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[upbeat music] Everyone, welcome back to the podcast. I'm your host, Scott Amenta.

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Today's guest is someone I've been following for a while now, honestly, long before I had the chance to actually meet him. Eric Nearlich has been one of the more thoughtful voices in the chief of staff space for years.

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And if you've spent any time googling chief of staff and landed on a really good blog post, there's a decent chance it was his.

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Eric started his career as an engineer, spent about a decade in startups, and then ended up at Google, where he eventually became the chief of staff for Google Search Ads, a role he held for over six years.

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And that experience is what eventually led him to where he is now, which is working as an executive leadership coach, helping leaders adopt what he calls the executive mindset.

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He also wrote a book titled You Have a Choice: Beyond Hard Work to Meaningful Impact. And honestly, we talk about it in this episode, and it could not feel more relevant to the moment we're all living in right now.

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So in this conversation, we get into AI transformation that's happening inside organizations, how leaders are supposed to build strategy when the world is changing faster than any planning cycle can keep up with, and where the chief of staff actually fits in all of this.

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There's a lot here. Let's get into it. All right, Eric, so nice to have you here. Welcome. Thanks, Scott. I'm excited to be here and talk about these issues that we're gonna talk about.

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I first came across some of your blog posts, I don't know what year it was, but it was early in the chief of staff world in the private sector.

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You've been one of the more, I would say, outspoken and knowledgeable leaders kind of in this space. You've gone on, obviously, from Google to coach multiple leaders, chiefs of staffs, executive teams.

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I'm not supposed to do your intro. I'm gonna let you talk a little bit about yourself.

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I just wanted to give a shout-out because I've learned a lot from you over the internet, but also at some events that you've joined us for. I'm very appreciative of it, so thank you.

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Well, thanks, Scott, and I appreciate the work you've done to help make this amorphous job of the chief of staff more accessible and more comprehensible to people that aren't inside it.

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Just briefly about me, I started my career in the tech industry as an engineer. Worked at several different startups for ten years before pivoting to the business side and joined Google on the business side of things.

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I was working actually in revenue forecasting and business analysis, and one of my product partners said, "Hey, why don't you come be my chief of staff?" I'm like, "What's a chief of staff?"

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This is twenty twelve, I think. I've never even heard of this position. What is that? He's like, "I don't know. You understand my business. I need somebody to help me un- run my business. Come help me run my business."

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I love that. You know, that's what-- how I ended up getting the job. People say, like, "Well, how do you become a chief of staff?" Like, I don't think you do it the way I did. Uh.

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[laughs] Yeah, they don't just fall into people's laps anymore. I mean, sometimes, but not that way.

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This is a guy I'd worked with closely doing his business modeling for three years, so he knew me and trusted me, and I ended up being the Google Search Ads chief of staff for over six years by his side, and it was quite a formative experience.

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I mean, I'm in the room where it happens. I'm doing all the budget and headcount planning. I'm organizing the strategy planning sessions.

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I'm involved in all of these kind of decisions about, like, where's the business going, and where should we put our resources?

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It was kind of a master class in leadership because this is the essence of executive leadership. How do you deploy your limited resources to the opportunities you have available?

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So I did that for over six years and really enjoyed it, but then took the opportunity to step aside from Google and become an executive leadership coach to take what I'd learned about how these leaders thought, what I call the executive mindset, and help other leaders, up-and-coming leaders in the tech industry, be more effective and impactful by applying those principles.

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So that's what I do now. I work as an executive coach helping leaders adopt this executive mindset and make more impact in the world.

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We're gonna talk a little bit about some of those learnings that you've had along the way in your executive coaching profession.

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Before we get into it, though, let's talk a little bit more about your chief of staff role just to provide some more context to our listeners.

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We were joking that it kind of fell into your lap, but there were clearly some things that you were doing already along the way, and, and one of the words that you used was obviously trust, which is arguably one of the biggest factors in becoming a chief of staff is, you know, can you establish a trusted relationship between yourself and your principal?

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And for someone that's hired internally, the benefit there is that that trust is built over years or months of working together and can be established, you know, outside of just a six-part interview process, which is arguably never enough.

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Talk to us a little bit about your career as an engineer, product management on your way into this chief of staff role.

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Were there things that you were doing that kind of felt chief of staff-y at the time, even if you weren't calling it that?

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So I was in an interesting position where I was on the revenue forecasting team at Google, which meant that I was in all the discussions about revenue because I was the one analyzing the revenue.

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So I was in a weekly meeting where the ads leaders would sit down and say, "What's happening with revenue this week?"

