Chief of Staff: The Strategic Partner Who Will Revolutionize Your Organization

Paul Adams interview Tyler Parris

Hello, and welcome to Sound Financial Bites. I’m your host, Paul Adams, as well as president and CEO of Sound Financial Group. Today, we’ve got a unique guest. He’s the author of the book, ‘Chief of Staff: The Strategic Partner Who Will Revolutionize Your Organization’, Tyler Parris. Tyler, welcome to the show today.

Hey, thanks, Paul. I really appreciate you having me.

You’re welcome. Your book, ‘Chief of Staff’, is about being able to create somebody or hire somebody in your organization who becomes this totally different role from what most of us have in corporate America. Before we get into the book and some of the ­ what I know is for savory tidbits that are already applying to our organization could you tell our readers a little bit about your background and what got you the place where you ended up writing the book?

I’m a Hudson certified executive and leadership coach and I left the corporate world about a year and a half ago to start my coaching practice. I had done career coaching on the side of my day jobs for about 12 years, and those day jobs included operations management at intellectual ventures, program management at Advia Inc.,technical editing at Microsoft, and I also had an eight ­year stint in the Marine Corps Reserve as a computer networking specialist. At Intellectual Ventures is where I encountered the chief of staff role. I really had not heard of it before that. I didn’t know what it was for. I know that a chief of staff there was transitioning out of his role and was talking to various people in operations management at the company to find his replacement and that’s how I ended up getting into it and tapped for the role eventually, and I stayed in that role for about 2 years. I worked for the president and chief operating officers at Intellectual Ventures and helped her manage an agenda for the company from the ground level up and also from the board down into the organization.

Right on. How Tyler and I originally met is kind of interesting: ­ he stood up at an organization that we both attend on a regular basis. It’s a prayer breakfast here in Seattle called Kairos. At Kairos, there was an occasion where he had shared what he did, and we do these round table discussion on what our marketplace calling is. He brought up that he coaches chiefs of staff how to hold that role, which is an all-too-overlooked role inside most organizations. He totally caught my attention, so I pulled him aside after, reached out to him and began to ask him a series of questions.

He and I met and I began asking him these questions before he had finished writing the book. I’ve got to tell you that one of the first things that most resonated with me, Tyler, is we talked was this idea that the chief of staff, one, is not a fancy name for an EA, and it sat with me after that call. This idea that the chief of staff is somebody who holds the executive’s or owner’s concerns and then operates holding those concerns within the organization. Could you just pick up there and go back to what you shared with me a year and a half ago?

I talk a little bit about this in the book, of course, that there’s a short answer to what a chief of staff is. I think it’s really a catch-all role that’s filled with somebody that has exceptional organizational skills, people skills, who handles all manner of tasks that are not necessarily covered by an existing member of the CEO’s staff or tasks that go across different departments and functions.

You used the term ‘translational ability’­­ when you talk about somebody being able to move across roles in the organization, which I had to ruminate on for about a month to figure out.

Exactly.

But is that what you mean when you’re saying the ability to talk across all the different departments?

I think so. There are certain tasks in your organization that you might give to your sales departments, certain tasks that you might give to your finance departments, certain tasks you might give to your HR department but, in many cases, there are tasks that don’t neatly fit into a particular department’s purview and you need somebody to be able to manage those special projects. You need to able to have somebody who can work either within the departments or understand where different departments are supportive of a particular task or work stream that needs to get done or where they’re resistant to it and find out what that resistance is about and help them work through it so that everybody’s moving in the same direction.

What I think the translational ability really is about is taking the CEO’s intent and passing it down, making sure that gets carried out in the organization the way the CEO intended for it to be. I think, sometimes, CEOs think that when they say, “Do something,” they’re expecting everybody to jump and just get it done and that doesn’t always happen. Because the different departmental leaders have their departmental focus, that may or may not jive with exactly what the CEO said, or it may be new and they’re not quite sure if it’s A or B that the CEO was really talking about when this directive was given. So the chief of staff can be the person who stays behind after the CEO says, “Let’s get this done,” and talks to the staff about what that really means, how are we going to make it functional, and, in that way, they serve as that translation layer.

Yes, and not just, “What are we going to do to get done?” but, “What did everybody understand?”.

