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[upbeat music] Hey friend, it's David Nebinski, 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 Slack with over nine hundred people in it. Learn more about our membership, events, and programs at chiefofstaff.network.

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You can also learn more about our upcoming New York City Brain Trust on Thursday, February 13th. The Brain Trust is a proven mini conference focused on peer-to-peer learning and problem-solving.

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It works, so we keep hosting it. Also, Kyle Hege, a chief of staff at Morning Brew, will be speaking there.

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After listening to this episode, listen to the prior podcast episode that we recorded with Kyle called How to Be an Effective Chief of Staff.

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In this episode, you'll hear from the one and only Scott Amenta, the founder of the Chief of Staff Network. Yes, Scott, the founder of the Chief of Staff Network.

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You'll learn about Scott's first chief of staff role, starting the Chief of Staff Network, those first in-person meetups, reflections from our twenty twenty-four Chief of Staff Connect, a two-day conference here in New York City, and how we're bringing Chief of Staff Connect to three cities in twenty twenty-five: San Francisco in May, New York City in October, and London in November.

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You can learn more about all this at chiefofstaff.network. Excited for you to level up as a chief of staff. Here we go, Scott. Scott Amenta, welcome to [laughs] the Chief of Staff podcast. Good to be here.

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[laughs] Um- Feel like we're welcomed into our own podcast here. [laughs] Yeah. Um,

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so, uh, yeah, we like to start each podcast episode about how did people get their, a chief of staff role or their first chief of staff role and, um,

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you were, you know, an early pioneer in the space in, in, in many different reasons. So I would love to hear that if you can remember back in the day, what was, uh-- how did you get your first chief of staff role?

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I, I've told this story many times in, in vari- in, in varying capacities, so, uh, I'll, I'll do my best to give a, a compelling version of it here.

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[laughs] Um, m-my chief of staff journey began what, what feels like a lifetime ago back in like two thousand thirteen, two thousand fourteen. Uh, I was walking down the street.

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I, I bumped into an investor friend of mine. He was on the phone, said hi very briefly,

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and for some reason, I don't think he even remembers this, said, "Hey, by the way, like, we're looking at chiefs of staff as being like the next generation of entremer- uh, entrepreneurs."

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And, and I walked away from that two-second conversation thinking, "Okay, chief of staff is the thing that I wanna be."

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Um, you know, how do I, how do I find a role that is going to give me the most exposure and, and depth across the whole organization kind of at the executive level?

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And at this point I'm in my early twenties, and so, you know, that was kind of a, a tough position to kind of find myself into, um, you know, at that stage of my career.

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And I, I ended up, you know, joining a company as the fourth or fifth employee, and my initial pitch to the CEO when I joined was, "Hey, I wanna be your chief of staff."

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We, we both kind of agreed that we didn't know what to make-- how to make sense of that at a five-person company, um, but we, you know, did agree that I would spend thirty to forty percent of my time kind of working on priorities that were that CEO's, you know, fifth or sixth thing kind of on their to-do list.

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And, um, that very much kind of turned into, over the next two years, what we started to define kind of more and more as, as a chief of staff role.

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Um, it wasn't until we were kind of closer to fifty, sixty people, we had kind of closed our Series A, we were a growing business, that we kind of formally put the, the stamp on it, gave myself the title, um, and then all in kind of one motion I realized very quickly that, you know, even though I thought I knew what I was doing, I actually had no idea what a chief of staff really meant.

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And, uh, you know, I needed more than myself to kind of be the proxy for figuring out kind of what that was going to look like at especially early stage startups.

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You know, the only examples that I had seen kind of at the time were, you know, people like Brian Romeo at LinkedIn.

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Um, there was a notion of chief of staff at Google, but, but most of them were more like product managers than they were like operators.

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And so early stage startups at, at this time, like two thousand and fifteen, two thousand sixteen, not a lot of chiefs of staff to find out there, certainly not people posting about the role on-online.

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And, um, it was at the behest of one of my mentors to just post about my own experience and start blogging about it, and, and those early blogs turned into dozens of people reaching out to me saying, "Hey, I'm thinking about this role as well," or, "I, I'm about to call myself a chief of staff internally, and I also, like, feel very lonely in trying to figure out what that means.