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And I was the one tasked to figure out, like, if there was anomalies, if, like, we were doing better or worse than expected. Who would go figure it out? It was, it was me and the people on my team.

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So if you're the one person that everybody goes to to talk to about money, turns out [chuckles] that's very valuable to a leader, and you have to earn a lot of trust to do that.

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So it was, like, weekly meetings with these VPs that earned me that trust over the course of three years. If you've just sat there staring at these numbers like, "What, what is going on here? What makes sense?

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Let's explore this together," and do a few of those exercises, that earns you a lot of trust.

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I think the other thing was I had the, uh, wonderful experience of coming onto the revenue forecasting team in the fall of two thousand eight, which you may remember is the start of the Great Recession.

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I was, in two thousand nine, during the depths of the Great Recession, every month, I'm being-- standing in front of Larry and Sergey and the entire Google executive leadership team going, "What's gonna happen with the economy?

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What's gonna happen with revenue?" I'm like, "How should I know?" But that was my job was to figure it out. So, like, it was a really stressful time. I worked an insane number of hours.

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But it was also a pretty exciting time for me personally because the Google leaders were depending on me to figure this stuff out. I don't know if I did the best job, but I made it through, and I got some answers.

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And like you said, that built a lot of trust. So then a few years later, when one of these VPs was like, "Hey, I think I need somebody to help me think about running the business.

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There's this guy who already knows my business." [laughs] Like, it was an easy decision for him. Yeah, interesting.

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Prime position, right place, right time in some ways, but clearly you were doing a lot of the work to kind of set yourself up for that. Yeah.

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Interestingly, of the people on that revenue forecasting team, I think, like, five of us went on to be chiefs of staff because it was just such a clear, easy fit.

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So, like, I went on to be the search ads chief of staff 'cause I was my business partner. The YouTube guy went on to YouTube chief of staff.

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Like, every single person went on to become a chief of staff because it was just, like, an easy fit for their product leaders to get somebody that already knew their business inside and out.

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Is there a Google revenue turned chief of staff mafia?

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I wouldn't say mafia, but yeah, like, the people that were on that team from, like, two thousand and nine to two thousand and twelve, we were very closely bonded 'cause it was a tough time.

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We were working very long hours, but we were figuring a lot of stuff out together, and, uh, every now and then we get together and talk about where our careers have gone since then.

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What's worth acknowledging here is that this is pre-AI time, and so, you know, you could not just turn to Gemini at the time and ask what the strategy should be based on where the economy is going. It's not that easy.

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Still not that easy, but I'm s-oversimplifying things. Still not that easy, and you couldn't just say, like, "Oh, you know, drop, you know, five different revenue models and do this for me."

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Like, we actually had to construct our own algorithms and do our own spreadsheet analyses and all that kind of stuff.

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So a lot of those skills I had then are not very useful anymore 'cause it would be faster to turn to AI to do it now, but the process of thinking through those models was very helpful.

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You can generate the output easily, but I think the way I learned to think by spending hours and hours struggling to put these models together, I think is really valuable.

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Which I think brings us to exactly the conversation that we were planning to have, right?

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Which is talking about the leaders that you're coaching and the work that they're doing today is so fundamentally different than the way that they were operating even one to two years ago.

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I think that's causing, in some ways, a lot of learning pain, a lot of growing pain, steep learning curves.

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Talk to us a little bit about what you're hearing through the grapevine in your conversations with executives about just kinda where the world is today and the type of work that they're doing, right?

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Producing strategic visions over the next, like, six, twelve, eighteen months, and finding those visions to be almost obsolete the following day. [laughs] How does that impact just the mindset of an executive?

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It's such an interesting time right now because, I mean, I work with CEOs and leaders of startups and people at big companies like Google and Meta, and everybody's basically in panic mode constantly.

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It feels like there's a huge inflection happening. It feels like there's a gold rush happening, and nobody wants to be left behind.

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I was talking to a guy yesterday, he's like, "There's gonna be the haves and the have-nots, and I wanna be on the side of the haves." And [laughs] I mean, that makes sense.

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Like, nobody wants to be left behind, and it's a real concern. We're seeing unprecedented number of layoffs across the tech industry 'cause they're like, "Oh, we don't need people anymore.

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We're just gonna do it all with AI," and you don't wanna be on the wrong side of that line. So everybody's working harder than ever.

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I have one founder CEO that's working at an AI startup, and he's like, you know, staying up till two AM every night. And I'm just like, "It's not healthy." He's like, "Yeah, but I can't let somebody else get ahead of me.

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Like, this could be the difference." So it's just this interesting time when everybody is racing and going as fast as they can to try to capture the benefits of this new way of working with agents.

