Navigating the EA and Chief of Staff Relationship with Maggie Olson

Jeremy · 0:00

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Speaker 2 · 0:48

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

Jeremy · 1:04

Hey friends, welcome to The Leader Assistant Podcast. It's episode 260, that's right, 260. You can check out the show notes at leaderassistant.com/260. Today, I am speaking with my friend Maggie Olson from NOVA Chief of Staff. Maggie and I have a bunch of topics that we're gonna cover over the coming months on the show. And we chatted about her Chief of Staff certification course in episode 255. And then we more recently chatted about the transition and journey from EA to Chief of Staff and how to level up. That was episode 257. And then today, we're going to dive into the Executive Assistant and Chief of Staff relationship. And before I hand it off to you, Maggie, I just wanted to share that like, you know, over the years, I've talked to assistants who, you know, this question comes up often where it's like, hey, we just hired a Chief of Staff, and I don't know if I'm going to get fired because they do similar things that I do or because I've been doing some of that work. Does that mean I'm a failure? Or another example would be the other day, it's like, hey, we hired a Chief of Staff, which is great, we needed help, but our roles aren't very clear and distinct, and so there's causing a little bit of drama, and we're stepping on each other's toes and all that. And then kind of the last example I'll share is, you know, I remember there was this long coaching client of mine, you know, I had for months would speak with her at a very large organization, and there was just drama, drama, drama with the Chief of Staff, because the Chief of Staff had been there forever, and the EA was coming in to this dynamic relationship and dynamic environment where the Chief of Staff had been set in their own ways. And so anyway, my point of sharing all that is I know there are people listening who, whether they're EAs or Chiefs of Staff or want to be a Chief of Staff or want to work with one or don't want to work with one or being forced to work with one, I know there's a lot to navigate and balance when it comes to, hey, we're kind of working in this triangle, the CEO, the Chief of Staff and the Executive Assistant, and how the heck do we navigate that? So that's what we're going to talk about today. That's what Maggie's going to talk about today. I'm going to hand it over to you, Maggie, for your TED Talk on the EA and Chief of Staff relationship. And I'm excited to take some notes and listen in.

