How to Go from EA to Chief of Staff

Are you an executive assistant who thinks you might be a good Chief of Staff? Kristina Willis, EA turned Chief of Staff at We Are Rosie, shares her advice on making the transition.

Recorded at EA Ignite Fall 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, recorded at the ASAP event, EA Ignite, we talked to EAs and chiefs of staff about the nuances of their respective positions and what has helped them to be successful. Our guest today is Kristina Willis, who will share her journey in going from an EA to a chief of staff role. I loved getting into this topic with Kristina, and I hope you take away some new information and inspiration, too.

Hi, I'm Leah Warwick, Editor for ASAP, and my guest today is Kristina Willis, Chief of Staff to the CEO at We Are Rosie. Welcome to the podcast, Kristina.

00:00:48                     

Kristina Willis: Thank you for having me, Leah.

Leah Warwick: It's so good to see you in person and to have you here.

Kristina Willis: I am excited. I am very excited.

Leah Warwick: Welcome to EA Ignite.

Kristina Willis: It's been wonderful. I've only been here for a few hours, and it's stunning – from the venue to the coordination and the communication, it's just been seamless, so thank you.

Leah Warwick: Oh, that's really nice of you to say. We're just so happy to have you here and to be doing this event at all. It's our pleasure. I want to start getting into some questions with you, so we'll start with a little bit of background on you. You began your career in recruitment and then you transitioned into being an executive assistant, and now you're a chief of staff. How did you make these leaps, particularly from EA to chief of staff? What helped you to stand out and succeed?

Kristina Willis: I really think success is like [the] "it takes two to tango" analogy. I think there's how we show up as individuals, and I also believe there's, like, someone reaches out a hand, acknowledging what it is that you're putting out there. So, from a tactical standpoint, I would say, little things: Showing up not just on time, [but] early to work. Not having a hard stop at 5:00. Getting the job done and deciding what those boundaries look like for myself, that give and take.

00:02:09

And it was equally being recognized by the leaders that I worked with, who said, "Hey, I see this. Have you thought about that?" Having that hand reached out is definitely what played a part in the transition from EA to chief of staff. In fact, my founder and CEO at We Are Rose, my first week I was at We Are Rose, we met in person. It's a fully remote company. So, we met up in person. We're both in Atlanta. And she looks at me and she goes, "I can see you being a chief of staff one day." I had never heard about the chief of staff role. This was February 2021. So, someone just speaking it to me sparked an idea. Nothing happened for the foreseeable future, but there was definitely support from my leaders that played a part in the leaps that I made throughout my career. 

00:03:01                     

Leah Warwick: It sounds like they saw something in you, but because you were going outside of your comfort zone already – you were raising your hand to things. And we hear that a lot, of the balance between boundaries but also knowing when you take on new opportunities, because sometimes people don't know what you can do unless you get outside of your bubble a little bit and say, "Hey, I'm going to try this project," or "I'm going to work with this team," or "I'm going to raise my hand for this project." That can really help a lot.

Also, in the move from EA to chief of staff at We Are Rosie, what were some of the biggest differences you noticed in your daily work? What surprised you? 

Kristina Willis: That's a good question. I mean, I think one of the things that surprised me the most was realizing how much more I needed to speak up. So, I think the very thing that helped make the transition, which was me not just capturing conversation but contributing to it as well, I think that very thing, that was me coming out of my comfort zone as an EA.

00:04:06

That helped define what my thoughts were, how I think, how I approach things. Leadership now knows that I have a voice of my own. I think that very thing became a muscle I needed to build as a chief of staff, a muscle I did not have, a muscle that I would flex once in a while and just happily let go because it's intimidating. 

I think one of the things that surprised me was how much more of an advisor I needed to be to my CEO. That comes with being comfortable and honest. It requires transparency. You're also being mindful of: You have to count your words, because if your CEO holds the weight of your words as they should or as you want them to, you have to be mindful of what you're saying, because you're kind of wielding influence in a way that should be done very carefully and thoughtfully. 

