What Exactly is a Chief of Staff? (with Maggie Olson)

Speaker 2 · 0:05

The Leader Assistant Podcast exists to encourage and challenge assistants to become confident, game-changing leader assistants.

Jeremy · 0:23

Hey friends, the Nova Chief of Staff certification course is one of the most popular professional development resources for growth-minded leader assistants like you. With dozens of templates, self-paced learning, multiple instructor touchpoints, and peer engagement, Nova alumni walk away empowered and confident to level up as an assistant or even negotiate a promotion to a Chief of Staff role. With well over 500 students across 22 countries, Nova is the top spot for Chief of Staff learning and development. Join the movement today at leaderassistant.com/nova. That's leaderassistant.com/nova. Welcome to The Leader Assistant Podcast. It's episode 308. You can check out the show notes for this conversation at leaderassistant.com/308. Today, I'm excited to have my friend, Maggie Olson back on the show. Welcome back, Maggie.

Maggie · 1:24

Thank you. Happy to be here.

Jeremy · 1:27

We are going to dive in to the question of what exactly is a Chief of Staff, and the basics of the Chief of Staff role, the differences between EA, Chief of Staff, COO, CEO, etc. And then maybe who makes a great Chief of Staff. So, yeah, we're excited to jump in. We've had a lot of great conversations over the last several months. And a couple of those that are related to this topic that might be good for listeners to go back and check out are episode 257. That's from EA to Chief of Staff, how to level up. And then episode 298 is Chief of Staff, the next step for EA. So those are some good conversations that you guys can go back and listen to and fill in some of the blanks for today's conversation.

Maggie · 2:31

Yeah, I'm so excited. We've gone into a lot of specific tactics and how to be an excellent executive project manager, for example, or kind of more specific questions. And today we're going to step back and just sort of level set on what even is a Chief of Staff. And I don't understand the difference between Chief of Staff and EA and who makes a great Chief of Staff and what does a Chief of Staff do all day. So I'm excited.

Jeremy · 2:58

Awesome. Perfect. Well, we'll jump in then and I'll let you kind of lead the way as you're the Chief of Staff Guru.

Maggie · 3:05

Okay. That's a big title to live up to here. So we're just going to start with the easy question here, which is how do I define a Chief of Staff? So I define a Chief of Staff as a business leader's strategic thought partner who's excellent at execution and allows the business leader to focus on what's most important, vision, strategy, growth and leadership. So just like an EA, a Chief of Staff supports the leader directly, but in a highly strategic role that at its core is focused on driving the leader's many, many business initiatives forward quickly and efficiently, solving problems and removing roadblocks along the way. The Chief of Staff often also acts as a proxy for the leader, driving alignment across the leader's executive team and leading major cross-functional projects as necessary. So, that's a lot, that's a lot of words, a lot of jargon. But at the end of the day, the Chief of Staff is the right hand to the business leader and they are helping drive alignment across their leader's team. They're taking on projects, they're filling gaps, they're looking at the business both with a 10,000-foot view, like a bit more in a strategic kind of removed way. And then they're also able to be excellent at execution. And they're doing both constantly. So from here, I'm going to dive into the differences between EA and Chief of Staff. But first, I'm going to talk about how a Chief of Staff and an EA are similar. So both roles exist to support a human, to support a person, versus their own scorecard or business category. For example, like a COO or CMO, marketing role. Both roles are highly organized and very planful in their work. Both roles can be seen as the glue that holds the team together. Both roles have a major impact on the leadership team in the company, and both roles are really kind of the right hand or left hand to that business leader. But at the end of the day, these two roles are very different. You will rarely ever find the core functions of admin work in a Chief of Staff role. And those core functions are calendar, inbox, travel, expense, logistics. Those just generally are not part of the Chief of Staff role. However, where it gets a little bit murky is there's incredible EAs out there, and many who are reaching and grabbing for a strategic project here and there, or maybe solving a company problem, of course, and taking on some of those responsibilities that might live more within the Chief of Staff role. So that's why it can get a little bit murky, but they are two very different roles. I'm going to pause there, Jeremy, because I know we both have this conversation a lot. Do you have anything to add around kind of the differentiation between Chief of Staff and EA, and how you talk about the two?