Maggie · 4:06

Awesome. Thanks, Jeremy. So happy to be here, as always. You know, it's funny, too, because we can almost role play. Jeremy, as a potential senior EA, Maggie, Chief of Staff, we can maybe even approach some of these situations that way, which would be interesting and fun. But I think this topic does come up a lot, and it should. I think when you're sitting as an EA, generally you have been in the role, and a new chief of staff is coming in. So there's going to be this natural fear of like, is my job going to change? What's going to happen? Who is this person coming in? Do they care at all about what I'm doing? Do they want to know what my goals are? Do they want to know all the cool things that I've accomplished for this business? Who is this person and what are they doing when it comes to a new chief of staff stepping in? And that's usually the dynamic. It's usually existing EA, relationship, probably for many years with their principal, and a new chief of staff role comes in, and there's not a lot of awareness or understanding of what that role is and what to expect. What I tell chiefs of staff is that one of the most important relationships, if not the most important relationship you will have as a chief of staff, is with the EA. The two of you are in a perfect state, very much in lockstep. You're very much aligned on the priorities that you are both serving this leader in X, Y, Z ways. You understand each other's jobs really well. I could go on and on, but that is absolutely the ideal blend of the relationship between an EA and a chief of staff. The EA is also probably going to be the closest ally in the chief of staff role and most likely the most utilized resource for a chief of staff. So not only is it important on a relational perspective for the two people to get along and work together, but it's good for business. It's good for business to have a strong relationship and to understand each other. So what I'm going to do is kind of talk through some of the different ways that we can do this both as an EA and as a chief of staff. Cool. Okay. So when a new chief of staff role is introduced, one of the biggest pain points can be navigating this relationship between EA and chief of staff. So I will talk about first from a chief of staff perspective what I suggest. First, approach humbly and assume the best. So what does that mean? It means I'm a chief of staff. I might be coming in with like guns blazing. I'm so excited. I want to make all these changes and I want to have a big impact and people to recognize me for the things that I'm doing. I tell chiefs of staff to really slow down and breathe and use these first few months to learn, approach humbly, assume the best in everybody and kind of adopt that learning mindset without changes for the first few months. Additionally, shadow your EA enough to truly understand what you do every day. So Jeremy, can I sit with you for a few hours for the next three days or three days over the next week or two, maybe at different times of day, and we can go over the things that you think would be most important for me to learn. So what does Jeremy think as the senior EA is most important for the chief of staff to learn? This is really, really important, both directions to truly understand each other's jobs and have that kind of base level foundation built for the role before you get into all the things that a chief of staff is going to want to do right away. I think additionally, like understand the EA's goals in their role, their likes, their dislikes, what's going well, what's not going well. Normal things, these are all things that sound easy enough, but when you're in it, it is hard to slow down and truly think about what is the most important way to approach the relationship. And finally, understand that the EA is probably a little bit nervous about their role changing. Think about it. And I know a lot of people listening are EA's and we've got chiefs of staff listening too. If you're a new chief of staff coming into an environment where an EA and a principal have a long-withstanding relationship and there's not a lot of clarity around what the chief of staff role is, there is going to be natural fear, natural loss of control, natural concern over their job changing, and you potentially being a catalyst for that change. So I think that emotional intelligence is incredibly important for any kind of a person or chief of staff to step into an existing environment where they will probably ruffle feathers and it's how to do that in the least, you know, in like the least aggravating ways possible. So from the executive assistant perspective, you have a new chief of staff starting. How do we do this? Again, we assume the best. Expect a driven achiever who wants to make an impact quickly. That's kind of a good term. Terminology use for chiefs of staff. But assume the best. Assume that this person and you have aligned goals on supporting the leader in the best way possible. And I think one of the most important things that I coach on this subject is approach the relationship as an EA with a teaching mindset. So the chief of staff is approaching with a learning mindset. Show me everything. What do you do? I really want to learn. If as an EA, you can adjust your mindset to truly say, okay, I'm going to help this person learn and I'm going to show and teach and demonstrate the things I do, the way the office runs, the current state of things. You'll both be able to adopt an understanding of kind of this current state before a chief of staff is going to say, okay, now maybe we can make a few changes and make a few things better. Teaching mindset, help the chief of staff learn how things work today before kind of, I guess, maybe having a more closed mindset where you're nervous and fear-based and worried about losing control. Be aware of those things, but try to work through that through teaching and showing. Be prepared for process improvements and some change. So that is a goal of a chief of staff and a goal of a lot of people. I think there's a lot of EAs out there who are excellent with process and efficiency and finding solutions to problems. Chiefs of staff, a huge part of a chief of staff's job is to make things run smoother and better and quicker and leaner and more efficient. I don't believe a chief of staff is going to be successful by stepping in and doing this right away before they learn a business. However, expect that some of that will begin to happen and jump on board if you can. How can I help or what are you thinking here or do you mind if I jump in and give you a suggestion on that? I don't know if I agree. Open the dialogue, but expect some change and it will come easier if you expect it. Finally, from the executive assistant's perspective, understand and learn that chief of staff's goals both professionally and probably personally. Where do you want to go after this chief of staff job? What are your number one things that you think you're going to address as a chief of staff? Oh, well, what about this? I've identified this. Should we work together here? It's an opportunity for you to get to know each other through asking good questions and kind of setting yourself up together to approach kind of what's next in terms of the transformation of the office that you're in. So for both the EA and the chief of staff, some of these are a little bit repetitive, but I'll repeat, intentionally build a relationship and get to know each other. Kids, family, hobbies, favorite lunch options, quirks, ideal weekend, travel spots, get to know each other. It can be hard to do those things when there's a little bit of tension and anxiety, but we all know the better we get to know each other, the more human we see each other and the better we can work through some of that anxiety and conflict at work. Again, assume the best, again, learn each other's jobs. I haven't touched on this, but truly over communicate. No one likes to be a micromanager, and I think that EAs probably can feel sometimes that chiefs of staff just want to know everything and want to see the business in all the ways. Be okay with over communicating, especially at the beginning. Get yourself and each other on each other's pages. Share maybe more than you think you need to. Figure out what each other wants to understand and learn and what maybe isn't as important at the beginning. Over communicate at the beginning and really kind of find your rhythm as partners. So simple enough, definitely not easy. This is a hot topic. It's an important one to spend time on. I'm sure we'll come back to this at different points throughout the year. But hopefully that was helpful to those listening around how to navigate the EA and the chief of staff relationship.

Jeremy · 13:26

That's awesome, Maggie. Thank you so much. And I really like the idea of just kind of the if you're new to the situation, you're the listener versus the teacher. And too often you hire new team members or you join a new team and you come in and you're trying to teach everybody what you know and you're trying to, you know, insert yourself and make a name for yourself, kind of those high ego moments. And I think that's very valuable, whether you're the EA or the Chief of Staff. If you're new to the to the triangle, then, you know, it's always best to listen and have that season of listening and learning versus teaching.