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This wasn't possible a year ago. September of last year is when the new version of Cloud came out that allowed agentic work, and now it's just, like, default the way to work.

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And it's so interesting how quickly that shifted how everybody worked, and nobody knows what that means yet. And that's the interesting part.

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It's like, what does it mean to be a leader when you're leading people running agents? And I don't think we have a good model of that yet.

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The way that we kind of thought about value previously, going from nothing to good, good to better, better to great, the amount of time spent in between each one of those kind of nodes has been massively constricted.

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The amount of time spent on a project is not necessarily indicative of how good that output is. Yes. One of the people I work with said the fundamental shift is code is cheap now.

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You can make a completely custom application, do what you want, and throw it away tomorrow, and there's no sunk cost 'cause you'll make it better tomorrow 'cause the AI is getting better every week.

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So like, you know, people keep reminding me, "This is the dumbest AI will ever be today. It's only gonna get better and faster from here. If it's possible today, it'll be trivial tomorrow.

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If it's just barely out of reach today, it'll be possible tomorrow." So that's the interesting part, is we're at the frontier every day.

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But, like, that idea that code is cheap just completely changes the calculus people have of, like, what's worth doing. There's that annoying task I spend two hours on a month. Eh, I could spend two hours.

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Now it's like, no, I can spend two hours and vibe code it and never have to deal with it again.

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That's pretty cool, and in the process, I'll learn how to make an app and do all the things I need to do to make-- never worry about it.

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And I mean, when I was chief of staff, there were all these, like, little things I would spend a, an hour or two a month kind of sorting through, and now those can be automated, and that's pretty cool.

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And, like, if it changes next month, that's fine. I'll just update it. It's not that big a deal. So I think that's one of the real shifts in mindset.

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It's like our bar of what's worth doing goes way down when it's this easy to code. I think it also has presented one of the more interesting opportunities for chiefs of staff.

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One, for the point that you just made, where some of the work that feels maybe less strategic at times or repetitive can be automated, and can be automated relatively quickly and automated in a way that's, like, highly personalized to your situation, the way that your team is operating against, like, a certain cadence or the way that your principal wants something written, right?

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These things can be pretty specific now to your particular setup. The other opportunity, though, is chiefs of staff helping to drive that AI transformation forward themselves.

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And, you know, for every chief of staff that's told, "Look for the biggest, hairiest problem that your company should be tackling now, and, like, go focus on that," in some ways, this all fell into every chief of staff's lap, uh, overnight.

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I will acknowledge that, you know, I think many are afraid of the work to come and still have this feeling of potentially being replaced by the tools themselves. That's rippling across all organizations today.

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In a world of constant momentum and change, what is your opinion, mindset of how do you find solid ground as a chief of staff, as an executive leader in these companies?

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First, I wanna reflect on what you said before that of like, yeah, automating some of the smaller things. When I was chief of staff, I loved the job, but I didn't love operations.

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I didn't love doing budget and headcount planning. I didn't love OKR planning and trying to coordinate six spreadsheets across five functions to make sure that everything was aligned. That was just painful, tedious work.

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But doing that work was what allowed me to be in that room with the leaders to say, "Where are we going from here? What matters? What's important? What's worth doing?"

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And I joke that part of the reason I got into leadership coaching is now I skip all the operations. I just have that one hour with the leader, which is kind of the great part for me.

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So, like, that's the stuff I love doing. Now I mostly do that. But if you're a chief of staff now, like, that's the stuff to embrace. It's get all this other stuff out of the way.

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Like, this was a mistake I made as a chief of staff in my first year. Because the job was ill-defined, I was like, I thought my job was just to be helpful.

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And people would come to me and say, like, "Hey, can you do this?" I'm like, "Sure, I can do that, and I can do that." And I loaded up my time with all sorts of low impact, operational, boring work, basically.

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And it sucked. It was not a fun job. After a year, I was like, "I'm ready to quit. I hate this job." But before I quit, I sat down with my principal and my VP. I'm like, "This is the kind of work I'm doing.

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It doesn't feel very impactful or valuable, and there's some strategic stuff right here that I feel like I would be really good at, and I have no time to do." He's like, "That's dumb." [laughs] Like, "Stop that.

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I do not want you doing this operational stuff.

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I want you working on the strategic value stuff, and I will find other people to go do that other stuff, 'cause that's where I want you to spend your time, is on the strategic, valuable, where are we going work, not just keep the lights on work."

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Sometimes just saying it out loud is the most important thing. I mean... Yeah. I mean, once I had that mandate from him, then it was easier for me to kind of just shift my attention.

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But if you're a chief of staff out there, like, take that mandate for yourself. Your job is to add strategic value and direction to your principal, not to do the keep the lights on work. Find other ways to do it.

