Leveraging Leadership

Founder of Chief of Staff Roundtable Phil Burns

September 09, 2024 • Emily Sander • Season 1 • Episode 104

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In this episode of "Leveraging Leadership," Phil Burns talks about the crucial role of the Chief of Staff and the risks of not defining it properly. He and Emily discuss the differences between an Executive Assistant and a Chief of Staff, emphasizing strategic thinking and rebranding for those transitioning roles. Phil also shares about the Chief of Staff Roundtable, a community providing resources, peer learning, and discussions on key topics like executing business rhythms and solving big problems.

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Who Am I?

If we haven’t yet before - Hi👋 I’m Emily, Chief of Staff turned Executive Leadership Coach. After a thrilling ride up the corporate ladder, I’m focusing on what I love - working with people to realize their professional and personal goals. Through my videos here on this channel, books, podcast guest spots, and newsletter, I share new ideas and practical and tactical tools to help you be more productive and build the career and life you want. 

 

Time Stamps:
01:21 Phil's Path from EA to Chief of Staff to Founder
06:59 Challenges and Realizations in the Chief of Staff Role
12:45 The Birth of the Chief of Staff Roundtable
14:05 Growth and Evolution of the Roundtable
22:01 Membership and Offerings of the Roundtable
27:18 Understanding the Tools of the Trade
28:42 Membership Benefits and Access
30:19 Networking and Peer Learning
31:25 Diverse Membership Base
32:41 Role Clarification and Career Pathing
47:49 Strategic Conversations and Trends
53:25 Connecting and Learning More

Welcome back to Leveraging Leadership, where we unpack the art of business leadership. I'm your host, Emily Sander, Chief of Staff turned Executive Leadership Coach. I work with people to help them step into effective leadership and realize their professional and personal goals. If you have known failure and success, if you have had good bosses and bad bosses, If you are a high achiever and want new ideas, and if you want the practical and tactical side of things, then you are in the right place. This show is all about finding your points of greatest influence and leveraging them to better serve those around you.

Emily:

And today we are joined by guest Phil Burns, who is a former chief of staff himself, and now the founder and CEO of Chief of Staff Roundtable. Phil, welcome to the show.

Phil:

Hey, glad to be here, Emily. Really excited to, to have this time with you and talk about what's brewing at the roundtable. Excited.

Emily:

So first of all, we'll, we'll rewind a little bit. So you were chief of staff and

Phil:

Yeah.

Emily:

As I understand it, a round table was born out of the fact that you were scrambling and grasping for resources and information and what is this role? And how do I do this role successfully? So just take us back there for a little bit and maybe do a brief recap of your time as chief of staff.

Phil:

Totally. I'd love to go there, uh, to set the stage a little bit. I think it's. Helpful to provide some context for my, of my kind of career journey and the roles that I've found myself in. Um, so I've, I've worked alongside leaders in a lot of different capacities, a lot of different kinds of roles in a lot of different industries and. I was actually telling someone just earlier in the day that I, for whatever reason, I just always felt my leader was like a magnet where I was just always like, like ended up right beside them and always usually compelled by some version of their vision and wanting to make that a reality. So little did I know I was really in the chief of staff headspace, um, for most of my career. And so naturally, you know, hindsight 2020, it makes sense why this role found me as it was, you know, um, coming out of the traditional context where it's well established, like government military into the more non traditional context, like the business world. And so eventually it found me. And so the circumstances around me officially branching in and into this community or this profession is I was, um, I was working in the president's office at a university here in Atlanta, Richmond graduate university. And when I entered, um, my first role was I was, I was just an admin in the president's office. It was a stopgap job. I just needed something to find my next thing. And I'd always envisioned maybe being professor one day. And so I was like, you know what? I'm going to give this higher ed thing kind of a, uh, I'm going to get under the hood and kind of see if this is the kind of place I would want to be. Well, I found out that I did not want to write for a living, at least at that level, um, and constantly publish and constantly present papers. So I was just like, you know what? This is not for me. But I did get exposure, um, to the highest levels of leadership that I had up until that point. And so, When I came into the organization, the current president CEO announced his resignation two years, two months later. And so I was like, Oh, cool. Um, and so I helped keep things together as the board. I was working with the board to find an interim. And so through that process, I kept the trains on the tracks. Like I didn't, I had no idea what I was doing, but it was, the mandate was like, Phil, just keep it together. You know, no one even told me that I just assumed that responsibility, that ownership. And so the interim was named. And so I helped onboard her and get her, you know, for her, the time that she was interim, get her going, get her focused on the right things. And she ended up not being the permanent, uh, president candidate. So, she rolled off into her previous role, and then the, the then permanent CEO was established, and so I was a part of the process in getting him onboarded. And so I developed this reputation at the organization where like Phil just keeps things together. Phil keeps things going. Phil doesn't say no. Phil, I say Phil doesn't say no. It's not Phil has boundaries. Whatever needs to get done, Phil jumps in and just takes care of it. He finds a way, right? And so the new presidency at the time was like, wow, feels really, you know, a pretty, uh, pretty key part of this operation. Um, and obviously I need him to help me, you know, start my tenure as a chief, as a CEO, new CEO, uh, well, and so six months into my time and being his direct support in like an executive assistant capacity, it became really evident that I, I was capable of much more. I'd already demonstrated this for probably 18 months at that point. And so he was like, well, I'm a new CEO and you know, I don't want to lose Phil. And so, you know, I've worked with chiefs of staff in the past, haven't had my own before. I would like, this was what he was thinking. I would like building them be my chief of staff. Little did he know I was doing my own career planning at that point. And I was thinking like, based on my background and you know, the narrative thus far in my journey, like what is the next role? Like what is the next thing for me? Based on my very early research. I think I read like the Harvard Business Review's article on the Chief of Staff. There wasn't a lot back then. This is just 2018, so not that long ago. But there really wasn't much out there, um, about the role outside of government and military. And so whatever was out there, I started to educate myself around. And I was like, I really like this. I really feel like this fits me. This fits, um, this makes sense from a career arc standpoint, but it also makes sense Long term of like me wanting to possibly run my own organization one day and be an executive. And so I was like, this is the perfect kind of, um, platform or career, you know, ladders accelerator for me where I wanted to go. So I was thinking chief of staff, he was thinking chief of staff. And then I remember scheduling time with him to talk about opportunities for me. And. In that conversation, we got to the point of like, well, what could it be? We both said chief of staff and it was like, we actually did it in real time, but it was this cool moment of like, he was thinking that I was thinking that this must be, you know, meant to happen. And so, uh, this is early 2020, 2018. And I was so excited. I was like, this really did feel like, uh, I'd reached the peak, like of that, of my journey up until that point and all the roles I had, like this was, I finally hit this really core milestone in my, my professional journey. And so it was about 30 days or so before I officially transitioned. I was actually getting married that spring as well. So a lot of big changes were happening. A lot

