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[upbeat music] Hey, friend. It's David Nepinski, the community lead at the Chief of Staff Network.

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We help chiefs of staff through the three Cs: cohorts, curriculum, and community via a Slack with over nine hundred people in it. Learn more about membership, events, and our programs at chiefofstaff.network.

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You can also subscribe to our newsletter there to stay in touch as well. This episode of the Chief of Staff podcast is with Anna Buckley. Anna's a two-time chief of staff at Barstool Sports, the popular media company.

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In this episode, you'll learn about how she got her roles, how an EA role can turn into a chief of staff role, complementary skill sets between the principal and a chief of staff, and so much more.

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So excited for you to level up as a chief of staff. Here we go with Anna. Cool. Uh, Anna, welcome to the show. Thank you so much for having me. Excited to be here. On a Friday. Um,

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so, um, I don't know if we should talk about dogs first or not. Um- [laughs] Okay. Why did that come to mind? Um- You know I have two foster puppies at home at the moment. Did I tell you that?

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Uh, I've heard about that, yeah. Okay, yeah. I think you emailed about them. Oh, possibly, yeah. Yeah, yeah. Oh, yeah, on the-- when I was connecting with Chief of Staff Network.

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Um, yeah, we've two foster puppies at home, Friday, Friday and Rufus, twelve weeks and- Got it... fifteen weeks. So they're a bunch of work, but it's good fun. [chuckles] Okay. Um, uh, when did you get them?

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Like three, four weeks ago. Oh, wow. Feels like an eternity though because it's been so much work. Oh my gosh. Okay. Yeah. They were babies when they came to us, so the training is, is going, is going. Okay.

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That's about it. [chuckles] Okay. How do you compare that to chief of staff role? [chuckles] Um, great question. Uh, a lot of chaos definitely. [laughs] A lot more cuddles. [laughs] Very different, I would say. Okay.

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Um, and then speaking of chief of staff roles, um, how did you get your chief of staff role? Yeah.

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Um, so to go right back to the start, my parents both were entrepreneurs, um, more so in the traditional sense versus the modern sense.

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Um, but so when I was growing up, I had, like, very little exposure, I suppose, to the corporate world.

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Uh, worked very hard, you know, attained great grades, went to Trinity, which is the number one university, um, in Ireland, but felt that there was very little resources available to me in terms of a career development, um, standpoint.

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So that's actually something I spend a lot of time on now, is trying to help other high-potential talent from Ireland coming over to the US in, like, their early career and figuring out what first steps look-- might look like for them.

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Um, so in, in college, I studied business and economics, so pretty generalist degree.

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Um, when I was looking at, you know, paths I might wanna pursue, consultancy was one that came to mind, um, given it is, you know, generalist in nature, and you get exposure to the full, full realm of the business.

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Um, uh, but I guess I was a little bit hesitant around that because I was aware of the fact that I am pretty impatient by nature- [laughs]... I would say. And, um, maybe was a little bit arrogant at the time- Okay...

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and really wanted to go into a role where my scope was defined by the value that I could bring to the organization- Okay... versus being predetermined by, like, your years of tenure. Okay.

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Um, so chief of staff was kind of emerging, emerging title in terms of, um, private and public businesses at the time, you know, five, six years ago.

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Um, it was interesting to me because the role seemed to be more reliant on intangible skills, so your ability to build networks from within, um, your, you know, some of the soft skills, um, that didn't necessarily come from experience.

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So just being, like, solution-oriented by nature, being very analytical, being able to operate with humility.

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Um, and I thought that if you went into that role, you would get exposure and a seat at the table when I hadn't necessarily earned it at that point in time, which is really what I was interested in doing.

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Um, so I came to the States. I'd spent a lot of time in New York during the summers, uh, through college. How many years ago was this? Uh, this is twenty eighteen- Okay... twenty nineteen.

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Um, spent a, a bunch of summers here throughout college. Love New York.

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Um, love the pa- the pace of New York, love the diversity here, and I felt if you could make it in New York, it was kinda the epitome of success- [laughs]... as corny as that sounds.