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Delegate it. Influence other people to do it, or get an AI to do it now. So all that comes back to your real question was, like, how do you navigate when things are changing so fast?

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The way I'm coming to think of AI is just like it's a boost in productivity. It helps you get things done faster. It's like you're adding horsepower to whatever you're doing. But it doesn't tell you what to do.

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That's the thing that matters. Like, where are you going? What matters? What's worth doing? Who are you serving? Those are questions AI doesn't matter 'cause they're value questions. They're mission questions.

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They're purpose questions. AI can't tell you that. It can't make value judgments for you. I mean, you can ask it to, but I think it's a terrible idea.

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Only you and your principal can really decide, like, here's what we're here to do as an organization. Here's who we're serving. Here's what matters. Let's focus on that.

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Then you can figure out, okay, for that audience, for that purpose, what's the most valuable thing we could be doing this week? Then you put the agents on that.

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And this gets back to one of your other questions I think you shared earlier.

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It's like, I mean, I used to run the annual planning process at Google, which we'd start in freaking July for the next year to start coming up with strategic questions, organize an offsite, have people write position papers, do a month of budget requests and headcount requests, and resolving all that so that we could have something resembling a finalized headcount and budget by December.

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It's ludicrous now to spend five months trying to set a strategy that's supposed to stay in place for a year because the whole ecosystem can change in five months. So, like, what do you do?

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That whole process is obsolete. I mean, I'm sure they're still doing it at Google because there's a lot of, uh, momentum there, but, I mean, because you still have to allocate headcount and decide who gets to hire whom.

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But with the resources you have, I'm starting to believe it's just matters much more like, what are you gonna do this week? How are you gonna move things forward this week for your purpose?

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Because next week's gonna be different. So the plan you had this week may change in a month or may, may change next week.

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Like, you have-- So I think it becomes very important to get clear on, like, what are we trying to do here together? How can I move that forward this week, and how will I measure progress so I'm still on track?

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If you start to do that, then it doesn't matter as much. Like, what's gonna change next week?

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Like, it doesn't matter if the new model comes out that obsoletes everything 'cause, like, okay, with that new information, what am I gonna do this week to serve the purpose, to serve my customer?

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I think what's relevant here is the things that you're choosing to do this week won't change.

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You're actively choosing to do things that have less of a likelihood of being impacted by the broader landscape changes happening around us, and these things are moving fast, and they're hard to plan against.

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What do you think that looks like in practice? Like, when a senior leader asks, "What should our strategy be for the next three years?" What do you actually say? "Don't bother with the strategy.

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Just focus on, you know, what you have in front of you"? We're gonna talk about your book in a second, which is all about choosing impact, and this is, I think, kind of the heart of the conversation here.

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I think on the, like, what should you do this week, like, this is actually something I learned when I was a chief of staff because I would send an email to my principal every Monday morning like, "Here's what I'm focused on this week.

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Here's what I'm getting done this week." The first few months I didn't do it, and he'd be like, "What are you working on?"

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[laughs] Like, we'd go sit around one-on-one, and he'd be like, "This is what I needed you to work on. Why are you working on this?" So it's like I learned I needed to sync.

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Like, what are the top three things, like, of all the things I could do, 'cause my to-do list became eight pages long as a chief of staff. Like, of all those things, what is most important?

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And just syncing with him, like, "Here's what's most important to both of us," that he signs off on each week. "Okay, that's what's most important," helped us stay in sync.

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And the good thing about having that sync on Monday morning was, like, something new would come in on Wednesday. "Okay, we have, we need this presentation for the CEO." "Okay, here's what I was working on, A, B, C.

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What can wait or get dropped so I can work on the presentation?" And I was fortunate to work for a leader that could prioritize like that. Not all can. Many, many can't.

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Most leaders are like, "Well, do it all," but then you do it badly, and he understood that. He was like, "I'd rather have it done really well, and if you don't get to this, that's fine. I can wait on that."

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But that kind of weekly thinking really permeated my thought and was so useful to just really focus the week.

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If I get through the week and I haven't gotten those three things done, like, that week was a failure, and it really forced me to prioritize. Somebody asking for this? That's gonna wait. That's gonna wait.

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Is it on my top three list? No. Or if it's-- seems important enough that it should be on my top three list, talk to my principal, chat it out, figure out how it stacks up.

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So to your question about, like, what should the leader do when they-- we're talking about these one-year plans or three-year plans, I think of it these days as, like, that question I mentioned of purpose, of who are we serving?

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Like, what is our North Star? What's guiding us? What's gonna help us rank all the fifteen things we could be doing?

