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The Emergence of the Chief of Staff and What Lies Ahead for the Position
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The Emergence of the Chief of Staff and What Lies Ahead for the Position

On Season Two of Aspiring Ops, we’ve been fortunate enough to sit down with nine Chiefs of Staff from companies of every size and stage. Combine these guests with the four Chiefs of Staff from Season One, and you’ve got a who’s who of incredible leaders defining the Chief of Staff position today and what it will look like in the years to come. 

And while we certainly plan on having more Chiefs of Staff in upcoming seasons, for the Season Two Finale of Aspiring Ops, we wanted to take a step back and better understand why the Chief of Staff position has become such a prominent role for today’s high growth companies. 

To help us take stock of the Chief of Staff landscape, there’s no one better suited than Scott Amenta, Founder of the Chief of Staff Network. 

Scott's professional journey began in the early days of the New York startup tech scene at Foursquare and Techstars. After his initial exposure to working with early stage companies, Scott decided to make the jump to a four-person startup called Spring where he pitched the idea of joining the company as a Chief of Staff. Although he didn't come on immediately as the Chief of Staff, he gradually made the transition into the role, and his career path played a pivotal role in the emergence of the Chief of Staff position as we know it today. 

On the Season Two Finale of Aspiring Ops, Scott shares how his experience as a Chief of Staff led to the creation of the Chief of Staff network, and why the position is becoming more prominent across businesses today. Scott also shares how the position has evolved, and what he believes the future has in store for the role.   

From advice for first time Chiefs of Staff to guidance on how veteran Chiefs of Staff can continue to grow in the role, this is an episode you won’t want to miss. 

Our Takeaway

Similar to any leadership position, as the Chief of Staff role continues to evolve, so will the responsibilities and nuances expected of the position at different stage companies. As Scott shares, the Chief of Staff role is unique to every company, and it’s important that companies are setting the position up for success by accurately defining expectations and responsibilities.

Over the course of the past two seasons on Aspiring Ops, we’ve met with a number of Chiefs of Staff that are in very different stages of their journeys. From first time Chiefs of Staff in two-year rotations to seasoned veterans building out entire departments, the Chief of Staff position comes with a vast range of experiences and responsibilities. 

To help account for this wide range of experience for the position, the Chief of Staff Network has been at the forefront of building out a Chief of Staff Leveling Framework. As Scott and his team share, the purpose of this framework is to help provide a blueprint to how the role progresses from IC execution to strategy and thought leadership at the most senior levels.

Similar to Chiefs of Staff looking to leverage this framework as a way to measure their experience, influence, and ownership at different levels within their role, companies can also use this structure to better understand what they should be looking for in candidates. 

Just as there are CMOs, CROs, and even CEOs that have the background and experience to thrive at different stages of a company’s lifecycle, the COS position can have varying degrees of influence or experience as well. 

As the COS role continues to evolve, we look forward to continuing our work alongside companies like the Chief of Staff Network to provide insights, practical steps, and solutions to help Chiefs of Staff and all strategy and ops leaders as they continue to build their companies. 

Interested in learning more about the Chief of Staff Network? Check out their site here

Want to learn more about how Elate is working with other strategy and ops leaders? Request a sneak peek today.

Scott Amenta - Aspiring Ops Transcript

Brooks Busch: [00:00:53] Hello, and welcome to another episode of Aspiring Ops. My name is Brooks Busch, and I'm joined here today by Scott Amenta. Scott [00:01:00] thanks for taking the time.

Scott Amenta: [00:01:01] Yeah, thank you, Brooks. Appreciate you having me.

Brooks Busch: [00:01:03] Yeah, absolutely. So really excited about today's episode because as a lot of folks know over season two, we've been meeting with a ton of chiefs of staff across the country.

And time and time again, we’ve spoken to how this is a role that continues to be on the rise, especially in high-growth companies. We're seeing that this role is evolving. It's continuing to take new form. And so for today's purposes, I thought there would be no one better Scott than you to take us through a little bit of what you're seeing for those that don't know Scott.

He co-founded the Chief of Staff Network, which is a network that we've had brought up multiple times in past episodes and past guests. So Scott, maybe to kick things off here, we'd love to just hear a little bit about your background, how you ended up founding the chief staff.

Scott Amenta: [00:01:49] Yeah, of course. So, you know, I started out really an early stage startups, really kind of in the heyday of the New York tech scene as it was really coming into its own.

So this is back in like [00:02:00] 2009, 2010. I was in college at undergrad at NYU. And, uh, yeah, really found kind of my way into the startup scene through university. And immediately after college joined Foursquare as a, as an intern and worked as an associate there for a handful of months and, uh, decided I didn't really want to work in a, B to C startup at that point, even though Foursquare was really the prime example for a successful New York startup at that point.

