[upbeat music] Hi, everyone. Welcome to the Chief of Staff Network Podcast. I'm Scott Amenta, your host for today.
I'm joined by three of my colleagues, all kind of current and former chiefs of staff. I'll let them introduce themselves quickly. Rahul, you wanna start with yourself? Thanks for having me on today, guys.
Uh, Scott and Tom hired me to be GM of the Chief of Staff Network three years ago. It's been an incredible ride, and I've been privileged to see the growth of the chief of staff role and our specific community.
So glad to be on the pod today. Hi, I'm Tom. I'm Scott's co-founder and the president of Chief of Staff Network, and then we have Lauren. Hi, guys. Um, I'm Lauren.
I've actually been a member of Chief of Staff Network since twenty twenty-three. I'm a former and current chief of staff, but also a head of growth at Chief of Staff Network. So excited to talk with you guys today.
So today, we're talking about how to position yourself as a chief of staff.
And, you know, this episode I think specifically goes out to people that are especially looking for roles, maybe have not been a chief of staff before and are considering this as a pathway, uh, as part of their career.
And we're gonna talk today a little bit about what are the ins and outs of kinda the skills that you need to build, the factors that go into building kind of a very credible resume to get a chief of staff role, what does the interview process look like and how to prepare for that, and if a chief of staff role is even right for you.
There are lots of other kind of similar roles out there, maybe not necessarily with the same title, but certainly a lot of maybe overlapping responsibilities, and so we'll talk a little bit about that from our own kind of career histories as chiefs of staff or in similar positions and kinda what that means in the market today.
Lauren, I'll kick it off to you because you've been hosting kinda multiple office hours with our members and, and the broader audience, both chiefs of staff and non-chiefs of staff alike, and you've been hearing these questions.
Tell us a little bit about what's been coming up in those office hours that is kinda most critical at this stage today. Yeah. So thanks for having this conversation.
I think it's one that is coming up a lot in the conversations that I'm having both with current chiefs of s-staff members, um, but also folks that are outside in the broader community that are working their way into a chief of staff role, um, and wondering, you know, how do I position myself given how competitive things are today.
Um, and there's a lot more popularity in the chief of staff role, and these w- uh, job descriptions that are coming up are getting more and more specific and tailored.
Figuring-- you know, looking at your own history, and I think a lot of folks are in this situation of I've been in these really cross-functional operator roles, I've been serving as a strategic right hand, but my title was, you know, strategy and ops or, you know, business operations manager or even, you know, in a more traditional people function.
And they're wondering, "How can I prove that I can do this role? How am I going to stand out from this stack of resumes? Or if I do get that interview, what are the things from my background that I can play up?
How do I position my experience in a way that's, you know, giving credit to the things that I've done and the ways that I have operated, even if I don't have, you know, the little checkboxes or the, you know, chief of staff official title previously?"
That's something that's kind of near and dear to my heart, obviously.
I never had the traditional chief of staff title before I started working as a chief of staff, um, and, you know, kinda joke was on me that I had been functioning in this way the whole time.
It took so many different people to call me a chief of staff before I realized I was one.
Um, and that's because, you know, I think previously when I first entered into more chief of staff, uh, traditional roles, they weren't very common outside of, you know, politics in the US is the one place where it meant one inherent scope.
Um, and everyone that I had seen doing it was kind of doing it differently, having a different experience, and that was maybe not the way that I liked to operate or the roles that I like to fill with organizations or partnering with principals.
Um,
so I, you know, stayed away from it and very intentionally took different titles in strategy and operations [chuckles] or, you know, client services or, you know, but serving as that kind of strategic glue across operational disciplines to drive things forward, keep all boats pointed in the same directions and all the other kind of cliché things that I [chuckles] use to describe the work that I do.
Um, but yeah, so I think that's something that a lot of our members are dealing with, um, but excited to hear everyone's perspective.
Rahul, I'm gonna kick it over to you for a second because you've reviewed thousands of chief of staff resumes or, you know, prospective chiefs of staff. You helped build our, our resume review tool.
You helped create the leveling framework, which we'll talk a little bit about.
