What It Takes to Be a Chief of Staff

We talked to Maggie Olson, founder of Nova Chief of Staff, about the qualities and skills needed for an admin or EA to become a Chief of Staff.

Recorded at APC 2024 and produced by the American Society of Administrative Professionals - ASAP. Learn more and submit a listener question at asaporg.com/podcast.

Leah Warwick: Hi, everyone. I'm Leah Warwick, and you're listening to "The Admin Edge." This season was recorded at the Administrative Professionals Conference, also known as APC, in Colorado. Our first guest is Maggie Olson, Founder of Nova Chief of Staff, and she will bring the Nova Certification Course to all ASAP events in 2025, including APC and EA Ignite. We could not be more excited. Now, let's listen in to my conversation with Maggie at APC 2024.

00:00:40

Hi, I'm Leah Warwick, Editor for ASAP, and my guest today is Maggie Olson, Founder of Nova Chief of Staff, which is being offered here at the ASAP event, the Administrative Professionals Conference. Welcome to the podcast, Maggie. 

Maggie Olson: Thank you so much. I'm so honored to be here and here at the event.

Leah Warwick: We are so happy to have you. It's very exciting to have Nova on site, here at APC. First, tell me a bit about you, your background, [and] what led you to founding Nova.

00:01:08                     

Maggie Olson: I had just left my corporate chief of staff role for a major telecom company, and I was talking to my mom about how crazy it is that there are thousands of project management certifications out there, and nothing for chiefs of staff. And she said, "Well, why don't you build it?" So, here we are, a couple of years later. It took me a year to build the Nova Chief of Staff Certification Course. We have over 600 students at this point, across 22 countries, and this is our first in-person event, here at APC.

Leah Warwick: Wow, that is incredible. It speaks to an appetite, I feel, and that kind of leads to my next question. We have a lot of EAs and admins here at this event, and a lot of them are interested in becoming a chief of staff. So what does it take for an EA or an administrative professional to become a chief of staff?

00:01:57                     

Maggie Olson: We could talk about a lot of things. We could talk about intrinsic qualities. We could talk about kind of the hard skills, but I'll start with sort of the soft side. A great chief of staff can be described as a few things – and this counts for EAs looking to be chiefs of staff: Achievement-focused, driven, loves breadth versus depth, great at a lot of different things, curious, growth-minded, loves supporting senior leadership; kind of okay behind the scenes – like you've got to be able to speak up and represent yourself, and have that component of executive presence, but you're essentially putting that leader up on stage, and you're behind the scenes making everything come alive, right? So those are some of the kind of behind-the-scenes qualities of a great chief of staff.

00:02:41

When it comes to a little bit more of the hard skills, I usually lead with what I call executive project management, so a really strong ability to track all of your leader's initiatives, follow through, prioritize, speak up and represent those initiatives, lead them at times, and really kind of offer that transparency and visibility to the full leadership team to help the leader's executive team ensure that they're all pointing in the same direction, towards that leader's goals, and really all of that comes down to executive project management and then a component of business planning, of course, which is sometimes heard as the "rhythm of business." 

00:03:17                     

Leah Warwick: And what do you think when someone is transitioning – from an EA role, let's say. What are some of the common roadblocks that you hear, whether it's from the company itself or from the EA, where they may need to develop some new skills?

Maggie Olson: The number one most common roadblock for an EA transitioning to chief of staff, or evening thinking about moving into the chief of staff role, is confidence – the confidence: Can I do it? Am I good enough? Am I focused enough? Does my leader see me as this strategic leader? Do I have the skillset? Can I learn? The answer is yes. Yes, you can. If these are things you're thinking about, if you're the kind of person that it taking on more responsibility and your leader is relying on you for a lot more things outside of those general core admin functions, you probably just have a little bit of a lack of confidence, which we can work towards.

00:04:09

And that's really how I built our course. It's hands-on practice doing the things chiefs of staff do every day, because I believe that hands-on practice leads to confidence so that you can say, "Hey, I've built a brief. I've put strategic recommendations together. I've led complex off-sites and all-hands, and I've ghost written for my leader, and I've practiced this executive project management." I could go on and on, but the hands-on practice gives you the confidence and validation that you can do the job and that you can walk into your leader's office or an interview and say, "I can do this. I've done it before. I have the skillset, I have the tools, and I'm ready." 

00:04:41                     

Leah Warwick: Yes. And about confidence – that relates definitely to research that we've done that we're going to talk about tomorrow, because we survey our membership. We ask them what their key responsibilities are, what their skills are, and a lot of them are doing chief-of-staff-level work already, and their title has "assistant" in it. So it's about saying, "I'm actually doing a lot of this work now, and I need the confidence, I need the roadmap." That's part of what Nova does so well, providing people with the roadmap and any additional training to get to the place they want to be, to get certified, and then bring that to their company. So what kind of stories have you heard from your Nova Chief of Staff enrollees about any successes that they've had?

00:05:20                     

Maggie Olson: Yeah. I think you nailed it. It's really about figuring out, having that ah-ha moment of, "Okay, actually, I'm doing a lot of chief of staff responsibilities here, but what's next? How do I present that to my leader?" That's what we work on a lot with our students. I talk with all of our new students. I've got kickoff calls weekly, and it's something that comes up a lot. "Okay, so how do I have that conversation?"

00:05:44

What we talk about is [to] bucket your work, analyze. What are all the things that you're doing? What falls into core admin functions? What falls into more of that chief of staff, like strategic gap-filling, extra responsibilities? And then how do you take that information and talk to your leader about it? Maybe it's, "Hey, Leader. I am doing all of these responsibilities over here on the strategic side. I think you would agree that my time is best spent over here. And if that's the case, I'd love to propose backfilling for my more admin-focused responsibilities." So we kind of roleplay. We talk through that. There's so many successes. I think my favorite success – I just posted about this today on LinkedIn – is that I hear from executive assistants who are moving into chief of staff roles that their leader was going to combine executive assistant and chief of staff into one role, but that they've heard my messaging. They've seen the strong messaging – for example, on LinkedIn – that those two roles should really not be combined, and they are listening. 