Exactly. Clarifying what was heard, clarifying what was intended. That’s a lot of clarification and checking the assumptions in the room, that sort of thing.

For our readers, one thing that showed up for me and certainly was there in reading the book is that what most people think this chief of staff role is for companies that are bigger than mine. The thing that I had that was a bit of a luxury was the opportunity to get to know Tyler a little bit, a little bit about his philosophy before reading the book so I didn’t know any better. I came back to my organization and started thinking about the conversations Tyler and I had, and I began saying, “We’re going to have a chief of staff.”

I rolled it out to a few key people and we started talking about it, started building a role based upon ­ that conversation we had that day and a couple of follow ­up emails you had sent me. What I discovered is that it set loose a whole different set of performance from what we had before and in two ways. One is it allowed the person who was my executive assistant prior, the level of horsepower she is. Number two, it gave her a role that she’s continuing to live into and step up to. She still has learning to do in that role but just giving her the authority and changing the way I even coach her to be a chief of staff has changed.

One of the ways I related to it was you had talked about the chief of staff’s role to hold that owner’s concerns. What I realized what I had related to my EAs in the past is that there are tasks that they were to get done for me consistently, but if somebody came to them with a concern, their answer would be, “Well, I don’t know. We’ll have to ask Paul.” Now it’s becoming, “I don’t know that answer, but Corey does, our Vice President, or Sherry,” and she’s directing traffic now and, most importantly, directing away from me and protecting me, all the while, my concerns.

Something else that you said in one of those conversations we had ­ ­ was that idea that if something is weird in the company, it has a cultural thing going on, or there’s some key player that’s upset. Then it’s the ability for that chief of staff to just be able to sit down, have a cup of coffee with that person, take him out for a beer, and say, “What’s really going on?”. You talk a little bit about that and how they act as a buffer between the owner and those people.

Well, the chief of staff trade sin confidence, right? I mean, our political capital, if you want to call it that, involves keeping certain conversations confidential and that sort of thing. So, for the chief of staff, I think it’s really important for them to be able to sit down with department heads, or even people further down in the organization who are responsible for getting work done where they might be running into issues, as you said, to figure out what’s really going on there. You want to hear the no-BS version of the story, what they’re really concerned about that they might not tell the boss. The boss doesn’t want to hear no or they perceive that the boss doesn’t want to hear no, even though, in reality, sometimes the boss doesn’t mind hearing ­­ it wants to know if it’s a bad idea. But he wants to hear it in a certain way, so they may not be very comfortable messaging to the boss when they have objections or resistance. I think the chief of staff enables them to figure out how to get stuff done and also if there is something bubbling up that the CEO needs to know about, the chief of staff can, in a way that protects that person’s position, also share that information in a way that it’s received. The CEO can actually make better decisions or different decisions knowing what reality on the ground is. Does that answer your question?

Yes. The ground truth, as they say in the military or Susan Scott­ — author or ‘Fierce Conversations’ — who does a great job of talking about what is the ground truth.

This last year, we got over 40 total folks between advisers and staff and what I noticed is there’s conversations that go on that I can’t be a part of. If I could be so bold as to give a slight modifier, the chief of staff trades in confidence and competence. Meaning I, as the owner of the company, have to feel confident enough in her to not need to know exactly what was said in confidence to her. So it’s this and I need to know that I can say whatever I need to say to my chief of staff and they are not going to go out and bleed those exact same words but move with the intent as you so aptly put it.

The other thing that I realize is it’s created a protection for me, meaning there’s things that I used to, for a lack of a better way of saying it, how we’d look at the hierarchy in your organization. You’d walk out to the front line, and you’d say something to somebody like: “Why isn’t this getting done?” and now suddenly, somebody who shouldn’t report to me is suddenly telling me about tasks they got done.

Right.

Even though you were trying to help them to do their job better, now suddenly, there’s this loop of communication that’s coming back to you. You as the owner or executive, that shouldn’t be coming back to you, and now I’ve got to go break affinity with that person to stop the lines of communication. Versus having somebody that’s the chief of staff where I can, if I ever have to go to the front line and do something, immediately tell my chief of staff and they intervene and say to that personnel, “By the way, when you’re communicating about that, you send that to me.” So it’s keeping me out of those conversations as well.