00:04:58

So definitely having to speak up more was a – I wouldn't say it was a surprise, but it was something at the forefront of my mind of like, "Oh, this is one of the things that must differentiate what I did as an EA versus now." That thought partnership was expected of me across senior leadership as well, so that would definitely be one of the areas that stood out as different for me, personally. 

Leah Warwick: Yes, like a muscle you had to flex a little bit more in the role that said, "Oh, okay, I am…" And you found you could do it. It just required a little effort, a little trial and error perhaps.

Kristina Willis: Absolutely trial and error because also, if you think about it, as a chief of staff you are a leader by influence. But how else do you influence? It's how you show up, but it's also what you say, and then it's what you do after what you say, but you have to be confident, even when you're not.

00:05:53

I think it's the same as an EA, right? It's like when someone says – and I'm not going to derail us because I talk a lot. Did I tell you I talk a lot? 

Leah Warwick: I love it – keep going!

Kristina Willis: But even as an EA, if you think about it, you're the one that's always like, "I've got it. Sure." Never mind all the million thoughts going through your head of like, "How am I going to actually do this?" But you have to put on that brave face. It's very similar as the chief of staff. It may look differently, but it's still that same confidence in my ability to do. I can. And that became much more – that's something I just had to build in my chief of staff role.

Leah Warwick: Yes, building that executive presence, that executive energy. It seems like that's even more important in a chief of staff role if you have to be that strategic advisor. You really have to match your executive and the executive team you're working with in that way, which is really important. So, what are some other skills that someone in a traditional EA role would need to develop or add to their toolkit to really thrive in a chief of staff role?

00:06:56                     

Kristina Willis: So, I would say – you touched on this a little – executive presence is something that needs to be built. As an EA, your direct tie to the executive you support is where much of your success lies. As a chief of staff, it's a much broader reach. Your CEO, for example, as the chief of staff, may be very like – you may have a great rhythm. But those relationships with senior leadership, key stakeholders – everyone at the company, actually – are equally as important because that's also where your ability to come in and point things out to your CEO, give feedback – that comes from trust being built. Again, I keep using the word "visibility" because it's so important. The more you're in the front of, the more people think of you.

00:07:41

So building the executive presence is definitely a skill. I would also – when you think of like project management, there's things that you're now owning as a chief of staff. As an EA – it's funny; I was talking about this earlier today – you seek to prioritize the executive you support as a human being. And then, supporting them exceptionally well, you unlock their opportunity or potential to maximize what it is – their time and energy. 

As a chief of staff, you're looking to prioritize your executive's priorities. That calls for a different type of balance, so some things that you would've either shed light on for your CEO or executive as an EA, you're now owning alongside, or running much further down the field than you would've as an EA, bringing it back. 

So, I would say executive presence is one. I would definitely say project management. And then also what that project management looks like – the scope gets broader. You're not just – let's say your executive says to you, "Hey, I want you to get this thing started. I want you to put together an outline. I want to get my team together. Get time on the calendar. Put together an outline." 

00:08:56

Great. You do that. You get the time on the calendar. You give the context as to why. As a chief of staff, you're providing far more context to the meeting than you were as an EA. Your CEO says, "Hey, I want to get this team together so that we can brainstorm on X." Now you're looking for all the data you can find. How do you want to drive the conversation? You're now saying to everyone else, "Hey, this is what I need you to bring to this meeting." You're kind of running it. Then you're owning the outcome. So, your CEO is almost like looking to you to double his effort and not just his or her time, if that makes sense. 

Leah Warwick: It absolutely does. That really matches with research we've done, talking to EAs, talking to executives, HR, and subject matter experts. We just put out the "State of Executive Administration Report," and we found it's really a continuum of assisting, supporting, partnering, and leading. So, a chief of staff would be an example of someone who's really leading in an administrative role – like you talked about, prioritizing the priorities.

00:09:59

So you are, in some cases, a proxy for your executive. You need to double them. Often, you are driving initiatives. Like you said, owning initiatives. You are a strategic advisor. And, of course, project management is huge. 

Kristina Willis: Huge.

Leah Warwick: And then on the communication side, the executive presence and confidence to carry those things.