Jeremy · 5:58

Yeah, I mean, I think the biggest thing I would just want to add that we've talked about before is just that there's such a difference in these titles and roles. But there's a difference between how people... Let's put it this way, there's a difference between the difference, depending on the industry and depending on the company size and depending on the, even the CEO's preferences on how they want to organize their leadership team. And so what some people will see as, oh, this is a very, this is very clearly a chief of staff, you know, job description line item. Other people might see that as, you know what, actually, if you're in a small nonprofit organization, they actually might put that line item in the executive assistant to the CEO job description. So it's kind of fluid depending on the organization and depending on the industry and depending on the company size and all that kind of stuff, which can be part of the problem because there's a lot of confusion and there's not a lot of clear levels when it comes to, you know, how much should I get paid for a chief of staff role or how much should I get paid for a senior executive assistant to the CEO role and all that. But I just wanted to throw that out there. I know we've talked about before, but it's just always good to consider the context of the situation. And the conversation.

Maggie · 7:41

Yeah. Yeah. You know, there's just so much variety and range in both of these roles depending on the business. And you could be in the same size business, in the same industry, and still have this massive difference in just the day-to-day operations of your role, or maybe the seniority level, or, you know, any of those things that Jeremy, you're just talking about. So it, you know, it's one of those, whenever you're supporting a human, because we're all so different, the role can just be very, very different. But I always come back to, at the end of the day, any Chief of Staff role, regardless of industry or size or your seniority level or who you're supporting, the core purpose of the role is the same. And that's what I talked about earlier. You know, the core purpose of the role is to be that leader's right hand, to help them execute, to drive alignment across their leadership team, to fill gaps and drive execution and, you know, manage all their many initiatives. That's the purpose of the role. And when it comes down to it, because, and we'll get into this in a minute here, but because the breadth of the role is so wide, it can just day to day look very different depending on where you're at. So, and often I'll chat with an EA and they'll tell me that they're doing all the things that a chief of staff is doing. And I tell them that they probably need a promotion to chief of staff and to offload the admin responsibilities in their role so that they can be as effective as possible as a chief of staff. So all sorts of things happening out there, lots of going on. Let us know what bucket you're in and how we can help you. I know Jeremy and I are both really passionate about this and helping everybody who's kind of in the middle trying to figure it out.

Jeremy · 9:21

Yeah, definitely.

Maggie · 9:23

Okay, so what are the differences between chief of staff and chief operating officer? Now, this comes up a lot because both roles are highly operational and often both roles support, let's say, a CEO, right? I mean, chiefs of staff can support directors and VPs and business leaders. But in this example, it can be murky because maybe you're both supporting a CEO and they're definitely both operational roles and at times, you can potentially work on similar projects as a chief of staff and COO, but that's really where it ends. So the key difference is that a chief of staff exists to support a human, to support a person and the chief operating officer exists to support the company. When we think about COO, they have their own organization, their own scorecards, their own problems to solve, their own true business within the business, business within the company, and their own real operational categories of a business. So a chief of staff exists to catch all of the initiatives from the business leader, not just open initiatives for the company, the business leader's priorities. The chief of staff usually doesn't have this giant org chart or category of business, of ownership. Instead, they support the CEO or business leader in everything and anything they need to help that leader stay focused on what I mentioned earlier, which is looking forward, vision, strategy, leadership, growth. So those two can get pretty murky. And at times, there seems to be a lot of overlap, especially in a small environment, like let's say a startup with not a ton of people. And a chief of staff is potentially operating in a chief operating officer kind of world, they're just out there solving company problems. Now, if that chief of staff is really actually just jumping on the things the leader wants them to jump on, they're supporting the leader in terms of kind of their engagement planning and their rhythm of business, and it's much more tied to that human, tied to that leader, that is the chief of staff role. Now Jeremy and I touched on this a little bit in the discussion around EA and chief of staff and how we define the role, but the role is growing in popularity. And truly, you can find a chief of staff in like every single industry. You can imagine, I've talked to you all, people from all these industries, which is super exciting, and the chief of staff role really exists under lots of different titles and different leadership levels. So there are leadership, let's see, so we've got chiefs of staff for CEOs or head coaches or directors, sports, entertainment, media, product companies. It's clearly a role that's in the C-suite supporting, you know, VPs and SVPs and presidents. And the role can really range from manager level to director level to C-suite level even. But again, you know, I'll just keep bringing it back to the core purpose of the role is the same, which I've been which I've been chatting to. So, okay, Jeremy, if if you think I should go here next, I'm going to chat through who I believe makes a great chief of staff. If you've been following Jeremy's podcast, heard me before you, this list may sound similar, but it's my favorite. So I'm going to dive in if that sounds good to you, Jeremy.

Jeremy · 12:45

Yeah, that sounds perfect.

