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[upbeat music] Hello, and welcome back to another episode of the Chief of Staff podcast. I'm your host, Scott Amenta, founder of the Chief of Staff Network.

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What if the thing that made you great at your job is also the thing holding you back? Today's guest has spent years studying that tension and also living it.

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David Kirby is a former chief of staff at Ford Motor Company and the author of The Ultimate Chief of Staff Guide: The Art of Navigating Power, People, and Priorities, released in twenty twenty-five.

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He's worked across some of the most complex organizations in the country, from the automotive industry to utilities.

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In this conversation, we get into the doer trap, why being a high performer can actually stall your growth, and what it really means to shift from execution to orchestration.

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We also talk about proactive gatekeeping, operating across multiple altitudes, building leverage in your career, and the three ingredients that make or break trust in this role.

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We end with a question that every chief of staff should sit with: What does it actually mean to build something that runs smoothly even when you're not there? Let's get into it. Hey, David. Welcome to the podcast.

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Hey, Scott. It's great to be here. Thanks for having me. You've written the book on chiefs of staff. I mean, there's multiple books, but this is probably one of the better ones I've read.

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So I appreciate your insights and everything you're gonna share with us today. Before we get into that, just give us a little bit of your background, David Kirby, in a nutshell. Yeah.

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So admittedly, it's a very nonlinear, nontraditional path, but I think it has lended itself nicely to being able to navigate a role like a chief of staff role.

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And ultimately didn't see that path ahead of me, but was really excited whenever I found a role like this and an opportunity like this, and that was just a, a really strong match between skill set and role that I've just really enjoyed over the years.

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So a quick background is I went to law school in North Carolina, thought that my career was gonna be an attorney down South, bounced around quite a bit all over the country, and ultimately ended up in Detroit, where I did a number of different things and was an entrepreneur for a number of years, owned a grocery store of all things here in the city, but ultimately spun that around to a career in advertising and then one of the large automotive companies here in Southeast Michigan, where I ultimately landed as the chief of staff.

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So that was my first foray into super large global companies, and then ultimately went back to school, got my MBA, continued to operate as a chief of staff for a number of years, and now have taken a recent pivot, ended up in the utility industry here at the beginning of the year.

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So I keep pivoting. I keep trying to sort of find my path, but the years that I've spent as a chief of staff have been some of the best memories that I've had in my professional career so far. Yeah.

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I mean, industry agnostic, but always looking for a new challenge. Let's talk a little bit about your time as a chief of staff. How did you get into the role? Was it something that the business was already looking for?

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Were you pitching it? It was an internal hire, right? You were already working for them. Yes. It was really one of the first times that I felt confident enough to take a calculated risk.

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And, you know, as we continue to get deeper into this conversation, I think the theme of calculated risk is gonna come back time and time again.

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But ultimately, what happened was I was involved in an organization that was in the midst of a reorg.

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A new executive was coming in from the outside, and, you know, everybody felt like, "Oh, boy, there's a lot of dust that's been kicked up. How's, you know, this gonna really all shake out?"

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My first one-on-one with this new executive, I realized that the old role that I was in really wasn't gonna transfer to this new organization.

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And so I quite literally, Scott, I took a swing, and I said, "Hey, if you're thinking about a chief of staff or you're thinking about some type of force multiplier in a role like that, please consider me."

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The executive said, "Thanks. I'll think about it." [chuckles] And maybe about a day, but certainly before the end of the week, he said, "Yeah, let's do this."

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A couple of sort of external things were happening at the same time.

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Number one, the chief of staff role was quite prevalent across the organization, so it did help that we were seeing this title in lots of different departments.

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He was being introduced to a number of peers at the leadership level and their chiefs of staff, so it was certainly sort of primed for the right time and the right opportunity.

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But truly, Scott, I kind of manifested my own destiny in that respect, asked for the job that I wanted, not really knowing the implications or consequences of it, but it worked.

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I'm very privileged for it to have worked out, but I will also admit that my story, my journey has lots of anecdotes of where I've taken risks, and it hasn't worked out, worked out.

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So please don't take, you know, this idea that like, "Oh, we took a risk, and it worked out, and everything's great," but it was a confluence of the right time with the right person and the right organization that all sort of coalesced into me speaking up.

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And I think that that level of confidence really, really was a, a lesson for me that now I've carried on in the rest of my career. I think you're absolutely right.

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The stars do have to align in some regard for that opportunity to present itself, but it's very much on the person who's raising their hand, seeing that opportunity for what it is.

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And in your case, maybe you couldn't foresee all the things that might come with that role, but stepping in or stepping up to position yourself to kind of take advantage of that opportunity when it was there is, I think, something that every listener should take away from this.

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There's more principals and companies out there without a chief of staff today than there are with, and many are either not actively thinking about it or have heard it in passing and, you know, need that person to raise their hand and kind of present the idea and show them why it matters and what kind of impact it's going to have.

