Maggie Olson is the Founder of Nova Chief of Staff, the premier destination for Chief of Staff education and development.
In this episode of The Leader Assistant Podcast, Maggie Olson dives into EA career paths, transitioning into the Chief of Staff role, EAs who make great Chiefs of Staff, and more.
CONNECT WITH MAGGIE
ABOUT MAGGIE
Maggie Olson is the Founder of Nova Chief of Staff, the premier destination for Chief of Staff education and development. As the first Chief of Staff to a president at a Fortune 40 company — who led a multibillion-dollar business with 5,000+ employees — Maggie built the president’s Chief of Staff model from the ground up. Maggie has 20 years’ experience leading large teams and has spent her career focused on both customer and employee experience at companies including T-Mobile, Nordstrom, and Starbucks. In addition to operating the Nova Chief of Staff Certification course, Maggie is a fractional Chief of Staff focused on helping mission-driven, for-profit startup founders scale their businesses quickly. In her spare time, Maggie loves spending time outside with her husband, their animals, and their 1-year-old, Max!
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Calling all Executive Assistants: Are you looking for a way to elevate your skills or earn that promotion you’ve been eyeing? Nova Chief of Staff’s online certification course provides you with the knowledge and confidence you need to stand out on the job. Whether you want to land your dream position or level up in your current role, Nova’s self-paced course gives you hands-on practice doing what Chiefs of Staff do every day.
Visit leaderassistant.com/nova to learn more and secure your spot!
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LEAVE A REVIEW
If you’re enjoying the podcast, please take 2 minutes to rate and review the show on Apple Podcasts here. Each review helps me stay motivated to keep the show going!
THE LEADER ASSISTANT BOOK
Download the first 3 chapters of The Leader Assistant: Four Pillars of Game-Changing Assistant for FREE here or buy it on Amazon and listen to the audiobook on Audible. Also, check out the companion study guide, The Leader Assistant Workbook, to dig deeper.
LEADER ASSISTANT LIVE EVENTS
Check out our constantly updated schedule of events for admins and assistants at LeaderAssistantLive.com.
JOIN THE FREE COMMUNITY
Join the Leader Assistant Global Community for bonus content, job opportunities, and to network with other assistants who are committed to becoming leaders!
SUBSCRIBE
Subscribe to The Leader Assistant Podcast so you don’t miss new episodes!
You can find the show on Apple Podcasts, Spotify, Google Podcasts, Pandora, and Stitcher.
Join my email list here if you want to get an email when a new episode goes live.
LEAVE A REVIEW
If you’re enjoying the podcast, please take 2 minutes to rate and review the show on Apple Podcasts here. Each review helps me stay motivated to keep the show going!
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EPISODE TRANSCRIPT
00:00:05.915 –> 00:00:13.495
<v SPEAKER_2>The Leader Assistant Podcast exists to encourage and challenge assistants to become confident, game-changing leader assistants.
00:00:23.235 –> 00:00:30.455
JEREMY: Hey, Leader Assistants, have you heard the NOVA Chief of Staff Certification Course is about to see a price increase?
00:00:30.455 –> 00:00:37.375
JEREMY: But don’t worry, you can enroll now, lock in the current rate, and start whenever you’re ready with lifetime access.
00:00:37.375 –> 00:00:41.415
JEREMY: NOVA’s mission is to give you the ultimate student experience.
00:00:41.415 –> 00:00:54.835
JEREMY: 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.
00:00:54.835 –> 00:01:02.035
JEREMY: With over 500 students across 22 countries, NOVA is the top spot for Chief of Staff Learning and Development.
00:01:02.035 –> 00:01:06.235
JEREMY: Don’t wait, enroll today and join the community at leaderassistant.com/nova.
00:01:08.835 –> 00:01:11.795
JEREMY: Hey friends, welcome to episode 298.
00:01:11.795 –> 00:01:33.435
JEREMY: 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?
00:01:33.435 –> 00:01:40.215
JEREMY: So I hope you enjoy Maggie’s great overview and catch you on the other end.
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MAGGIE: 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.
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MAGGIE: So as a CEO, ideally, I like to share this visual.
00:01:55.535 –> 00:02:11.795
MAGGIE: 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.
00:02:11.795 –> 00:02:23.815
MAGGIE: 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.
00:02:23.815 –> 00:02:32.215
MAGGIE: Often CEOs, as you all know, are actually heads down chasing tactical items that they shouldn’t be spending their time on.