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I'm glad to hear I'm not the only one." And from there evolved what we now see as the, the Chief of Staff Network.

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Um, it's gone through very many iterations kind of since two thousand and fifteen, um, and, and you've seen kind of the, the latest and greatest version of that over the last couple years.

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Um, and, and that's-- yeah, that's where I started kind of my chief of staff role and, and where the community, uh, you know, started as well. Yeah. Um,

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I think that's really interesting and helpful advice on, like, you knew you wanted to be it, um, you know, didn't, didn't have the title in the beginning and but was kind of working your way into it and then were, you know, connecting with other people to, like, better understand the role, and you were like, "Hey," like...

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[laughs] Wait, what did you, what did you mean by you didn't really fully understand what the chief of staff role was, and why did you need to connect with other people? What, what, what, what part there?

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Well, well, chiefs of staff, as, as we both know, can, can wear, uh, many, very ha- um, very many hats. And, you know, for, for me, I, I started out really calling myself, like, business development.

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Um, and, and business development at this company meant a combination of external partnerships and so, you know, helping to drive kind of-- it was a marketplace, so helping to drive the, the supply side of the business.And, and from there emerged, like, other strategic opportunities that were not anything that the kind of core team was going to focus on, but things that we thought could make or break the business if we- Mm...

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if we pursued one or more of those, of, of those opportunities.

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And so from there, like, kind of those strategic initiatives, you know, those are very much things that typically end up on a CEO's plate that again are, like, not the core priority, but are certainly things that they should be spending some time and attention, if not more.

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Um, and so to answer your question, like, what, what did the chief of staff role mean, it, it was taking on lots of different shapes and sizes kind of as the company was growing.

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And I thought that, that was the most interesting part of the role. It was also the scariest part of the role because I, I knew coming out of it that the biggest fear I had was

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as much as I've explained what this position means to our other, our other employees and, and my CEO and are in, are in agreement in terms of the definition of it, at least in this current state, um, how am I going to label this and define it and, and describe it to other companies, investors, et cetera down the road when I go to find another job?

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Like, is this going to be a, a black mark on my resume, um, or is this truly going to be, like, the accelerant of my career that, that I expected it and kind of hoped it would be?

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And so, um, you know, I think the, the idea of finding other chiefs of staff w- was really in helping to define the role for the whole industry. Mm.

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I, I don't think any one person can say what a chief of staff is or is not at this point because it does take on, still today, a lo- lots of different types of responsibilities and has lots of different shapes depending on the business.

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Yeah. And so it's the community that has defined it, not, not any one person. Yeah. And so then you started hosting meetups, um,

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in New York City, uh, based upon prob- it sounds like this, you know, internal interest but probably external interest because of these blog posts.

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Um, talk to us about what were some of those, like, first meetups there and, and then why you wanted to start the Chief of Staff Network.

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So most of the early roundtables were, you know, uh, hosted at, um, other chiefs of staff or, or my own office.

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You know, we would, uh, tap into whatever food supplies the startup was paying for, you know, on their dime and, and usually order some pizza and beer, you know, on our, on our own.

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Um, so this was not a, you know, not a money-making entity. It was really just a, a community for community's sake. And- But if you're a sponsor and you're listening to this, uh, definitely reach out to us now.

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[laughs] Of course. Yeah. We're, we're a very different, we're a very different beast now, so nothing's free in this game. Um,

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and, and yeah, so and th- those meetings were, you know, anywhere from, let's say, eight to 15 chiefs of staff huddled around a, a kind of boardroom table,

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usually talking about, like, some of our most intimate professional and, and, and sometimes personal challenges, um, you know, inside and outside of work. And

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what emerged from that was, one, a feeling of kind of understanding. Like, okay- Mm...

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the, the things that I'm seeing day to day, you know, my, my challenges with my principal or, you know, challenges between different teams that I'm responsible for helping to, you know, orient out of, um, I'm not alone there.

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Like, actually lots of companies have very similar growing pains.

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And, um, and, and there are different, you know, mental models and frameworks and, and approaches and, and communication styles to help solve those problems.