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And that impact can be had without the title as well.

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I think that's the other thing worth talking about is there are things that you can do before you're a chief of staff that help align you to the types of, uh, work that you would be doing as a chief of staff with the actual title.Yeah, that's exactly right.

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You don't have to have the formal title.

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In a lot of ways, I mean, we can get into this, and I see this a lot in the conversation around chief of staff, just sort of in the ether, right, out there in the world, that the role is very ambiguous.

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Some of this might be if an organization doesn't have a role like this, the leadership team or HR or whomever is thinking about, you know, the right roles and the right positions, like, might not even understand the power of a chief of staff if leveraged in the appropriate way.

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And so I know this conversation is sort of chief of staff one oh one, but if you look at the broad spectrum, and I talk about this a little bit in the book, of sort of a, a quote-unquote "glorified admin," acknowledging that executive administrators are a deeply valuable and highly, highly leveraged and incredibly important role in the organization, but a chief of staff is not that, all the way to sort of a mini general manager.

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A chief of staff is sort of inherently ambiguous, and it really needs to be customized in a way that is best suited for the organization in which you're operating, and frankly, even the executive in which that you're serving.

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So for a person who's thinking about this, but they're looking at their organization and saying, "Well, we don't have a chief of staff," some of this might actually just start with educating the right people to say why this is an important role and how best they can sort of fill that role, a candidate can fill that role to best support the organization to achieve its goals.

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I think this is one of the topics that you cover so well in the book, is really that path kind of along the chief of staff spectrum, moving from the more junior elements of the role, let's call it, to the more senior leadership aspects that I think a lot of chiefs of staff, and this kind of emerged from our first conversation, are somewhere stuck in the middle of that and are having difficulty either redefining or reestablishing what the role means in the context of their executive team and their principal in the more senior realms.

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One of the things that you brought up is there's kind of this idea of the doer trap, where, you know, being a great doer, right, someone that's, like, executing constantly, actually is a place where you ultimately get stuck.

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It's kind of a provocative thing. It's, like, you kind of put it front and center at the beginning of the book. Let's talk a little bit about that. What do you mean by kind of the doer trap?

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What does it mean to think about yourself as someone that's, like, highly operational, high capacity for execution? Where do those chiefs of staff get stuck on the road? Uh, it's a great question.

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And so it's a bit of a contrived sort of first stab at this answer. Really successful, highly impactful chiefs of staff no doubt have a long history or a substantial history of doing, right?

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They've created a lot of impact in their role, and now they're been identified to step into a role that is a little bit more broad and s- sort of operating at a different altitude.

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And so I talk quite a bit about the different altitudes that a chief of staff has to operate in.

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And I think by and large, other than the executive in which they serve, that altitude shift is sort of representative of how it's different than just a plain old doer.

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The idea is if you're really good at a thing, you will be rewarded with doing more of that thing, right? If you are a really good illustrator, people are gonna come to you and request more illustrations, right?

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It's just inherent in the value that you provide.

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And so for somebody who's trying to look into stepping up into or being successful at a chief of staff role, they have to understand that the skill set has to start with the foundation from what you've built as a doer, but then you have to step up into those altitudes and understanding that you're not just operating in kind of the let's fight fires or let's use my skill set to understand, like, this sort of contained universe.

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It's far broader than that. And so the altitudes that I talk about are the sort of the hundred-thousand-foot view, the fifty-thousand-foot view, and then even really, like, the one-foot view.

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And lots of examples of how you have to go between, even day to day, all three of those altitudes. A doer is primarily focused on a task and then accomplishing that task.

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Uh, you set off KPIs or you manage this through lean processes, whatever else, but it is about accomplishing a goal. With the chief of staff job, it really is more about orchestration. You're still doing things.

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I mean, doing is still inherent in the job, but is doing with the lens of orchestration that really optimizes that job to maximize its impact.

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The other thing that we talk about, and I know that a lot of people talk about this now, is the idea of an-- or concept of a force mu- multiplier.

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But I think that that really gets to the heart of a doer versus a force multiplier. Doers, by and large, it's like one-to-one.

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One input, one amount, one unit of effort gets one sort of input to that same level of output. The force multiplier, its nature, its definition has to be more. So you have one input.

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It's you and it's your contributions, but the output has to be significantly larger than what you can accomplish alone.

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That is an inherently different skill set than just, like, rolling up your sleeves and trying to get a task done.

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The other phrase that comes up a lot when you describe chiefs of staff is this concept of, you know, connective tissue within the organization.

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In your opinion, is the force multiplier this version of getting multiple people aligned around a similar vision and executing in tandem kind of against that mission more so than would happen without that person linking those dots together?That's the ideal state.

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The chief of staff is seeing around the corners, seeing what's coming, trying to avoid firefighting, although that is generally unavoidable at all.

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But it is really around being able to see what's coming and putting the right pieces together.

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Because ideally, by the time something reaches an executive level or the executive specifically that they're serving, the kink should be worked out of the system.