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Um, so came over here after college, and when I started looking for chief of staff roles, instead of, you know, my...

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I suppose my approach in the organizations that I was looking for, I was more so looking at, um, unconventional criteria as opposed- Mm-hmm. Like, I wasn't looking at industry or product.

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I was more so looking at the teams. So I was really interested in working with seasoned executives who had worked at, you know, more established, traditional companies, but also had built and scaled startups.

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Um, I was looking for startup culture for sure, no matter what, like, how old the company was or what stage it was at.

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It was really that culture I was after because I figured if I could get my foot in the door and there was less definition because of the startup culture, it would offer me the opportunity to take more on.

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Um, and then I also wanted an organization or a business that was backed by investors that were experts in their field.

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Um, I clearly, coming out of college, didn't know anything about anything, and I thought if I could lean on the investors who'd made the investment in terms of they understood the industry, they understood the market, they understood, um, what was going on there, they were advisors to the business, and they'd done their due diligence as well,

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um, and, you know, saw the opportunity enough to make that investment, that they were kinda some of the criteria that I was looking at, um, when I was looking for the, that chief of staff role.

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So one of the organizations that I came across, um, now obviously I'm from Ireland and this accent, which we were just joking about- [laughs]... if anyone hasn't caught on yet. Um, so I...

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Barstool Sports has no audience in Ireland. Um, you know, it's, our audience is all in North America, so I know noth- knew nothing about Barstool Sports when I went in there.

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Um, but they, Deirdre Lester, who was the chief revenue officer, she was hiring for a as- an assistant, and I likened a lot of the responsibilities of an EA with an early, um, chief of staff type role.

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And I figured if I could get in, get my foot in the door, take that role, and succeed with some of the, those, like, early tactical initiatives, um, then I'd maybe be able to scope out a bigger role and move and elevate into a chief of staff type role.

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Um, and it's funny because I know even the study that, that you guys did, the Chief of Staff Network did a couple years ago, when you look at the transition from EAs to chiefs of staff, I think it was, like, twenty-five percent- Mm...

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of chiefs of staff originated in an EA type role, um, which was re- it seemed really high to me, and I wonder if that just happens organically. Whereas I think that it's a very...

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it's very unusual for someone, an aspiring chief of staff who wants to go into a chief of staff type role, um-Proactively seeking out an EA or an assistant type opportunity.

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You obviously need to have a low ego to that, um, but really going in with that intention and then scoping it out- Yeah... um, and moving into that role.

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Um, so the early years, like I spent a lot of time working mainly on more so the EA type, or 30 months I should say, excuse me, um, spent more time working on the more administrative logistical type tasks, so calendaring, travel, um, tactical priorities, like preparing Deirdre, um, documenting notes, and had some quick wins early on.

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Um, definitely Barstool obviously was pretty chaotic at the time and kind of still is to this day.

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[chuckles] Um, so it was easy to have some quick wins from, uh, I suppose like a logistical standpoint, particularly with Deirdre, who was overseeing a really big organization.

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Um, so she was, as I mentioned, was the chief revenue officer, so she was overseeing everything from pre-sale, pricing, marketing, sales, right through to post-sale, ad ops, client solutions.

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It was a really big organization. She was being pulled in a lot of different directions, and in those early months I was able to spend a lot of time really optimizing her time.

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Um, and from there, I think there was like a couple of things that happened, just some natural and some luck. I think from a, like, natural standpoint, obviously- [laughs]... work ethic.

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You have to have work ethic, um, especially in a chief of staff type role, and especially in an organization that was lean.

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Like Barstool always operated incredibly leanly, and I tried to lean into those areas that they needed additional help so that I could better understand the business and get exposure to different areas of the business.

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And what does that look like? When you say it's like very lean, does that- Like- Like how does that affect your day-to-day? Yeah, just like v- like very like startup culture-esque, really hard to get headcount approved.

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Um, we were like profitable very early on, which is pretty un- unusual, especially in that timeframe.

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Um, so one example of that is there was a really impressive lady called Ashley Buah, who was our head of pricing and planning at the time, and we were probably doing like tens of million dollars of revenue at this time, twenty nineteen-ish, and she was a one-man band overseeing pricing, responsible for every single deal that went out the door.