Um, tell me, like, after reviewing kind of all these resumes and seeing kind of the gamut from good to great candidates, what do you think kinda really stands out as being a, a top-of-the-line chief of staff or, or candidate for chief of staff role?
I think some of that is difficult to answer because we still know the chief of staff role is highly variable. That's why we have the leveling framework.
But the thing that really stands out to me is the person can tie whatever it is they're doing to commercial outcomes, right?
And it's rare that a chief of staff is a seller, but the chief of staff should know that I'm doing X thing.
X thing makes the company more efficient or makes the CEO more effective, or it does-- it has these long-term impacts on the profitability of the business.
And that matters because as a chief of staff, you're being entrusted with a stewardship role. You're not just a line employee where you can come in, clock in at nine AM, do whatever it is you're gonna do, and then leave.
Like, you're helping pilot the ship. You're the first mate. You need to know where the ship is going, why it's going there, what planks and timbers need to be replaced on the ship, so on and so forth.
And so what really stands out to me when I've seen resumes is not just when someone says, "Oh, I prepped the board decks," or, "I ran the monthly all hands," or, "I did..."
you know, whatever it might be, but it's tying that to some sort of commercial outcome, right?I led the board meetings and convinced all of our investors to follow on to our next fundraising round,
and that round was, you know, oversubscribed by this percent." Um, or something like, "Hey, I ran all the all-hands, and we had retention of our staff above and beyond what is expected for our industry."
So ultimately, all of it boils down to that concept, which I like calling it commercial rigor. Other people might call it something else. Um, but typically, that's what it is, right? Pretty simple, and you...
Easier said than done maybe, but pretty simple. Yeah, but I think the, the typical profile of a chief of staff is not typical at all, right?
We, we tend to call them great generalists, but generalists can come from lots of different backgrounds.
I, I think what I look for in a great chief of staff is someone that's confident enough to know kind of the depth of skills that they have in any particular area.
So I've talked to chiefs of staff that I would consider very good in their role who come from sales backgrounds, marketing backgrounds, product backgrounds, and they all admit to that upfront that, you know, they might be great generalists, but they also have this other skill to kind of lean back on, and that tends to be, you know, usually in line with what their principal needs from them as well, right?
So someone coming from a product background may be reporting into a CTO or a CPO now.
Someone coming from, you know, more of a sales background may be reporting as a chief of staff into a CRO, and it doesn't mean that they're now selling, but it does mean that they can kind of walk the walk, talk the talk with the teams that they're orchestrating and, and helping to align.
Tom, do you see kinda similar profiles? Like, what does a great generalist mean to you? I think it's so hard because we can, uh...
Like, what chiefs of staff look like after the fact, after they're hired and see a lot of similarities, right?
But when principals are hiring chiefs of staff, often they're looking for something quite specific, even if they can't describe it, uh, very well, and, you know, often that's the case.
I find the principals say like, "Oh, I just re- want somebody really smart," or, "I want somebody, you know, who's done this before," as like a, as a heuristic for cutting through the noise.
But I, I think there are a few categories that, that are pretty common, or at least that I would look for if I were hiring a chief of staff today.
Um, the first would be, you know, horsepower, so analytical skills demonstrated in, in some way, and often a good proxy for that is, like, have you been through a high-quality training program in banking, consulting, something along those lines.
Uh, that, you know, the... Historically, that was the most popular entry route into the chief of staff role.
I think that's changed a little bit, but still, like, the last few founders that have reached out to me saying, "Hey, can you help me hire a chief of staff?"
It's been, "I want somebody who spent two years at McKinsey, two years at Blackstone," kind of thing, right? Um, which great, lovely. That... I mean, if you can find that person, wonderful.
I think sometimes they're the perfect fit. Sometimes they're, they're not. So analytical rigor is one. The next one is people skills, and the way that's demonstrated depends on the level.
Again, like, a, a level one or two chief of staff, um, is going to tend, you know, uh, you're gonna demonstrate that in, in the interview mostly, versus, like, on the resume.
And then if you're a level four or five, you should be showing, you know, some leadership experience and management experience, um, and the results that, that come with that.
The next couple things really depends by company, and those are industry experience and stage experience. Typically, CEOs don't want to hire a chief of staff that needs training wheels.