Emily:

happening during that time. Yeah. Oh

Phil:

yeah. Oh yeah. So, so. As, as excited as I was to take on this role, as ready as I felt as I was, um, what I wasn't ready for was the face plant that happened the like literally weeks after taking the role and the face plant kind of, uh, element of, of, of how I tell this story is a little odd because I already been at the organization for two years at that point. Yeah, two years. And so I knew my way around. I had a reputation, like I knew the stakeholders. But for whatever reason, the shift to become the chief of staff, um, his chief of staff, uh, was a really jarring experience. And I equate that to just a kind of a cluster of, um, of competing, not competing, um, of misaligned expectations. So I had certain expectations of what the role Should feel like based on what I had learned, he had a set of expectations that he envisioned for the role. The organization had a set of expectations, um, because this was the first time for all of us. First time he had achieved his staff. First time I was a chief of staff. The first time the senior team had worked with the chief of staff. And so, as I tell folks, the learning curve was straight up on all fronts. I didn't realize that of course. Um, and so the face plant happened when I just came face to face with this reality that I really don't know what I'm doing. I did all this work, but like in the thick of it, looking at all that needs to be done and trying to assess like, well, what are the skills that I, you know, I've brought to the table? What are the skills that I need to acquire? What are the resources I need to get what I need to, you know, plug in to, to make headway where I feel like an ad value. That whole experience was so, um, confusing and, you know, he's, as most leaders are, it's like, if they feel like they need, um, Help, you know, because leaders operate at a much higher level as they should be. It's like, once they plug it in and from their standpoint, it's like, you know, forget it, move on to the next thing. And so, so that's basically what happened to me. He promoted me to chief of staff and it was just like, he was off to the next thing and it was just like, wait, Whoa, there was no, you know, there was no sort of onboarding and again, it's, I'm not blaming anyone. It was first for all of us. So it's like, we didn't know what we didn't know, but there I was. You know, very excited for this opportunity in this role, but also from, from the very outset, very confused, very isolated. Um, and I was in this kind of perpetual kind of free fall face plant for a year, just trying to figure all this out on my own. And at the time there was very little cheapest to have resources. Like when I thought about, you know, well, if I don't have the resources, you know, intrinsically or within my organization, it's like, well, probably you see that. Maybe is there anything out there? Like, is there anything out in, are there other others that have gone ahead of me or in the same stage in my chief of staff journey that I could learn from? And what I realized was. There wasn't really anything formalized at that point, um, and really what I was looking for, I wasn't looking for, you know, another article to read, um, because I'd read all those. I wasn't looking for another book to read. I read all those. Uh, there weren't many books at the time. There was Tyler Paris book, and I think The Gatekeepers by Chris Whipple, who he, he talks about White House Chiefs of Staff. And then there was a slew of articles in, on the internet. I devoured all that, and I was like, You know, that satisfies, that satisfies some of the conceptual, like, uh, categories about the role. When it comes to, like, learning from, like, those that have, that have worn the shoes, that, you know, have the battle scars, um, I needed that. I needed, you know, I didn't need, you know, I needed, like, a cohort. Like, I needed just, like, a group that, that felt like a safety net for me. Like, that felt like, you know, they had my back in a lot of ways, and I could, you know, Process the challenges that I was going through in real time. Um, and get real feedback in real time. Because you didn't

Emily:

have that, you reached out on LinkedIn at the time. Yeah. And just started, just started cold messaging people saying Oh man,

Phil:

sure did. Yeah, I was desperate. I literally remember this It's weird. I was desperate, but I was also really motivated. I remember at the year mark feeling this desperation and resolve. Desperation for like, man, I just need to be in my group. Like, I just need like a table. Like, I just need a consistent pattern.