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And really get clear on that, to use that to rank what are we doing this week or month to move towards that vision.

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And that question of how will we measure success is so important because it's like very easy to say, "Oh, we're doing this to serve the customer." Like, how do you know? This is one of the great things...

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Another great thing about AI is, like, observability is easier than ever. Like, you can actually get access to the data.

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I have a startup CFO client who couldn't get any engineering resources, and they wanted to look at the budget. He's like, "Wait, I can just five-click some dashboards." So he did. Now it's very easy.

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Everybody can just see their budgets and their headcount and everything, like, lined up in front of them, and it's like, then it can very, very clear. Like, okay, we put budget here, we're not getting results.

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And he's having that conversation with the other C-suite leaders at startup. Like, "We're putting this much into marketing. Here's the acquisitions we're getting. What's going on, guys?" And he can do that in real time.

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That's pretty cool. But it makes it very clear, like, if that's not happening, let's examine those assumptions. We thought that if we put money in this acquisition channel, we're gonna get this result.

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We're not doing it. Let's talk about that. Those are the kind of conversations we can have now with AI that were very hard. I mean, I used to put together business-- like, manually put together business dashboards.

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It took me, like, a week to put together that kind of information of, like, SQL queries and accessing databases, and now it's just, like, click, there it is. Pretty cool.

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But what that enables is getting out of the muck into these questions, what are we doing to serve our vision this week?

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You wrote a book that in some ways, I won't even say has stood the test of time yet, but it's definitely come into a time where the book feels more relevant than ever, even from when it was initially published.

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The book is called You Have a Choice: Beyond Hard Work to Meaningful Impact.

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Talk to us a little bit about kind of the framing of the book and how has that translated to the world that executives and chiefs of staff find themselves in today.

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The premise of the book is you really only control one thing- Mm-hmm. -which is the next thing you do. That's it. You can't change the past 'cause it's already happened. You can beat yourself up about it.

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You can spend your time now beating yourself up about the past or looking for who's at fault for the past, but that's not really productive.

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You can make plans for the future, but as we're discovering now, the future can change really quick for things that are outside your control, and the whole world can shift.

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So spending a lot of time planning when the future can change in that wave is, in my opinion, not that productive. So what will you do with your next action is the thing to focus on.

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And to be clear, this is not, like, a unique philosophy to me. Stoics say the same thing. Buddhists say the same. Like, every major spiritual tradition says the same thing. So this is not new to me.

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But the lens I put on it was I burned myself out at Google during those-- through that recession trying to do everything, and the part that felt so frustrating about it was I didn't feel I had a choice.

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I was trying to earn a promotion. My manager said I had to do more work to get the promotion. Now, I had to get a promotion.

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I had to do what my manager said, and the work just kept coming, and I started working hundred plus hour weeks, working eight AM to midnight every day, including weekends.

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And after a couple of years of that, my body gave out. Not surprising. I basically was in bed for a week, which sucked. And I was, like, lying there in bed going, "What am I doing?

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What is so important about this promotion?" Well, I feel like I wanted to prove that I belonged at Google. I'm like, "What else can I do to prove it?" Like, [chuckles] "This is not working for me."

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And for some reason, something clicked for me that week I was in bed, and I was like, "What if I didn't have to go for a promotion? What if I stopped doing everything my managers told me to do?"

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And I was like, "Is that possible? Can I do that?" And I was desperate enough, I was ready to quit, that I was like, "Okay, let me try this. Like, if they fire me, fine. Like, I'm ready to quit anyway."

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And so I had a conversation with my manager. I'm like, "Hey, this doesn't work for me. I don't want to work that much anymore." And they were very confused.

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They're like, "What do you mean you don't want to work that much?" I'm like, "I just... That was too hard. Can't do it." They're like, "Well, that's the job. If you can't do the job, you're not gonna get that promotion."

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I'm like, "Okay." "If you can't do the work, I'm gonna find somebody else that can." I'm like, "Okay."

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They took away half my team, my performance rating got slashed, but, and this was surprising to me, the world didn't end. I was still here. [laughs] I still had a job.

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I was working forty or fifty hours a week because they took half my work away. So instead of a hundred hours a week, I'm like, "Oh, that's actually kind of nice. I get paid. I only work forty or fifty hours a week. Huh."

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I mean, there were consequences. That is the key, uh, thing of the book. It's like we have choices when we can accept the consequences.

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I hadn't been willing to accept those consequences, that my performance rating would get slashed. That's why I thought I didn't have a choice.

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Once I opened the aperture and said, "Oh, okay, there's consequences to doing that. I don't like those consequences, but I can accept them," everything opens up I hate my job. Okay, quit your job.