Kristina Willis: Yes. And that's where I would also add: driving alignment becomes a skill that you must possess as a chief of staff. That alignment is such a delicate balance. Alignment is not a destination. It's every day. As an EA, you may be privy to a lot of what's not aligned. You're in the meetings. You're talking with your executive. They're coming to you and they're like, "What do you think? Did you pick up on this? Did you pick up on that?" You're giving feedback, but you're not driving the alignment. You're seeing it. You may even have ideas around like, "Hey, maybe this is what's off."

00:10:53

But as chief of staff you now own the alignment that exists or doesn't, and that's due to communication. It is a whole art to wrangle. 

Leah Warwick: What, in your opinion, are the pros and cons of an EA role versus a chief of staff role?

Kristina Willis: I'm so biased because I think both roles – I think the pros for both would be the opportunity for expansion. I'm mindful of how I use the word "limitless," but, for lack of a better word, I really think, be it the depth and breadth of potential that lies within both roles – I think it's huge. So, I would call them both pros.

I think, for me, more than the cons between each, I think a con that stands out instantly when you ask this question is the uncertainty between the two, or the misunderstanding that exists between the two roles. And the potential of, if you do muddy the water, you can do a disservice to both, or one.

00:12:01

That, I think, is very unfair. I think I've seen the chief of staff potential to be "better than." I don't like that. I think that's a con. That's not true. The chief of staff role is one of many opportunities that an EA can expand into. So, I think the cons, for me, would lie more around how the roles are built out, described, talked about, and the accuracy around speaking about the roles. I think until that's fully fleshed out and there is a true sense of understanding behind the two and what makes them different, what makes them complimentary to each other when a chief of staff and an EA work together, I think that's always going to be a con, in my mind. I think there's a lot of work to be done around solidifying what each role is and how one does not replace the next and one does not trump the next. 

00:12:50                     

Leah Warwick: Right. It seems that, because in a lot of companies there is a lack of career progression for EAs, so then they think, oh, I have to be a chief of staff. I think it's really important that we, as an organization and through our training, and through great work from people like you, show that chief of staff is a career option. It is a role that you might be a good fit for. But also, how can we expand the EA role? How can we create promotion opportunities for someone in an EA role? Maybe it's an executive business partner title. Maybe it's a function that could be created, a business function, where it's more of an executive operations model where you could become a manager, a director, a VP of executive administration, and then you work with the chief of staff. The EA/chief of staff relationship is a very important one, and I think talking about that, too, and how that relationship can be strong, is important.

00:13:41                     

Kristina Willis: Yeah, absolutely. I agree with everything you just said, and you probably said it way better than I would've said it, too, so thank you.

Leah Warwick: No, you're crushing it. I'm just – listening to you talk about all of this stuff is really solidifying to me the importance of providing career pathways for administrative professionals in general, but especially for executive admins. It is a very widespread problem that there is no career progression, so we need to make sure that we're advocating for that and talking about the different roles that might be a good fit. So, I'm glad you're here to talk about that.

My last question for you (before we get into our listener questions) is: What is the best advice you've received that has helped you in your career? 

Kristina Willis: When I started out at We Are Rosie as an EA, it was maybe three months into my role. I was so paralyzed by the fear of making a mistake that I was holding myself back. I wasn't moving as fast as I could. I was being a little too calculative, like, if I can do this task perfectly, that was my goal – no matter how long it would take.

00:14:48

My founder and CEO, she saw what was happening and one day – it must've been – It was a day when I had only asked her maybe a thousand questions. She said to me, "I think you underestimate the amount of runway that you have and the trust that I have in you. You are going to make mistakes, and there's no mistake you make that we can't come back from; I am certain of that. So, just go." 

I kid you not – I have chills saying it – I remember where I was. I was at my desk, but I could still picture my pink laptop, and I could just picture the environment I was in. I was home. It was quiet. And I just felt these chains that I had put on myself – no one put them on me, to be clear – I felt them just like fall. That was such an empowering moment. I thank her to this day. Once in a while, I think about it and I'm like – they were so – the words were so freeing. 