They want somebody who can operate autonomously from day one.
They want somebody who can, like, add value to them from the beginning, and that process is a lot quicker if they've been there before or at least can analogize pretty well.
And then the last two things I'd say, one is, is relatively new that I've seen popping up in the last year or so.
It's real AI capabilities, you know, a, a portfolio of AI projects that they can bring to the table and say like, "Hey, I will help level up the organization along this, along this dimension."
Um, and then the last piece is, is really kind of the f- the, the, the final filter that determines whether you get the job or not, which is do you vibe with the principal? Are they gonna be happy spending time with you?
Are they gonna be happy having you as their proxy? So those are the big things I'd look at. Um, and again, I think you can demonstrate those very well without having had the chief of staff title specifically. But
it's harder if you're going through a recruiter or if the CEO or, or principal has in their mind, like, "I wanna hire somebody who's done this role before." So that's my two cents. Yeah, I love the framework.
I, I think it's interesting that for many of the chief of staff job descriptions that we see, just to echo one of Tom's first points, many of them are very generic, right?
And, and this role being so tied to the principal, the job description rarely does justice to kind of who that person is, how they work, how they communicate, a-and really what they're looking for.
Um, it's not enough, right, just to be asking for a very smart person, generalist role, who, you know, kinda has the horsepower and people skills, et cetera, to kind of r-run the position.
Um, that would be fine if it was just an organizational role.
But because this role is so tied to the principal, you know, I think one thing that we would all like to see is more companies doing the hard work to, like, really distill not just what the role is, but how the role is going to work with the person they're reporting to.
Um, Lauren, I'm, I'm curious, as you've been kind of hosting these office hours, h-has that come up from our members as people are going through these interview processes?
Do, do they feel like they're reading something on a page and then walking into something totally different, uh, in, in real life when they go into the interview process? Yeah.
I think, one, that challenge of, like, this is so generic. How do I, you know, without having that title, how do I position myself because it is so broad?
But the other thing is that it is so tied to the principal, and then they're going in there and hearing from the horse's mouth something totally different about the way that they like to operate or do something else.
So I alwaysI always say that like chiefs of staff are all kind of personality hires to a certain degree, where you're not only figuring out like what, what does this specific organization need?
What does this specific principal need?
But then also, you know, there is that kind of like magic sauce between a principal and chief of staff that like makes that partnership really powerful of like, how do we gel together? How do we...
Are we on the same page? Do I understand where your brain is going and how to translate that into priorities and strategic initiatives across an organization?
Um, so there is that, you know, kind of push and pull between how, you know, maybe the principal articulates that to whoever is writing the job description, and then, you know, that there can get stuff lost in translation there.
And then when they're in these rooms, it's, well, yes, but, right? You're trying to get to the heart of the actual problem, not necessarily the solution that's written on a job description.
And I think in any kind of situation, there can be a, a disconnect between those two things if you really dig in.
Yeah, and I think that the challenge in terms of what that principal might be looking for, you know, in an ideal world could be distilled down to a set of metrics or proof points that like demonstrates how ready is this person to be my chief of staff.
That obviously is not going to be so cut and dry. Just le-let's use Tom's kind of framework as, as an outline here, uh, or, or Lauren or, or Tom jump in.
What, what metrics or proof points do you think best demonstrate COS readiness?
Like out of the horsepower, uh, you know, ability to use AI, uh, people skills, et cetera, what thing would you kind of lean into the most if you were interviewing for a role today?
In baseball, there's this concept of a five-tool player. I think you kind of have to be the same way as a chief of staff. You've got to check all the boxes. And you can have, you know, varying strengths in each of them.
You don't have to be world-class analytically, world-class people, world-class industry expertise.
But, um, you have to stand out in some way because the fact is that each of these roles, if they get listed publicly, they're going to get minimum hundreds but likely thousands of applications, and you have to be able to stand out.
And we can have a separate conversation, we should, about, hey, is there any point in actually throwing your application in the ring through, through those, uh, those cattle calls?
Uh, you know, but I, I think it's you've got to show that you can do all of them because once you're in the role, you're going to have to demonstrate industry expertise, uh, stage expertise or develop it fast, right?