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And, and very often having someone that's seen it or done it before or is doing it at the same time, uh, makes it that much easier to go to work the next day to, to try to execute it, right, and, like- Yeah...

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really, like, drive that operation forward. Um, the other thing is just, like, navigating professional careers. Th- that part of the loneliness was, was almost immediately gone, right?

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It's like, all right, hey, I'm actually, like, moving on from my chief of staff role. I'm interviewing now or I'm talking to my CEO about what that internal transition might look like.

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You know, here's how that conversation has gone. Here's what I learned from it. And, you know, that feedback in, in real time, um, is im- immeasurably helpful.

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And so we, we very quickly took those roundtables and, you know, realized, okay, we can't just do this, you know, every couple weeks.

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It's better to also just have real-time feedback and, and that's where the Slack community kind of emerged.

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And, and we were and have always been and, and remain today very protective over the kind of sanctity of that part of the community, right? It's, it's very much a what is said here is private.

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You know, nothing gets shared kind of publicly.

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Um, you know, we're very careful about people being open to sharing challenging circumstances at their businesses and, and getting real-time feedback from dozens or hundreds of other operators.

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Um, and, and I think that's really critical. Yeah. Okay. So then from those meetups then a- and the starting the community, then, you know, last year in 2024, um, I think I helped produce

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60 in-person events, uh, globally. Um, and then we also-- And that's not including Chief of Staff Connect, um, which was a two-day conference here in New York. Um,

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I guess, like, Scott, what was it like to see that two-day conference with over 100 chiefs of staff gather back in New York where you no, you no longer live anymore, but to see that from...

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I can imagine you had some reflections to those early, you know, those early roundtables. What was it like seeing that? Oh, at, at...

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I, I, remember even at some of those roundtables, I think, you know, what-- Rachel Peck is a good example because she was a very early member.

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Um, we had definitely joked around about wanting to, like, have a big conference, but at that time there weren't even enough chiefs of staff to have a big conference.

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And so to, to, I guess, watch the, the industry evolve and, and the profession evolve in a way that-You know, hundreds, thousands of companies have come to see the role as being an important part of their leadership teams.

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That by itself, I think, is like really valuable and, you know, I, and I feel grateful for that, that has happened kind of in the industry.

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Um, then to see all those people come together under one roof and, and really share like this kind of core sense of belonging and, you know, very overlapping reasons for being there and, you know, just a, a shared understanding of kinda what the role was evolving into, um, and what their responsibilities were, what was, was incredible.

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And I think, you know, that, that is, um... It, it can be achieved virtually, but it does not feel the same as being in person.

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A-as you clearly know, you know, having hosted dozens and dozens of, of events last year of all different sizes, right?

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And, um, you know, I think Connect, for us at Chief of Staff Network, is really like the culmination of those events, right? Brain trusts and mixers and, and different types of summits.

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You know, these local events are great because we get, you know, small groups... small, medium-sized groups of, of chiefs of staff together.

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Um, but to see all of those people come together, you know, under one big roof is, is really, really impactful. Yeah. And, um, I know we wanna talk about what we're thinking for 2025 on the Connect side.

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What, what other, like, either reflections or learnings did you have from that two-day conference last year, Chief of Staff Connect in New York? What other, like, either reflections or learnings did you have?

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So I, I think, you know, in terms of like what chiefs of staff can expect this year based on what we learned last year, one of the big things was r-really focusing on depth kind of over breadth.

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Um, so, you know, we're inviting speakers this year who are like true industry pioneers. They're, they're experts in their field.

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Uh, we wanna give them the space to share their thoughts and, and have an audience that's also like actively participating in each event. And so, you know, think more workshop driven versus keynotes and panels.

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The, the speakers and panelists that we had at 2024 shared incredibly valuable insights, but I think we didn't give them enough time each on stage to really get into the depth of their, their real understanding of, of, you know, different types of operations.

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Um, so that's gonna be a kind of a core focus this year. The other thing is just connections, right? We, we learned a lot about how people connect at these types of gatherings.

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Both of us have attended n-numerous conferences and, and, and events ourselves. You know, we kind of know what works and what doesn't work.

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And, and this year we're gonna focus very heavily on, you know, one-to-one matching, right?