00:15:51

From there, it's like I could see myself start to move like 100 mph. Not recklessly, but I just could see myself moving with more confidence of like: You've got this. Why are you acting like you don't? And I've carried that with me to this day. 

Leah Warwick: It's amazing what the words of others can do and how you remember them. That's inspiring me to tell people in my life, "Do you know how great you are? Do you know how much I trust you and believe in you?" That's very powerful.

Kristina Willis: It's empowering.

Leah Warwick: I love that. I'm so glad. I'm so glad to hear that. And now we have a listener question submitted by one of our community members. They write: Are there specific projects or types of initiatives you recommend taking on to showcase readiness for a chief of staff role?

Kristina Willis: I don't know if I would bucket this as an initiative, but I would definitely say this is something to go about very strategically, if you're not doing it already. So, if you are doing it already, hats off to you.

00:16:46

As an EA, your calendar is filled with meetings that your executive is attending, many of them that you don't necessarily attend. Start to attend the meetings that you schedule, as much of them as you can. Maybe not the one-on-one with your CEO's direct report or something like that, right? [chuckles] But start to attend the meetings that you're scheduling, whether that's the financial reporting meeting, whether it is that leadership meeting that recurs biweekly, whatever it is. Start to sit in on them because that's when you get to hear everything in real time. You get to start forming thoughts of your own, right? And that's where your contributions come in. 

Your view of the business and what's going on is yours. The more you sit in on these meetings, the more you start to speak, everyone at that table is going to realize: Oh, my goodness. This perspective is missing, and it's only sitting with you. But you cannot showcase that if you're not in them. So, raise your hand, ask, "What meetings can I shadow? I want to come in and listen. I'll even throw you in a bonus. I'll take the notes," right? Depending on what it is. 

00:17:59

Or maybe you're in the meeting, taking the notes, and that's all. That is important work. But maybe it's debriefing with your executive afterward. Maybe it's saying, like, "What's the level of flexibility for me to contribute in real time?" Establishing that boundary, making sure you and your executive are on the same page, but sit in the meetings. Contribute to them. That's how you learn. That's how you get to listen. And that's how you get to amplify your voice. That's how you get to now build influence, and all of those things make a very important part of being a chief of staff. It's so much emotional intelligence. It's all the non-tangible things that come from you just being in the room. 

00:18:43                     

Leah Warwick: And the qualities that the executives in the room have that you need as well, and you belong at that table.

Kristina Willis: Yes.

Leah Warwick: That's a big hurdle sometimes is, no, you belong at that table, too, at that executive table.

Kristina Willis: One hundred percent. If the seat has been pulled up for you, do not just warm it. Sit there, shoulders up, and own it. If it has not been pulled up for you, raise your hand and say, "I want to pull it up for myself. Can I scooch in?" And I'm hoping that the listeners have leaders who support this kind of stuff. That's a part of it, too. That's where the "it takes two to tango" comes in, because there are limitations when you have a leader who may not understand how best to leverage and utilize you as an EA. So, I'm hoping that more people are listening who have leaders who are like, "Absolutely," and they're very open. I just maybe need to be more proactive.

And if you don't have a leader that's very open, there are still ways to bring the value and prove the value, but it still involves being confident, articulating yourself very clearly, explaining why this is important for you – even if your leader can't see why it's important for them, tell them it's important for you. 

00:19:55

"Maybe you don't see why, but I know I need to be here, and until I'm here, I can't prove to you what else I can actually do, so just give me a shot." You know what I mean? So, I'm hoping there's more listeners who have very supportive executives than not, but even the ones who may not understand, you have an opportunity to influence them because you're an influencer. 

Leah Warwick: Right, yeah. Do what you need to do to get a seat at that table, to raise your hand and get that seat. I'm so glad that you spoke to this. It's so, so important. Thank you so much for coming on the podcast. Where can our listeners find you online?

Kristina Willis: Oh, my goodness. You would think I'm prepared for this question. LinkedIn would be the best place to find me. If you look me up under Kristina Willis, Chief of Staff to CEO at We Are Rosie, you'll likely find me there.

[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.