You've gotta... You're gonna be analyzing stuff all day long or working with AI to do that, and you're gonna be dealing with people, um, at least until AI takes all of our jobs.
So, you know, that's the, that's the reality of it. There is something to be said about positioning here as well.
You know, I, I see lots of people that were not chiefs of staff, um, and maybe doing something similar to a chief of staff role indirectly, uh, now calling themselves fractional chiefs of staff.
Lauren, I'm gonna call you out here even though I know you were doing a kind of proper chief of staff role, maybe without the title, but you've been doing fractional chief of staff work for at least the past year.
Talk to us a little bit about that transition and kinda how you thought about, you know, wearing this new hat as a fractional chief of staff and has that positioning helped you as you've, you know, been talking to other employers, et cetera?
I think it, you know, calling myself a fractional chief of staff, um, it took-- You know, I started meeting with folks, and when I thought about, okay, where do I wanna go next? What do I wanna do?
Here's how I like to operate. And every kind of person I had a conversation with said, "Sounds like you're a chief of staff." And I said, "No, no, no. Like [chuckles] I'm, I'm not," right? "This is what I do instead."
And they're like, "Yeah, you should look into this more." And that's when I met with Rahul, and he said, "Yeah, you're definitely a chief of staff, and, you know, you probably have been for a while now."
I said, "Okay, cool. Um, so let's give this a go." I think it's starting to mean something to other people.
Um, but the way that I position myself and is, yes, I think, Tom, all the things that you mentioned are like up there, right? And that's what you need to be able to do.
But how you position that to another person, something that comes up so common, and it might just be because I tend to partner with organizations when they're going through like, you know, inflection points and needing that additional support.
The pipes are bursting, right?
So that comfort and ambiguity of like, whatever it is, I'm gonna come in, solve this, figure out what the problem is, figure out the right solution, and do that kind of analytical horsepower, and then execute through whatever, you know, different tools are in my tool belt to make sure that you're moving forward in the best possible way.
So that comfort and ambiguity, being a builder, being able to translate, like really understanding where they're going, what their vision is, and not only like the outputs of that but like why and the, the reasoning behind it, so that way you can pull that into the day-to-day now.
And so I think there's like these broader things of like, you know, it's hard to explain or, you know, define like, "Oh, I want someone that can take what I'm thinking and make it happen," but proving out, "Yes, I can do that.
I've done that numerous times before.
I've worked across numerous disciplines to make that happen, and I can do that for you using, you know, my AI toolbox, using my, um, you know, analytical horsepower, using all these different skills that I've, you know, built up over my career and flexing those muscles."
So that's been the way that like I've been positioning myself, which seems to be going pretty well and helps me also work across industries.
So, um, that, that way you can take it, you know, obviously my corporate career was in digital media and advertising, but now I work specifically with, you know, high-growth tech startups, with nonprofit organizations, with, you know, mission-driven things.
So being able to flex those muscles and saying, "I have this skill set, I could do it anywhere," is something that I think is resonating with founders the most.
That makes a lot of sense, Lauren, and obviously anybody would be lucky to hire you. I think the fractional thing is tricky, right? Because in some senses, you're just selling a... Well, in general, not you specifically.
In g- you know, you're selling a product if you're, if you're going out as a fractional person. And people are used-- companies, CEOs are used to buying a fractional chief of staff. They have a model for that.
So that's, uh, it makes sense to position yourself that way.
I do think that folks who haven't been in the chief of staff role going and positioning themselves as fractional chiefs of staff is in some waysThere's a little bit of intellectual dishonesty there unless you have, um,
shown commercial results and worked directly for a principal, right? Because the principal relationship thing is such a big piece of being an effective chief of staff that
to say you're a chief of staff without having that is, is a little bit, um, uh, it's just I, I'm not sure how accurate it is. Um, so I, I don't know.
That may be a bit of a controversial statement, but, um, what do you think about that, Lauren? No. So I, I do think that also makes sense, right? So I guess caveat to that is my experience is always revenue.
So I've always been tied to commercial functions and having those as like key metrics that I use. Um, I do think, you know, that is something that like chiefs of staff generally get... need to be better at.