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Whoa. We had hundreds, if not thousands of partners. [laughs] And Ashley was responsible for, um, auditing every single, like, package or plan that went out the door. Yeah.

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Um, also defining the capacity, which was probably a multiple of what we were selling.

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So, um, was kind of ti- ti- tied myself to her, um, early on and tried to help her out where I could, and she was an incredible mentor to me and still is, and is a great friend now. Mm-hmm.

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Um, she's gone on to do great things.

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Um, so yeah, I think just like with an oper- with that like kind of startup culture, it presented a lot of opportunity for those that were green and were hungry and were willing to help. Um, so that was one piece of it.

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I think also as well, something that really is not talked about very much, and I'm really not sure why, because obviously New York is so diverse, and when you look at leadership teams now of any organization, you know, there's so much diversity there.

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Um, the only executive I've ever heard speak out about it is Sarah Friar, the CFO of OpenAI. Um, she was the CEO of Nextdoor beforehand, but she's a, a fellow Irishwoman, and- [laughs]...

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she speaks a lot about how, you know, if you want to stay in the US, you've a huge amount to prove in a very short period of time in order to get that sponsorship- Mm-hmm...

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and to get the backing, um, behind you to, to get your visa to stay here. Um, so that was also weighing on me that, you know, my- Mm-hmm... my American peers didn't necessarily have.

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So of course, there's like innate work ethic, but then also the, the pressure of wanting to stay here in the long run.

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Um, and then on the other side of that, I think those immigrants that have stayed here, stayed in the US for a prolonged period, like you're getting someone who is exceptionally good at what they do, um, and has shown a lot of resilience in order to stay here.

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Um, so yeah, that's definitely, that pressure was, was definitely weighing on me, and it was why I, why I wanted, um, to continue to take more on, not only because I was eager to learn and wanted, you know, to have a pretty steep career trac- trajectory, but I also wanted to stay in the States.

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Um, and then the other thing at play there, I would say, moving from the assistant to the chief of staff role, but then up within the chief of staff role, um, because obviously there's a lot of levels within chief of staff, it can mean different things in different organizations, um, was the fact that Deirdre, and this is just more so luck, but Deirdre and I's, um, skill set really complemented each other- Mm-hmm...

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very well. So she is an incredible leader and ga-- you know, really believes in her people and really gave me the reins to take on what I wanted to.

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So that coupled with my own kind of hunger and curiosity meant that I got to take on much more than, um, than I ever could have imagined, to be honest with you.

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Um, and then there were other skills that complement each other well. So Deirdre is a, you know, amazing visionary, and she needed a more tactical operating partner to really execute on her vision.

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Um, she's also outgoing, client-facing chief revenue officer [chuckles] obviously. [laughs] Um, I would describe myself much more as like an introvert, and- Okay...

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I think like that good listening skill, um, meant that I was able to sit in the room with her and then really able to go and run, run the projects kind of back office, um, behind closed doors and, and keep things moving for her.

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Um, she's also an incredible storyteller, and I'm much more analytical and data-driven. So I think those skills, you know, complemented each other very well and allowed me to progress through the chief of staff role.

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Um, I think it's harder to understand the principal-chief-of-staff fit when you aren't an internal, um, like a promotion from within.

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Um, I think there's some questions you can ask when you're interviewing for that role, um, around, you know- Yeah, say that a little... What, what's the, what's the part that's tough there?

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Um, figuring out like your principal and chief of staff fit, like really- Mm... truly knowing someone's ways of working, knowing what their qualities are, knowing that you're gonna make a diverse team ultimately.

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And I think, you know, often people hire like-minded people or people from similar backgrounds. Yeah. It's just the nature of human... It's just human nature.

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Um, but I think Deirdre was pretty intentional about finding someone that was going to complement her. Mm.

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Um, and we made a great duo then, um, which was incredible and was, um, really helpful and meant that I could take more on, I suppose.

