Building a Stronger Business: The Impact of a Chief of Staff on Strategic Growth

Intro: Broadcasting live from the Business RadioX studios, it’s time for Women in Motion. Brought to you by WBEC-West. Join forces. Succeed together. Now, here’s your host

Lee Kantor: Lee Kantor here. Another episode of Women in Motion. And this is going to be a good one. But before we get started, it’s important to recognize our sponsor, WBEC-West. Without them, we wouldn’t be sharing these important stories. Today on Women in Motion, we have Keziah Wonstolen with Vannin Chief of Staff. Welcome.

Keziah Wonstolen: Hi, Lee. Thank you for having me. I’m excited to be here.

Lee Kantor: Well, I am excited to learn what you’re up to. Tell us about your firm. How are you serving folks?

Keziah Wonstolen: So, at Vannin Chief of Staff, we provide chief of staff talent in a couple different ways. So, we have a fulltime search. We will provide interim chiefs of staff, as well as we train and coach up chiefs of staff that are existing in the business. So, we work with, typically, CEOs and founders that are running businesses 20 million and above, and we can service… we provide talent and coaching across those three areas. We’re based in Denver, and we’ve been doing it for about five years now.

Lee Kantor: Well, do you mind if we get to the beginning, like people have heard-

Keziah Wonstolen: Yeah.

Lee Kantor: … of the term chief of staff, but maybe they don’t really have an understanding of what are the kind of the role and responsibility of someone’s chief of staff.

Keziah Wonstolen: Yeah. So, a chief of staff is someone who sits to the right of the leader and is able to do three things in how we defined it at Vannin Chief of Staff. They’re really there to align and execute and amplify that leader. And that can look differently across different sizes and scales of businesses. So, at Vannin, we’ve worked with companies from solopreneurs, providing them a chief of staff, all the way up to fortune 100 companies. And you can imagine that that chief of staff, when they go to align, execute and amplify that leader’s vision, it looks different across those variety of different companies.

In reality, what they’re doing, from an aligned perspective, they’re running all of your strategy strategic planning. So annual quarterly planning. From an execute perspective, they’re running the operating cadence of your business. So, setting… You know, with that strategic plan, they’re developing an operating cadence, tracking KPIs, establishing a KPI or OKR framework, and then running that operating cadence. They’re also under the execute bucket. They’re really running your special projects. So, as a leader of a company, things come up all the time. They’re not predictable. And so, to have someone to really help you execute and strategically project manage those initiatives, it’s really important. And then, amplify what they’re really doing is trying to amplify the leader across their impact, influence and communication. And that’s really what the chief of staff role does. And we can talk more about it, but that’s at the highest level.

Lee Kantor: So, what would be the difference between a chief of staff and an executive assistant or a chief operating officer? Like where are the lines drawn?

Keziah Wonstolen: Yeah, that’s a really good question. And it depends on the size and the scale of the business. But what we generally find is that at around 10 million, a hundred people, either one of those milestones that you hit, you can have a chief of staff and a COO together. They start to delineate the responsibilities. But under that size and scale, you can have any… you don’t need both essentially. So, a COO and a chief of staff are playing the same role. We see companies choosing the chief of staff role because it generally comes in as a director level. It’s a little bit more moldable than the COO. You can aspire. You can have that person on a trajectory to become the COO, but you’re really bringing them in to, kind of, use them as like a leadership path that they can go on.

So, generally, the two core differences we see as you begin to have two of the same, like you bring on a COO and a chief of staff, is that the COO generally has the talent reporting to them. So, they own all the operational talent, they own the cost metrics, they own the P&L. That’s what a COO is doing versus a chief of staff then really stays aligned with that align, execute, amplify, running annual strategic planning, cross-functional project management, and then the amplify piece. That’s the difference between the COO and the chief of staff.

Between the EA, we generally don’t see a lot of overlap because it’s a completely different role. As you, kind of, just heard me talk about with the COO and a chief of staff, those are much more similar in the way that you need to… that we kind of think about the role. And admin is really… it’s someone that you bring on. They’re very, very important. But if you’re looking for someone to help you in a transactional way, right – emails, calendaring, logistics, travel – if you think about as a leader, you need to outsource certain things to elevate you to make sure that you’re spending the right time on the right things, the way I think about the difference between EA and a chief of staff is that if it’s a strategic thing you need to outsource, a chief of staff is a really good partner. If it’s transactional and it’s repeatable, then an EA or an admin is a really good partner that you can use. That’s the difference. We get that question all the time, and I think all of them are really important, but just kind of depends on what you need in the business.