And, uh, yeah, I ended up deciding to join Techstars as an associate as well. And cut my teeth there for about four months, writing pitch decks, helping startups go to market and working on marketing business development and partnerships, and really just kind of figuring out what I liked at early stage businesses.

But I think more than that, seeing all of the. Kind of similarities that these companies were going through in terms of the types of growing pains, the types of decisions that they need us to make. And, uh, you know, the types of kind of [00:03:00] generalists skills. And I wasn't using that term at the time that they really needed to just execute.

And as an undergrad business student, I didn't really feel like I had any real skills to offer, but those interpersonal skills, those relationship skills ended up playing a huge part of the rest of my career. And, uh, you know, that's really where I started to. I recognize the importance of those things, you know, at these businesses.

Brooks Busch: [00:03:23] So for those that aren't familiar with the Chief of Staff Network, just quick high level, uh, the network is the leading private membership network designed specifically for chiefs of staff, for operators coming in and helping to scale these businesses, working directly alongside leadership teams, the CEO at a company.

And as we've talked about multiple times, and I'm sure we'll dive into here on today's show, that role can look significantly different based on the company, based on the individual, based on even where the company's at in their life cycle. But just walk us through, if you don't mind, Scott, kind of the, the origins of how the chief of staff or [00:04:00] came to be, what were the early ideation parts of that, which you said look I think there might be something.

Scott Amenta: [00:04:07] Yeah. So I ended up joining an early stage business called Spring. It was a marketplace, you know, building in the kind of home goods and, and fashion industries. And my first position there was in partnerships and business development. But I remember walking into my first meeting with the CEO at the time.

The company was four employees. Uh, actually the first thing I pitched to him was being a chief of staff. And, uh, granted I had heard it, you know, emerging from companies like LinkedIn and Google over the years as to these much larger established technology companies. But it didn't really exist at the very earliest and in growth stage businesses, the CEO at Spring was a man named Alan tit.

Uh, and actually his brother, David Tisch from box group is the one that initially kind of put that ear worm in my head of a, what a chief of staff could be. And, you know, the reason he said it was, Hey, look, we're looking [00:05:00] at a lot of chiefs of staff emerging from some of these larger tech companies and they're going off to start amazing companies.

And I always felt myself to be on that kind of entrepreneurial journey and really looked at my career as an opportunity to learn all of the ins and outs of what it took to get a company. A to B and then B to Z and felt like the chief of staff role would give me enough of a, a wide enough purview to get good breadth of experience across different divisions of the company and the best knowledge kind of resource I could get from some of the most senior leaders at a quite early stage of my career.

And you know, it wasn't until, uh, Two years later after working in kind of partnerships and business development at Spring, and kind of leading the supply side that we really decided, Hey, we should call us the chief of staff. Now, you know, you've been spending 40% of your time on all of these other things that we assumed that chief of staff should be doing.

And we can get into that in just a second, that the role became official for me. And as soon as it did, you know, crossing that [00:06:00] line between. Not having a title and having a title, even though I would argue that titles are not very important in this case, it actually felt pretty important because the chief of staff title was not something that anybody understood, no one at the company I was working for.

And certainly external to that, you know, I knew the immediate risks of putting this on my resume and it not being, you know, well interpreted from kind of the outside market that I would ultimately be interviewing in recruiting. Potentially starting a company in and having to tell investors what a chief of staff was.

And, you know, that was a risk that I very much perceived from day one and was encouraged by another mentor to just start writing about my experience in the role. And, you know, a few months in, I started posting some blog posts about things that I was working on. The things that I felt like a chief of staff should be good at doing from a kind of skills development standpoint and where I felt the role was kind of growing within these types of [00:07:00] companies.

And that was the initial kind of kickoff for what has now become the Chief of Staff Network. Was a handful of other people in similar shoes as my own, we are reaching out and say, Hey, I'm also doing this, you know, maybe we should meet. And, uh, you know, that, that first dinner that we hosted at the smile and like the end of 2016, then turned into a summit series where we would meet kind of once a month round table format.

Pizza and beer, and really just talk about, you know, one that types of challenges that our companies were going through on a day-to-day basis, but to more importantly, and I think this continues to be the glue that holds the community together is what's just generally going on in our careers. And how do we best navigate this position, define the role and make the most out of the experience while we have.

Brooks Busch: [00:07:47] I, I love how, and it just plays in so well, to folks that we've seen take on this role of you kind of evolved with it and you helped shape it. You, you helped shape the community by saying, look, I'm going [00:08:00] to put out content and see if anyone's interested in this and help almost add some structure to what I'm doing here within Spring.

And you ran with it. From there, you, you took it on as like, this is, this is a project that I'm going to own, which is just a skill set. It feels like a lot of chiefs of staff have to have, which is a curiosity, but also a drive of just look, I'm going to go figure this out and learn and get it to a point where it's, it's something that's sustainable.