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And we can use kind of our, our internal knowledge about our members and, and the attendees here to really like hone in on who's the right match for, for other people based on challenges and industry and kind of career state.

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And, um, yeah, I think that's gonna make this conference kind of really stand out from the, you know, very generic kind of events that, that you can attend.

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And nobody wants to walk into a room with hundreds of other people and not be told what to do or how to get the most value out of it.

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And, and that's, I think, what we've always done really well is like we handhold our members through every event.

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Nobody leaves without feeling like they got, you know, some kind of critical, uh, value out of that, that, that time spent. Yeah.

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I think it's so interesting when we, when we get feedback that says like, "It seems like a chief of staff planned this." [laughs] That...

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Like, I think that is like the feedback that I, that we're looking for [laughs] or I'm looking for. It's like when I...

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Uh, I, I think that's just like a, a really great, um, testimony when that happens, and I've definitely heard that from the last one.

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Um, and I think the other thing I just wanted to add on that, that I think, you know, it's... I guess it's the implicit here is like it worked, um, and, um- It's still working. [laughs] Yeah.

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And so Chief of Staff Connect 2024 worked. People, um... Yeah, the attendance, the, the sa- like, the registration, et cetera, and I think both of us were surprised by, um...

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We didn't really market it as like a global event, but it brought people from around the world, um, which I think like we'll, we'll touch upon is how that ties into 2025 Connect's vision.

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But like, I think that was like a big takeaway is like people showed up two days, you know, and people came in from Canada, parts of Europe, California, um, you know, Washington, DC, et cetera.

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And I think, like, that was a surprise to me because we didn't really necessarily like market it as a like, "Hey, this is a call-calling all chiefs of staff globally, come together for this thing."

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And I think that that was, um, kind of a learning and a surprise in a good way that I had. So as we're thinking about 2025, and speaking of piggybacking off of that, like the global interest, et cetera,

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um, you know, we're having three Connects this, this year instead of, instead of one. Talk to us a little bit more about like the vision behind that and, and where those are, et cetera. Yeah. So as, as you said, it...

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The Chief of Staff Connect in New York in 2024 was a global event on, you know, unsolicited by us. We were mostly planning on East Coast chiefs of staff to, to show up there.

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Uh, instead, we had people from all over the country a-and the world. There were people coming from London and, and Germany, and, and so that was incredible.

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And what we realized is, well, you know, the goal for this year is not necessarily to make that one event bigger, right? It's not to shove more people into, into one room.

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Uh, instead, it's about, you know, how do we take kind of a, a core theme, a topic, and, and bring kind of a similar flavor of that event to different parts of the world and, and make it more accessible to our members and, and our audience generally, um, you know, a-across those cities.

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And so this year we're bringing it to San Francisco in May-Uh, New York in October, our kind of flagship event, two days, and London also in November, uh, which will be a one-day event.

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So we, we chose New York, San Francisco, and London because of a few reasons. One, they're, they're major hubs. You know, many of our pro members come from these cities.

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We want them to have a convenient place to, to assemble.

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Um, and, and two, like, frankly, some of the most exciting technologies and companies are being built in these cities, and, you know, we want that to be, um, you know, reminiscent of, of many of the speakers that, that also attend to kind of share their insights and, and learnings.

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And so, um, we're starting with these three cities. Uh, I can't promise that we won't add a fourth, but, uh, we will definitely keep everyone posted. Follow us on LinkedIn if you wanna see those updates.

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[laughs] Um, and so you mentioned, you know, more workshop-y, more depth, more connection. What el- what else can people, like, expect related to Connect? Yeah.

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So th- this year's theme is a little bit different than last year. Last year we focused on chief of staff, uh, company blueprints and toolkits.

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It was really about kind of frameworks and mental models, and, and people walked away with a lot of, like, tangible assets. This year is r- really focused on what we're calling the art of human alignment.

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And so what, what does that mean? Our, our thinking is that the world is quickly becoming dominated by AI, if it hasn't already.

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Um, and it makes sense to kind of explore how people within companies will succeed together and alongside these new technologies.

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So our goal is to dive into the, the very things that make these organizations unique, right, their people.