Um, because when you're the output of like, "I'm really successful in this job if the person that I'm partnered with is better than they would be without me," that's hard to measure.
Um, so getting, you know, if you are thinking about going into a, a fractional or, you know, transitioning into a chief of staff job, having those metrics kinda locked is important. And then the principal relationship.
So yeah, and even if you've worked really closely with specific teams, right, or with specific leaders or cross-organizational, um, leadership teams, I think is also important.
I didn't necessarily have, you know, thinking back on my own experience, I was, you know, a right hand for that person more in function than title and, and name, right? It ended up working out that way.
I think a lot of folks though have maybe had that experience where they're like de facto the right hand of their superior or their, um, you know, the VP, the, the CEO, the CRO, whoever is the, the top person and kind of building that relationship, but that is something that a lot of folks, um, are looking to build when they, they come to Chief of Staff Network, right?
So that is a lot of the conversations that I have. That makes sense to me.
I, I think you also like don't have to stretch your experience too much to say you're a chief of staff to present a good application for some of these roles, right?
Like, if you haven't done the chief of staff role, don't claim that you have because it's gonna be pretty apparent to anybody who's been exposed to that before that it, it was not quite a chief of staff role and that you're stretching the truth or you're just trying to position yourself.
Own the experience you have, own the expertise you have, and present that against the, um, the competencies that the, the principal is recruiting for, and then maybe in the meeting you can say, "Hey, you know, I see a lot of similarities between the work I was doing and this chief of staff role," or, "I served in a quasi chief of staff function in my, in my past couple jobs."
But, um, I've seen resumes as well where people just distinctly did not have the chief of staff role and, you know, in parentheses or in italics or whatever, like chief of staff role, and it's like n-no.
The ca- the, the, um, the tasks you were doing bore little resemblance to what a chief of staff would be doing a-and that's ultimately not gonna serve anybody well.
So something Lauren said was like hear what they want and present a narrative of how you've done that thing.
I actually try, when I talk to people about how they're positioning themselves, I tell them, "Write a cover letter. In that cover letter say, 'Here's exactly what I can bring to your team as your chief of staff.'
Copy/paste the actual salient bullet points out of the job description, bold them, and then tell that story with some sort of commercial outcome." Right?
'Cause then you're bonking them over the head with, "You want this thing. I have done this thing." If you cannot come up with that cover letter, the exercise should show you that role is probably not a fit, right?
As Tom was saying, like don't stretch yourself or stretch the truth if there's not an obvious fit. 'Cause, you know, we do know that thousands of people are applying for some of these roles.
You want the one that's gonna be a slam dunk, not the one where you have to stretch like fifty percent to try and make it. Yeah, I think that's a really good point. The, uh...
and, and if the job description obviously has enough detail to do that, go for it and right, making sure that you're tying it back to your actual real world experiences.
I, I think if it doesn't though and you're still interested in the principal, this organization, you know, it's not wrong sometimes to take a guess as to what the company might be going through with enough understanding of the market, right, enough diligence of their competitors and the product that they're building that you can take a swing and say, "Hey, look.
Here's what I think probably is important to you. Here's item six, seven, eight, nine, ten that you're not getting to every day. Here's where I can help you."
And, you know, I think that can be incredibly effective because you're proving, you know, upfront that you know your value as a chief of staff and you know exactly where you're gonna step in on day one.
For most organizations hiring a chief of staff role today, many of them are doing it for the first time, and that presents a little bit of a risk both to the principal who has to now manage this person and also to the company, right?
The HR team is probably questioning who this person's going to be and, and what the laddering or leveling is going to look like.
The chief of staff that comes to the table knowing more about the role, knowing more about how they're gonna fit into the organization, knowing more about how they're going to scale within the company, what's gonna happen eighteen, twenty-four months from now when I might wanna do something else, the person that has that story lowers that risk profile for the company making this hire for the first time.
And so, you know, I think for any prospective chief of staff out there, go do your homework, not just on the company, not just on the principal, but on the role itself.
The more history you know, the more chiefs of staff that you talk to, the better prepared you are to have these conversations and hit the ground running, you know, day one i-in this new position.
