on it really, really hard and I remain far away from the finish line of whatever goal it is I’m working on, I finish the day feeling like I have been filled up rather than drained?”
So, I think those types of pursuits are always things you want to be seeking out. Like, even if you’re not perfect at it, maybe you’re training for a marathon like I am right now, and trust me, I’m horrible. I’m not doing this because I have any hope of winning anything. Hopefully, maybe hope you are. But just think about that, of what fills you up and fills you with joy regardless of the outcome, that you don’t want to be measuring those rejuvenation periods on the same scale as you are with your work or performance.
Okay. And then I’m curious, so let’s say you’re doing all these things and you’re just rocking and rolling, delivering value all over the place, and it seems like, unfortunately, the meritocratic forces in your organization are broken. It’s like, “Oh, you can’t be promoted until someone dies or moves to another role, and they’re probably not going to do that for six years.” How do you think about that when you’re there?
Been there, done that. I absolutely know that struggle intimately. As I mentioned, I worked at Google for 12 years so it was really on me to have to reinvent myself, and I tended to do it in kind of three-year cycles. I would be challenged in the beginning and learning a lot, then I get into my zone of genius and start doing it really well, and then, after that, I would start to get the itch of like, “What’s next?”
And nobody, even at a company as innovative and driven as Google, nobody ever came to me once and said, “Oh, Ann, I’ve noticed you’ve had this untapped talent or interest, and I’ve been thinking about how to apply it.” That just doesn’t happen. That’s your job. So, I think it comes back to having that conversation with yourself and knowing exactly what you want to go for.
So, after about, let’s see, six years at Google, so halfway through my tenure there, I had this idea for a role that I think would really elevate not only my work but the work of my manager who, at the time, was Eric Schmidt, the CEO. And I had seen, we were doing a lot of policy work at the time, and I had seen this role of chief of staff in government, at the White House, in military, for example, and I thought, “That is what he needs.”
I had been this business partner for him, I’d been kind of a thought leader with him, I was kind of that safe space for him to debate ideas, and I thought, “If I could take my job to the next level, it would look like chief of staff.” Eric thought it was a good idea, had me brainstorm, write the job description. I took it to HR and it literally took me three years to fully realize what I wanted in that job.
And so, in the end, I was the very first chief of staff at Google ever, and now it’s pervasive throughout tech and now moving beyond that. But I can tell you right now, I had a conversation, in fact, with my HR rep the day I left for Christmas holidays and it made cry because she, basically, just squashed it and said, “If you want that type of thing, you might want to consider looking elsewhere,” and I wasn’t ready to do that yet but then, eventually, I moved on.
So, I’ve had those really hard conversations but I think it comes back to that knowing what you want, seeing how that solves a problem for your manager, and proving how that’s best for the company. In the end, either you’re going to get it, which I did after a couple of year’s fight, and then, eventually, I needed to move on in order to have the kind of growth that I wanted. So, you can feel both of that. Sometimes it’s wait and work really and prove yourself, and then eventually, sometimes, the answer is that growth opportunity might lay elsewhere.
All right. And not to dig too much into the minutiae of your story, but I think it will be resonant for folks who encounter resistance. Okay, so the CEO wants it, you want it, what’s HR’s problem?
Thank you. I literally said that to him after I got the “No, no, no,” and he kind of…he shrugged, and he’s like, “Gosh, we’re truly a big company now.” But what it was, the part that made sense to me, a lot of it did not, but the part that made sense to me was Google, by then, had had to operationalize, stream-wise, and make sure everything was done with ultimate efficiency. That means that everything was done now on a specific job ladder.
I was trying to create a brand-new job ladder. So, I was trying to kind of merge a lot of this support structure, this skillset in communications and policy and project management, and create this hybrid role, and HR did not want to create a whole new job ladder or this hybrid role that they thought would be really nebulous, hard to write job descriptions, how do you measure for that, how would I be evaluated, how would you be compensated for that.
And so, it took years, and, rightfully, probably in the first year, I didn’t have a clear enough understanding of what the delegated authority level of that job would be, what are the delegated tasks, how would we measure and quantify the success and impact of that work. It’s a very, very data-driven company I did need to dig into the hard work and really make the case. And, eventually, I did but much slower than I had anticipated.
Okay. So, that’s a nice perspective. It may take some time or it may be hopeless. Any tips on how we can tell the difference sooner rather than later?
I think I pursued it for three years because I did see progress and I became more and more convinced of the value of it. What I ended up doing that sealed the deal in the end was I said, “How about we do an experiment? Let’s not make it official but of the job description that I’d outlined, with this delegated authority level, with this type of responsibilities, with this skillset, I’m going to act like I already have this title and this job,” which took a bit of buy-in from my peers because a big part of being chief of staff is acting as a surrogate, as a delegate of your executive.