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I know a lot of executives wanna be able to feel like they're rolling up their sleeves and getting involved and providing a point of view and providing guidance and direction, but it should be at an altitude where it is at a very strategic high level, not necessarily like the super boots on the ground kind of stuff.

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So I talk about, like, corporate flow or orchestration, but it is kind of seeing what's ahead, what is the right team cross-functionally or internally to be able to put together the right materials to present and have the right conversation with the executive.

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You know, a lot of the work that I'm doing now, and even a lot of the work that I was doing as an official chief of staff, it was, let's ensure that we're having the right conversations with the right people.

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You know, we can talk about doers again, right? The conversations doers have is fundamentally different than the conversations executives have.

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And so the implications, the accountability, and the strategic direction that's provided, you all have to do a lot of work upfront to drive that right conversation, to get the right outcomes, to provide the direction, and it's just like a continuous feedback loop when it's working well.

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There aren't bottlenecks. There aren't sort of stops and starts in the system. There's a flow to it. And a chief of staff that is effective is managing and orchestrating that flow to the best of their ability.

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I know it's easy to talk about these things in kind of abstract terms, and w-we use these fancy metaphors.

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Is there an example that you can point to in your chief of staff role at Ford or in your current position where you felt like you were really playing that orchestrator role on behalf of your principal and helping to drive, you know, some strategic project, some initiative forward?

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So to pull the curtain back a bit, of course, you shared some of these questions, and this is probably-- this is my second favorite question, if I'm being honest.

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And so I like the idea of, like, let's make this really practical. So yes, there are plenty of examples. There's lots of examples.

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The one that came to mind was around the planning cycle and the role of chief of staff serving the executive. We had P&L ownership, and so, you know, budget planning kicks off late summer.

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And so, you know, you are working through super cross-functional teams, finance and marketing and corporate strategy, product development, right?

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And really understanding the pipeline, your backlog, what's coming next year. And it is very much this like, again, this sense of different altitudes. You're focused on a certain task at hand.

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Let's nail down this budget for next year. But then you're also thinking ahead of, okay, well, what is feeding the pipeline for us to be able to actually develop our targets and then meet them?

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So while that's happening, you're pulling together a lot of different meetings, a lot of different stakeholders.

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And so, of course, there's a particular example where, number one, you're super boots on the ground in budget planning. And so you're bringing in finance partners, and you're about to have a cross-functional meeting.

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Something happens, a family emergency or whatever else, and the finance representative that is supposed to be coming to this meeting talking about projections can't come.

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So you're fighting that fire of, okay, well, can we have the meeting without this person? Do we need to reschedule without this person?

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Can we have an upfront meeting to be able to get the right data so we can still have the meeting? So you're really trying to, and, uh, you know, this is actually a, a real-life example. So I was trying to manage that.

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Then at the same time, you're still juggling, well, the executive has to give a presentation in two weeks to a small group of executive elsewhere in the company.

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And so you're planning what does that presentation look like? How are we pulling the materials together? And so it never stops. You're looking out ahead.

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You're looking out two or three weeks to see what's on the calendar that the executive has to take care of in the future, while also fighting the fires of today and how we are gonna keep the trains running on time.

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So it's constantly that scan of what's happening right now, what's up ahead, and how do I prioritize those two things so that I can, can accomplish everything that's expected of me.

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It also feels like you're actively deciding what information, in what format, and from who, for that matter, should the information come from on its way to your principal.

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In a lot of ways, you're a filter for that peer as well. You use a term in the book, proactive gatekeeper. When people hear the word gatekeeper, they often think a bottleneck.

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What you're describing, I think, is the polar opposite of that. Talk to us a little bit more about kind of where people get this notion of a gatekeeper wrong. What does getting it right actually look like?

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So getting it right, you know, I've tried to think of the right or at least a relevant metaphor here, but the best one that I can come up with is a shipping manager, right, at an Amazon warehouse, something like that.

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You're trying to understand delivery routes, and it doesn't make sense for a delivery driver to drop off one package on one side of the city, drive across the city, drop off another package, go back to the other location, drop off a package right next door.

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You have to orchestrate that it makes sense and maximizes the sort of the value and impact if we coordinate all these things all at once.

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Even in this conversation, I've talked about corporate flow a lot, but it is that orchestration. So a proactive gatekeeper is being really strategic about timing. Then that's ultimately the difference.

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A bottleneck is something that just inherently slows things down. A proactive gatekeeper might slow something down in the near term and ultimately speed things up long term.

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So you can think of the executive having one-off discrete meetings or coordinating and orchestrating a larger forum where in the pre-work that key we've talked about, you know, the executive level decision-making, a lot of key decisions have been made preemptively or at least aligned enough so that when you go to the executive, the conversation is at the appropriate executive level.It's no longer just kind of about the doer problem, it is about the orchestration problem.