Totally agree with that, and I think that remains an underrated way to get these roles is to do your own research, reach out with a very tailored note to, to the principal and say why you're interested and do it truthfully and do it compellingly.
You know, I, I think if you have...
if you're one of a thousand applicants through like a, an, a resume drop, even if you're in the top ten percent of those applicants, that's still a one in a hundred chance versus you'll probably be one of maybe five or ten people at most who are cold emailing a principal, especially if they don't ha- even have a job, um, open, uh, you know, but looking for a role.
Even better. And yes, it'll take you ten or twenty times a-as much effort to, to write a good-Kind of note there and, and show your work. But if you actually want the role, you have to be willing to put in that effort.
Um, and I think the outcomes are generally better too. I think you bring up so-something really interesting with the one in a hundred, right?
If, if those hundred, the top ten percent are high initiative and they email you, Tom, and say, "Hey, can I have fifteen minutes?" That's twenty-five hours of your time, which you rationally cannot spend, right?
You have other things to deal with as CEO of a company.
So instead, the thing that I found works, working with people and researching is, if I consume the artifacts you put into the world, right, podcasts, blog posts, et cetera, and say, "Hey, Tom, I read this article.
It had an impact on me. I used it in this way, but I disagree with this point. Can we talk about that?" Right? And smart people typically need to be right about the world to be successful over long spans of time.
So if someone reached out to me and said, "Hey, the chief of staff salary report is awesome. I negotiated for higher pay, but I actually think your data in my city is wrong or in my country is wrong. Can I tell you why?"
I'd probably take that call most of the time. And I think that's the way you sort of get in compared to those hundred people who are just saying, "Hey, Tom, can I have fifteen minutes of your time?" I agree.
I think the...
I'd complicate it a little bit and say, don't just disagree, have a, have a reason that you're disagreeing and, and good backup, because if somebody writes to me and just, you know, is, is, is ornery, I don't want to take that call either.
[laughs] I'll just delete it. Yes. Yes. Be principled, be genuine, right? Don't blow smoke up people's butt, but also, like- And show that you have some value to bring to the, the conversation, right?
You have to prove that you're going to be a, a valuable conversation partner there.
And, and maybe that means, like, you've used the product, um, you know, that, that the company produces, or you have relevant experience, or s- or you've done a, a research report or something like that, right?
It's, it's easier than ever to show your work now, so you gotta do it.
I'm curious from your guys' perspectives, we've talked a little bit about how to position yourself, how to kinda get your way into the door, have that first meeting.
I think what, uh, what often is not discussed enough is what questions should candidates be asking, right?
How do we make sure that this is actually the right full, uh, role for them as well, not just for the principal hiring them?
So from your own experiences, from working and kind of talking to lots of chiefs of staff, what should they do to clarify expectations, decision rights, success metrics? What are the questions that you would ask?
Always something that gives better understanding into, like, the CEO's or the principal's, like, long-term strategic vision for the organization and figuring out, like, where exactly you're gonna plug in to drive impact.
I think a lot of folks, right, like, generally go into job interviews, like, ready to sell themselves, but, you know, ultimately, you're gonna be judged based on the outcomes of the organization and how successful you are at driving things forward, showing that you're thinking about that big picture, where your CEO is gonna be, that principal is gonna be, um, and how they're gonna hit their benchmarks, um, I think is, you know, the first thing that's gonna set yourself up for success and know if that's work you're interested in doing, um, in a very tangible way, but also, you know, when you're gonna hit those milestones.
I would even go so far as to create essentially a reverse job description for yourself and be very explicit about what you are seeking in the role. This is just for you.
This is not, I, I think, to share with anybody except maybe an external recruiter that, you know, is reaching out to you.
But, um, say what kind of work you want to be doing, say what your comp expectations are, talk about the responsibilities you wanna have, talk about the path that you want to create over the next couple years forward after this role.
And then whenever you end up having one of these conversations, compare the results or compare what you're hearing versus that, that job description, the reverse job description, because if nothing else is true, good founders are really good salespeople, and they will convince you to take less money and less responsibility and a lower title and all this stuff because giving away all those things is costly to them.