So from going through that experience, even firsthand at Spring of evolving into the chief of staff role, you mentioned that those general. Qualities that early on you didn't really recognize, but started realize were really important to the role. How did you even identify that a chief of staff position or strategy and ops was where you wanted to go in your career?

Because as you mentioned, you started on more of the business development and partnership side of things.

Scott Amenta: [00:08:57] So I think the first, the first thing that was [00:09:00] important to me was, was broad exposure. And even when I was in a business development role, quote, unquote business development, to me, he felt like the broadest title that I could apply to the business card that I was carrying around in my pocket at the time.

And I didn't want to get type casted into. A sales role or a specialized marketing role and to be fair strategy and ops doesn't really exist at these very early stage companies. Like it feels a little bit nebulous to say I'm working on strategy and ops at a five person startup. So. You know, business development felt like the kind of opportunity to say there's a lot of different things I could work on in BizDev.

It could be partnerships, it could be focused more heavily on product. It could be focused on marketing those partnerships and developing an into the product. And so a lot of cross kind of collaboration that needs to go on. As an early stage business develop, Minch kind of professional. I think that was probably the, the most natural evolution [00:10:00] to my then saying, well, how do I just continue this career path?

And is it always business development or is there something else that I should be leaning into to kind of continue getting exposure at the most senior levels of these companies? Especially as, as they grow very quickly. And so, you know, it's Spring, we went from the five people when I joined to the 80 to 100 people when I became chief of staff only in less than a two year period.

So that was, you know, rapid spurts of growth that I hadn't really experienced before and knew that I wasn't. Ready to be a COO. I wasn't ready to, you know, lead product, you know, I wasn't ready to kind of fully head up the sales organization at a hundred, 150 person company, but wanted to kind of not keep the power, but it was more about keeping the kind of eye on how these different parts of the organization were growing.

Again, getting back to country. My initial goal of growing a company, myself, and wanting to rely on those broad experiences to, to do that.

Brooks Busch: [00:10:57] That's super helpful. And [00:11:00] again, it plays into chiefs of staff have to be able to connect different area of the business. And frankly, they have to have a desire to flex between how sales and marketing product and engineering, how it's all connected.

But let's step back into, as the Chief of Staff Network was starting to form, you mentioned so much of the glue that brought you all together was just building the role, going through life, going through the different challenges that the role offers at different stages of companies.

History and starting to figure out, okay, what are commonalities or what are learnings that we can share that are going to be applicable to, to other folks in this chief of staff role. I'm guessing that even from your time, when you first stepped into the role and seeing it evolve over the last few years, that it looks quite a bit differently.

Scott Amenta: [00:11:47] I'll start with my own experience. You know, when I started out at Spring, again, focused on kind of partnerships before taking on the chief of staff role. I had helped build out the supply side of the organization for the first 18 months. [00:12:00] You know, I'd built strong relationships across product engineering, marketing, and brand teams.

And those are relationships that I continue to rely on pretty heavily than as a chief of staff. I think one of the things that we're seeing today with the kind of evolution of the chief of staff role is as more companies are hiring for the position. They're hiring for that role externally versus internally first.

And, you know, I think in the kind of initial phase of, of chiefs of staff for merging at these early stage companies, it was very much like let's just take the most generalist person that's working closely with the executive team in one way or the other. And we'll turn them into the chief of staff today.

There is very much a, if you go on LinkedIn, you know, there's hundreds of sheets of staff roles available, you know, there's typically going to be one chief of staff per company today. We'll talk about maybe the evolution of what that looks like going forward. But I think that's one of the big changes that certainly that I've seen is just kind of external search for a chief of staff.

And that presents its own set of challenges. It's not necessarily the wrong way to do it. I would argue that an [00:13:00] internal recruiting process is probably. More effective for making that chief of staff successful in their first kind of hundred days, but there are certainly ways to bring in outside operators.

And I think one of the changes that we're also seeing is Jesus' staff come from very different backgrounds and, and that's really important to this position. So there is no set profile that makes one person, a great chief of staff and the next person not well suited for the role because the position can be very.

Principal oriented at times, you want to bring someone in that compliments, that CEO, that CTO skills, right. And. Helps to balance the things that give that principal their energy, right? So if your principal is great at fundraising and loves writing pitch decks and, you know, loves just being on the road, pitching the company and, and, you know, building partnerships, that's great, but you probably don't need a chief of staff.

That's also very good at those things. And so, [00:14:00] you know, in my case, my CEO, didn't love to write pitch decks. I love writing pitch docs. And, uh, you know, we got along in that capacity. Both of us were good at crafting the narrative, but actually putting it down on paper and taking the time to like, think through that storyline was something that I really kind of appreciate that process equally for writing board decks and things like this.