Lee Kantor: Now, is there any advice you can give to firms that maybe aren’t large enough to hire you or afford a chief of staff today? Like, what things can they be doing to get kind of chief of staff results from their team? Or is that even possible?

Keziah Wonstolen: Well, one of the things we like to think about when we first start talking to a client is… and usually our clients are CEOs or leaders of organizations, we’re really looking at where should they be spending their time. So, we use this idea called the Zone of Genius, if you’ve heard of that. It’s by Gay Hendricks. But really, what is… where should you be spending your time in the business? And usually there are things that you should be… you know, that you’re excellent at or that you really thrive at doing, or really the business needs the leader to be doing. So, we start there. And then we look at the rest of the work that they’re doing, and then we start to see, well, where should that go? Who should own that? And if it’s a chief of staff, that’s great. But sometimes it’s not. Sometimes it is, like you said, an admin, or a CFO, or another person on the leadership team. But that’s where we always start with our clients of going, where do you need to be spending your time? And then, what falls out after that? that’s not a priority, but still really, really important to run the business?

And that’s how I would… you know, if I’m… if you can’t afford to bring us on, that’s what I always really recommend doing and starting there to figure out what are the bulk of activities that you need to then figure out who’s going to own them and then delegate within your team those areas. Because as a leader, you need to constantly be thinking about the strategic vision of the business versus, you know, the details. And that’s what a lot of leaders struggle with, is getting sucked back into the details and unable to sort of elevate them out to really focus on the things they need to be focused on.

Lee Kantor: Now, you talk about the term “zone of genius.” Is that something that a leader can kind of self-assess, or is this something that requires kind of fresh eyes to look at because they may not really understand what is truly their zone of genius and where they really need help?

Keziah Wonstolen: Oh yeah. I would recommend reading the book. It’s called The Genius Zone. And then, they can kind of read that and that’s a really good start to figuring out, you know, when you’re really thinking about how… if I’m growing a business, no matter what the size is, where… There’s always the best use of the leader’s time. Arguably, the… your leader, the CEO and the leadership team is some of the most expensive resources you have. So, prioritizing where they’re spending their time is really, really important. And that’s a good… You know, if a chief of staff is out of budget, then maybe start there and try to figure out how are we making sure that people are spending the right time on the right things?

Lee Kantor: And then, I guess looking back at your calendar is a good way to seeing how well you’re adhering to what you’re learning.

Keziah Wonstolen: Yeah. I mean, one of the things that we talk about chiefs of staff doing is strategic calendaring. So, they’re not going to be your admin, right. They… You know, I would suggest getting an admin if you need calendaring because, usually, chiefs of staff are more… you know, they cost more to bring on. But if that’s really… You know, you start there. A lot of what we do is, you know, at the beginning of an engagement, we kind of say, “Hey, what is the vision of one, three and ten years out that helps the chief of staff align – going back to kind of our framework around this role – align with the leader and what needs to get done that year. And so, they can help strategically calendar that leader with the admin to go, “Hey, this is our quarterly milestones. These are the metrics that we need to hit this quarter,” “Hey, you’re spending all of your time on something completely unrelated to that.” How do we align that, both just at the CEO level, but also across the leadership team? That’s really important. And that’s how we typically work with admins. And I think that’s why, again, they’re really important in the support of a leader.

Lee Kantor: And then, part of your role is not only kind of becoming that chief of staff for the organization, but it’s either training a new chief of staff or helping someone become a chief of staff.

Keziah Wonstolen: Yeah. So, what we… Depending on the size and the need in the organization, we can support in… one is just we have a recruiting business that you can hire us, and we will go, and we will find… we have a network of 5000 people. We go out and we recruit from that and we work with you, given our level of experience, in the role. We really try to customize that chief of staff role for you as a leader, and then we will go out and find that. Generally, we’re… we can place within 30-35 days. And that’s because we know the role, we know the people, we know the network, and we can do that quickly for you. So that’s a fulltime chief of staff.

If you don’t… typically, we see people doing interim chiefs of staff if they don’t really know what they need yet, but they want to trial the role. And so, that’s usually where we need to get in quickly. So, we have a team of 13 people in Denver and those chiefs of staff will go in for 6 to 9 months period of time. And I like to think of them as like the Navy Seals of chiefs of staff. We can go in, diagnose, get in the business, set up a… you know, what we just talked about, like operating cadences, KPI frameworks, get that rhythm of business running for you, and then try to figure out, “Well, what is the longer-term solution? Is it a fulltime chief of staff or maybe it’s something else, right? We’ve done engagements where in reality, it really was they needed a CFO and an admin at the end of it, but really took that, bringing in an interim chief of staff to sort of diagnose, and then figure out a path forward for that leader.