Emily:

Maybe a round table perhaps. I

Phil:

mean, maybe a round table, maybe something like that where like, you know, no one feels superior to each other and that we all bring like really valuable insight and can learn from one another in it. really dynamic way. I needed that. Um, and I, so that was a desperation piece. I also felt a lot of resolve that to really nail it. Like I, I literally distinctly remembering like, I really want to reach my potential in this role. I want to do the, have the most impact possible. And I knew, but I knew that that wasn't going to come from just pure will. Like I needed a round table to, to be the anchor point. I needed a safe space where I could process, not just process my challenges and have this kumbaya kind of like, we're all in this together moment. I needed a space where, Those that were along or that were with me in this journey spurred me on to become more than I was at the time. So, so, basically, I, I, I, I, feeling very desperate and feeling absolute resolve. I was like, I'm going to reach out to as many chiefs of staff that'll talk to me just to, just to learn a few things. Am I crazy? Am I incompetent? Or are we all crazy? And are we all incompetent? Is there a way forward? So, um, I did that 300 DMs, 60 phone calls later, after talking with a few folks, we were all like, we should just start a call. And we should just hop on to save time every month and just bring whatever challenges that we had faced over the last 30 days into that. for that. Forum and just talk about it, help each other out. Um, and so that's how the round table was born. That was 2019 when the round table first meeting was June that year. So we're actually coming up on our five year anniversary, which is really cool, a really cool milestone. A lot of cool things are happening, uh, have happened in the last five years and even cooler things are happening this year in the few next few years. But that's when it started. And so we kept the line open every month, um, and started inviting more and more folks to weigh in on the, on the conversations we were having. Um, it started originally as it was a hobby. Um, I was a chief of staff at Richmont. Doing the role best I could as I was learning from this community. And, and so fast forward, four years of really, you know, doing it on the side, more and more people started showing up the desire for more robust resources and programs and networking, you know, started to build. And so it became evident. Like, this is like real work, um, and it's work that was really exciting to me.

Emily:

Sorry to interrupt, but you went from like a call and it was just like, Hey, you got a handful of people. Would you want to jump on a conference call or a zoom call or whatever it was? And then that grew because people kind of told other colleagues or friends, Hey, there's this call that I joined that's useful around chief of staff. Is that how it grew? Or how did, how did the work? Yeah.

Phil:

Yeah, it's very organic. It was only organic. Like we didn't. Yeah. And it still very much is. Um, we're putting a little bit of money into marketing, but you know, over time we just really, the, the, the core kind of animating, I guess you could say principle, but ethos of this whole experience was from the outset and it continues to this day is that everyone has something to bring. You know, if you think of like the traditional, you know, King Arthur's round table, like that whole idea of, you know, everyone's equal distance, it's not that, you know, certain bits of information could be more valuable or practical than others, but that's certainly true. But the underlying belief, all that is that we all have something to bring because we all have something to give. And in that cycle of learning and sharing, um, everyone, the, the, whatever the topic is or whatever you're focused on, like everyone gets stronger from that activity, like from that experience. And did you have So that grew organically, for sure.

Emily:

Gotcha. Because of that experience. I love that round table, it's, it's, it's It's, you know, certain people may resonate with certain things more so than others at that given time. Um, but it's certainly that everyone is equal in the sense that they have something to contribute and they're at the table for a reason. Um, so I love that aspect of it. So in, in the kind of beginning period, or I guess when it started to grow, did you have dedicated topics? Did you pick a topic where people just like, Hey, what's coming up for you this month? And we talk about that. How did, how did that go? The topics? Yeah.

Phil:

So if I'm hearing you correctly, you're asking like, how did the topics and curriculum kind of develop of how we approached? Yeah, I

Emily:

mean, I assumed that at the beginning there wasn't even a curriculum. I was just like, Hey, that's right. That's right. That just, Hey, what are people going through round Robin? Or did we say this week's call or this month's call is about a rhythm of the business or how do I get my principal to engage?

Phil:

yeah, yeah. So originally, um, it was very, um, member or person challenge specific. So like we would all hop on and round Robin, like, Hey, what's your biggest challenge? And we would, we would, we would help each other out just based on our experiences of how to navigate that. And fast forward, that's actually still there, but not in our round tables, but as our. As a part of our peer learning cohort experience. So our round tables eventually became more topic oriented and they continue to that, to be that way around the kind of the core, most relevant topics that every chief of staff is going to have to navigate. So it, the, our round table, the focus of our round tables has become that. And so because we, but, but at the same time, because we value that, Like, well, I have a unique specific challenge that I'd like peer feedback. We've carved that out into another offering that we offer our members, which is the peer learning. Okay.

Emily:

So let's outline that for folks. So there's, there was the round table that morphed into, was it the peer cohorts based on common topics? And then there's also. Yeah.

Phil:

So let me back up. The topics that we eventually started choosing for the round tables mapped really against the larger questions that were happening in the space as it was growing. So if you remember, Um, If you remember, like it was a long time ago in 2018, there were only a few organizations that had a pretty well established chief of staff practice. Google, Intel, Microsoft, like, you know, had chiefs of staff for a while, but other than that, it would, you know, even to this day, it is still very much an emerging, it's still a very new role. And so there is this mandate to educate, like, what is a chief of staff? What is, what is a job description look like? What is the, how do you measure the success of the role? So a lot of those questions started. We were, you know, we had our ear to the ground of those that were joining of like, these are the questions that they're encountering, like with their leader, with senior leaders, with their friends, with their family. And so early on we realized like we really need to have like, like we really need to orient the discussion of these round tables around these meta level. Yeah, topics about what does it mean to be a chief of staff? You know, we started like, I remember, I actually remember, I think it was 2020. It was when we kind of officially transitioned to more of a curriculum mindset or with a quarterly focus. And then we would kind of look at, you know, what are the sub themes along this larger arc themes. I remember talking about what are the, what's the mindset of Achievement Staff? So we had a conversation around that. The next layer was what are the values? What are the values and drivers of Achievement Staff? We had that conversation. I remember pivoting into like, What are the core functions of the chief of staff? And like, this is pretty well documented, like gatekeeper and implementer and integrator and those things. So we had separate conversations around that. So we started really at that meta level based on where the conversation was in the space, kind of what, what was being talked about, but it, but those conversations and even to this day, it's not simply, um, Phil. Pontificating about what Phil thinks for an hour. Like the real magic of these forums comes from, yeah, I am setting up the conversation, but the real magic comes from the questions we're asking around the topic in the format of breakout groups. And so we'll, we'll. Even to this, so this actually started pretty early on and we just kept it because it worked. There would be the first little bit of the call would be just setting up why this topic matters, why it's relevant to Chiefs of Staff, bring in some compelling statistics just to help frame it, frame up the discussion. And then we stop, we break out, every breakout has a list of questions they process. We assign roles in each breakout so that we get as much engagement as possible from, from these, these forums and breakouts and we come back and then we learn together what was discussed and we put together that, you know, coalesce the picture of the answer to whatever the question or topic or, um, that we're exploring that day. So that was the format that we started back in 2020 and that's continued to this day. With the topic with the topics being at that more meta level of like what does it really mean to be a chief of staff? What does it mean to succeed in the role? What are the core aspects core skills? Um, how do you become a chief of staff again? Those really meta level questions but relying on the community to define Like what those elements are, what, you know, when you say gatekeeping, not relying on a bumper sticker definition, but hearing from those that are actually doing it and like getting really granular and really specific on what that means. Um, because what we found in the conversations I've had with chiefs of staff over these years, And even in these forms is that, you know, soundbites only get you so far. They may help like satisfy an itch of if you, maybe you feel stuck just feeling like, Oh, wow, that's a good direction. But when it comes to actually really doing the role well, like surface level understanding, they're like, you need to go deeper than that, but not on your own. And so that's, we've structured these conversations to go deeper together. So that's how we've. That's how we've approached that.

Emily:

And today, how many members of Chief of Staff Roundtable are there?

Phil:

Yeah, so we launched our membership program a little over a year ago, and before we launched our membership program, we had, goodness gracious, um, most of our growth in terms of those that are joining our events has been 99 percent organic. And we, on any given our forums, even to date, we have, you know, 30 to 40 individuals showing up and engaging as forums and we cap it around there because one, that's a lot of breakouts to get through. Um, if, if we're coming back to. To talk. So we cap it around 50 folks is usually what we're aiming for. Um, so that's what you can expect at any round table. We have upwards of 50 folks joining those.

Emily:

Okay. Let me back up for just a second. Sorry. What are there? Is there like a free level and then there's a membership level? Just give us the high level kind of overview. What are the buckets? Oh, sure. Yeah,

Phil:

absolutely. Yeah. So for, for Since it started in 2018, for the first couple years, anyone could join our forums. They were completely free. Over time, though, the nature of the conversations we were having were so insightful, so valuable, we decided that, like, you know what, and they were getting so, like, big, that there had to be a way that we gate, like, what, you know, how do we keep this experience as valuable as possible? And so, We started charging for those events. Um, I can't remember the date, but it's been a few years now and that we saw an immediate benefit. Um, and the quality of folks that would join the engagement rate of those that would join. Um, and so we, and then a year later, we did our membership program. So, so if you wanted to just come to one event. Like more of an ad hoc way. We charge per tickets$50 per ticket. Um, and that's just again, one of the, one of the tables that we offer. If you're like, you know what, like, I literally remember like when I decided to go all in on the chief of staff role, when I was my first time chief of staff, um, my mentality was just like, I'll do whatever it takes. Like if I need to go to a round table, if I need to get a cohort, if I need to do one-to-one coaching. Yeah, I'll do whatever it took. And so our membership, since we've been starting the program, we have around 60 members right now that are, that really have that mindset of like they're, they're bought in and what we love about our, our membership program is, and this, this definitely, uh, separates the round table from some other options out there, which I love, which are great. I know all the leaders at, at those other places is the flexibility we offer. And the tailored and personalization. So like when we, when we onboard a new member, we recognize that they have limited time, um, they obviously have limited money. And so we want to help them figure out, okay, wherever you are in your cheapest app journey. We want to help you figure out what's next and what are the resources that you need to get there. And of the, of the things we offer you as a member, which ones make the most sense now? And so we'll say like, Hey, commit to two out of X number of benefits. And that should help you find what you need to get where you need to go. And so to answer your question, We, we currently, uh, we give free tickets out to some of our forums for those that, that are maybe just discovering us, just as a way to give them a taste of what our community is about. But we're really serious about protecting that experience. Um, and so we still keep it capped at 50 per event. Um, now that's our round tables. I should, I should clarify. And then we'll give out free tickets for those that are just learning about us. Um, we also, we do offer a free event. They're called tools of the trade. I should have mentioned that a few minutes ago. Tools of the trade events are really where we get to showcase. Our partners and the platforms and services they offer. Um, and those are wide open, they're free. Um, and we get a really good engagement from those like over a hundred folks tend to buy tickets or buy tickets, get tickets to those. And the whole purpose of those forums is, you know, we're, I'm sure many, many folks listening have been a part of organizations that, you know, have 20, 000 sponsors and it feels like they're being sold something like every five minutes, like a commercial. We recognize some organizations that's their model and that's how they make it work. We, we were like, well, we would much rather put brands in front of our community that are highly relevant to their role in helping our members, you know, reach their potential. And so we're very calculated in the partners we choose. And so whoever we choose to partner with, we want to give them a platform to talk about how their service helps chiefs of staff, um, how their product helps chiefs of staff succeed. And so those are free events. And the way those are structured is the first half of those conversations are kind of the more like why this product is even necessary at kind of the higher level. Why it's super, why it's super relevant for chiefs of staff to be aware of and use. And then the last half of it is like a demonstration. But again, highly, um, you know, like how a cheapest app would use a tool like this. It's not simply like how to use Asana. It's like, no, this is how it cheaps. You should structure your workflow kind of thing. So, so in summary, tools of the trader completely free wide open. That's the, that's a platform for partners. And then our round tables, we give out free tickets to those that are just learning about what the round table offers. So they get a taste of it. But we gate it and make it a really high valuable experience for our members who have demonstrated they're really all in on their Chief of Staff journey and are willing to commit and engage in that way.