Maggie · 12:46

Okay. So as I think about this list, I often think about the people in my life that I've worked with that fit in this profile. And maybe it's easy for you to say, yes, that's me or that's partly me or, oh, that's my friend. She's just like this. So here they are. You're fast, you're driven, you're curious, you're growth minded, you have a strong executive presence, so you're on your way there. You're achievement focused, high emotional intelligence, loves breadth versus depth. I call this expert generalist, problem solver, solution oriented, graded a lot of things, learns quickly, asks great questions, collaborative, influential leader, wants more responsibility if you're looking towards what's next and you're not a chief of staff yet, and that you love supporting senior leadership. Anything else that you would add, Jeremy, from your side? I'm Maggie Olson, founder of Nova Chief of Staff Certification, the first of its kind online course for aspiring and existing Chiefs of Staff. With curriculum taken directly from on-the-job responsibilities, Nova's self-paced learning modules provides you with hands-on experience so you can feel competent and confident moving into a Chief of Staff-style role. It's the perfect next step for executive assistants. Head to leaderassistant.com/nova to learn more, grab the syllabus, and enroll today.

Jeremy · 14:20

I mean, that's a pretty good overview for sure. I think that if anybody listening is like, oh man, that describes me perfectly, then definitely reach out to Maggie. She'd love to chat.

Maggie · 14:37

Yeah. If this is you, it's a sign. If you've been waiting for what's next, not sure what it is, looking for development and Chief of Staff's been on your radar. These are the characteristics that make a strong Chief of Staff. I think these are far, far more important than, for example, having an MBA or consulting experience. I know that if I was interviewing somebody and it was clear that this described them, I would hire them over somebody else that maybe it didn't describe, but they had the credentials, for example, of an MBA or consulting background, which I do not believe are necessary for a Chief of Staff role. So, you know, characteristics are different than skill set. I think that when it comes to skill set, you know, we haven't talked about this yet, but I'm the founder of Nova Chief of Staff. We have a very successful Chief of Staff certification course that offers hands-on practice doing the daily functions of the Chief of Staff role, but, you know, the foundational skills necessary to be a Chief of Staff. Some of them were just mentioned in kind of those characteristics, but strong executive project management is really, really important in an executive back office. The ability to lead a meeting, so facilitation is highly relevant. Being comfortable networking, that executive presence that I mentioned, having good sessions and one-on-ones and kind of information gathering tactics to kind of who you are to get to know your surroundings, your leadership team, that learning quickly component. Confidence is a big one. A lot of the Chief of Staff role, people are concerned that, oh my gosh, well, what if I've never worked in that industry before? Or what if I'm not super confident from a financial perspective? We have a podcast episode we recorded on this. Jeremy, I know he'll put it in the show notes for us around building financial acumen. But the Chief of Staff role is about breadth versus depth. So what's important is that you definitely understand the most important parts of your business. But what will be a detriment to your success as a Chief of Staff is if you spend too much time going deep in one area, so you just can't be an expert in everything. You've got to be able to identify what needs to be learned, and the resources to reach out to when you do need to go deep, and that's a skill for sure. There's other skills depending on the role. You may be presenting often, and you may be facilitating the information flow and materials for board reviews, which I know a lot of executive assistants also work with, that board level management. Of course, there's the leadership component. Often, you don't have a direct report as Chiefs of Staff, but sometimes you do, and you're definitely an influential leader. The ability to get folks to do what you need them to do, when they may be more senior than you, and they may be an SVP and have a team of 300, and yet you need those slides tomorrow. And how do you get them? That takes some confidence, it takes good planning, it takes good follow up, and it takes some EQ, like how do you approach this situation and this leader based on what you know. That's a little bit around the tactics that would make a great Chief of Staff. And again, Nova, our course dives into a lot of the overview of how do you build a strategic recommendation or a brief or executive project management, a complex offsite, and you just practice doing those things. So anything on your end, Jeremy, that you would add from a skill set perspective?

Jeremy · 18:16

Yeah, I mean, I just want to reiterate your point about the people that have an MBA or formal education that does not necessarily mean that they have an advantage. And I think a lot of times, you know, and why I think why assistants are so interested in this role is because assistants have such vast experience from on-the-job training and being in those board rooms, being in those leadership team meetings, reading and filtering and managing a CEO's inbox. I think managing a CEO's inbox can be sometimes more educational than an MBA. It's just so real and raw and you just can absorb so much about the business. And so I think that's a great point that the skills required is kind of that gritty adaptability, that ability to context switch at a moment's notice. And you really don't get that skill, I don't think, unless you've got that on the job training and on the job real world experience.