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Um, and y- I th- then, sorry, to my point about the promotion from within and beingI think it w- it's much easier to find that fit when you're working with someone.

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Like, there are some questions I think you can ask, um, if you are hiring-- if you are interviewing for the role around, like what, you know, what makes them tick, what drives them nuts- [laughs]... or like a user guide.

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I've seen that. We don't do that, but I've seen that done elsewhere, and it works. It's a, it's a good way of doing it.

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So I think if you-- if there are any aspiring chiefs of staff, I'm sure you have a bunch listening, um, that's a good way to try and figure out are you and your principal going to, um, make a good team.

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And I think that's really imperative in order to have...

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be able to have take ownership and take agency, um, over different tasks so that it's no-not so much of an administrative role, but much more of a, um, senior, senior role. Yeah. Cool. Okay. Um,

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yeah, the fit really does matter a lot. Yeah. Um, and I think, just to be clear, it sounded like you said that it started off as an assistant and then got promoted.

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Um, but you're not sure as much, like, how frequent that is. But I, I've heard of, um...

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I know exactly, like, specifically, like, one example off the top of my head where someone saw an EA role and then was like, "Hey, like, I know that that's what you're hiring for, but I think you actually need a chief of staff," or, "I wanna be your chief of staff."

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Mm-hmm. And they ended up getting that role. Yeah. Um, so like- It's a really smart thing to do. Yeah. So I think that there's a lot of like, it's just like a classic, like,

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you know, whatever-- you don't have to take everything one hundred percent at, like, face value. Mm-hmm.

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Like there's like a opportunity there that there is a need, there's a problem, and there's something, and it's like up to you to... I mean, obviously, like, you know, this is like y- some edge cases.

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[laughs] But still, though, like you never know, and especially for these chief of the staff kind of roles, like there is, I think, like a little bit of gray area, um- Definitely... and you, you made it work. Yeah.

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And, and here you are, you know. Like in how many, how, how many years has it been? Um, five, six years now. Wow. Um, yeah, I think you're right.

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I think as well there are, you know, if you go into that EA type role, the beauty of a chief of staff role is that it's ambiguous. You-- to your point, you can craft it- Yeah... what you wanna make of it.

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There are also a lot of external resources that you can leverage to take it the direction that you want to take it.

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Um, even like the chief of staff network, like level, leveling up framework is really helpful in terms of how it's hard to get promoted in a chief of staff capacity unless you're moving up to like a COO type role.

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In terms of title, it's hard to get promoted. But it is definitely there are ways to increase your scope,

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um, and I think that framework is really helpful in terms of, um, a resource that can set the bench-benchmark of where you are now and where you wanna go.

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Um, there's a bunch of other resources out there, and I wish honestly I had leveraged them more at the time. [laughs] Which I didn't really realize.

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Um, but like Primary Ventures have the Mastermind, um, community run by Emma Balin and, and Devin Barben, which is great. Um, McKinsey have like their chief of staff forum.

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Um, Clara Maz, Ask a Chief of Staff, Nova Chief of Staff. There's a bunch out there. [laughs] Um, and like obviously you need to, if you're utilizing those frameworks or those resources- Yeah...

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um, you really need to bring your own like tacit knowledge of your organization and your role, um, and the kinda institutional knowledge that you've built there.

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Um, but those resources are really helpful in terms of if you do take an EA or an earlier stage chief of staff type role and you wanna elevate it into something, um, more senior. Okay.

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Um, it sounds like, you know, you've, you figured out that there was a strong fit, um, and like, uh, was there anything that you did to like ensure that that partnership was really working?

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Like, I guess, like what I'm hearing is like, you're like, she was a good storyteller, you're more analytical. Um, so like on paper, that sounds like great. Mm-hmm. Um,

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was there any like specific things that you two did to like really ensure that, that like, that the scoping and the projects and stuff like that, that like really...

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Like it sounds like you went to attended a bunch of meetings, like, but was there anything else that like you did to like ensure that like the workflow and the collaboration was like really like firing on all cylinders?

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Yeah. I think part of it just comes with time. Mm. Like the nature of like a interpersonal relationship, you build trust over time.