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Well, then I won't have money. Okay, which consequence is worse, hating your job or not having money?

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Now it's a choice, and that's the principle of the book is you have more choices than you think if you're willing to accept the consequences. But that's kind of the negative frame.

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The positive framing is like, and with that choice, what will you put your precious time on Earth towards? What purpose will you serve? What impact will you serve? Who will you serve? That becomes much more powerful.

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And in the process of doing my own reflection on that, I was still chief of staff at the time, that's what inspired me to go towards coaching, 'cause I was like, the stuff that I was getting measured off my chief of staff job was process work, operations work, putting together, like organizing people in project management.

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And I'm just like, "I hate that." What I love is helping people figure out what to do. I help people map out ways to get unstuck. And somebody was like, "That's coaching, dude. You should go do coaching."

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It's like, "Oh, that's a thing?" It is. I'm doing it now. I've been doing it... Left Google, what? Seven, eight years ago now, and it's been great for me 'cause I love doing it.

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I think I'm good at it, and I can make enough money to get by.

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So it's like the book is kind of my encapsulation of my own journey to finding my own meaningful impact and what I've learned in coaching other people to find their own meaningful impact in whatever leadership positions they're in.

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This idea of doing hard work, just going where we started this conversation, hard work in some ways is replaceable now by new tools and technologies, and so the definition of hard work has changed.

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And I, I wonder how that might have been employed by you when you've kind of found yourself in this chief of staff role doing more and more things, right, working hundred-plus-hour weeks.

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Had Gemini and Claude and these other tools been available, like, might that have been a different outcome for you?

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You may have ended up in the same place saying, "Well, this is not how I define meaningful impact, and therefore, there's another path for me."

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I think the other thing that is, like, very worth noting, coaching is a very, like, typical mode of a chief of staff, and it sounds like you were very early in the role in the private sector.

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I mean, Google was one of the first companies that I heard of having a chief of staff generally.

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Maybe because those definitions and kind of those guardrails, like how we describe the role today, like flash forward almost a decade, didn't exist.

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You know, this idea of, like, coaching as a chief of staff and what that meant in the context of working with your principal and other members of the team might have also been a different outcome for you, right?

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Like just in a different day [chuckles] of age.

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I just wanted to reflect on kind of those two points because I think it is interesting how much, like, time and kind of where you are today, looking back may have been very different decisions just kind of based on access to knowledge and tools available and things like this.

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Who knows? Like it's, it's a different time. But I think that point about hard work is really important because I used to think hard work was the point.

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Like my job is to work hard, and that led me to burning out [chuckles] because I was working hard, but not in valuable things.

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And I think that's a shift that a lot of people miss in their careers, 'cause working hard is its own reward early in your career. In school, there's a fixed goal, you work towards it, you get the A, and you move on.

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Early in your career, your manager gives you a task, you work hard on it, you exceed expectations, you get promoted. The value you get is working hard and solving problems.

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What tripped me up was that's all I knew to do is like work hard and solve problems or whatever my manager told me. I didn't have my own judgment for what was worth working on.

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So it's like you can work hard and be spending a lot of time going in circles. The effort's there. There's no progress. That's kind of what I was doing.

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And what I think is so important is that when you get further into your career, ten, fifteen years or whatever, your job is not to do what your manager says anymore. You need to have your own judgment.

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Here's what's important. Here's what's gonna move things forward towards our goals.

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What's really interesting right now is, like, everybody needs that judgment [chuckles] because if you're-- we're using AI, like everybody needs to be thinking in that way.

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Things are changing fast enough that we can't have a top-down hierarchy where everybody waits for their manager to tell them what to do.

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They need to have their own judgment to guide the agents to set up the work to do the right thing. I was talking with one of my clients who's a CEO. He had a all hands off site where he, like, made this case explicit.

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Like, "I need everybody to step up and understand this purpose, this mission, and have that in their head when they're doing their work. I can't be the arbiter anymore of the mission and purpose.

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I was able to do that before when we were smaller, when we weren't AI powered, but like now, things are moving too fast. You're making decisions at your level. I c- I can't wait.

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We can't wait for it to get up to me and back. So I need you to understand, this is what we're here for. This is what matters. These are the principles and values I want you to, to work within.

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These are the guardrails in some sense." And it was actually very well received by his team because they're like, "Okay, this makes it clear. Here's what's not changing.

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The whole world's changing very fast, but this, our guardrails, our principles, our values, who we're serving, those are not changing. Those are our guide stars through this chaos."

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I really think that's the way leaders need to be operating now. It's not telling people what to do. Micromanagement will not work anymore. It's, "Here's what we're going for.