Maggie · 19:37

Yeah, I totally agree. I have an MBA and I did not learn how to be a chief of staff for my MBA program, that's for sure. There were good things that I got from the program, I definitely got opportunity. I was placed into a leader to executive development program post MBA, and I kind of gained confidence around like, you can do anything, this tough mergers and acquisitions class, like you nailed it, you know, like you can do it. There was a confidence building aspect for sure. The hyper local network that you get from an MBA program, it's not for nothing, like that's great. I had my MBA in Seattle. I now have a network of hundreds of people that I could reach out to. I don't live in Seattle anymore now. So that's when I say hyper local. It is a local network if you're in person. You know, and then there's just, of course, like the benefit of learning for learning sake, just to focus on the learning, the philosophy behind something, the how to do something new and challenging, and there's benefit to it. But I tell everybody, like definitely did not learn how to be a Chief of Staff in my MBA program. That's for sure, it was all on the job, and it was not just in a Chief of Staff role. Absolutely not. It was from my past experience that then made me a good fit for the Chief of Staff role, kind of as I've talked about here with characteristics and skill set.

Jeremy · 20:59

Yeah.

Maggie · 21:00

Well, yeah. You know, one thing to note, Jeremy, you recommended folks listen to, I believe it was episode 257 for how to level up as an EA, if you're interested in the Chief of Staff role. We went through a number of tactics on that podcast that I won't get into on this one, but definitely go check that out if you're looking for some applicable hands-on things that you can do right now to help elevate yourself into the Chief of Staff role. You know, and then I think the last thing that I'll mention here, Jeremy, just to give folks an idea of like, what are all the things? I'm going to just list off a bunch of the things that make up Chiefs of Staff's daily functions. So, I can give examples of these as well, but we've got business planning, the rhythm of business, executive project management and prioritization, business process and efficiency driving. I mentioned removing roadblocks, problem solving. That's definitely a category on its own, building process. Filling gaps, Chiefs of Staff fill gaps across the board. As we mentioned, there's industry after industry that has this role. The gaps are going to be different everywhere, but some could be, oh, let's lean in a little more to employee culture. Hey, Chief of Staff, can you put a survey together and then pull some tactics and some next steps? It could be, can you cover this leave? You have a background in HR and our HR manager is going out on maternity leave. Can you cover this for three months? It's not really Chief of Staff-y, but we need somebody. Wow, we don't have an org chart. Nope. This isn't generally a Chief of Staff responsibility, but everybody's busy. So it's a sense of there are a lot of priorities, and a Chief of Staff is somebody that fills the highest priorities of that moment at times. And then the final example would be areas like, well, we mentioned board and investor relations, that's big, but a little bit more broad would be just kind of the oversight or maybe even the doing of the events and communications for your leader. So you may, as a Chief of Staff, you may be the person drafting the comm that your leader is sending out next month for some event going on or some national holiday. You may be drafting it or you might be approving it, but you're probably involved in some way. You're probably at least reading it through because you touch almost everything that that leader is doing. And the same thing from an event perspective. I know there's Chiefs of Staff out there running events and they're putting it all together. I know there's EAs out there doing the same thing. Often when you're in a larger company, there may be an events company that you work with, like a third party. The Chief of Staff is still in the know. They're still project managing everything to make sure that the leader isn't, because somebody has to be involved every step of the way and that person should not be the business leader. So the Chief of Staff often steps in on those major kind of cross-functional, multi-person projects and oversees a lot of what's going on. So those are some of the functions day to day of a Chief of Staff. But there's many, many others.

Jeremy · 24:05

Nice. Yeah. Well, and I think you mentioned earlier to the Financial Acumen, that was episode 296 for those listening. I'll put all those prior conversations in the show notes at leaderassistant.com/308. And of course, you all listening can reach out to Maggie or myself on LinkedIn, or on our websites, and all those links will be in the show notes as well. But yeah, thanks for chatting as always, and I love the work you're doing for the Chief of Staff community, and even the Executive Assistant community is really soaking up all of the tools and tactics and tips and tricks that you've been sharing for how to become a Chief of Staff. But even, as I've said before, even just assistants training themselves to level up in their role, it's always good to learn because you may work with the Chief of Staff one day, or even if you don't become one, it's good to know more about how they think about the role and how they think about the relationship between them and the CEO and the board and how that involves you as an EA and all the things. So thanks again for chatting about all this.

Maggie · 25:23

Yeah, thank you. It's always a pleasure coming on and anybody if you need anything, just let us know. You can email us at hello at novachiefofstaff.com.

Jeremy · 25:32

Perfect. Thanks again, Maggie. Thanks everyone for listening and we'll see you next time.

Maggie · 25:36

Take care.

Speaker 2 · 25:47

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