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Um, the other piece is like obviously just like overly communicating, like in the early days- [laughs]...

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um, particularly like when you start acting as a proxy or making decisions on behalf of your principal or of your executive, just like overcommunicating in terms of what the decision is, why you've made it, how it's in service of the overall org goals.

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Um, communication obviously is, is just key, and then trust, I think, just comes with time.

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Um, I think if you're having a hard time building trust i- w- in a, in any situation at work, it's if you can just provide the backup and your kinda way, your h- your understanding and what you looked at externally, um, to really be able to showcase, um, y-your way of thinking.

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Yeah. And then welcome the feedback. Mm. And of course it's gonna be iterative, um, and it will change, but I think just taking someone through your way of thinking and the how as opposed to the what is really important.

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Okay. And it's evolving. Yeah. Um, just like this podcast. [laughs] Yes. [laughs] We had an idea of what to talk about, but you know, we're, we're, we're evolving. You know, we're adapting.

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[laughs] We're seeing what's happening. Um, okay. So then you talked about how you got the role and like in great detail. That was like fantastic.

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You talked about the importance of the partnership and collaboration there. Um, you know, you've been at Barstool for a while, um, which is very impressive.

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Um, anything else related to like the role itself that you really like...

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Like we've been talking a lot about this, or like Arti, I don't know if you attended this one, um, workshop that she did, but it was all about this like chief of staff X factor.

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And there's like, there's certain pillars of things that are like pretty common or potentially like pretty-Similar things across some chief of several.

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So obviously there's like, you know, a lot of nuance, a lot of differences, but there's like certain thing that might be like an X factor, which is like the thing that like you really bring to the table, the thing that you really specialize for, um, the thing that like really like,

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yeah, that people always like come to you or trust you or rely on you for. Was there anything that like you developed, um, that like you'd wanna share? Yeah.

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So I was chief of staff both to Deirdre, the chief revenue officer, as I mentioned, and also Erica, the CEO at a later stage.

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Um, very different experiences just in terms of the organization being at very different stages. When I was working with Deirdre, we were really building and scaling.

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When I was working with Erica, we were trying to take the company through the sale, and it was really more so about the transformation and taking a, a brand or like a comedy brand and a startup brand- [laughs]...

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ah, to be, to be acquired by a company that was highly regulated, obviously being in like the sportsbook space, um, and was publicly listed.

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Um, so there's a lot of, I suppose, differences and difference in their, in our relationships- Mm... and their management styles respectively.

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Um, but the similarities, I think on, in terms of what I would consider my X factor...

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And it's funny, one of the things that comes up a lot when you're a generalist, um, I think being a generalist and figuring out what you're-- either where you wanna go next from a chief of staff type role or what your X factor is, people tend to want to put you in a box.

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[laughs] Um, or they want to... Like people will say as an organ- as an organization grows, you need to be, um, able to like specialize a little bit more. Um, I actually don't necessarily agree with that so much.

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I think if you've really- Hot take. [laughs] I think if you have really good first principles ways of thinking- Yeah... you can apply that to anything you do. Sure.

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And when you look at the, um, some of the skills that a chief of staff will have in terms of like analytics, stakeholder management, um, project management, like those are really adaptable and you can, you can move them into any role that you really want to.

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Um, I would say to answer your question in a very roundabout way, um, my X factor would probably just be the ability to take a vision, something really big picture, and be able to break it into really tactical steps on a timeline with, you know, people accountable and manage against that, and that's really the piece that means that the vision is realized.

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Um, I would say that's kind of- Mm... my- Vision is realized... vision is realized- I like that... is my, I would, I'd like to think- [laughs]... is my X factor anyway. [laughs] Um, okay.

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And so then for people that are like in the role- Yeah... that are chiefs of staff that, um, you know, are thinking about...

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And you talked about some of these like different like transitions and stuff and, and adjustments along the way. What else, what, what else comes to mind about chief of staff like transitions? Yeah.

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So I think, um, I mean, I know McKinsey did a study that was released earlier this year that tracked, I think it was like two hundred or two hundred and fifty chiefs of staff, you've probably read it, um, over an eight-year period and saw kind of what their transitions looked like.

