Maggie Olson - Is Chief of Staff the Next Step for EAs?

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, Leader Assistants, have you heard the NOVA Chief of Staff Certification Course is about to see a price increase? But don't worry, you can enroll now, lock in the current rate, and start whenever you're ready with lifetime access. NOVA's mission is to give you the ultimate student experience. They've packed the course with dozens of templates, self-paced learning, hands-on practice, multiple instructor touchpoints, peer engagement, and even guest authored assignments. With over 500 students across 22 countries, NOVA is the top spot for Chief of Staff Learning and Development. Don't wait, enroll today and join the community at leaderassistant.com/nova. Hey friends, welcome to episode 298. This episode features my friend Maggie Olson, and this is actually a clip from one of the Leader Assistant Premium Membership coaching sessions where Maggie walked through the Chief of Staff role and really the question is Chief of Staff right for me, or is Chief of Staff the next step for Executive Assistants? So I hope you enjoy Maggie's great overview and catch you on the other end.

Maggie · 1:40

The first thing that I want to describe is basically how the Chief of Staff, Executive Assistant and CEO work together, and then I'll dive much deeper into the Chief of Staff role. So as a CEO, ideally, I like to share this visual. Their head should be up, their eyes should be forward, and Jeremy and I have talked about this on his podcast and in other forums too, but eyes up looking forward, thinking about focused on future, vision, strategy, leadership, and growth. And really the major initiatives that they need to be pulling together to hit these goals and to continue to drive forward and follow that vision and strategy and growth and all those things. Often CEOs, as you all know, are actually heads down chasing tactical items that they shouldn't be spending their time on. And this is really where their support team comes in between Chief of Staff and Executive Assistant. As a Chief of Staff, a Chief of Staff should be able to focus on that strategy and vision, eyes up, looking forward, and be very good at and be able to focus on that eyes down, executional work. So, highly skilled execution, leading major initiatives for their leader autonomously, working cross collaboratively with other functions of the business, leading teams directly or influential, and building strategic plans that drive business forward. So, the CEO ideally is heads up looking forward, and the Chief of Staff is executing those strategic initiatives, helping pull information back to the CEO, focusing on the business process and efficiency, and oftentimes leading major projects. Then to carry through this visual from an Executive Assistant perspective, you all know better than I do, but tactical logistical support for the CEO, core functions of the role being calendar inbox, expense travel, and various executive team support. For the sake of the visual, I think about this as more of the heads down portion of the role because it's more tactical and executional. However, I think many of you, probably all of you and many EAs out there, approach their role very strategically, and often do fill gaps, fill strategic projects or other gaps for their CEO, but not normally on the same scale or for the same purpose as the Chief of Staff. That's the three, how they interact together. Now, popping back over, I'm going to now just dive deeper into just the Chief of Staff role, and I'm going to define it. And then we're also going to, so some of these are just sort of, I guess, for sake of not really having a better word, like more of a philosophical definition. And then what I will do is dive into the tactical things that a Chief of Staff owns and does every day. And if you need more clarity on any of that, just take a note and we can dive into it too. So a Chief of Staff is the business leader's strategic thought partner who's excellent at execution and allows the business leader to focus on what's most important. I just named them Vision, Strategy, Growth, Leadership, the future of the business. 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 and varying business initiatives forward quickly and efficiently, solving problems and removing roadblocks along the way. The Chief of Staff also often acts as a proxy for the leader, driving alignment across the leader's executive team and leads major cross-functional projects as needed. So I want to chat a little bit around, obviously, the differences between EA and Chief of Staff and what could make you a great Chief of Staff. But first, let's talk about how the Chief of Staff role and the EA role are similar. Both roles exist to support a person. So this is interesting because a lot of us have trouble understanding, like, what's COO, Chief Operating Officer versus Chief of Staff? They're both operational. They both report to the CEO in this example. What's the difference? Well, EA and Chief of Staff both exists to support the business leader versus a COO who has their own scorecard, their own business category. They exist to support the company. So the leader's initiatives, the leader's calendar, the leader, the leader, the leader. That's why the Chief of Staff and the EA both exist. So super similar there. They're both on the same back office team for that leader. Both roles are highly organized, or should be, and planful in their work. Both roles can be seen as the glue that holds teams together. Both roles have a major impact on the whole leadership team and often the company. And both roles are really kind of the right hand and the left hand to the business leader. Now, the core differences between EA and Chief of Staff, and I'm starting to repeat myself a little bit here, but I think it could be helpful to have different ways to talk about the same thing. A Senior Executive Assistant is a highly skilled problem solver, strategic doer, and the logistical mastermind behind the executive's calendar travel expense while acting as the go-to support lead for tactical items across the executive's team. Of course, there's going to be variance within these roles. There's many senior strategic EA's that are taking on some of those Chief of Staff responsibilities. But at the end of the day, most EA's have the same core functions of their role, which is different than a Chief of Staff. So those calendar, inbox, schedule, travel expense, those are generally never part of a Chief of Staff's role. Those are almost always part of an EA role. And then, let's see. So the reason it can get a little bit of overlap and understandably confusing is that sometimes, often, an EA is stepping in and leading some of those strategic projects. But like I've just mentioned, the Chief of Staff's almost never owning those core admin functions. So hopefully, that helps understand the difference just a little bit. And I think this is going to kind of answer a little bit of one of the questions around the levels of the Chief of Staff and my Chief of Staff at my company is very senior. Chiefs of Staff exist under many, many different titles and different leadership levels. There's different leadership levels among Chief of Staff work, and many different levels of leader have Chiefs of Staff. So you will find a Chief of Staff to a CEO. You could find a Chief of Staff to a director. You could find a Chief of Staff to a