And for me to represent Eric Schmidt in rooms he wasn’t in is a big deal and I needed his senior reports to kind of treat me accordingly even without formal title authority. Luckily, I had worked with all of them for more than a decade and I had that trust factor with them already. They knew that time with me would make their jobs better, and so I got that kind of peer buy-in that was essential. Had I not had that, those relationships of trust already established, I don’t think I could’ve converted on it.
But agreeing to do that six-month trial and then inviting extreme critique from all of those people I had worked for and got a 360-performance evaluation from them was the proof that they needed that this actually did, I think one of them described, 10x-ing our output by having me be able to represent him in more rooms.
That’s good. Well, Ann, tell me, anything else you want to make sure to mention before we shift gears and hear about some of your favorite things?
No, I am so excited for your listeners to really create this playlist for themselves, and then to be brave enough to say it out loud. Honestly, I think that’s the hardest part is just the first time you have that conversation with your manager, it’s awkward. I remember trying to expand the confines of my job description when I was working with Marissa Mayer, who was my first manager at Google.
She was employee number 20, first female engineer ever hired at Google, tough as nails, insanely smart. And I remember suggesting a couple of projects that were far outside the confines of my job description, and it was met with awkward silence at first. She literally did not respond. She didn’t even acknowledge she’d heard the words coming out of my mouth. But it was processing, that was kind of her thing.
So, I just wanted to put it out there. Sometimes it does, at first, be met with that silence because you’re trying to teach people to treat you and think of you in a different way so don’t let that deter you but be very clear and show the value of not only for yourself but for your manager and your team as a whole. I found it works pretty consistently.
All right. Now, could you share a favorite quote, something you find inspiring?
So, there’s two that come to mind, if I can cheat and choose two. One is from Maya Angelou. It is very apropos to what we were just discussing, where she says, “People may forget what you said, they might forget what you did, but they’ll never forget the way you made them feel.” And I think that absolutely resonates for me in my life, in general, and definitely in my career. I have worked for very driven dedicated sometimes terrifying people but they made me feel valued, they made me feel like they wanted to invest in me, and I’ve really tried to pay that forward now in this next part of my career.
And that leads into the second quote that I really liked that’s by Diane von Furstenberg, one of the first self-made female billionaires. And Diane said, “I didn’t know what I wanted to do but I knew the woman I wanted to become.” And I think a lot of people who have natural ambition and just feel like they were made for more sometimes can opt out because they don’t know what that looks like yet.
And I don’t want people to be deterred. That quote has inspired me because the woman I want to be has always been very clear to me. How I accomplished that came in very unexpected packages, and so I find that very inspiring.
And a favorite book?
There’s two I find myself constantly quoting to my clients and to just my friends that we talk about careers is. There’s one by Ben Horowitz called The Hard Thing About Hard Things. My favorite line in that book is full of so much wisdom. My favorite line is saying that, “As an entrepreneur, there are only two emotions: terror and euphoria.” And I find that to be very true in my work.
And another one that I find myself recommending nearly on a daily basis is one that’s written by John Doerr called Measure What Matters. It’s about the goal-setting moonshot system that is used both at Amazon and at Google for innovative thinking, and it’s very applicable to individual careers, not just those trying to become the next Amazon and Google, but it’s really about leading an ambitious life and pushing through the boundaries of your capabilities.
All right. And can you share a favorite tool, something you use to be awesome at your job?
Well, the first response that comes to mind is just all the things I’ve used to stay connected across the pandemic, especially since I moved to Spain and started my own company just before the pandemic happened, so I’d already set myself up for a bit of a learning curve. To be connected with global entrepreneurs while not face to face with them is tricky.
So, if I really had to choose something, it’ll probably be this little green light here on my laptop, like being able to be connected on these different platforms, these video platforms is 100% how I do my job now. So, if I had to pick one, it would be Zoom or Zoom-like features is how I’ve really stayed connected.
All right. And is there a key nugget you share that really seems to connect and resonate with clients; they quote it back to you frequently?
Probably the most quoted line from my book that people send me on Twitter or Instagram or otherwise, is “No life is too small and no dream is too big to be worthy of investment.” I really believe in that.
Yeah, thank you. I’m going to chew on that for a while. And if folks want to learn more or get in touch, where would you point them?
So, the best single stop is the book’s website, which is BetonYourselfBook.com. There you got links to all my social media and all the places you can buy it. I’ve got some nice free downloads there. And very active on LinkedIn. I post articles three or four times a week, and so you get little bite-size pieces of the wisdom from the book and things that I’m sharing consistently with my clients there, so you can find me there.
And do you have a final challenge or call to action for folks looking to be awesome at their jobs?
My call to action is start today. As you’ve been listening to this episode, an idea that you’ve been afraid to say out loud has come to mind. Take one little baby step towards that today. And if I could pick one for you, it would be say it out loud to somebody that is a nice sponsor for you that will keep you accountable and support you in taking those first brave baby steps forward. So, start today.
All right. Ann, thank you. This has been a treat. I wish you much luck in all your bets.
Thank you very much to you, too.