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Here's what matters," and use that to guide yourself through the ever-changing chaos [chuckles] that we're in right now.

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There's so much uncertainty in the world and so much change happening around us that I think the point that an executive needs to create some amount of certainty inside the organizations, like between those four walls, you can create an environment where certain things are a little bit more rigid, and everybody can align around a set of values, a mission statement, a vision for the product or service that they're delivering.

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That may change over time as well, but it's changing on their own terms, terms that may be reflective of the rest of the environment, but changing on their own terms nonetheless.

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It creates some safety for people because, like, in this world where everybody's getting laid off and stuff, it's like, well, what do I do to not get laid off?

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And this CEO is very clear that, like- If you're serving the purpose, I want us to serve the purpose faster. I don't want AI to replace you. I want you to use AI to serve our customers better and faster.

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That's what I want from you, and this is what that means. It kind of gives a sense of what the... in this case, what his employees could do to keep themselves safe in the world of uncertainty.

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Serve the mission, do it faster. That's what I'm asking of you. And, like, that's a powerful message. That creates, like you said, an island of stability amongst the chaos. This is what we're here to do.

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It kind of feels like, and maybe this is not happening structurally in the hierarchy of an organization-- of most organizations today, but it certainly feels this way, that there's this great flattening kind of happening across many companies where, yes, the managers might still exist, the C-suite team, of course, still exists, but those teams expect their employees to be making the decisions in terms of how they use these tools and how they do more hard work in conjunction with those technologies that align to that vision.

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And so what I'm curious about is, like, in your conversations with executives, A, do you see eye to eye with that statement?

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Like, is there a great flattening kind of happening, even if the companies are not necessarily calling it that? And two, where does the chief of staff actually play a role here, if at all?

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I think the great flattening is starting to happen. I mean, you're seeing it at, uh, Meta and other companies which are just ripping out the middle management layer.

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I don't think leaders have a clear idea of how to do it yet. I think we're in a kind of chaotic situation where, like, this is where it's going, but the best practices of how to do it are not there yet.

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Now it's kind of just throwing people into chaos of, like... I saw some announcement yesterday where, like, the CEO's like, "Okay, managers now have to manage fifteen people and be strong individual contributors also."

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I'm like, "Well, that seems like [laughs] a lot to ask." [laughs] You know, he should be able to do it all with AI. It's like, that seems a little, little wacky to me.

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And they gotta manage humans and agents and also do their own work. So... [laughs] Yeah, and also do the strategic planning vision work on top of that. It's like, okay, you just put three jobs on this person.

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Like, I mean, yeah, we're more efficient, but that doesn't seem plausible. So we're actually on a path towards more burnout, is what you're saying, rather than less.

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Like I said, everybody's in this mode where they, they don't want to fall behind, so everybody's in this mode towards burnout at the moment.

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Which is interesting because, like, I am not on the forefront of AI, but I read the people that are on the forefront of AI, they're doing the agent orchestration and, like, writing all these things, and it's like the agents are doing all the operational work, how to make things actually happen.

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So all I do is, like, the hard decision-making work of, like, what are we actually trying to do? And, like, that's exhausting.

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This guy, Steve Yegge, who's on the f- forefront of this, he's like, "Yeah, I got, like, three hours of that in me a day, and then I'm just gonna, like, fall over 'cause it's too much."

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Intense strategic thinking is really difficult. It's demanding. So it's kind of interesting that, yeah, we'll do this great flattening. Everybody can do this. Like, yeah, but that's not it.

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[laughs] Like, we have to also take into account human capacity of the brain. It's like making those decisions is resource-intensive for the brain, and we need time to rest and recover.

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I feel like we're in a situation where everybody's burning themselves out because we're asking too much of our brains and our bodies to handle this moment, but you don't want to be left behind. So it's a tricky thing.

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You said, like, how does the chief of staff serve in this moment? I mean, I think it's a few things. One, this alignment question is very much in the chief of staff wheelhouse of, like, what are we here to do?

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What's important? What are the principles and values that are guiding our decisions?

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How do we align those across the organization so that the engineer vibe coding on the front lines is aligned with what the principal is thinking at the top levels? It's aligned with the strategic vision.

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How do I communicate it? How do we enforce it? How do we keep tabs on it so that everything's pointed in the same direction?

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That's very much what I consider the chief of staff function is, alignment of the organization, because getting everybody pointed in the same direction is hugely valuable, 'cause if they're pulling in different directions, that's a lot of wasted effort.

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You could be working very hard, but if you have two parts of the organization pulling against each other, that's completely wasted effort. So that's one part. The other part is this question of, like, what is valuable?