Now, you know, there are some kind of skills that I think are. Absolutely necessary for, for lack of a better word. You know? So being, cross-functional being able to build strong interpersonal relationships very quickly and establish trust. Great at communicating. I mean, these are like the classic things that you see on every job description, but I think they really get amplified in these types of roles and yeah, just sleep.

I think having some kind of more tactical skill sets that you can rely on over the course of your chief of staff tenures. So you never really know what's going to be thrown at you. It could be any number of strategic projects that are either highly critical to the business, or will be highly [00:15:00] critical to the business down the road.

It could be any number of, kind of internal projects from OKR to annual strategic planning, to planning an offsite for the executive team or the rest of the company. And, you know, these are things that. Can be highly nuanced, no matter how much you read on every blog post around the web and we'll end up looking and operating differently at your business.

And yeah, I need someone that is kind of creative and open-minded and a well-established within the company to not just build the process, but then get buy-in to the process. That's the most important thing. And this is where a chief of staff can provide the most leverage to a CEO or an executive team.

It's really, you know, having that kind of cross-functional. Again, relationships. And we'll, we'll probably use that word a hundred times over the course of this podcast, but those relationships will become really critical in getting that buy-in and, you know, an executive team can push a project, push a [00:16:00] process, push values, et cetera, all day long.

But a chief of staff can be very good at straddling that executive team and the rest of the organization. And, you know, get that buy-in from the brand new junior employee all the way up to, you know, the vice-president that, uh, might see things a little bit differently, but, but trust that chief of staff, because of whatever work they've done together, like, you know, in the trends.

Brooks Busch: [00:16:24] I don’t think we've met with a single chief of staff who hasn't emphasized the need to build trust the frankly, aggressive or proactive in forming relationships and being able to work cross-functionally and having a desire to do so. So as you outline those three skill sets as well, Yeah, I would agree if you're not able to quickly build trust, proactively establish your relationships.

It's going to be really hard to thrive in that role where you're acting as a connective tissue between leadership and everyone throughout the organization. As you mentioned. One thing you did point out is kind of the evolution of [00:17:00] the role itself. And I think we're actually seeing this in the chiefs of staff that we work with and the companies we work with is the shift from almost entirely hiring internal folks to step into that role versus.

A shift towards externally bringing folks in. And I think it's for a couple of reasons, one of which is people are more educated on what the chief of staff role is and thus can build resumes, can pursue those opportunities at other companies. Whereas early on it was to your point, let's just. Put the best generalist or executer that we have as at the company into that role.

And even if it's a two year, three years stint, it's great, then we'll look elsewhere, but we're seeing that evolution. And I'm even just curious from your perspective, what are pros and cons of putting someone internally into that role versus externally bringing in someone to fill that?

Scott Amenta: [00:17:53] So I think that the pros are more obvious for the internal hires.

We'll go back to [00:18:00] the, their relationship word that we keep on using, you know, so having that established credibility with different team leads across the organization, having worked on projects and having the institutional knowledge that comes with, you know, having executed on those projects can be really critical.

And then I think there's something to be said about just being bought into the vision values and kind of mission of the company. From day one, versus as an external hire, having to be kind of sold on that. And, you know, sometimes it can take a little while to really get buy-in. On those capacities. And so I think there's the value of the internal hire is that person's already basically ready and rearing to go.

You're limited though, in terms of how big your company is when you end up hiring that chief of staff as to whether or not you have that person on staff to actually bring into the position. And I think a lot of companies are probably ill prepared to have kind of a number of generalists on the team.

Right. You tend to hire. [00:19:00] Pretty specialized positions, not in like at like 10, at a 10 employees, you're hiring so much generalists. And then shortly after that, you're hiring only specialists, at least in my experience. And so that leads into not being well-prepared to actually bring an internal hire as a chief of staff, unless it's something that has been discussed kind of early on when that employee first.

And so I think the, you know, the pros to hiring the external chief of staff is you can really drill into and be very specific about the types of characteristics and qualities that you're looking for in a chief of staff at this point, you know, the CEO or whatever principal that chief of staff is going to report to should have a better instinct and understanding of how they want to work with the chief of staff.

And again, what kind of qualities will compliment. And, uh, help provide more leverage to their day to day jobs. And then I think also like, as the organization scales [00:20:00] that chief of staff role tends to fluctuate between being very principal focused and very organization focused. And so having an eye towards how is the organization growing and how ultimately will the chief of staff.

Not fully move away from the principal, but also take on more of the organization's priorities at certain times. And how do we, how do we think about again, kind of those characteristics that we need in this future role?

Brooks Busch: [00:20:27] Yeah, and so even to focus on this part of it. One of the things that I've heard you mentioned, and you all are helping to spearhead this, this language about the chief of staff role is traditionally it had been chief of staff to the CEO because that is in a lot of instances. You're bringing in a chief of staff to amplify the CEO first and foremost. It can also be the rest of the leadership team, but the CEO has been generally where that chief of staff has focused their time and effort.