00:02:32.215 –> 00:02:36.335
MAGGIE: And this is really where their support team comes in between Chief of Staff and Executive Assistant.
00:02:37.995 –> 00:02:54.435
MAGGIE: 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.
00:02:54.435 –> 00:03:08.455
MAGGIE: 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.
00:03:08.455 –> 00:03:25.915
MAGGIE: 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.
00:03:25.915 –> 00:03:44.035
MAGGIE: 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.
00:03:44.775 –> 00:03:50.455
MAGGIE: 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.
00:03:50.455 –> 00:04:08.695
MAGGIE: 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.
00:04:08.695 –> 00:04:12.935
MAGGIE: That’s the three, how they interact together.
00:04:12.935 –> 00:04:21.195
MAGGIE: 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.
00:04:21.235 –> 00:04:30.215
MAGGIE: 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.
00:04:30.215 –> 00:04:36.615
MAGGIE: And then what I will do is dive into the tactical things that a Chief of Staff owns and does every day.
00:04:36.615 –> 00:04:40.915
MAGGIE: And if you need more clarity on any of that, just take a note and we can dive into it too.
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MAGGIE: 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.
00:04:49.535 –> 00:04:54.595
MAGGIE: I just named them Vision, Strategy, Growth, Leadership, the future of the business.
00:04:54.595 –> 00:05:08.935
MAGGIE: 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.
00:05:08.935 –> 00:05:18.975
MAGGIE: 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.
00:05:21.055 –> 00:05:28.475
MAGGIE: 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.
00:05:28.475 –> 00:05:33.295
MAGGIE: But first, let’s talk about how the Chief of Staff role and the EA role are similar.
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MAGGIE: Both roles exist to support a person.
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MAGGIE: So this is interesting because a lot of us have trouble understanding, like, what’s COO, Chief Operating Officer versus Chief of Staff?
00:05:45.415 –> 00:05:46.415
MAGGIE: They’re both operational.
00:05:46.515 –> 00:05:49.595
MAGGIE: They both report to the CEO in this example.
00:05:49.595 –> 00:05:50.795
MAGGIE: What’s the difference?
00:05:50.795 –> 00:06:01.055
MAGGIE: 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.
00:06:01.055 –> 00:06:04.035
MAGGIE: They exist to support the company.
00:06:04.035 –> 00:06:08.455
MAGGIE: So the leader’s initiatives, the leader’s calendar, the leader, the leader, the leader.
00:06:08.455 –> 00:06:11.335
MAGGIE: That’s why the Chief of Staff and the EA both exist.
00:06:11.335 –> 00:06:13.055
MAGGIE: So super similar there.
00:06:13.055 –> 00:06:15.455
MAGGIE: They’re both on the same back office team for that leader.
00:06:16.155 –> 00:06:20.935
MAGGIE: Both roles are highly organized, or should be, and planful in their work.
00:06:20.935 –> 00:06:25.255
MAGGIE: Both roles can be seen as the glue that holds teams together.
00:06:25.255 –> 00:06:31.215
MAGGIE: Both roles have a major impact on the whole leadership team and often the company.
00:06:31.215 –> 00:06:36.455
MAGGIE: And both roles are really kind of the right hand and the left hand to the business leader.
00:06:36.455 –> 00:06:46.835
MAGGIE: 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.
00:06:46.835 –> 00:06:59.415
MAGGIE: 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.
00:06:59.415 –> 00:07:01.875
MAGGIE: Of course, there’s going to be variance within these roles.
00:07:01.875 –> 00:07:07.875
MAGGIE: There’s many senior strategic EA’s that are taking on some of those Chief of Staff responsibilities.
00:07:08.155 –> 00:07:16.875
MAGGIE: 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.
00:07:16.875 –> 00:07:25.595
MAGGIE: So those calendar, inbox, schedule, travel expense, those are generally never part of a Chief of Staff’s role.
00:07:25.595 –> 00:07:29.035
MAGGIE: Those are almost always part of an EA role.
00:07:30.195 –> 00:07:31.815
MAGGIE: And then, let’s see.
00:07:31.815 –> 00:07:45.335
MAGGIE: 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.
00:07:45.335 –> 00:07:50.695
MAGGIE: But like I’ve just mentioned, the Chief of Staff’s almost never owning those core admin functions.
00:07:50.695 –> 00:07:54.315
MAGGIE: So hopefully, that helps understand the difference just a little bit.
00:07:56.715 –> 00:08:05.995
MAGGIE: 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.