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What are we actually trying to do here? It's so tempting to keep going and making things. Like I said, I talk to people that are on the, on the frontiers here, and it's fun. They're making stuff. They make a change.

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They make some more stuff. Like, the agents are doing stuff for them, and it's, like, kind of addictive.

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It's almost like, uh, playing a slot machine 'cause y- you ask it to do something, and it's like, "Will it get it right this time? Oh, not quite right. Oh, let me try again. Oh."

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It's like this intermittent reinforcement that's literally designed as like a slot machine. Like, sometimes you get what you want, and it's really exciting.

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But I've talked to a few people that are like, "Yeah, I'm also, like, burning myself out 'cause I'm staying up till two or three AM playing with AI, and then I'm not showing up as a great leader the next day 'cause I'm yelling at my team 'cause I'm exhausted."

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And I was like, "You gotta tell your AI to, like, tell you to stop pull requests at midnight or at least ask you the question, 'Is this next thing that I'm doing more valuable than showing up as a compassionate, calm leader to my team tomorrow?'"

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That's a great question. I think that's a very important question to ask.

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That's kind of what a chief of staff can do for the system at large, for the principal and all the people on his team, his or her team, is be that brake on the system, like, is the marginal value of this next little bit worth more than the well-being of our organization, of everybody here?

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Because we can push and g-- push a little more into that of what we can't do, of the next stuff we could do, but, like, pushing that more has a cost to our ongoing sustainability of work.

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And there's nobody that's thinking about that, which is why I think it's an opportunity for the chief of staff.

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It's an interesting one, not one that I was thinking about, but this concept of a chief of staff as, like, the culture maker, right? Taking a pulse check of the organization, probably more important than ever.

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As this world is changing, the humans are gonna feel that impact faster than anything, and organizations still today, for the most part, are made up of humans, and that's what we should be protective over. Yeah.

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I think that's partially borne out of my own experience as chief of staff is, like, I was that kind of release valve for people in the organization. Be like, "Hey, Eric, do you know about this? Here's what's going on.

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Don't tell your principal." Like, okay, yeah, but, like, you start to hear these reports like, okay, there's pressure in the organization. And they knew that if they got it to me, like, at least it would be in the room.

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There would be somebody in the room that understood what was going on. And being that kind of release valve of like, "Hey, the organization's under stress.

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It's kind of hitting into that yellow line, maybe crossing into that red line territory," that's important information for the leaders to know. I think a chief of staff's a great place for that to land.

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Going back to our initial points around, like, AI transformation and where the chief of staff plays a role there, I think this is very much it, right?

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It's not just about how do you push the change forward, it's about making sure that the pace of that change aligns with what the team is also ready and willing to adapt to.

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You need someone that kind of has enough context and no specific horse in any race, you know, functionally or across any P&L or any business unit to do that, and a chief of staff is positionally well-placed to do that.

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Now it's a question of are they behaviorally well-placed or ready to take on that leadership responsibility? And are they trusted by their principal to say, "Hey, we need to pull back here"?

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Like, that to me, that's a big ask.

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But I think this idea of sustainable productivity I think is really an important one for us to be considering in the age of AI, and I'm kind of making this up on the fly as we talk here, but, like, I do think it is something that the chief of staff can be well-positioned to monitor and advocate for.

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So I'm kind of inspired by this now. Gotta think about, more about how this can play out. Eric, we've answered a lot of questions along the way here over the last 40-plus minutes.

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We've left a bunch of unanswered questions between the two of us that I think we need to think about in more depth, and I'm sure by tomorrow the world will have changed again, and we will have to think about our statements all over again.

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I really appreciate the time today. We'll have to do it again soon. Sounds great, Scott. I really enjoyed the conversation.

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I appreciate what you do with the Chief of Staff Community, and I hope that our conversation today will help some chiefs of staff orient themselves and add more value and have more meaningful impact.

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Thanks so much, Eric, and we'll share your links to, uh, your coaching practice and your book in the description below as well. Thanks again. Thanks, Scott. All right. That's a wrap on today's episode.

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I hope you got as much out of that conversation as I did.

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I think what Eric said about the chief of staff being positioned to be kind of the sustainable productivity check inside an organization is definitely worth remembering.

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If you want to check out Eric's book, You Have a Choice: Beyond Hard Work to Meaningful Impact, or learn more about his coaching practice, we'll have links to all of that in the show notes below.

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Definitely worth a read, especially right now. If you've been enjoying the show, the best thing you can do is share it with another chief of staff or operator or leave us a review. It goes a long way.

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We'll be back soon with another episode. Thanks so much for listening.

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