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And over, I think it was over mid- over half, so the majority of chiefs of staff will be in a, in the role for less than two years. Um, I think that's for two reasons.

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I think first and foremost, um, chief of, chiefs of staff are very, uh, high achievers. And- Would you say that about you? [laughs] Uh, I'd say I put a lot of pressure on myself- Okay. Okay... um, to answer it that way.

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Um, but I think they-- when you start with an organization- Yeah... and you have such a broad amount of exposure, um, in the early days, your learning trajectory is incredibly steep. Mm.

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And if your organization isn't growing at a pace, at, at a, like a very quick pace, that learning trajectory obviously levels out or narrows- Yeah... as you, as you're there for longer.

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So I think chiefs of staff like to, being high achievers, challenge themselves, and that's why they move on. I think the other piece with that is it's r- you know, it's a high intensity role.

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You are the right hand and the strategic partner to your executive or to your principal.

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And you-- so you're there with them in the meetings, traveling, working the hours that they're working, but also you're responsible for preparing, you're responsible for following up.

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So naturally, you know, you're doing a huge amount of work, and that high intensity can be hard to sustain over a long period of time.

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Um, having said that, I think chiefs of staff are like very uniquely well-positioned to move on to other internal roles.

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Um, like you have an unrivaled view at an enterprise level, um, but also you have probably indirect reports or have been working with those on the front line and understand the true like operational day-to-day as well.

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Um, so you're, you're, you know, well-positioned to understand the broad strategic direction of the organization, where the gaps are, hence where the opportunity is.

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Um, you also have experience working with the executive team, so you know their ways of working, you know, um, how to go about approving resources with them, you know how to get their buy-in.

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Um, and for me, when I moved on from the initial chief of staff role with, with Deirdre, I saw, I suppose, the business need where the company obviously was performing incredibly well, um, but we were operating...

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The, the context in which we were operating, we were-- had almost like saturated.

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So we-- the business was like pretty transactional at that point in time, the advertising sales business within Barstool, whereby we were working with audio agencies and had a lot of like direct response advertisers, direct consumer brands that got on board with the podcast medium pretty early on.

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Mm. Um, and we were working with so many of them, but it's a very- And if you're listening, say hello. [laughs] Um, but when you're working with those, it's a pretty transactional business. Mm.

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Um, and I saw the oppor- In a nice way. Yeah. [laughs] Um, but I saw the opportunity, I suppose, like there was so much white space outside of that. Yeah. Mm. Um, and when you consider...

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I think first and foremost, when you are moving on from a chief of staff role, you have to look at what the business case is and where the business opportunity is.

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Um, don't get confused, I suppose, with your own agenda or what you're trying to do. Mm.But again, being a generalist, it's hard to know where to go from there.

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Um, so one thing I-- one framework actually I found really helpful at the time, it-- like not to get too philosophical, but there's this Japanese framework called Ikigai- Yeah...

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which like I don't know if you're familiar with it, but it's like very simply just like four quadrants of what you're good at, um, what the company needs or what the, what the world needs, where you can add value.

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Um, so what you, what you enjoy, what you're good at, what the world needs or what the company needs, um, and where you can make money.

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And I found that really helpful in terms of like an intentional point of reflection to understand where I wanted to go next. Um, I'd actually, actually say reflection is one of the key differentiators between- Mm-hmm...

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um, exceptional operators and mediocre operators.

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And, um, I think those that can take the time to think about not just when things have gone wrong, especially in a chief of staff role where you're working at an incredible pace, you probably have a bias towards action.

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So you're not used to taking a step back [chuckles] even though it's a strategic role, you're just like working at such an incredible clip.

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Um, those that can take the time to really reflect and think about, you know, where-- what success looks like to you, how, um, what you're good at.

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You've worked obviously cross-functionally on a bunch of different projects. What have you enjoyed? What have you not enjoyed?

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And doing that on a recurring basis can be really helpful in, in identifying where to go next.