Emily:

So just to recap, because I get tons of questions from Chiefs of Staff. Totally. You know, what's this platform and what's this association, what's this roundtable, what's this network and all that stuff. And so I want to, Be able to answer them myself, but also point them to some discussion. So just to recap in my own mind, it's tools of the trade are open to anyone. Those are relevant, applicable tools that chiefs of staff can use. Then there are. Events and you can get, you can either get a free ticket somehow, or you can pay the 50 bucks to do a one off attendance to an event. And then there's a membership level, which I'm assuming includes all of the aforementioned items plus. Other things. Is that kind of general mapping? Correct.

Phil:

You're doing the, you're in the Mac. I should probably back up a little bit and frame. It'll probably a little bit easier to understand. So we've been doing these round tables for almost five years now. Um, if you become a chief, a member of the round table, chief of staff, round table, you get all access to all of our round tables. You also get access to our peer learning cohorts, which happen monthly, which give you a chance to present real challenges in your journey and get that peer feedback. You also get access to one to one on demand coaching. It's not a program. But it's like, Hey, I couldn't make the round table. I couldn't make my cohort, but man, I really feel stuck. And I just need to talk through what's next. And so we give that option to our members and then all of our members get, you know, access to our resource library, which we have over 60 recorded forums, over 150 specific cheapest staff, um, tailored resources there. Um, so that's all included in membership. If you are, and they get obviously tools of the trade, if you're just learning about us and you're like, man. That sounds awesome. How could I get a taste? Then we give out free tickets to our round tables, which is just one of the benefits of being a member. Um, if you join our private LinkedIn group, so I probably should have done. So if you join our private LinkedIn group as a way to say, thank you, like give you a taste of what our community offers, we'll give you a free ticket. To our next roundtable. Um, and if you can't make that one, just a future one. So that you get a taste of that. We also, if you, if you're like, man Phil, I can't make any of those, do you have a recording? We'll give you a recording just to give you a taste of that. Because we really feel like those calls are a great experience and they're worth checking in, checking out. So, that's probably a more helpful way of framing it. So, membership, roundtables, learning cohort. On demand coaching resource library, and then curated networking. I forgot to mention that. That's actually what our members love the most because we re you know, we recognize like whether you're trying to get into the role. You're trying to grow in while you're in it where you're trying to exit. It's who, you know. That makes all that possible. And so we have a very unique approach to finding, connecting you with people that gets you to where you need to go faster. Um, and so I won't get into how we, how we roast the sausage. So to speak of how we do that, cause that's a really special aspect of that we offer our members, but that is another important benefit that we don't offer. Okay,

Emily:

so thank you, because that outlined helped a lot. I think if someone is just is listening and saying, I'm just starting, it sounds like the private LinkedIn group is the place to start. And that kind of gets you into, uh, into ecosystem, so to speak. And then once you're in, and you're talking about, I can connect you with people, and you have these cohorts and peer groups and all these things. Are those other current chiefs of staff? Are those Um, executives who work with chiefs of staff are those executive coaches who, who was included in those, those groups and forums you're talking about.

Phil:

You're asking like basically who makes up our membership base in terms of who's involved in active. Let's say I joined the private

Emily:

LinkedIn group. I get the free ticket. I attend the event. I like it. I sign up for the membership. I joined one of my. That's it. Right. Pure groups. Who, who is it?

Phil:

Yeah, totally. Uh, 60 percent of those that are in pure groups are current chiefs of staff. They're just trying to level up, you know, become better in the role. Uh, about 20 percent or so are aspiring chiefs of staff. Either that they're either becoming chief of staff for the first time, or They're a former chief of staff, but they're looking to become a chief of staff again. Maybe they have a different role. And so that's about 20%. And then 10 percent are are our partners or coaches that are invested in this chief of staff space. We actually have a several, um, Fractional chiefs of staff that have gone out on their own. And so I put them in a different category, even though they're doing the role. Um, but that, that is a unique, there's a unique challenge set around starting your own business, even doing chief of staff stuff that we want to, we want to help, you know, they can learn from the community as well.

Emily:

Do you help people, uh, Get placements in chief of staff roles. Do you do that part of it or is it more talking amongst ourselves about the different things that we're seeing the challenges the opportunities in the role all of those things.