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So the proactive gatekeeper was intended to be a little sort of pokey because you're acknowledging gatekeepers typically have a more negative connotation, and certainly in a, a corporate environment that is, [laughs] you know, a criticism of many organizations, whether it be intentionally malicious and control-oriented or otherwise.

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But the proactive gatekeeper is one that is trying to put the puzzle pieces together, so by the time, again, you get to the altitude where you're with the executive or they're trying to make that principle level decisions, it is this idea of, like, one plus one equals three.

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The value is more than just the meeting itself, it's the work that's been done prior, and it's the orchestration that's been done prior that leads to the best results.

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Do you feel like as chiefs of staff move into more senior levels of this role, they become...

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And part of this I think fits into this idea of proactive gatekeeping, they become more invisible to the rest of the organization?

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Like, the work that they're doing is not necessarily the final output of what might be seen, you know, that's reflective on the bottom line or in a board deck or what have you, but is very much the work that goes into the processes behind how work is actually getting done.

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And you talk about kind of invisibility as a feature of doing this role well. What does that mean? Do you actually become more invisible as you're doing the role even better and better?

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I mean, yes, that's certainly a possibility. I would slightly reframe it to say you don't become invisible or more invisible or less seen, but when you are seen, the impact is far more strategic.

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And so you're exactly right. So, like, a lot of this work and orchestration and putting meetings together and putting stakeholders in the right room to have the right conversations, you're exactly right.

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That's really hard to put down on a lean bowler and measure over time. But when you are doing it and the impact is felt, you know, I talk a lot about it's really around timing.

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So if you're totally invisible, it's a major problem, [laughs] right? Like, people will straight up forget about you. You don't want to be totally invisible.

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But at the same time, inherently you're not completely visible. I mean, your executive is, right?

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And maybe even the teams that are working on a particular initiative like a board presentation or something, they should be very visible.

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So as a chief of staff gets deeper into that job and they're thinking about the visibility and the impact that they're having, the impact and how they're communicating that outcome of the work that they're doing, it is about strategic timing.

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You have to be able to tell your own story. You have to be able to communicate the impact that you're having.

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It's not just the being about, like, I set this up, and then I let it run, but it is about the guidance, the orchestration, the flow, and the relevant strategic timing of when you're showing up and how you're communicating your impact.

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I think a lot of chiefs of staff thinking about kind of this notion of invisibility and how more strategic work gets done, it may not always be seen, but it's certainly felt.

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The chief of staff then can point that towards, "Okay, I'm a strong performer across kind of XYZ domains." And as you said kind of at the beginning of the episode, a lot of that comes from the doing first, right?

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What are the skills that I carried with me into this role?

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I've talked to lots of chiefs of staff that come from product management backgrounds, engineering backgrounds, ops backgrounds, strategy backgrounds, go to market.

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They've all carried something with them into this role that marries well to what their principal and what their organization needs.

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There's a lot of talk, I think, among the chief of staff community about what is the skills gap that it takes to really move from junior mid to, like, very senior chief of staff.

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This is not necessarily hard skills that we're talking about. They're soft skills, right? Or I like the phrase power skills.

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These are things like communication and leading without authority and negotiation and the human act of working with other humans.

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What is your opinion about how you grow in the role based on how the role might be structured? Is it a skills gap? Is it a positioning gap?

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Of course, right, acknowledging up front that some of this might be reflective of the individual and the individual experience, and so my answer is gonna be just sort of inherently broader. For sure.

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And I think that's the best caveat, and one of the reasons that this podcast exists is, is every opinion [laughs] is a little bit different, and that's okay. [laughs] Right. Exactly, yeah.

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So, you know, I mean, of course, if you're an individual and you've got a difficult relationship with your executive, and you're just n- sort of not being supported in that growth, that's just your own unique challenge, right?

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But broadly, you know, again, sort of seeing these questions and thinking about this question, I think in other conversations you've had and acknowledged this difficulty broadly, this macro sense of being able to go from that mid to the upper.

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I wanted to try to acknowledge maybe two elements that might not be as popular in the discourse, right? Or seen as a data point in the discourse.

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Number one is, fundamentally, if there is a super large organization or a large enough organization where there are multiple chief of staffs running around and operating, and everybody's operating relatively at the same level, and there is no path up where the chief of staff itself, the job, the role, is moving up to more and more senior level positions, then frankly, I do think some of that is a reflection of just the organization and its belief of where the role is and where it belongs in sort of the, the hierarchy.

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So if you're sitting there and that is your world, and you're looking around, and chief of staffs are, you know, at level X, and you want to be able to get to that next level, there is fundamentally a conversation to say, "Is this still the right organization for me, or do I need to be able to look elsewhere?"

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That's just the truth.

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In sort of the same vein or kind of a variation on that theme when we're talking about the relationship between the chief of staff, yourself, and the organization and the executive in which you serve, I know this is kind of like a very touchy subject, but frankly, I also think it's a matter of leverage.The times when I've been able to really move in my career was when I had the greatest amount of leverage.