Maggie · 14:07

Absolutely. I couldn't agree more.

Jeremy · 14:10

So awesome. So then I guess one thing that kind of came up, how have you seen with this relationship? Have you seen in your experience or, you know, the Chiefs of Staff and EA that you've spoken with, the job descriptions and the org chart, you know, questions or, you know, hey, my job description is pretty similar to your job description. How can we fix that? What's maybe, you know, a few minutes of thoughts on that whole dynamic, because I know that can be an issue, too, where it's like, hey, we think we need a Chief of Staff, so we bring them on. And it turns out their job description, there either isn't a job description or there is, and it's very similar to the EAs. And then it's just like, OK, how do we actually get this sit down and get this on paper to where it's clear?

Maggie · 15:06

Yeah. You know, I usually suggest starting with an audit of what you're doing. So if, let's say, you're an EA in this example and you're like, gosh, I'm doing a lot of EA work. I'm an EA. I'm a senior EA, for example. But I also feel like I might be doing some Chief of Staff work. And maybe there's already a Chief of Staff or a Chief of Staff that's new or coming in and you're a little unclear about your role and how you're going to work together. Put everything that you do into Excel as an example of a tool. Open Excel, put everything you do into a different box all the way down. Column A, for example, all the way down one through. Let me guess as an EA, like 75. Then take Column B and put an X, or let's say a C for something that might be Chief of Staff related and an A for something that's definitely maybe more administrative and leave it blank for the things that you don't know and you can kind of work through those later. But basically, what kinds of activities are you doing that fall into the very general understanding of an executive assistant? And we know that there's so many different definitions out there, but for example, calendaring and expensing and travel, those items, what are you doing that are executive assistant responsibilities? And then what are you doing that's outside of that? What are you doing that's a little more planning focused, a little more strategic focused, a little bit more analyzing a business or putting recommendations together, a little bit more collaborative, getting everybody on the same page for things, preparing, briefing. Hopefully you can kind of see some of the differences there and look through your audit, put time to the activities that you're doing if you can and use that information to inform your next step. So if you believe that you are doing more chief of staff style responsibilities, whether or not you want to be a chief of staff or you want to move in outside of like an EA role, you can do this activity to propose an increased scope or propose maybe a title increase, adding senior or adding executive business partner or special assistant to the president. There's so many options. Do the audit, put a proposal together, have the conversation. If there is a chief of staff involved in this scenario, sit down, talk to them about it, have them do the same kind of audit. I think that a lot of times one piece that's missing in these conversations is the recommendation. So often an assistant will say, I'm doing these things and I know this to be true, and I've already done all this, but what do I do with it? So-and-so is so busy, they're not ready, they can't listen to me, they're off doing their own thing, whether it's the chief of staff or the principal. Put a recommendation together. Maybe it's an email, maybe there's a couple slides in a PowerPoint deck where you say, this is what I'm seeing, this is what I think I can do, here's how our roles could differ, here's how maybe there's some overlap that we should address. I suggest we do this. And then you've suggested a recommendation, you're seen as a thought leader, you're seen as somebody coming with a solution to something, and hopefully you'll feel better about the way you're analyzing your time and potentially fixing a problem of maybe some overlap and duplication.

Jeremy · 18:24

Love it. Well said. Thank you, Maggie. That's great. I love the starting with the audit. I have people, executives reach out to me all the time, say, I need to hire an assistant, but I need help. I don't know how or I need to hire a chief of staff. And it's like, OK, well, what do you want them to do? Like, well, I don't know. I just I think I need one. And it's got to start with that. Like you said, just list out everything that you're doing and make a list. So well, well said. Well, Maggie, thank you so much. Great conversation, as always, and great tips, as always. I'm excited to dive into more topics over the coming weeks and months. And the let's see, we're going to talk about networking. We're going to talk about the negotiation skills and interview strategies, financial acumen, managing executive engagements, building confidence and more. So stay tuned, everyone, for future chats with Maggie Olson. And be sure to check out the show notes at leaderassistant.com/260. And you can find out more about Maggie, connect with her on LinkedIn, and obviously check out her course at leaderassistant.com/nova, leaderassistant.com/nova. So thanks for listening. Thanks again, Maggie, and we'll talk soon.

Maggie · 19:51

Can't wait. Take care.

Speaker 2 · 20:03

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