However, we're seeing larger [00:21:00] companies, especially starting to hire chiefs of staff to be specialized for the CTO or the CRO or other members of leadership. And thus saying principle is almost a requirement because it's going to help represent the specific member of the leadership team that, that chief of staff.

Works with and is designed to kind of help facilitate their ability to represent their voice and their opinions throughout the organization. So, That's something that I'd love to get your thoughts and perspective on is we're seeing more and more companies starting to bring in chiefs of staff, multiple in their business for these C-level executives.

Do you expect this to continue to gain momentum? Or is this one where look it maybe for a certain size, it's going to make sense, but we don't see it as a long-term trend.

Scott Amenta: [00:21:50] Yeah. So going back to, you know, the different professional backgrounds that chiefs of staff often come from, as you were talking about before.

Yes. I think it makes a lot of sense for [00:22:00] chiefs of staff to ultimately report into various parts of the executive team. And ideally they have some of those skills that would be required across each department. So, you know, you would imagine, and we're already seeing this. If you're reporting into a chief product officer.

You're probably coming from a product operations or even a product management background. You know, if you're reporting into a CTO, you're probably coming from maybe not a full fledged engineering background, maybe you're just great at no code or maybe you're, you know, working in QA for example, but you have familiarity working with engineering teams and the way that those teams are structured and the types of processes that would be important.

Those departments. I think it makes a lot of sense for executives to have their own chief of staff. And as you said, we're definitely already seeing this at much later stage companies, you know, I would caution early in growth stage businesses below sales. A few hundred employees of [00:23:00] trying to hire a chief of staff for every C-level executive, you know, all at once.

I think it's a lot for still today. I think it's a lot for an organization to really wrap its head around how this chief of staff is working, not just with their direct principal, but then across the executive team and then across the wider team as well. And how. That person can provide leverage for their principal, but can also remove roadblocks and work on cross-functional projects without people feeling like he or she is stepping on their toes or.

There to take their jobs or, you know, there to spy on them on behalf of the CEO. And, and these are real, these are real things that a chief of staff goes through. That is not really something that you can easily point to another role having to deal with. And so, you know, I think it, it, it takes a little bit of a learning curve for companies to understand how to, how to best leverage the chief of staff.

I think as soon as the company has gotten kind of buy-in across the organization for that. It does start to make sense [00:24:00] very quickly to think about having chiefs of staff across the C level. And then, you know, be even at some of the very large companies like HPS or Microsofts of the world, or even seeing chiefs of staff at the vice president level or even the director level, which is interesting because what that also means is the kind of clarification of chief of staff leveling as well.

Is also becoming a little bit more clear. So a chief of staff that's reporting into a director is maybe not as senior, as a chief of staff reporting into the C level in theory. And so I, you know, I think that same model will ultimately end up applying to many of the startups that we see out there. The only other thing that I would advise and hiring multiple chiefs of staff, and this also applies to hiring your first chief of staff is you also want to have probably an executive assistant or some administrative assistant in place as well.

And ideally first before that chief. Comes into, into office. The [00:25:00] reason for that is a CEO that is used to working with an administrative assistant that understands kind of where they can get the most value out of that person, managing their calendar, thinking about their day and kind of weekly structure.

Thinking about how to prioritize different meetings and just things coming in from, from the team internal or external, we'll give them a lot more leverage when they actually take that chief of staff to not just fill in the kind of hundred percent of their day or week, but then to double their capacity to the next a hundred percent.

And. Often without that administrative assistant, the principal can, you know, easily fluctuates to kind of treating the chief of staff as the admin assistant. And that's not a knock on executive assistants. It's an incredibly important role, which is why I'm suggesting to hire at first, you know, before the chief of staff.

But, uh, you know, I think the two complemented balance each other really well, and it's important to have it in most cases, it's important to have.

Brooks Busch: [00:25:58] Even heading into this conversation. I [00:26:00] didn't think of this question, but now it comes to the forefront of my mind because you work with so many different folks in this role that you see a w well, a lot of times, but you also probably see it done poorly a lot of times.

So if you were. Advising or giving someone stepping into that chief of staff role advice to help see around the corners of things to avoid or, or pitfalls that you've seen companies fall into in the past. What would some of those be?

Scott Amenta: [00:26:27] Yeah, so I think that the first thing is we talked a little bit about the role being very principally oriented at times, a lot of the challenges that can emerge from the chief of staff role, even early on.

They start really, even in the job description. So when you look at a lot of chief of staff job descriptions today, you know, they talk about the types of qualities that they're looking for, the types of skill sets that they're looking for. Maybe they even go so far as to talk a little bit about the type of work that you might be doing.