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I know this sounds kind of Machiavellian or like playing a game, but fundamentally, like, if you don't acknowledge that where you are with your career development and the leverage that you have, you're not looking at your entire toolbox.

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And so, you know, if you're thinking through, "How do I get to that next level?"

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So for instance, you're operating sufficiently at a chief of staff job, just as I said earlier in the conversation, like if you're really good at X, then you're just gonna get more of X.

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And so if your executive is saying, "Wow, Scott is just killing it. He's operating, he's meeting every expectation.

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He's just really, really good at this job," there's no leverage and there's no incentive for that executive to support you into that next level, 'cause what does that mean for that person, right?

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It means, "Oh man, maybe I have to backfill this person," or maybe, "Scott's gonna go on and start to lead more. Maybe it's possibly a threat ultimately to where I'm at and what my role is."

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And so leverage can be used thoughtfully. In fact, I know it's a little counterintuitive, but it can probably used a little benevolently as well.

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And so to be able to use what you have, frankly even like if it's a counteroffer, if it's an offer to leave, if it's an offer to go to a different part of the organization.

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But you may be able to have to say, "Listen, I really need X. I'm deeply invested in my development. This is an important role and this is an important step-up opportunity for me." That's how you get people to move.

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I've seen it time and time again where somebody has strung along even for like multiple years where they're saying, "Hey, great, you're a high performer. We really want to get you into that next job."

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But you know, there's a lot of stasis in that aspect of their career 'cause, like, you're doing great. [laughs] So again, you're actually disincentivized. The organization is disincentivized to move you along.

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I have truly seen, I'm not making this up, I have truly seen situations where a person has been in a role for at least a year, possibly years.

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They've gone off, they've gotten some leverage, they've got a counteroffer they've gotten, and a move has been made within twenty-four to forty-eight hours.

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Now, I mean, I think that that is problematic in its own way, but it does show you that when people are motivated to support and make change, they will.

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I like the point that you started with around organizational structure can be an impediment for a career move generally as a chief of staff, you know, upwards in the ranks.

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And I think it's something that most chiefs of staff are taking for granted, this idea that, well, every role has a career ladder, and therefore, this one should be no different.

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And my principal and the people ops team or whoever's making the decisions will kind of see my value for what it's worth and naturally move me along as the years go on.

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For one thing, every chief of staff has the same title, even though the levels may be dramatically different.

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And so I think there's plenty of companies out there that actually have not established, "Hey, where does this chief of staff sit within the hierarchy of the organization?"

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And then it's just left a little bit unclear to everybody. That is a problem all by itself.

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I think the other issue is the chief of staff role coming from military and kind of political worlds is a lot more rigid in its structure and kind of where it sits in the hierarchies of those departments, and it is almost a very senior role every time.

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And that is very different than the way that it has been adapted or adopted into the private sector, where organizations are living, breathing entities, and they change all the time, and people come in with different viewpoints and different ways of working, different ways of thinking about how the organization should be structured.

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I think it's probably the most interesting thing about companies is that they are literally all different.

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[laughs] And therefore, you know, it's such an ambiguous role, I think it's impossible for any one person to say, "Well, this role is going to be the same across every company, and therefore, is always gonna be the most senior or the most junior."

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It is open to interpretation by company and by principal.

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I think the second point that you made is also really valid, that, like, the principal needs to have your back kind of first and foremost to even make those opportunities possible.

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Then your ability to have some leverage to really, like, force that conversation if it needs to be forced and give yourself, you know, the opportunity to move where it may not have been immediately top of mind before.

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That leverage can go a long way, and I think you're right. Like, it doesn't need to be done in a malicious way. In some cases, it can actually be really good for the company. It's just, it's on you to prove it, right?

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Yes. And this goes back to the first part of our conversation, like this act of doing, this act of execution. It is a little bit of a trap because all of those things that you're doing then need to be backfilled.

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They need to be replaced. In your capacity, your ability to open more capacity for yourself to do that more strategic work, to be that force multiplier can't happen.

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You know, I think the other trap that we haven't talked about, but you did write a little bit about in your book is this kind of like concept of reactivity versus proactivity, right?

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And a chief of staff that is solely putting out fires. And that's not to say that, like, you won't be putting out some fires as a chief of staff. That is a natural part of the role.

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But if that's all you're doing, if you're spending ninety-plus percent of your time just reacting to whatever the company throws at you, you're kind of doomed to failure.

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Not failure in the role, but, like, you're not gonna move forward in that capacity. Yeah.

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If you're putting out fires constantly and you're making everybody's life easier because you're just putting out fires, again, you're just gonna get rewarded with the same thing over and over again.

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The journey that I went on, because it was a new organization, it was going through this reorg, I actually experienced... To go back into the altitudes, like the altitude shift, the percentage shift over time.