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And, you know, while also ac- acknowledging that organizations are about to go through, you know, very rapid change, that they're evolving so fast that most people can't keep up with it.

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But we know from the research that we've done, from the conversations that we have on a day-to-day basis, that, that chiefs of staff are really at the helm of this change.

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They are the ones kind of guiding and shepherding their teams through these organizational, uh, this organizational evolution, and, you know, will be responsible for thinking about h- how, how AI sits alongside their people.

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And so this conference is about, you know, focusing on the people while also, uh, learning about how to kind of shepherd that change with these rapidly evolving technologies. Cool. Um, and so for, for people...

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And, like, we're literally, like, just announcing this, like, right now. So for people that wanna get involved with this, like, how...

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We mentioned there's three cities, and also I wanna, um, share that, like, people can attend all three, right, Scott? Yeah. That's right. So people can attend all three, and, and there's a few ways to, to grab a ticket.

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Um, I guess the first thing is go to chiefofstaffconnect.com. Uh, you'll find all three events, uh, there on that website.

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The, the second thing is e- early bird tickets are live now, so, uh, go there quickly because they are selling out fast.

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Um, we're also planning to select one special early bird ticket holder to join our podcast in a special interview. Um, so stay tuned for that. You'll have the luxury of being with David for, for that interview.

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And, uh, lastly, you, you don't have to stop at the single conference, right? As, as David mentioned, you can buy multiple tickets to all three conferences. We're, we're happy to have you.

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Um, but you can also buy a bundled offer with our Chief of Staff Connect Pro membership. Um, what this gives you is an annual membership to the Chief of Staff Network.

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Uh, as David mentioned, we hosted over 60-plus in-person events globally last year, with even more on the radar for this year, and so there's lots of ways to get involved on a regular basis, both online and offline, in the Chief of Staff Network.

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So you can buy that bundle, attend Connect, but then keep the party going in the Chief of Staff Network after the fact, um, and, and get all the access to our members a- and resources and programs throughout the year.

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Love. Um, keep the party going. Um,

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so is there anything else about C- anything else about Connect that you wanna share, and/or is there any advice that you wanna share to, you know, existing chiefs of staff or aspiring chiefs of staff that you think that we didn't get to cover?

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I, I think the, the, the main advice that has been kind of most helpful for me in my career, right, both as a chief of staff, as, as a founder, a- as a, uh, a person leading a product team now, is, you know,

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be understanding of change, and recognize that you're the person that needs to shoulder that change. And, and not everybody is going to be comfortable, as comfortable as you will be with that change.

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And, you know, I, I mentioned that companies are changing fast, but, but, but teams change quickly too. Priorities change. Strategies change. You know, communication is lost in the shuffle.

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Um, when you're with a leadership team day to day, you might see kind of the whole view of, of, of the whole picture of the company. Most people do not.

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And so, you know, shepherding that change i- is a talent, and, and it, and it takes a lot of skills to kind of do that well.

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And, and I think that's the most critical thing that a chief of staff can be, you know, day to day at a company. So practice it. Uh, you know, spend time with, with your other colleagues.

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Like, acknowledge that there are real fears and misunderstandings, um, and that these things can be overcome. And, and, and overcoming those things makes companies that much more successful. Cool. Well, we can...

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As you mentioned, we can keep the party going. Um, so people can keep the party going, um, uh, at chiefofstaff.network. Learn more about membership. Learn more about Connect.

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As Scott said, we've got a bunch of different in-person events, uh, virtual events, in-person event happening tonight in New York- Nice... um, and also in Dallas. So two events tonight. San Francisco on Thursday.

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So I, I know that by the time this episode goes out, uh, you'll probably miss those, but, um, just letting you know- Or late in February. [laughs] Yeah, exactly.

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Just letting you know h- how, what the, the activity's like. And, um, yeah, reach out. We wanna hear from you.

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We've been getting a lot of great feedback from people like you that are listening, so let us know, uh, what you took away from this conversation, what questions you have about Connect, what questions you have about Chief of Staff Network.

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Uh, we're here. We wanna hear from you. Um, thank you so much, Scott. Yeah, David, thank you very much. Appreciate it.

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