Phil:

Yeah, so we don't we don't have a official placement service. But what we do what we do. Is we know who all the players are in the space that are doing that and we like, literally, I'll be on halls with members are like, man, I'm really trying to get into a chief of staff role. And I'll ask them a series of questions. What kind of role are you looking at? What industry, you know? Um, and I'll be like, you know, you need to talk to. You need to talk to Clara Ma because she has a much better sense of like what's happening in that, on that side of things. And I'd be happy to make an introduction for you. So that's the approach we take with services that we don't immediately provide is because we know there are a lot of folks in this space that are doing really great work and, and we want to be able to support them and push people, um, wherever they need to go. And that, that is, You know, in terms of our whole approach to because we obviously we're all about these experiences, these events, um, whether it's the round table, a cohort or coaching. But if you, if we zoom out a little bit, a lot of it, actually, what we really feel like. The roundtables mandate is is as much growth has happened in this space and will continue to happen. We feel like there is a really visceral need in the community to for there to be an anchor point, like some sort of a, um, an organization like a roundtable where there's this centralizing element to, to keep the space coherent, um, to bring the very best resources and provide platforms for them. Um, and really make sure the space grows in a coordinated collective, um, and mutually Um, edifying way. And so, uh, we, we, we have ambitions to form relationships with every, every group that's out there in some form or another because we recognize they're, they're doing really great work. And it would make, it makes only a ton of sense on so many levels that we work together to bring the very best resources and support to chiefs of staff who really need it and you really need to find their path to success. So does that answer your question?

Emily:

It does. And I agree with you. I mean, you and I were talking earlier and I've always said The chief of staff role is well established in military and political arenas, and it's emerging in business, but it's kind of scattershot, you know, throw something up in the air and like see where it falls down. Yeah, that's right. I think in the next five to seven years, it's going to settle into something. And I think you, me, Claremont, others in this space are trying to let it, trying to get it to settle in a strategic way. C level position, which the role truly is not something else. That's, uh,

Phil:

yeah, well, you know, that that's an interesting perspective cause it's, it's, you know, when you think of where it's traditionally. Understood and use. There is only one version of it, like in terms of who has given the title, like if you're a chief of staff in the military, that is, there's a rank on your shoulder, like there's some way to know that like, Oh, that that's what that person does. So when you walk in the room. It's a very consistent, um, experience for those that are on the receiving end of, of you in that role. Um, the government, you know, probably would be where things start to level a little bit because you'll have Chiefs of Staff to local official, officials who will carry themselves differently than Chiefs of Staff to United States Senators. So that's where you're starting to see some, some where the scope kind of goes out a little bit. So I wouldn't say that, that, um, I definitely feel like there is a need to determine where is the role at its optimal, like scope and leverage. So I think the conversation needs to be oriented that direction for folks that find themselves early career, um, that are chiefs of staff that are, that whose roles are highly tactical, not so strategic. It doesn't mean they don't have a path to that. It just means that, That, um, you know, we're thinking about the vitality of the profession as a whole, like that's where it needs to go because I feel like when it when it means everything to everyone, which is we're kind of in that state now where a leader could slap this title on anybody in any stage of career because they feel like they can, um, that dilutes. What the best version of the role in terms of the most value it can bring a leader in a team. And so we're having all the right conversations. And so I definitely, yeah, when I

Emily:

say I want it to settle in a certain way, I want it to answer the questions you had and the challenges you had when you first got in the role where My expectation, my CEO's expectation, and my senior leadership team's expectation was misaligned because it was the first time they had heard, those parties had heard about it. So I want it to become, it's becoming more and more ubiquitous in the market. I speak with so many chiefs of staff and I go, how did you first hear about the role? Or if their boss, heard about how did they first hear about the role? Well, they knew someone or they had a friend or I have a friend who was the chief of staff or, you know, someone told me about it. So these conversations and little mentions of it here and there, it's, it's out there, but people aren't quite sure what it means. And you're right. I was speaking with a us marine Colonel chief of staff. He's like, Emily. In the Marines, you are at least a Colonel if you're a Chief of Staff and you at least have 25 years tenure. So when I say I am the Chief of Staff for, you know, so and so unit or so and so general, that carries with it a very high rank and high connotation. I was, uh, I was, worked for a Congressional office and our Chief of Staff freaking ran that office. She was like, Everyone knew internally, everyone who was important knew who ran that office. And so I think it's very well understood in political terms when you say, this is my chief of staff. Oh, got it. You run stuff behind the scenes. I think in business, there certainly are those. Various job levels that you were talking about, certainly junior chief of staff or associate or deputy or level one or whatever you want to call it. And there's also a lot of scope and breadth to the role because in a startup or early stage is going to be very different than later stage or, or large multinational firm, but I still think there's room for that to. Kind of solidify into, oh, I know what a chief of staff is, this kind of fits in here and, you know, it depends on the company and the principle and the need still, but it's still more, what do I say, concrete or defined, like, oh, it's chief of staff, got it, not, you know. Okay. That sounds cool.

Phil:

Yeah.

Emily:

What? What does that mean in your case? So anyway, that's, that's my visioning of the role, but we'll all see how it shakes out in the next several. Yeah.

Phil:

Yeah. I mean that, what's so cool about that, Emily is, is what's I tell folks all the time, you know, we're in, we're at an exciting point in how this role is emerging because it's, Like you is that you've experienced the value of the role firsthand. I've experienced the value of the whole firsthand. I've talked to dozens of folks that, that are driving real value, um, in a very discreet way, you know, chief staff, like we were, we're in the shadows, right. And it's a special kind of human that's attracted to work like that, you know, like, and special, not in like an elevator way, but just like, that's unique in that, you know, it's not for everyone. And. I think right now, and maybe this is just because I'm in this space 24 7 and, you know, I tell folks the space is about this big and the whole landscape. So we need to keep that in mind when we're talking about our role. We are important, but not in the grand scheme of things. We have our purpose. Um, what, what excites me is how much energy and excitement is, is around roles, a role like this and what it can unlock for leaders and teams. The flip side of that. Is if, if we don't clarify, if we don't clearly define, if we don't, you know, draw hard edges around, this is what it is and this is what it isn't. You risk, you risk muddying the waters and diluting the value it can really provide. Um, and that's not an indictment or it's not a slight against those that may find themselves in the role and maybe they, they don't need to be in the role. It's because at that point it's, it's on whoever scoped the roles fault at that point, you know? So we're at, we're at, I think we're at a tipping point in the next couple of years of just like where things will settle.