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And so if you're in a new organization, for instance, or you're brand new chief of staff, you're gone through a reorg, or the role is new for the company, like it's gonna be a lot of firefighting, right?

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But then as things hopefully stabilize, you've put governance in place, you've put systems in place, you've been able to put cadence in place where, you know, things become more predictable, that percentage shift of altitude changes over time.

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That's the ideal state.

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I will also say the opposite is true.If you're only working on the big strategic stuff, you're only working on what's coming ahead in six months to a year, like you're also not fulfilling the roles and duties of a chief of staff in its entirety too.

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It is about that balance, right, of going across multiple altitudes and being sort of the proxy. I mean, frankly, in a lot of these roles, once enough trust has been built, you can operate as a proxy for your executive.

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And the executive in a general management role has to go through all those altitudes all the time. I think through like the Mike Tyson quote, like everybody's got a plan until they get punched in the mouth.

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It is great to be able to design systems and governance where things feel like you've got everything under control, but the sort of like most brutal truth of life is that like we have very little control over anything.

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And so it is having the adaptability and flexibility of understanding that your systems and governance are in place for most of the time.

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You've worked really hard to build that system so that the trains are running on time most of the time, but being prepared for the craziness that comes with corporate America and just dealing with fires as they come.

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But you have to be able to do all three, and if you find yourself stuck doing just one, you've got a major problem.

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I've heard from other chiefs of staff who I would say are operating at like some of the most senior levels of, of what the position has to offer.

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As they've moved through those ranks, their focus has become more on the organization's priorities than the principal's priorities. I think there's a lot of merit to that argument.

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I do think that your framework kind of across these different levels also holds a lot of weight because you're, you're never actually just operating only at the organizational level, only thinking six months to a year ahead strategically.

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Like you have to be in the day-to-day as well to have any of the context within the company that will make that more strategic work actually valuable and useful.

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It truly is kind of the movement between those atmospheres that makes it what it is.

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I completely agree, and that comment about the enterprise, it's the relationship that the principal has with the enterprise is really interesting.

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You know, in a perfect world, everything cascades down from these are the L zero goals, and you go down to the next layer, the next layer, and hopefully all of your objectives, KPIs or targets, whatever you use to measure progress is all nested.

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If that is the system in which the chief of staff operates, your life can be a little bit easier, right? Because you can understand the principal's objectives. You can see the enterprise objectives.

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You can start to work through, okay, what is the connective tissue that aligns, you know, and ensures the success of my specific principal or executive with the broader organizational goals.

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But go back to leverage, and it's not just about career navigation, it is about impact inside the organization too.

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So again, using very specific examples, as a chief of staff, I was responsible, and the team was responsible for P&L. And some of the P&L targets were tied to company-wide bonuses.

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And so to go through and fight the fight around product backlogs and product development to say, "Hey, if you want to get your bonus at the end of the year, like we really need to prioritize X, Y, and Z."

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I mean, that is enterprise level leverage that you can then use to the service of your principal or executive and team.

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So understanding the context, um, both well below at the working level and above at the enterprise level, that is a super successful chief of staff that can sort of hold all of those things in context all at once and see the right pieces and, and levers to pull.

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What do you think about in terms of measuring impact? We've got these different atmospheres that we're working across. They call for different stakeholders, different types of work, different mental modes.

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I like the idea of an impact journal, right?

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Just something that like I'm reflecting on in terms of conversations that I've had with peers and executives that may have moved the needle in one direction or another for various projects.

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And I think that's something that's like helpful to look back on on a quarterly basis, on an annual basis. And first and foremost, just for yourself, right?

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Like there are lots of things happen in a chief of staff world that may feel inconsequential, and then three, four weeks, three, four months down the line, you know, it turns out that conversation or like that meeting that was held actually had a lot more weight in terms of delivering, you know, the final output.

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What do you think about in terms of like impact measurement? There's no kind of clear defined KPIs for a chief of staff. They're going to vary based on, you know, how that role finds itself in the company.

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What are things that you've done that have been, uh, helpful for yourself?

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Measuring impact in the chief of staff or any sort of strategic role when something is non or harder to quantify is like one of the hardest challenges that I think anybody's faced with.

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I hear this across the board with, you know, strategy roles, chief of staff roles, roles where you're not tied to objective performance targets. It's just very difficult. I like the idea of a journal.

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I've said in our conversations I like the drive for specificity. Maybe you'll say I'm being too specific in this one, but I will tell you specifically how I deal with it. I've been doing this for years.

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I've always found success with it. I use OneNote.

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The companies that I've worked for have Microsoft Suites, use OneNote, and I have a tab, the annual tab, where every single thing I've touched, influenced, informed, that's uploaded in some type of copy on a shared drive or whatever I hyperlink to.

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And so I can go back by date, and I can pull up that page in OneNote, and I can go by date starting January first of this is the deck. It's hyperlinked here. This is the impact.

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And then when I'm doing weekly reviews, it is a visual management chart for my executive. When I'm doing quarterly KPI updates, I can go back and actually see. It's very much not about quantity.