You know, sometimes they, they, they do [00:27:00] mention, Hey, this is going to be a role rotation. Here's how we're thinking about the position. That's all great. But what they often, miss is. This notion of who are you actually working for? What does that person's qualities and traits? What, what are their personality nuances and what are the, you know, descriptive adjectives that we can use to help a potential candidate better understand who that person is and who they're going to be working with over time.

And this is a really important thing because. In most roles. Sure. You have a manager, but you know, you have your kind of day-to-day job. You have your tasks and that's all well said and done. Even if you don't get along with your manager, you can still do a really good job in a chief of staff role. You're often choosing the principal even before you're choosing the company.

And this is what I tell a lot of future chiefs of staff, people that are looking for the position is, yeah, you should be interested in the industry. You know, you should be bought into the mission or vision of the business. You should have a strong belief in [00:28:00] the things that they're building. But the most important thing honestly, is look for a principal, look for a boss that, you know, you will get along well with that you believe you compliment their skill sets that you believe you can provide a lot of leverage for.

And that, you know, you, you genuinely can trust in and build a strong relationship very quickly. If that first coffee chat feels at all awkward or, you know, not as fun as you wanted it to be. You know, it doesn't get any better over the next two years. Like you have to really trust your gut instinct on that relationship.

So that's the first piece of advice. The second pitfall is not spending enough time upfront building relationships now, not just with your principal, but first with the rest of the executive team. And then as a very close follow-up to that with as many of the rest of the. Kind of colleagues across your company as you can.

And that can happen in a few different ways. It can be in one-on-one coffee [00:29:00] chats where, you know, you're doing the majority of listening versus talking, and you're really only there to kind of probe and ask questions to better understand. What are the things that your colleagues are working on? Where are the problem areas that they feel they can't do as good of a job as they, as they should be doing?

And how can you best support them? And this is an area that most chiefs of staff will spend maybe one or two weeks on, you know, when they first get started, you know, it's part of the. Onboarding process for any employee, go have a few coffee chats with people across the company, but it's really something that has to be drilled in over the first three months.

And one could argue that that first three months should almost only be focused on that. Like you should have one or two projects where you can prove your capabilities and prove value very quickly, but most of your time should really just be sent, spent on building those relationships because that leverage will then.

Amplified a hundred acts over the next 18 to 24 [00:30:00] months of your tenure versus not having those relationships and having to kind of go back to square one, if you will, later on, we run a foundations track and the Chief of Staff Network, it's a four week track and it's pretty much exclusively focused on building relationships.

And, you know, you might question, how do you fit four weeks of content just on that one subject, but that's how important it is.

Brooks Busch: [00:30:21] Well, it's interesting. You bring this up and I actually don't question that you have a four week Jack because. It is time and time again, something where we hear chiefs of staff spending, even their first three months at the company, just meeting with as many folks as possible.

We talk to Grace Sutherland, who's the chief of staff at Yext, and she mentioned how that was basically the bulk of her job early on. Ben Battaglia is an incoming chief of staff at a company called Lessonly. And he's setting up basically a tour of the company meeting with every individual that he possibly can across all those different departments.

Because as we've mentioned in [00:31:00] the past, it's so much of the role is based on the information intake that you have available and the amount of information you can process. And then from there put together patterns, find opportunities within the business. The only way to increase that top of funnel of getting that information in.

Is first put yourself in positions to do so, but then also establish those relationships and that trust to have the channel open for future conversations, where folks feel comfortable coming to you, helping them feel as though look, when they're bringing opportunities to that chief of staff, it's in a manner of problem-solving or taking opportunities and running with it versus them feeling.

They are scared that that information is going to be used against them. He ties back to this whole conversation of the relationship element of it that we've talked about throughout Scott.

Scott Amenta: [00:31:50] Absolutely I would remind the listeners that that sounds like a relatively easy thing to do. Like, just go have coffee with a bunch of people that you work with, but, um, really the, the amount [00:32:00] of context switching and information overload.

And, you know, personality management that it takes to do that well is I think not something to be taken for granted. It's, you know, something where as you alluded to before, you know, you have to maintain a certain level of trust. But that's now trust across the wider organization, but also at the most senior levels.

And you know, the most senior levels want to hear what's happening across the wider organization from the horse's mouth as well. And so, you know, understanding what should and should not be said in what context, uh, is something that has to be really balanced very well, because as difficult as it is to build trust, it's significantly easier to break trust.

Brooks Busch: [00:32:42] It just takes that one misstep. So all this being said, Scott, you again, have that front row seat to the evolution of the chief of staff role across such a wide variety of company sizes and different verticals and industries. But I'm curious where [00:33:00] you see the role evolving to in the next five years, we've talked about chiefs of staff that are.

Highly specific to their principles. We've talked about chiefs of staff being at earlier stage companies. So all of that being said, and even some areas, I'm sure we haven't talked about where do you see the next five years going for this, this position?