00:08:07.275 –> 00:08:12.975
MAGGIE: Chiefs of Staff exist under many, many different titles and different leadership levels.
00:08:14.015 –> 00:08:21.775
MAGGIE: There’s different leadership levels among Chief of Staff work, and many different levels of leader have Chiefs of Staff.
00:08:21.935 –> 00:08:24.535
MAGGIE: So you will find a Chief of Staff to a CEO.
00:08:24.535 –> 00:08:26.355
MAGGIE: You could find a Chief of Staff to a director.
00:08:26.355 –> 00:08:29.095
MAGGIE: You could find a Chief of Staff to a startup founder.
00:08:29.095 –> 00:08:39.455
MAGGIE: 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.
00:08:39.455 –> 00:08:43.375
MAGGIE: They’re going to be different levels, and the rules are going to look a little bit different.
00:08:43.375 –> 00:09:05.635
MAGGIE: 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.
00:09:05.635 –> 00:09:12.535
MAGGIE: But Chiefs of Staff exist across every single industry, and I’ve talked to so many in these industries.
00:09:12.535 –> 00:09:24.555
MAGGIE: So sports, media, entertainment, big business, small business, non-profit, healthcare, startup, higher education, food and beverage, I could go on and on.
00:09:24.555 –> 00:09:26.795
MAGGIE: Chiefs of Staff exist in these places.
00:09:26.795 –> 00:09:37.215
MAGGIE: And in almost every industry, the structure of the Chief of Staff role is the same when it comes to the reporting structure.
00:09:37.215 –> 00:09:48.115
MAGGIE: 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?
00:09:48.115 –> 00:09:52.315
MAGGIE: All their direct reports on their executive team, and they all report up to that CEO.
00:09:52.315 –> 00:09:56.735
MAGGIE: And then off to the side is EA, and off to the side is Chief of Staff.
00:09:56.735 –> 00:10:02.615
MAGGIE: So there’s a lot of influential leadership, often over those execs that report to the leader.
00:10:02.615 –> 00:10:13.975
MAGGIE: 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.
00:10:14.795 –> 00:10:17.875
MAGGIE: Except for in our political government.
00:10:17.875 –> 00:10:26.235
MAGGIE: So I spoke to a Chief of Staff recently to a US Senator, and this is the only place it’s different.
00:10:26.235 –> 00:10:38.715
MAGGIE: 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.
00:10:38.715 –> 00:10:46.295
MAGGIE: So just a fun fact, not highly relevant, but interesting to see the different reporting structures, but the Chief of Staff role exists everywhere.
00:10:46.295 –> 00:10:47.335
MAGGIE: It’s going to look different.
00:10:47.335 –> 00:10:55.755
MAGGIE: 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.
00:10:55.755 –> 00:11:04.975
MAGGIE: 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.
00:11:06.895 –> 00:11:11.555
MAGGIE: Okay, so who would make a great Chief of Staff?
00:11:12.595 –> 00:11:13.815
MAGGIE: I’m asked a lot.
00:11:13.815 –> 00:11:15.075
MAGGIE: Do you need an MBA?
00:11:15.075 –> 00:11:17.595
MAGGIE: Do you need consulting background?
00:11:17.595 –> 00:11:18.835
MAGGIE: What are the skills required?
00:11:18.835 –> 00:11:20.295
MAGGIE: What do you need to be able to do?
00:11:20.295 –> 00:11:32.235
MAGGIE: 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.
00:11:33.415 –> 00:11:46.495
MAGGIE: 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.
00:11:46.495 –> 00:11:49.435
MAGGIE: And I talk to our new students every week.
00:11:49.435 –> 00:11:51.775
MAGGIE: I talk to them at the beginning of their journey and at the end.
00:11:51.775 –> 00:11:57.955
MAGGIE: And on these new student kickoff calls, I’m hearing more and more and more that folks are moving into Chief of Staff roles.
00:11:57.955 –> 00:12:04.695
MAGGIE: 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.
00:12:04.695 –> 00:12:09.155
MAGGIE: And I’m hearing, like, a handful of these folks each month that this is happening for.
00:12:09.155 –> 00:12:10.715
MAGGIE: So it’s not required.
00:12:10.715 –> 00:12:15.635
MAGGIE: It’s always easier to move into a Chief of Staff role or move into any role in your own company.
00:12:15.635 –> 00:12:20.775
MAGGIE: It’s always harder to network outside of your current environment and figure out where to go.