Emily:

Well, I mean, you, you yourself went from an EA to a Chief of Staff. So you know firsthand those roles are very different. Very different. And so the HR, uh, team member gets those confused because they're not quite sure Then they don't put people in the right seats on the bus, so to speak. So I want people to understand, Oh, if we're doing chief of staff, then we're doing chief of staff and we're not getting that confused with EA or senior EA or EA plus, I love EAs. They, they run the world and they are critically important to a leadership team, but the. Executive assistant and chief of staff are two completely separate roles.

Phil:

The one thing they are, the one thing I will say, since, you know, we think about those that get into the role, right? Um, there are a few, well, I don't want to say well established, but traditional paths. Like, you know, if you were to interview a ton of chiefs of staff, what are their backgrounds? Well, they may have a background in project management. They may have a background in program management. They may have a background in consulting in some capacity. You know, then you have the administrative background, high administrative background, executive assistant, office manager, um, fill in the blank. And what I love about that, that mosaic of pathways into the role is it really accentuates basically what you really need to know to really do the role well. And it lets you identify, like, if you're coming from this path, this is the value you're bringing into the role. Like this is the knowledge that will be highly relevant, but it also illuminates what you don't know. Like you need to like shore up this and this is how hard or easy that will be. For example, if you're an EA and you're becoming a chief of staff, what is something that you know that none of those other folks know, you know, what it takes to run a leader's life. Right? To keep the leader focused at the highest level so that they're not having to worry about all the spinning things that are happening in their immediate orbit. You get that critical function. So you bring that into the role and my, my, um, what, what, what an EA doesn't bring, right? So that their, their opportunity to learn is operating more at that higher level, asking higher level questions using language that is then a management consultant. Or maybe a program manager would be more comfortable using, you know, around. You know, all of it, all the higher level things that you need to talk about strategic strategy goals, you know, blah, blah, blah. So that's the opportunity for you as an EA. You have to, you have to use different language and carry yourself differently when you walk into a room, um, because people will, will sense. The difference, whereas, so that's the opportunity for EAs. Like that's something that EAs need to think about if they're becoming a chief of staff, if you're not an EA and you're coming into the role, you're coming in without the knowledge of what it takes to get a leader's world running, you know? So that is the opportunity you have to think about and making sure you've plugged in the right resources around your leader to make sure that their world's taken care of. And then you can turn your attention where, where it should be, whether it's with the team helping optimize and the talent there helping them, or if it's, you know, driving bigger initiatives across the organization. But the way that I talk about, um, You know, you've probably seen, um, Rob Dickens wrote an article a long time ago, 2017, I don't know, 10, 000 hours in a cheapest app role in tech. When he breaks down the three orientations of the role, that article saved my life as a cheapest app. That was one of the first ones I encountered when I decided like to go all in. And it was so grounding for me because it gave me a framework to think about The scopes or circles of influence that I have it in my role, the first being the leader, the second being the team, and then the organization. And just gave me scaffolding just to think about when I wake up today, where should I start? Start with my leader. Is he taken care of? Is he good to go? Okay. All right, next, you know, usually a lot of the issues Chiefs of Staff encounter isn't so much with the leader, it's with who the leader's leading, right? It's that immediate team is usually where a lot of, you know, folks spend a lot of the time as they should. Um, so anyway, that, that, that's how I would approach the pathing question. Um, it's not that some paths aren't legitimate, it's you just have to know what you're going to have to learn to really excel in the role and the gaps of knowledge you need to fill.

Emily:

Well, I think part of what you're touching on is the fact that you can have a diverse set of background experiences and be effective, be very effective in the chief of staff role. So people ask me all the time, Emily, what degree or what career path should I take to get myself to chief of staff? And I'm like, I don't know. Whatever you have so far is, is good because you can use all of your various experiences and pull from, but to your point, you have to know where you're strong and what you're good at, and you have to know what you don't know. And you have to be willing to learn that even though it's scary. And I think in EA, I've had clients who have transitioned from EA to chief of staff and they're like, Emily. I'm in the exact same meetings with the exact same people. And we're talking about the exact same project. They see me as an EA and I go, of course they do, because they've known you in that role. But like you mentioned, Phil, you have to show up differently. So instead of I'm going to take minutes, I'm going to make sure people have their slides and I'm going to reformat the slides. It's asking those strategic questions. Okay, you know, John and Steve and Rachel, I'm hearing, I'm hearing us talk about this. I just want to soundboard that what happens if we do that in 18 months with this team over here, or with, you know, this, this potential new technology in the marketplace, is that worth considering? So you're in that meeting.

Phil:

That's right.

Emily:

Same people talking about that same project, but the way you contribute is

Phil:

wildly different. You're just thinking about, you're asking questions at a different level. Um, and that's what it takes.