And then, if you have someone existing in your organization that you think would be an excellent chief of staff, usually their head of ops, they’re kind of rising leaders within the organization, we have a framework, we call it the Chief of Staff Accelerator Program, that we then train the chief of staff up in to be excellent because one of the risks we run with this role is that it’s not clearly defined when you bring the person in. And what we found over the years, because our leadership team has 40 years of experience in this role, what we’ve learned is that if you don’t have a framework as a chief of staff, you run the risk of just being dilutive across all of the things that need to get done. And that’s not a good match for the leader. It’s not a good fit for the CE… the chief of staff. And that’s what our framework does is bring that structure to the role that a lot of chiefs of staff just don’t have.

Lee Kantor: Now, what are some of the symptoms that a leader is having where getting a chief of staff would be the right solution, but they… you know, maybe it’s not even on their radar to consider that role?

Keziah Wonstolen: Yeah. So, we get pulled in for lots of reasons, but one of the biggest reasons is that CEOs are really struggling to be strategic, to get ahead of the business. So, you know, if you think about the role of the CEO, it’s really to guide and lead the business, but a lot of CEOs get sucked back into the weeds of running the day-to-day, whether they have… you know, they’re struggling with their leadership team or, you know, certain aspects of the business, but they cannot get ahead. And that’s usually when we get pulled in where we need to just elevate, support the elevation of a leader. We get pulled in by board members, we get pulled in by the CEO or the CFO, who has a lot of visibility into kind of the ways of working of the leadership team. That’s one example of why we get pulled in.

The other reason we get pulled in, especially on the interim side, is that they just need a good kind of like athlete in the business, right, that we… projects are being delayed. We need someone in there to sort of PM and make sure that those projects are on time and on target. And that’s how we drop in, a lot of the times, an interim capacity. There’s been a couple studies done on the way CEOs spend their time, and there’s some really interesting facts that… I can share the study, but an average CEO works over 63 hours a week. They, 70%, report no time to focus on strategy, and 36 to 40% of them are always in reactive mode. And then, again, there’s this stat that says that 58% have imposter syndrome and stretch beyond their abilities.

There’s a lot of reasons that we’re seeing CEOs in this way at this point in 2024, and that’s to do with like the changing technological landscape with AI coming on board, there’s post-COVID, there’s the political landscape. There’s so many reasons why being a CEO is so much more complicated than it used to be. And that’s why we’re seeing the rise in the trend of the chief of staff role within organizations.

Lee Kantor: Now, about what percentage of organizations of the size you serve have chiefs of staff?

Keziah Wonstolen: Well, the ones that we serve have them because-

Lee Kantor: Right. Obviously, yours is 100%. But out of all the universe of businesses that size, what percent have chiefs of staff?

Keziah Wonstolen: So, we see them a lot. I mean, I would say a lot of the time. And I don’t have the exact percentages. But in tech, professional services, you know, you’ll see them in government organizations, as well as political organizations, they generally have this role, and it’s become more of a blueprint role in the last five years. When we started the company in 2020, a lot of people didn’t know what this role was. And now, we get calls, you know, on a daily basis going, “I need a chief of staff. I know I need one,” whereas five years ago, it was a little bit more inquisitive of like, “What is this role? How can it help me?” And so, in those industries, we are seeing that it’s usually a blueprint role on the org chart. Emerging markets that we are seeing right now are really around like manufacturing companies and scaling large enterprise professional services. More and more, we see this role. And, you know, I personally… clearly, I’m a fan of it. So, I could argue with any leader anywhere could really benefit from this role.

Lee Kantor: So, why was it important for you to become part of the WBEC-West community?

Keziah Wonstolen: I’ve always been passionate about women in business since I started. My background was at a management consulting firm, and I always found a way to get involved in how do we support women scaling companies? You know, in the last five years, I’ve gotten involved in investments and angel investments with women, and how do we continue to elevate them? And so, for me, as a majority owned women business, it was really important to be a part of WBEC-West only because they serve to elevate women and business across North America, which I just find really exciting to be around. My first interaction with the group was at an event, you know, a few years ago. And I just remember being like, “This is incredible.” The amount of support they’re able to provide women and the connection they have into corporate enterprise and government is phenomenal as a woman-led business to have that opportunity.