Scott Amenta: [00:33:18] So the Chief of Staff Network recently developed a leveling framework and we did this because we’re used to staff entering, as we we've discussed at various points in their career with very different experiences. And yet they all have the same title, chief of staff. There's no kind of pointed direction in terms of, uh, how much experience they have under their belt, what they've done previously, and really where in the organization they sit.

And that could mean that they are a active stakeholder in the exact, within the executive team, it could mean that they are straddling the executive team. It could mean that they sit kind of outside the executive team, but maybe still have an ear in, but not a voice. And a lot of this has to do [00:34:00] with the kind of leveling that needs to go into this notion of a chief of staff, most chiefs of staff that we see today, at least within the network and more broadly, I would say, tend to be leveled.

Two to three, you know, maybe at the high end, the level four. And what that means is we're seeing a lot of chiefs of staff kind of early in growth stage companies enter relatively earlier in their career. And I think where the chief of staff role will go over the next five years is we'll really start to see that level five role emerge as a chief of staff as a true executive.

No within the C-suite working side by side with the CEO and, you know, still doing a lot of similar functions, but at a much more senior level. So there's always going to be a role rotation, you know, especially in earlier stage companies where it's, it's easy to get burned out on the role. But I think at a later stage company, it's possible that we see more career chiefs of staff that ultimately stick to the position and continue to level up within it.

[00:35:00] And, and for that reason, we'll see a much more level kind of five Chief of staff emerge over the next years.

Brooks Busch: [00:35:05] And, and that's one question that I'd love to press into here in a moment. The difference between folks that view the chief of staff role as a two to three-year stint, where then they flex into a specialized area within a business, versus those that view it as more of look, I'm stepping into this role for the longterm, whether it's with this company or to be the chief of staff at another organization.

But even before doing that, I Scott, I've seen a lot of the work that you all have done of this leveling framework. And it sounds like it's levels one to five. Is there like a quick synopsis or a quick recap that you would provide to what each of those levels kind of entails or looks like for an individual?

Scott Amenta: [00:35:44] Yeah, sure. So, you know, I think we've talked about this a little bit, that the role tends to ebb and flow between being very principle oriented and more organization oriented. And what that means is the. [00:36:00] The goals of their, of your principal, don't always necessarily align directly with the goals of the organization.

So, you know, where your CEO, maybe spending loads of time on fundraising. That doesn't mean the rest of the organization is spending loads of time and fundraising. Um, and so what we found is, and this is through, you know, working with the chiefs of staff in the community and beyond. As the role shifts from the more junior level one to a more senior level five.

At first, it's really about kind of strategy and execution for the principals. So the chief of staff is really there as a kind of brute force. Get it done for projects that me, you know, as a generalist, I can take pretty much anything and do it at roughly 80% as well as like the, the specialist in that area.

So then as a chief of staff moves into, you know, level two level three at that hierarchy, the role really starts to become more about optimizing [00:37:00] decision-making across the company. So they're now starting that shift from being very principle oriented, too. You know, starting to dip their toe into what's happening kind of across the rest of the organization.

This might mean that they are taking on more cross-functional projects, that they are working on. Things like right. That touch a lot of teams, ultimately what that means that they start to become a real thought partner to the principal. Right. So they're able to. Leverage those relationships, aggravate information, deal with high amounts of context, switching and bring all that information back to the principal or the rest of the exhibit.

Give team. What that ultimately becomes, you know, as, as this chief of staff is now moving to level four, level five, it's really about communicating and implementing strategic vision. So at this point, They've got their own projects. They're starting to take on their own priorities. They're starting to really dictate what those projects are versus it being kind of directed work.

And, you know, they really manage their own roadmap. This is I think, where we start to [00:38:00] see chiefs of staff building out this like office of the CEO type function that might include program management. It might include BizOps or other things of that nature. And you know, it could include an associate chief of staff, for example.

Take on some of that more principle oriented kind of brute force work at the more junior level. And I think this is where the role really starts to kind of emerge as like the true leader within the organization that can provide a lot of leverage across the whole executive suite, but also maintains kind of their own projects and priorities as an exec themselves.

Brooks Busch: [00:38:34] Yeah. And I love how you start to apply what it actually looks like to be in each of those levels for the chief of staff, because I think that's something. That's so often lost in this role is just. What is the evolution look like? And I'm not saying it needs to be as a traditional department, would where you go in sales as an example from BDR to AEA, to manager, to director, to VP of sales.

But [00:39:00] I think it adds a level of not just value and impact that that role can have across the organization, but it also helps anyone stepping into that role, understand what success is going to look like based on the differentiation of each of those levels themselves.

Scott Amenta: [00:39:16] Yeah, I think it's incredibly important.