startup founder. Two very different levels if you're looking at a corporate Fortune 50 company, CEO with the Chief of Staff, and then a startup founder who's bootstrapping and their Chief of Staff. They're going to be different levels, and the rules are going to look a little bit different. Now, the core purpose of the Chief of Staff role is going to be the same everywhere, which is kind of what I've explained here, to maximize that leader's time, to drive alignment across the executive team, to really allow that leader to stay focused on the vision and take on the strategic execution and managing a lot of those initiatives. But Chiefs of Staff exist across every single industry, and I've talked to so many in these industries. So sports, media, entertainment, big business, small business, non-profit, healthcare, startup, higher education, food and beverage, I could go on and on. Chiefs of Staff exist in these places. And in almost every industry, the structure of the Chief of Staff role is the same when it comes to the reporting structure. So if you are imagining an org chart, we've got, let's just use CEO, could be a business leader further down on the org chart, but CEO at the top, and then they have their line to all their execs, right? All their direct reports on their executive team, and they all report up to that CEO. And then off to the side is EA, and off to the side is Chief of Staff. So there's a lot of influential leadership, often over those execs that report to the leader. But unless the Chief of Staff has their own team, or for some reason the EA reports to the Chief of Staff, which is less common, but does happen, the Chief of Staff does not have a direct report of the executive team. Except for in our political government. So I spoke to a Chief of Staff recently to a US Senator, and this is the only place it's different. In politics, the executive team, all the people leading all the initiatives for the Senator, actually report up into the Chief of Staff, and then the Chief of Staff reports into the CEO. So just a fun fact, not highly relevant, but interesting to see the different reporting structures, but the Chief of Staff role exists everywhere. It's going to look different. The levels are going to be different depending on the product or the industry, who they're supporting, and just the needs of the business and the gaps that they're filling. So the role can look different in a lot of ways, but hopefully through my various definitions, you can see the difference between Chief of Staff and EA. Okay, so who would make a great Chief of Staff? I'm asked a lot. Do you need an MBA? Do you need consulting background? What are the skills required? What do you need to be able to do? These are good questions, and you will find job descriptions out there that require MBA, require consulting, require previous Chief of Staff experience, and you will also find many positions that don't. And I think we can chat about this a little bit later on this call, but as the founder of NOVA Chief of Staff, we have a online course that we've got almost 500 students through in the last year. And I talk to our new students every week. I talk to them at the beginning of their journey and at the end. And on these new student kickoff calls, I'm hearing more and more and more that folks are moving into Chief of Staff roles. Like, for example, a senior EA is moving into a Chief of Staff role with their leader's full support, and maybe their leader even brought it up. And I'm hearing, like, a handful of these folks each month that this is happening for. So it's not required. It's always easier to move into a Chief of Staff role or move into any role in your own company. It's always harder to network outside of your current environment and figure out where to go. But it's absolutely happening, and it is not required to have an MBA. Personally, I do have an MBA, and I can tell you that I would hire somebody that checks all the boxes on this list I'm going to read to you for what makes a great Chief of Staff before I hire someone just because they have an MBA. I did not learn how to be a Chief of Staff through my MBA program. I learned mergers and acquisitions, negotiation. I mean, I don't know, like some good things. Networking, I had a great local Seattle group of people that I met. I found opportunity for sure through job placement post-MBA program, but I learned on the job through my previous experience Chief of Staff and then as a Chief of Staff, just figuring out how to do it. So there's definitely some skills required. We can talk through that, but who would make a great Chief of Staff? I'm going to list some things off here. Fast, driven, curious, growth-minded, executive presence, achievement-focused, high emotional intelligence, loves breadth versus depth. I like to call that kind of an expert generalist. Problem-solver, solution-oriented, graded a lot of things, learns quickly, asks great questions. Collaborative, influential leader, wants more responsibility, wants to move into a new role, what's next, and loves supporting senior leadership. I'm sure a lot of you are like, oh, that kind of sounds like me, or maybe it sounds like someone you know, if it's not you, which is fine. And EA is a great next step path towards Chief of Staff, but Chief of Staff is not the only next step for EAs. There's also no need for an EA to feel like they have to go on to some other role. An EA is a great role. And there's a lot of other jobs that could lead well into the Chief of Staff role. And I think somebody mentioned, asked about this. So what are other paths besides EA into Chief of Staff role? Business operations, project management, future entrepreneurs will make great Chiefs of Staff because they want to lead a company. And so they're going to learn next to somebody who is leading a company and figure out what they need. And they're minded as a CEO, as an entrepreneur already, which is a great skill. It's honestly, you know, business school students, for sure, there's a tenacity and a drive and an achievement focus there, which does make consultants and MBAs good candidates if they are, if they match this list of things. So it's a little bit more about your character, like what kind of person you are, what you're drawn to, what you love to do, how you show up, versus the exact experiential background. And I know that a lot of EAs have a very different experience than each other even in their own roles, and the experience they're given and the work they're given to build skills and all of the things is very different than each other. So it really kind of depends on if you want to go after the Chief of Staff role and if you feel well suited for it, then I think it's a really fun role.

Jeremy · 15:43

All right, there you have it. Some great insight from my friend Maggie Olson at NOVA Chief of Staff. And I hope you enjoyed it. If you want to hear the full entire session with the Q&A and more interaction and more in-depth, you can join the Leader Assistant's premium membership. You can go to leaderassistant.com/membership to learn more about that. We'd love to have you. The full recording of the entire session is in the Members Only Library. But otherwise, yeah, definitely be sure to check out Maggie's certification course, the NOVA Chief of Staff course at leaderassistant.com/nova. And I hope you enjoyed the snippet and keep leading well.

Speaker 2 · 16:44

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