00:12:20.775 –> 00:12:25.115
MAGGIE: But it’s absolutely happening, and it is not required to have an MBA.
00:12:25.115 –> 00:12:38.575
MAGGIE: 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.
00:12:38.575 –> 00:12:41.795
MAGGIE: I did not learn how to be a Chief of Staff through my MBA program.
00:12:41.795 –> 00:12:46.795
MAGGIE: I learned mergers and acquisitions, negotiation.
00:12:46.795 –> 00:12:49.295
MAGGIE: I mean, I don’t know, like some good things.
00:12:49.295 –> 00:12:54.975
MAGGIE: Networking, I had a great local Seattle group of people that I met.
00:12:55.975 –> 00:13:09.375
MAGGIE: 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.
00:13:09.375 –> 00:13:10.775
MAGGIE: So there’s definitely some skills required.
00:13:10.775 –> 00:13:14.295
MAGGIE: We can talk through that, but who would make a great Chief of Staff?
00:13:14.295 –> 00:13:16.955
MAGGIE: I’m going to list some things off here.
00:13:16.955 –> 00:13:29.015
MAGGIE: Fast, driven, curious, growth-minded, executive presence, achievement-focused, high emotional intelligence, loves breadth versus depth.
00:13:29.015 –> 00:13:31.815
MAGGIE: I like to call that kind of an expert generalist.
00:13:31.815 –> 00:13:39.575
MAGGIE: Problem-solver, solution-oriented, graded a lot of things, learns quickly, asks great questions.
00:13:39.575 –> 00:13:49.015
MAGGIE: Collaborative, influential leader, wants more responsibility, wants to move into a new role, what’s next, and loves supporting senior leadership.
00:13:50.455 –> 00:13:56.835
MAGGIE: 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.
00:13:58.015 –> 00:14:07.875
MAGGIE: And EA is a great next step path towards Chief of Staff, but Chief of Staff is not the only next step for EAs.
00:14:07.875 –> 00:14:11.895
MAGGIE: There’s also no need for an EA to feel like they have to go on to some other role.
00:14:11.895 –> 00:14:14.255
MAGGIE: An EA is a great role.
00:14:14.255 –> 00:14:19.175
MAGGIE: And there’s a lot of other jobs that could lead well into the Chief of Staff role.
00:14:19.255 –> 00:14:21.435
MAGGIE: And I think somebody mentioned, asked about this.
00:14:21.435 –> 00:14:26.515
MAGGIE: So what are other paths besides EA into Chief of Staff role?
00:14:28.015 –> 00:14:35.975
MAGGIE: Business operations, project management, future entrepreneurs will make great Chiefs of Staff because they want to lead a company.
00:14:35.975 –> 00:14:40.395
MAGGIE: And so they’re going to learn next to somebody who is leading a company and figure out what they need.
00:14:40.395 –> 00:14:49.975
MAGGIE: And they’re minded as a CEO, as an entrepreneur already, which is a great skill.
00:14:49.975 –> 00:15:04.535
MAGGIE: 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.
00:15:04.535 –> 00:15:16.915
MAGGIE: 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.
00:15:16.915 –> 00:15:29.575
MAGGIE: 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.
00:15:29.575 –> 00:15:43.155
MAGGIE: 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.
00:15:43.155 –> 00:15:43.995
JEREMY: All right, there you have it.
00:15:43.995 –> 00:15:49.135
JEREMY: Some great insight from my friend Maggie Olson at NOVA Chief of Staff.
00:15:49.135 –> 00:15:51.615
JEREMY: And I hope you enjoyed it.
00:15:51.615 –> 00:16:05.435
JEREMY: 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.
00:16:05.435 –> 00:16:11.035
JEREMY: You can go to leaderassistant.com/membership to learn more about that.
00:16:11.035 –> 00:16:12.135
JEREMY: We’d love to have you.
00:16:12.135 –> 00:16:19.055
JEREMY: The full recording of the entire session is in the Members Only Library.
00:16:19.055 –> 00:16:28.895
JEREMY: But otherwise, yeah, definitely be sure to check out Maggie’s certification course, the NOVA Chief of Staff course at leaderassistant.com/nova.
00:16:29.455 –> 00:16:33.295
JEREMY: And I hope you enjoyed the snippet and keep leading well.
00:16:44.205 –> 00:16:46.545
<v SPEAKER_2>Please review on Apple Podcasts.
00:16:52.987 –> 00:16:54.687
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