Lee Kantor: Now, what are some of the qualities that make a good chief of staff?

Keziah Wonstolen: That’s a great question. We find that there are three types of chiefs of staff, and I call them archetypes. So, when you start to look for a chief of staff, you’re looking for one of these three. And there’s the operator, which is essentially the junior CEO that we talked about at the beginning of the call. Then, they manage the operating cadence, goal setting frameworks, more of kind of like that junior CEO, head of operations type person. The strategist is really around being a thought partner, advisor to the leader. They support the alignment and execution of all cross-functional projects. And then, you have a proxy. And that proxy is really an extension of the leader that can, you know, replace them in meetings, you know, just that they could replicate that leader. We generally see more senior chiefs of staff acting in that capacity.

So, across those three archetypes, there are different things that are important, but the common threads that we see that make a good chief of staff are they have really high EQ. They are very, very good at building relationships because a chief of staff generally doesn’t have direct reports. So, they have to get and, you know, coordinate work being done by building relationships with people, and it’s really important. They’re very, very good communicators, and they’re excellent project and change management. Generally, we see good chiefs of staff being grown up in their career as, you know, project or change managers, because that becomes so important as you’re organizing and coordinating the vision of a CEO.

They’re also, generally, problem solvers and curious, and they’re ambitious in their profile. And so, one of the things I always guide CEOs, if you’re going to hire a chief of staff, you need to have a career path for them thought through, right? It doesn’t have to be very specific, but you need to be… this person generally will stay in the role for 2 to 3 years, and then will want to move on, and it’s really a good way to kind of create a leadership funnel for you if you want to move them into a leadership opportunity elsewhere in the business.

Lee Kantor: Is there a story you can share that maybe don’t name the name of the company, but maybe explain this, the challenge they were having where they called you and you were able to help that organization get to a new level?

Keziah Wonstolen: Yeah. One of the stories that I’ll highlight, and I have a couple, but one was that we had a client that was struggling to transition out of the role that they were playing. So, they had the role as the leader of the organization but, really, it was time to move on to their next plan, their next move onto the board. So, what we did, they brought us in as the chiefs of staff to really stabilize the leadership team, to stabilize and build the operational infrastructure before they could pass it on to a new leader. And that was the call that we got is going, “Hey, we need to, basically, stabilize our operational infrastructure. We need to create an operating cadence, a predictable operating cadence of our business that will allow a new leader to take on and not sort of immediately drown in all the things that needed to be fixed.” So, that’s why that particular client called us in. And they were able to, within the nine-month period of time, successfully transitioned to a new CEO, move on to the board, and our chief of staff stayed in there, and then handed off the role approximately three months after that. And it worked. It was really great. It was a great use of the chief of staff role.

Lee Kantor: So, what do you need more of? How can we help you? Do you need more chiefs of staff? Do you need more board members to know about your service? How can we help?

Keziah Wonstolen: So, we always open the conversation to folks that are interested about how a chief of staff can help them. So, whether you’re a leader, a board member, a CEO, or even, you know, in the C-suite of a company, and you think that the chief of staff role could help you, we have free 3- minute consults that we offer. And we… you walk away with what is the right… you know, given the company size and the situation you’re in, what is the right type of chief of staff that we want to look for now, and is it a good fit? So, we offer that for free. You can go to our website at vanninchiefofstaff.com and do that. And we also love getting to know chiefs of staff or aspiring chiefs of staff. If this role has ever been interesting to you, we want to know you. And so, you can go to our website and connect with us to make sure that you’re getting all of our role opportunities that we share out to our community. And we host events specifically in Denver. And those are the two ways that would be really helpful.

Lee Kantor: And if somebody wants to learn more one more time, the website or the best way to connect.

Keziah Wonstolen: Yeah, it’s vanninchiefofstaff.com, if you Google vanninchiefofstaff.com but that’s where chief of staff, we will show up and that’s the best way to connect. Or you can send an email at hello@vanninchiefofstaff.com. And we will get back to you within a day.

Lee Kantor: And that’s V-A-N-N-I-N chief of staff dot com?

Speaker4: That’s right.

Lee Kantor: Well, thank you so much for sharing your story. You’re doing such important work and we appreciate you.

Keziah Wonstolen: Thank you so much for the opportunity to be here.

Lee Kantor: All right. This is Lee Kantor. We’ll see you all next time on Women in Motion.