There’s a section of your book that’s called ‘­ I am sorry, I don’t remember ­ where the box is’. The boxes in the book are…?

The call ­out boxes are ­­ the universal competencies.

Universal competencies. Those are the kind of thing that for me, as an owner and entrepreneur, I am able to go back to in the book. Even reading it once, then working with my team to implement what’s in the book and then all I have to do is go back and read the call ­out boxes to revisit the information over time. That was a key part of the book for me, this idea that the chief of staff’s role is going to be to keep me in my specific skill set which, right now, also acts as my EA, but the objective is to move her to a full on chief of staff.

I mentioned earlier you’re going to read Tyler’s material and you’re going to see that he’s really targeting that chief of staff conversation for much larger companies. Some salary type studies you had done, you interviewed over 60 chief executives and C-­suite executives for the book. Some of the companies were Microsoft and who else?

Microsoft, Boeing, Intellectual Ventures, SCYNEXIS, Barclays, Banamex.

All huge companies, and the one thing I thought when I read the book was this was all too big. I’m of the belief that if you’ve got over 40 people and you plan on getting bigger, you probably have to have a chief of staff to do that, maintain your freedom and autonomy as an owner and not be trapped by your company.

Well, you touched on an interesting point there because one of the things I try to tackle in the book is: is this there an ideal size or organization dynamic where it really starts making sense? I tried to find what I called the tipping point but I couldn’t really find it in a formula. But what a couple of folks have hinted at is exactly what you’re talking about: when you can’t remember everybody’s name in your organization, it’s time to start thinking about a chief of staff. You may not be as close to the ground truth ­ ­ as you used to be or you think you should be, and I’ve heard that from a couple of folks in my interviews. A woman named Melissa Wingard ­Phillips wrote a paper a couple of years ago or a guest blog post on my small organization. She’d used the chief of staff and she points to examples like Reid Hoffman at LinkedIn using one when LinkedIn was a startup. I think it was the advice of a Greylock partner board member and that sort of thing. There can be a number of good reasons that small organizations can use chief of staff as well as not just a big company tool.

We’ve noticed that people relating from the outside differently with that role. People are relating on the inside of our organization differently to that role and it doesn’t mean it’s easy. Whether you hire somebody in from the outside or you promote through the inside to a new role that’s never existed, you end up with some amount of conflict or jealousy. You’ve talked about some of the things that a staff person can do or a CEO can do to facilitate that if something goes wrong. Would you mind speaking about that a bit?

Well, I think it can happen anytime you promote somebody. You can have some dissension in the ranks or maybe resentment toward that person for carrying new responsibilities. Perhaps especially where you have an executive assistant which is often associated with a traditional set of very limited in scope responsibilities: filing, reception ­type work, concierge for the CEO, filing expense reports, and things like that. There are these traditionally associated tasks with the executive assistant role and when somebody can step out and beyond that into broader leadership roles, it can cause some people to either question their ability to do the new job or be jealous that they’re doing it.

There are things that the individual can do like just working with their peers at some level to address those issues, not respond in kind in a number of ways. If somebody’s sabotaging your work or spreading rumors or something like that, you don’t respond in kind. You play the better person. But, as far as the CEO’s role in that, at least to some degree, is facilitating that a little bit. You can set up a situation where people who are at odds can talk to one another and do what I would call peer coaching where they talk about each other’s strengths and areas for improvements. They work together on it because then your star performer stays motivated and finds ways that they can ­­ finds areas for development that can keep them a star performer. Then your person who didn’t get the promotion into a broader leadership role can find out why and maybe learn from their experience and move on. At the end of the day, that’s what you want for all of your people; to be more engaged in the roles that are most effective for them and to move the organization’s goals along.

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Paul Adams is a Registered Representative and Financial Advisor of Park Avenue Securities LLC (PAS). Securities products and advisory services offered through PAS, member FINRA, SIPC. Financial Representative of The Guardian Life Insurance Company of America® (Guardian), New York, NY. PAS is an indirect, wholly-owned subsidiary of Guardian. Sound Financial Group is not an affiliate or subsidiary of PAS or Guardian.

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