And so you wanna make sure that you're able to take a, kind of a, a principal negotiating stance and make sure that it's actually the role that you want and is the right step for your career versus just getting, um, you know, in that kind of tractor beam of a, of a great founder and, uh, and taking a role that doesn't get you where you wanna go.
I think the tractor beam thing is really interesting, and I think one of the ways to get around that is to just talk about the ninety-day plan very tactically.
And so if the CEO can't or the principal can't articulate what it is they want done in ninety days, even if they have a really great strategy in mind, they might not be able to connect it to tactics.
And so I personally wouldn't want that chief of staff role where I don't know what I need to be doing in the org to affect the outcomes that are desired.
Similarly, if the person really sells me and they're super charming and they convince me of all these things, but they can't articulate, "These are the things you need to do to be successful," I would similarly be a little bit nervous about that role.
And, you know, time and again, we talk about the ninety-day plan, uh, for chief of staff, 'cause unlike many other roles, you get a lot of ability to write your own ninety-day plan, whereas, you know, your average salesperson or ops specialist or whatever might not get that.
Yeah, I think it's a salient point.
The, the last thing that I would add, which is maybe the most obvious, is make sure that you're entering a chief of staff role, or at the very least interviewing for a chief of staff role that is at the level that you're looking for.
And I think this is one of the biggest problems with chief of staff roles is they all have the same title, right?
You may be able to differentiate slightly based on the responsibilities that are outlined, uh, maybe based on the requirements in terms of years of experience, maybe the salary, uh, but it's critical to have that conversation with the principal, with the hiring managers about where does this sit on kind of the leveling framework.
If they don't know what the leveling framework is, they should use the Chief of Staff Network leveling framework. I think it's the best one.
I think we're all probably a little bit biased, but, um, it certainly has been very helpful for lots of chiefs of staff out there already.
But, you know, that will helpPut people on a level playing field of, okay, what is this role going to be?
What are the shape of its responsibilities and decision-making powers and relationships with the rest of the team, both executive and broader organization?
And you know, you don't wanna find yourself walking into what they've constructed as a level two chief of staff, while in your head you're more a level four or five chief of staff, and all of a sudden you feel like you're doing much more administrative type responsibilities or just don't have the same kind of strategic access or decision-making powers, um, as you would in a, in a more senior level.
And so I think it's important to have that conversation early.
Again, you know, the, the more kind of instruments you can bring to the conversation in hand helps them to de-risk the hiring of this role and especially for you, who kinda has the history and knowledge of, of what it's gonna look like.
Yeah. And, and this... I think this last part of the podcast is gonna feel like a little bit of an anti-pitch on the chief of staff role, and I think all four of us are, are big proponents of, of the role. But
I think you've gotta go in with an open mind and a really clear view of what you wanna get out of it and, and how it's gonna contribute to your career.
Because I've-- I think we've all talked to a bunch of chiefs of staff who are still at sea about what they want to do next. Like an MBA program, right?
If you, if you're spending two hundred thousand dollars, or if you're spending two to three years of your life, you know, working really hard towards on this specific problem, in this specific role for a founder or for a principal, and you get to the end of it and you're like, "Well, wait a second, like, I'm not any closer to knowing what I wanna do," that's not a good use of time or effort, unless it's a massively successful company and the, the founder's hugely influential and all that stuff.
But you can't always count on that being the case. So there are lots of ways to get the-- get to the next step, get the experience that you want without having that chief of staff title.
Um, you should go for it for sure, but know also that there are a bunch of other paths that are really compelling.
So keep your, keep your mind open, keep your eyes open for, for other roles as well, and don't, um, don't fixate too much on that.
And, and actually, I, I would say, like, the most valuable roles are actually the ones where you have commercial responsibility, and most chiefs of staff want to graduate into owning a P&L.
So if you can find a way to own a, a P&L or part of it, you know, that's a great thing to do instead. Yeah, chief of staff is obviously an excellent stepping stone into many of those roles.
But I think for all of the stories that we've heard of people graduating from chief of staff into general manager, COO, VP of strategy, et cetera,
they're all coming into the position knowing what they want out of it and being very explicit and tactical about raising their hand for the projects they know will lead them to that next step.