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Um, so for me, when I looked at, you know, the business context and where I thought my strengths and interests lay, um, there was like one obvious function that kinda stood out to me, and that was like a revenue strategy and operations function.

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Um, so I worked with Deirdre, who was my principal executive at the time, um, to build out that function- Mm-hmm... and stand up that function. So I was responsible for...

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You know, I really was interested, I suppose, in analyzing the competitive landscape and the marketplace and understanding where we fit within that.

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Um, as I mentioned earlier, like being able to define your long-term goals, but also break that down- Yeah... into really like tactical steps for execution.

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Um, and, you know, within the ecosystem more broadly, given we were so reliant on the transactional business, is taking a step back to look at, you know, what is the ecosystem? Who are the key players?

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Where are those customers spending their money? What do our d-- what does our deal structure look like compared to that? And really organizing ourself around that.

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So like territory planning, comp planning, um, and annual planning, which obviously I was well-versed in given the chief of staff experience.

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Um, and I got to work kinda cross-functionally then, which is what I really enjoyed doing. You know, I always think y-you are the company you keep, and you wanna- Mm-hmm... surround yourself with smarter people.

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And that gave me the opportunity to c-continue to be surrounded with much more experienced peers than myself.

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But it also gave me the opportunity to build out a team and manage a team, which is something personally I was interested in doing.

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Um, and, you know, scaling our operations in terms of, I mentioned I'm very data-driven, um, building out and making sure that there was clean data in our order management system and our CRM system, um, so that that data was being aggregated, and we could really understand, um, on-- like really detailed understand where the business was succeeding, how we could further leverage that, where the white space was, where the opportunity was, and how to go after that as well.

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Um, so I think that was helpful in terms of figuring out what I wanted to do next, and then positioning it. Like, like I mentioned, obviously, chiefs of staff have like a bunch of transferable skills.

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Um, so, you know, it's just articulating, you know, those skills and really, as I mentioned, first and foremost, making the business case and showing the value that that's gonna drive for the organization, um, for the or for your executive.

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Um, one other thing, actually, another kind of hot take, [laughs]

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Is I was at a, an event recently, a chief of staff, like a panel, and it was-- I can't remember what the topic was, but it was something to do with the dynamics between a principal and their chief of staff.

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And one of the questions that was asked is by the audience, um, obviously, the chief of staff role is incredibly ambiguous, um, and it can be really difficult to define success for a chief of staff. Yeah.

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And someone asked that question to the, to the CEO there, and the CEO said that ultimately it's pretty subjective, and the chiefs of staff-- chief of staff success is the ability to, I suppose, like open up time or extend the reach of the chief executive, which I do agree with.

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But I think your success can't be anecdotal, and it has to be quantifiable. Mm-hmm.

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You have to be able to, to my earlier point on reflection, like document your wins, be able to articulate and quantify those wins, show how they map up to the overarching, um, strategy of the organization, and then you can use that when you're making the case obviously for promotion or making the case in terms of moving function.

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Um, I think that's like something really helpful, helpful to, to do when you're making that change. I can only, I can only imagine the spreadsheets [laughs] That you have. Yeah. The like Miro boards.

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I don't even wanna know. [laughs] It's like Notion connected to Zapier to connected to HubSpot. Like, I don't even... Like, yeah. [laughs] Um, which is all to say it's like super impressive. Um, okay.

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I know we've covered a lot of ground here. You talked about the company that you keep, et cetera. Um, you recently came to a chief of staff network event. Yes. Um, yeah.

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I guess like what have you noticed about like, I guess, like the chief of staff ecosystem and like the importance of like building relationships and connecting with other like chiefs of staff?

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What have you like learned from that, or how have you thought about that over the years? Yeah.

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I think, as I mentioned, like obviously you're just pulled in so many directions, being a generalist or being a chief of staff, and if you're working at a company that's growing pretty quickly, it's very difficult to take your head up.

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Um, I did it in some ways, um, in that I was like really interested in what was happening more broadly across the like media landscape- Mm-hmm...

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and what that meant in terms of, you know, strategic initiatives that we could implement, but not so much from a mentorship or... I had internal mentors.