00:06:40

And so these assistants are telling me, "My leader is not combining the role now, and they're keeping it separate, and we are hiring for two separate roles, and we're not just shoveling in the chief of staff responsibilities for the admin role." Because often the pay is not there, the title is not there, the recognition is not there, and the burnout will be there. 

00:06:59                     

Leah Warwick: That leads me right into my next question, which is about common misconceptions about the chief of staff role today. I'm sure you've heard them all, but what are some of the top ones that you've heard?

Maggie Olson: Well, the title "chief of staff" doesn't lend much help to the mystery of the role. I would say, anecdotally, about 70% of chief of staff roles actually don't have direct reports, so when the title is "chief of staff" it's a little harder to understand, "Wait a minute. Who are they the chief of the staff of?" So that's an interesting thing to note. Many chief of staff roles are individual contributor roles. Second: Chief of staff is not an executive assistant. Executive assistant roles are made up of the core functions of admin work being scheduling and travel logistics, expense, inbox – really important work that assistants can approach strategically, but it's tactical, foundational, executive assistant work.

00:07:51

Now, just like any excellent employee, an EA may reach and fill strategic gaps, and they may take on more responsibility and show their worth in new and different ways. But chief of staff roles rarely, if never, hold those core admin functions. So that is a really, really big, important differentiator between the two roles that's often not understood. 

Leah Warwick: Yeah, I would agree with that. But there are a lot of, as you mentioned, transferrable skills that you can take from an admin role, from an EA role, and then apply it to a chief of staff role, which is a different role – we will be clear about it right here – but definitely a place on the career path to venture down, if that's something you're interested in. And we do have a listener question for you, Maggie, submitted by one of our community members, and they write: "What advice would you give to someone who is in a smaller organization, where the chief of staff role doesn't exist, but they want to start building those responsibilities?"

Maggie Olson: Yeah, you're not alone. The chief of staff role and the title "chief of staff" is often not used, even in big companies. We have a blog – it's our most-read blog on Nova's site – "The Many Titles of a Chief of Staff." There's 20, 30-plus different titles used for the chief of staff role, things like business operations and business planning and all of that.

00:09:03

Now, I say that because sometimes there are people in chief of staff roles without the title, and it's helpful to identify who those people are so that you can see yourself on the path to chief of staff, even if it's a different title. Those folks are the ones behind the scenes. They're running the all-hands decks. They're delivering the work for the executive when, let's say you're the EA, and you're asking all of your CEOs/direct reports for the slides for a strategy meeting. They may be the person behind the scenes actually sending you those slides. That is the chief of staff role, the human supporting the leader, maybe under a different title. 

So when you're in a smaller organization, keep a lookout for that. That might be the case, where there are some people doing chief of staff work. The other thing is there's no reason not to pitch that your leader still needs strategic support. Chiefs of staff exist across all levels of sizes of business, industries, products – I could just go on and on. The chief of staff role is everywhere. 

00:10:01

And then also you could walk into any of these businesses and not find the chief of staff role being used. So it's about awareness. It's about education. I still think it's important for this listener to highlight the strategic impact they could have taking on more responsibilities in that chief of staff space, and still potentially backfilling for their more junior admin responsibilities. I still don't think it should be combined. You might be a smaller company with a smaller team, but if you're a fast-paced leader with tons of competing initiatives and you're spending too much time heads down, chasing follow-ups, execution, you need a chief of staff. 

Leah Warwick: Yes. I love that you outlined the responsibilities and that, yes, there may be someone doing chief of staff responsibilities with a title like "operations manager." And we see here there are hundreds of titles represented here at APC and in our community. And so instead of the title – Ann Hiatt, our keynote speaker today, talked about this – focus on the impact that you're having, the strategic impact that you're having, the value that you're adding back to the business, and align that with the conversations you have with your leader about your next steps.

00:11:01                     

Maggie Olson: One hundred percent, absolutely. Just tailor your approach dependent on your relationship with that leader. Maybe that leader needs a little bit more of a formal approach. Maybe that leader just wants to have a casual conversation. Maybe they need an email first. Maybe they need a full presentation. You know your leader. And one of the first things I tell all assistants thinking about transitioning or adding value, or how to add value, is to pause and step back from the business and really reflect. Reflect on what's going on. What's your leader talking about a lot? What are the pain points? And how are you best suited to add value, and what are the biggest priorities for you to tackle? And then present the information in a way that they're going to accept it.

Leah Warwick: That's excellent advice and a perfect place to end. Thank you so much for joining us on the podcast, Maggie. Tell us where listeners can find you online.

00:11:47                     

Maggie Olson: Absolutely. So if you're interested in Nova Chief of Staff, check us out at novachiefofstaff.com. If you are curious at all about our course, I always recommend diving into the syllabus as a first step. We outline every single thing you're going to do – 20+ hands-on assignments. It's a great place to start. If you're looking maybe to connect with me on LinkedIn, Maggie-Olson-COS, and I post every day about the chief of staff role.

Leah Warwick: Thank you very much.

Maggie Olson: You're welcome.

[music playing]

Leah Warwick: Thank you for listening to "The Admin Edge," produced by the American Society of Administrative Professionals, original music and audio editing by Warwick Productions, with video and audio production at our events by 5Tool Productions. If you like this podcast, please leave us a nice review, five stars, and subscribe. If you'd like to submit a listener question, you may do so on our website at ASAPorg.com/podcast.