If you're coming into the chief of staff role because it's a hot role that people are talking about, that's probably not the right reason and, you know, something to consider, right?
There are better paths for great generalists that don't have to be the chief of staff.
Someone was just bringing this up in, in the community, like, the other day, so [chuckles] it's kinda fresh, where she was like, "I'm, I'm graduating," right? "We're moving into another role.
Like, what should my title be?" Kinda the feedback from everyone was like, "Well, what do you like to do? What work do you enjoy? Where do you wanna go?" Right?
Like, you've probably done go-to-market, you've probably done, like, you know, finance, you've probably done HR. Like, what do you want your future to reflect in really sitting with that?
So I think if you don't know what you're hoping to get out of a role or where you're looking to go, it's probably gonna be hard to figure out if it's the right fit. Totally agree with that.
I-- There's this concept called zone of genius, which is what is energizing to you and what are you world-class at, and find the Venn diagram of those things.
Um, but the other point I was gonna make is that I, you know, I would admit I was actually a pretty bad chief of staff, and I was internally promoted out of biz ops manager, and then I actually went back to biz ops after my chief of staff role.
To Tom's point, you know, there are like five traits I think you can be... You need to be excellent at at least one. You could probably be weak at one.
And for me, the thing that I was weak at was actually, like, the interpersonal dynamic stuff. Like, dealing with people all the time was very exhausting to me.
And so going back to a more pure ops, project management, strategy type role where I could have a backlog of things to work on and mostly be left to my own devices was better.
And so sometimes you learn the truth by doing the thing itself. But hopefully for other people, they can figure it out before they do the chief of staff role for a few years.
It's amazing that you say that, Rahul, having now been the GM of Chief of Staff Network and having led the community this far. [chuckles] Uh, obviously a very people-focused role.
So y-you clearly learned a lot in that first chief of staff position. I'm glad you carried it with you.
And I think that's one of the best things about chief of staff is, is the learning, the learning machines, the people that can, uh, you know, really take on a lot more.
So I wanna end here by asking you all, you know, if someone takes kind of only three actions this month to position themselves for a chief of staff role, what should they be?
I would say think about your own experience, go to the leveling framework, and figure out, you know, aside from titles, right, what work do you enjoy, what work are you dangerously good at, and what work would you...
And, and pick some examples, right, that lad- ladder into the things that are gonna be interesting and, you know, where you are uniquely qualified to do that.
And that's gonna help you more than just looking for random chief of staff title jobs and throwing your resume against the wall.
I would say show how doing those things has advanced the company towards its goals, not just you towards your individual goals. So I think laddering what Lauren said into, like, the actual commercial impact of it.
I would say
sit in silence for an hour or go for a walk and think really hard about what do you want out of life and what work do you wanna be doing, because I think too few people have actually spent that time to do the introspection and then kind of find themselves thrust into this kinda whirlwind job hunting process and desperate to find something without knowing where they're going.
So do that, and then I'm gonna cheat and offer a, a, small addendum, which is get really good at AI fast, because I think you have to do that now in order to
be competitive and, and have a good job in, in the next few months and few years. I agree, and I, I'm glad you said it, Tom, because I was also going to say it if no one else did. But instead, I will share...
You know, I, I think the most important thing is, like, find community, find other people that are looking for roles. Even people that are looking for chief of staff roles are not competition to you.
They're opportunities to learn. Talk to chiefs of staff in the position.
It'll make you realize faster than ever whether or not this might be the right fit for you and, you know, at what stage company, what size organization, reporting into what type of principal.
That's the best way to figure out how to position yourself and go craft your story. And the last thing I'll share is join Chief of Staff Launch Pad. Uh, it's coming from the Chief of Staff Network.
It's a six-week cohort program.
We welcome prospective chiefs of staff that are currently interviewing for the role, but also current chiefs of staff that are typically in their first hundred days and ramping up, getting up to speed with their principal, who really wanna hit the ground running.
It's taught by, uh, many of the people on this call and a number of other executive coaches and, and former chiefs of staff. Um, so yeah. Tom, Rahul, Lauren, thank you for joining us today. Appreciate your insights.
Thank you. Thanks. Yeah, thanks. This was fun. Bye, everyone.
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