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Like I mentioned, Ashley was like really instrumental to my growth. Um, but more soMentorship externally, and also just like it's so rewarding being able to give back and pay it forward.

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Um, and just like the power of connecting, like you're-- It can be so challenging being in a chief of staff role in that, yes, the entire organization is your team, but in reality, you are an individual contributor.

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Yeah. Um, like when I was working with Deirdre, I-- her assistant, when we backfilled the assistant role, I was responsible for managing them. Mm-hmm.

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But it really ultimately is majority of the time a, um, particularly in a s- in a smaller company or m- small to medium-sized company, it's an individual contributor type role.

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You're working on probably pretty sensitive topics that you can't talk internally about. Yeah. Um, so just being able to leverage the community in terms of, you know, how did you tackle this?

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Um, you know, they, uh, the, your community generally doesn't care about the, you know, really details of what's going on in your organization. [laughs] So, you know, you're able to share with them as well- Mm-hmm...

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which I think is great. Um, and that's something that I wish I had leveraged more, um, during my time as a, as a chief of staff. Also, like you're just at a different stage to your peers, you know.

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They've got twenty years more experience. They've got functional expertise. You probably have a little bit of imposter syndrome because you're the most junior person sitting at the table in terms of years of experience.

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Um, so just connecting with other people that are, um, really growth oriented and in a similar, working in a similar capacity to you is really valuable for your own career, but also being able to leverage those frameworks with your own intrinsic knowledge internally.

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Love, love, love. Um, we covered a lot of ground here. [laughs] Um, including some hot takes. [laughs] Do you have any hot takes on the chief of staff role? Uh, that's a whole nother podcast episode. [laughs] Um, yeah.

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We'll, we'll save those for another one. Um,

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I, I, I think that your-- Like, what you brought up though is definitely something that I think, like I wanna, like I guess just double click on is like the importance of just like being able to articulate and communicate your value.

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Like, I've talked to people that are looking for new roles, and they're like, "Here's my resume." And I look at the bullet points, and it's like, "Worked on cross-functional projects." And I'm like...

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What does that mean? [laughs] Yeah. [laughs] Like, I think there's a little bit more to that. Yeah. [laughs] Um, or like I, I would, I think you should probably add a little bit more to that. Yeah.

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Um, so yeah, just some of those things. But it's tough, like- Mm-hmm... so I get that.

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But I, I think like on that stuff, it's like, I think talking about like who d- who did you work with or like who's in the room, how many people, um, like what, what's the team's impact on or like the partnership or the collaboration there.

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Mm-hmm. Um, but yeah, definitely like... And I do this on my own. Like, I have like a, um, in Notion, I have like a, I, I, I save like compliments. There's not a lot, but I try to save them when I get them. You did that.

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[laughs] Um, [laughs] and I also try to save like what I call like highlights, which is like sometimes it's kind of, it's related to work, but also it's like kinda personal too, which would be like, had this like really great unexpected conversation and like, I don't know.

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It's things like that that like helps you, like gives you context to when you like reflect back on like- Mm-hmm... the month, quarter, the year, et cetera, um, in a way that like sometimes is hard to remember. Yeah. Um,

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so yeah. That, that's like, I just wanna like double click on your like hot take there. Mm-hmm. Just like your, your advice- Mm-hmm... basically.

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Um, anything else that you definitely wanna share about the role, your experiences? No, it's been great. Like, I really feel like I've seen the full evolution of the company. It's been great experience.

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I think the chief of staff role is second to none.

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Um, I definitely think taking that assistant type role and trying to level it, level it up to chief of staff is worth pursuing if you are an aspiring, um, chief of staff.

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There aren't that many chief of staff roles out there, and they're pretty competitive. So that's one way to kinda differentiate yourself. Mm-hmm. Um, and like you said, like it's, I love being able to help people.

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So, um, definitely like connect with me on LinkedIn. Include a note so I have some context.

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[laughs] Um, but more than happy to help other, um, aspiring chiefs of staff or connect with chiefs of staffs that are in the role at the moment. Amazing. Thank you so much. Amazing. Thank you for having me.

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