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Like I'm not trying to get to hundreds of SharePoint links on this one particular deck.

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But I can go back, and it's also a really easy file management process too.To understand, oh yeah, back in January I was working on this, or I need this slide from that deck, here it is.

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So this is probably the most specific [laughs] advice that I can, I can give on this podcast. If it's not OneNote, but just some type of organizational tool that's hyperlinked or some way linked to the work product.

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It's really, really easy then to have conversations quite literally showing anybody what you've done and what you're working on.

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And then also it has this sort of other benefit of a file management system where you know where all of your files are and you know what you've been working on. Yeah.

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It's very poignant advice, and something that I think most listeners, most chiefs of staff are not doing well today.

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I think because measuring impact feels so ambiguous and is not a conversation that's had enough with principals. It feels like more finger in the wind, uh, you know, someone will tell me that I'm doing it well.

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That's not necessarily the right path for growth. Yeah. And it's the invisibility thing, right?

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So like if you're spending a lot of time orchestrating, putting meetings together, trying to put people in the right room together, how on earth do you measure it?

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You're not gonna take like a videotape and say, "Hey, this is-- here I am putting these meetings together." I mean, it's very, very difficult. And so, again, a huge skill set around impact is storytelling.

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You have to be able to tell the right story that resonates with the executive or principal to say, "This is the impact that I'm having. I'm saving you time. We're being more efficient.

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That doesn't always necessarily show up in a quantifiable way, but here's what I'm doing and here's the work that I'm doing," so that it is not invisible, that your value is felt and understood, even if it's not quantifiable all the time.

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One of the last things that you kinda talk about in the book is trust. And trust is another thing that's very difficult to measure, right?

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Because it is truly this, like, relationship between you and principal, you and the rest of exec team and the whole organization.

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You wrote that trust is kind of built on three factors: competence, integrity, and benevolence. I think most people probably get the first two. Right? Like, how competent am I at actually doing the work?

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Does my principal trust that I can go execute these things? Let's talk about benevolence, though. What does that actually mean in the chief of staff context?

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So now we've hit on my favorite question that you've asked, so the trust question. I love this topic. I think it's fascinating. It's endlessly fascinating. Trust is an outcome, just as like you're saying.

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It's really, really hard to measure. I believe very strongly that if you were to go out right now and ask ten people what is trust, you'd get ten different answers, and probably ten very different answers.

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When you look at the research of trust, it is an outcome or an output of three inputs: of competence, integrity, and benevolence.

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And so, you know, instead of focusing, if your ultimate goal, and it should be by the way, is to build trust with your principal executive, the working level teams, the teams above, like trust building is core to the work that a chief of staff does, then you have to understand the inputs, right?

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Exactly what you're saying. Frankly, are you good at your job? That's your competence. Are you being honest, telling the truth, you know, having the right values that align with the organization? That's your integrity.

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The benevolence thing is interesting.

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I mean, the definition of the benevolence is you're looking out for the greater good, or you're looking out for others' best interests or a group's best interest rather than your own self-interest, and that manifests in lots of different ways.

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And so are you really trying to look out for the team's best interest, your principal's best interest?

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Or frankly, I mean, 'cause it's come up a couple of times in this conversation, like, or are you just trying to get ahead and look out for your own career and you as number one and forgetting about the, the interests of the organization?

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That benevolence mindset of we're trying to maximize impact, we're trying to do the most good for the most amount of people, we're trying to look out for the best interests of the people that I serve, which is not just the principal, but it's the entire team that the prin-principal's responsible for, and then ultimately, I think, the whole enterprise, but are you really trying to look out to maximize the impact of the group rather than yourself or the individual?

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Countless examples, I can get into specifics, but the idea of invisibility is wrapped up in that benevolence where you're not just sort of like pumping up your chest and talking about how great you are.

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It's not just about always talking about the impact that you're creating, but it is if you're operating as a thoughtfully invisible orchestrator, a proactive gatekeeper, then ultimately what you're doing is acting in benevolence because you are trying to work out the impact of the whole organization and be that force multiplier.

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That's how you get the trust. That's how you get more empowerment.

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And, you know, as we sort of mirror this with the career conversations, the more trust that you have built, the more empowered you can become, the more sort of independent or autonomous decision-making that you can create, and that is a self-reinforcing cycle.

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So if you're thinking through, like, "Well, how do I make it to that next level?"

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You have to demonstrate that you have the capabilities, the competence to get to that next level, and it's done through being trusted, being empowered, and being able to operate in an autonomous way because the trust has been built over time.

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So, you know, again, you have to have a long track record of looking out for the greater good, and that is ultimately what benevolence means in this context.

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I feel like your statements around trust just linked everything we've talked about throughout this episode. [laughs] We should've just started there probably, David. That would've been a very quick podcast.