It's still, I think we're still only scratching the surface of what this really looks like, you know, over the next few years. And this is why I think it's very important that we continue to share different chief of staff stories, you know, and any format, whether it's written or audio or video. Because it really helps to kind of unlock some of the nuances of the role and those individual experiences together amount to what the ultimate definition and the way that future leaders and companies will kind of apply this role within their organizations.

Brooks Busch: [00:39:50] So Scott, maybe to, to wrap it up here, the one other question that we get a lot and it's, it's something you touched on already, and I think it even ties into this leveling framework. Yeah. [00:40:00] Folks that are thinking about is the chief of staff role, a rotational opportunity for me, versus a career opportunity where I see myself continuing to evolve in this.

If you were giving advice to someone, maybe evaluating the position, evaluating what the position should look like for them, what are the main things you would call out of someone thinking of a chief of staff role as a career role versus more of a two to three years?

Scott Amenta: [00:40:28] The first really is know your skills, understand how you'll be able to leverage them as a chief of staff and you know, where they're most applicable within the size of organization that you're joining the type of principal that you're going to be working for.

And ultimately where that company is going. You know, the, the 50 person startup that you joined today, maybe 150 tomorrow. Those skills will apply very differently. Get ready for high amounts of ambiguity in your role and high degrees of context. Switching. [00:41:00] I think that is something that is much more easily said than done, and is something that you have to be really comfortable with going into the role from day one.

And that's that there's a two-sided issue there that the first is you don't really know where the role was going to evolve over the. Over your life cycle as the chief of staff, and even with a definitive role rotation, the company having hired probably their first chief of staff also doesn't really know where that role is going to evolve.

And so together that is a conversation that will be had over and over again, and needs to have an established level of trust that you're both there to figure it out together. And you're both comfortable. Not really knowing what the future holds. Right? So in, in the other positions that, that you typically see with like very standardized at this point career ladders, it's relatively easy to understand what are the skills that I need to develop.

What's the competency profile that I need. [00:42:00] To, you know, move from, uh, you know, manager to director within the chief of staff role, it's much less clear. And so that path has to be taken together with your principal, with, you know, the people ops team with this notion that you're, you're both there to, uh, to help solve it.

One last point. For an aspiring chief of staff or someone that's new to the role is you really want to understand why you want it to be a chief of staff in the first place. And ultimately what you hope to get from the experience. This is also a conversation that you'll have a lot with your principal.

It is the thing that you'll rely on as you. Level up into the chief of staff role and pick and choose the types of projects and priorities that you take on that will ultimately lead you to that next step. I think a lot of companies will continue to have a role rotation within the position. I think that's great because it provides a definitive end date to a certain degree for a position that is very easy to get burnt out on.

But I think there's [00:43:00] also loads of opportunity as companies grow very quickly. Where that chief of staff can continue to level up in the position can continue to add new roles and responsibilities can even add head count and kind of direct management experience to the role, which is something that, you know, most chiefs of staff won't get in kind of 18 to 24 months of tenure.

And, uh, yeah, it can really unlock a lot of other value in the position that we're not really seeing so much today, but we're starting to see, you know, very early signs of.

Brooks Busch: [00:43:31] Well, I was just even thinking of it from the context that you, you shared at the beginning, which is you, you had to propose this role internally to the company, because it was something that just wasn't well known.

What is the chief of staff? What does success look like for that individual? And you're not the first individual that we've heard say that they had to propose the role internally and the company didn't bite on it to begin with, but then circle back to. And now I think we're at a point where companies are starting to [00:44:00] realize, look, this is a required role.

It's a role that has, can have such a significant impact on our direction and where we're going now. It's okay. Well, how do we add structure to it? Which you, the leveling framework allows for. I think it's a constant revisiting of why did you want to step into this role in the first place? And is this a role that you want to continue to flex into?

Because to your point, there is a high degree of burnout because it is just such a high tempo role. That's working across so many different areas, so many different relationships across the business that, that it's easy to just simply get burnt out with all of the projects that you're continuously taking on.

Scott Amenta: [00:44:42] Yeah, absolutely. It's definitely one of the big risks to the role, not a career risk necessarily. You're still going to learn a lot in that experience, but it's something that you have to really keep an eye on from a mental health perspective, especially is, uh, you know, how do you balance the two, getting the most out of the experience as you can, [00:45:00] but, uh, also not being so heavily involved that you lose sight of some other things that are important in life.

Brooks Busch: [00:45:04] What y'all are doing at the Chief of Staff Network is amazing. We love being able to see you all continue to support. Folks in the chief of staff role as they grow in their career. And even as they step into their role, getting good visibility into what it was, is going to look like what success is in the role.

But thank you so much for taking the time to come onto inspiring ops and share your perspective and experience.

Scott Amenta: [00:45:27] Thank you Brooks, for having me, it was really great.

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