Emily:

And I think sometimes it's the perception, right? You have to rebrand yourself, literally. You do. It's a rebrand of, of yourself and your role and how people interact with you. Yeah. As we round out, I want to definitely want to get to, I know you had mentioned early on in the Chief of Staff Roundtable, We kept getting these questions over and over, or these themes kept coming up. So we kind of put them in more of a curriculum, um, kind of a quarterly cadence, what trends and patterns and questions are coming up in round table these days? Are there something like, Oh my gosh, like this is coming up all over the place.

Phil:

Yeah. So just so I understand what you're asking, um, what am I hearing? with our community and the things that matter to them. And how are we using that input to frame kind of the conversation? I love that. So, you know, it's interesting. A lot of it maps to kind of the higher level conversation as the space has grown. So it's, you know, for the longest time, it was like, what is this role supposed to be? And like, we're, we're, we're solidifying what that picture is. The next layer down is, all right, I know what I'm supposed to do. Um, What, you know, how do I, how, how do I do that? You know, it's like getting much more tactical. And so for instance, like our, our themes throughout the rest of this year, um, in Q1, it was all about how to crush your 2024 plan. You know, every chief of staff sat in. Who knows how many hours worth of meetings in Q4 last year, into Q3 and Q4, of building this nice, shiny, robust plan for 2024. You start the year and it's like, okay, we'll see how long this lasts. Um, and so we're like, that's real. We heard it from our advisory board. Uh, you know, which is a, uh, a centralized, centralized, um, a core group in our membership who are chiefs of staff from every major industry category and org size demographic. And they're really the, the. The, the filter and making sure we're, we're asking the most relevant questions in the space that they are providing input and insight into. Does this match against chiefs of staff in your industry? Is this what they're encountering? If not, let us know. And we'll, we'll tweet, we'll tweak the direction there. Um, so I, I did want to mention that because they're a really important part of what we're building at the round table. We're all, we're obviously, obviously we have a lot more seats to fill. So if you're chief of staff and you're like, you know what, I want to help represent and advocate for chiefs of staff in my industry, there's an opportunity for you To be maybe an advisory board member. So we're open to talking about that. But to answer your question, Q1 was all about how to crush your 2024 plan. The three topics we covered was the first one was called all in how to mobilize and excite your team around the plan. So that really had to do with buy in. How do we get the optimal level of buy in from all stakeholders around this plan that we just created. So we talked around strategies to do that. Um, the second conversation was tempo, how to own and execute a business operating rhythm. As you know, that typically is probably the most explicit thing a chief of staff can own. Like, um, and so we talked about how to do that effectively. And then the last conversation was pivot, how to evaluate and adapt your strategy to win. So this whole year, like the last two years have been very high level defining. These are the core functions of the roller course skills needed out of measure success. And it's like, how to do this stuff. Like, how do you actually do this work? This quarter, our focus is the compound effect, you know, why little things drive big results. So as chiefs of staff, we often think, you know, what's the big thing, the big rock I can move today to make impact. And we realized that there's not very many of those because there's probably a leader who's responsible for that big thing. So we're just flipping the script of like, what are the little things that only I am well positioned to do? You know, the only I can really execute against. And the three things we're focusing on this quarter are We just did our session on triaging, how to prioritize and execute what matters most. We just talked about popular frameworks for prioritization for your own work, but also key questions you can ask yourself and your leader and your team about what's the work that really matters, what doesn't, and having, um, ability to navigate that, those dimensions in your org. The second conversation is called Loops, uh, How to, uh, Surface and Solve Big Problems. So this is how, basically, how do you solve problems, like, you know, how do you set up systems and feedback loops to, um, get at that root cause and solve for that. So we're going to be talking about that this month. And then our final call this quarter is called Memo, How to Curate and Deliver Essential Information. We all know the chiefs of staff. Um, we are a reservoir of information, very important information. And so it's basically, what do you do with that? Like, how do you, how do you take what you know and deliver it in the right ways to the right people at the right time? And so we're going to talk about how to effectively do that. Um, so that's, that's how we approach kind of this whole year is we're really focusing on like, you know, where the rubber hits the road in your role, how to do those things well, and I'll just tease. Q3 is going to be all about, I think the name of it is, um, like tough love or tough, we're talking about candid conversations, like how to have really constructive, but candid conversations. Cause that's, that's real at all, or it all matters, right. It's relationships and how to do that well. So it's exciting. So that's the level we're operating. We're talking about now is really. What is it? What is how does this role manifest as practically as possible and providing resources and and insight around doing that? Well,

Emily:

very cool. All right. I wish we had more time because I have so many questions on that on the last couple of topics you mentioned, but um, I will respect your time and let you get back to your busy day. But if, if people want to learn more, let About chief of staff roundtable. If they want to connect with you is linked in the best place to go. We're totally for that.

Phil:

Yeah. LinkedIn. If you want to connect with me, happy to talk about I always like to hear about folks journey in the role challenges they faced and wherever stage they're at, helping point them in the right direction. And if that's membership for the roundtable, we'd love to have you. Um, there's a ton of opportunity for you to learn, but also a ton of opportunity for you to give back and help others find their way. Thank you. Um, cheapest app around table. com. If you want more information around about our programs, we are redoing our website. So, um, look for an updated version in the coming weeks. Really excited about that, but, uh, yeah, DM me on LinkedIn or get our website or heck join the private group. We'll get you a free ticket to our next event and, uh, we'll see you there.

Emily:

Sounds good. We'll have all of those links and information in the show notes. Phil Burns. Thank you very much.

Phil:

Thanks so much, Emily. See everybody.

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