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It does boil down to that one word. I think it's maybe one of the most critical themes within a chief of staff world and just generally in business, right? Like, are you a good actor?

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Are you thinking about the organization and the team more than you are about yourself?

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You will oscillate between kind of those two worlds sometimes, but this role is built on trust and being a very principle-oriented position.

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The only way to succeed is to establish a strong relationship where your team and your principal know you're doing the work, you know, on their behalf and, you know, kind of for the greater good, as you said.I think it's also important to note that, like, benevolence does not mean just rolling over.

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Maybe I'm being a little too dramatic, but, like, you can be very aggressively benevolent, [laughs] right?

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Like, if you strongly and fundamentally believe in what is best for the greater good, that does require some level of confidence to go and push back, right?

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Where you're seeing that you have actors or you have conflicting interests that are misaligned to sort of the broader vision.

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So, you know, benevolent is this sort of soft or thoughtful, maybe you could look at it through the lens of, like, a passiveness. Like, "Oh, okay, I don't want to rock the boat."

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But that is very much not what benevolence can mean in a context like this. No, I think you're right. The most senior and most effective chiefs of staff are confidants to their principals first and foremost.

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And confidant does not just mean being a yes man. It means pushing back with the context and with the ideas that might make a difference in a decision.

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And that's only done obviously with an amount of trust where that person's willing to listen and, and maybe change their mind. That's right. David, I want to end with a statement that you kind of end your book with.

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You talk a little bit about what success looks like as a chief of staff. You say the highest compliment to a chief of staff is not, "We couldn't live without you," it is, "Things run smoothly even when you're not here."

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For someone listening that kind of wants that to be their story, what are your words to them?

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How do they position themselves in a way where their team can live without them, and that still feels comfortable [laughs] in the position?

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This is a bit of a cop-out answer, but it is the most honest one that I think I can think of, is just start. Just start anywhere.

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[laughs] I think back to, I know I've used a, a couple of sort of anecdotes and stories to drive home the point, but I think of Chris Rock.

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Chris Rock has a great little story of, you know, when he was starting out and really struggling. He was dead broke. He was driving from show to show, and his car would break down, right?

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If he just stood on the side of the road with his thumb out trying to hitch a ride, nobody would stop. But if he got out and he pushed the car, you know, cars would pull over constantly to help.

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And so you have to be able to help yourself. You have to start, and then people are going to jump in because they see the enthusiasm, they see the work, they see the commitment. There is no right place to start.

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If you're thinking through, "Where do I apply leverage? How do I act benevolently? How do I be a force multiplier? How do I build trust? How do I start as an orchestrator?" Just start.

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If somebody wants to reach out and we can have those conversations, I love it. But I've had conversations where we can say, "Okay, well, let's start with the smallest possible thing."

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You see a broken process or you see a gap in governance, go in and design a system and try it. It might not be perfect, but then you can iterate. Or the exact opposite in your context can be the truth, too.

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Go work on the biggest possible problem. All the small stuff is not worth it. Let's go-- Something is fundamentally broken. Let's go work on this huge boulder that we have to move out of the way to move forward.

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So the answer is, if you want to either move more deeply into this role, be a more successful chief of staff, or you're thinking, "How do I break into becoming a chief of staff?"

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Truly, the answer is just start with the idea that I want to build trust with a senior level executive. I want to be able to be a force multiplier for that leader and the organization in which they operate in.

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I want to serve the greater good of the enterprise. And there are things that are not working.

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What are pain points within the corporation that I can start to work towards to be able to maximize that impact and show my value?

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And so for anybody listening who is thinking, "Oh, gosh, it's like jump rope, like double Dutch. Like, ooh, I just got to get the timing right." It's not just about timing. It's just start.

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Start right now saying, "I've identified this pain point," be it small or large. "I'm going to lean into this, try to work it done." And then, you know, tell that story.

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Be a storyteller of your impact, and that momentum will build. It might not be overnight, but that momentum, as long as you're remaining consistent with that point of view, it will build over time.

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David, thanks so much for joining us today. Thank you, Scott. This was great. I really appreciate you. Okay. There's a lot in this episode worth revisiting.

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I especially like the idea that being rewarded for doing just sometimes gets you more doing. The one-note system that David uses to track impact over time was especially meaningful, and also that reframe on trust.

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It's not soft. It's a measurable output of competence, integrity, and benevolence working together. If there's one thing I really want to leave you with, it's what David said at the end.

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If you're trying to figure out where to start, whether that's breaking into the role, moving up within it, or just doing it better, his answer was simple: Just start.

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Pick a pain point, lean in, tell the story of your impact, and let the momentum build from there. If today's conversation resonated, the best place to continue it is with other chiefs of staff who are living it, too.

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The Chief of Staff Network is where that community lives through events, connections, and conversations with other chief of staff practitioners at every level. You can find it at chiefofstaff.network.

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And if you haven't subscribed yet to the podcast, do that now so you don't miss what's coming next. We'll see you next week.

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