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  • Writer's pictureZaharo Tsekouras

Inside the Office of the CEO with Dan Glenn, Chief of Staff @ GoodLeap

Recently, I had the opportunity to sit down with Dan Glenn, Chief of Staff at GoodLeap, a sustainability fintech that has raised $800M by notable investors including Brookfield, WestCap, NEA, and Mubadala Investment Company. Here’s a glimpse into our conversation and Dan’s unique perspective on the Chief of Staff role:

Z: Your career journey is anything but standard. You entered the Navy, pursued a Master’s degree in China as a Schwarzman Scholar, ran a family office after that, and finally ended up in the Chief of Staff role. Tell me more.

D: My career path is psychotic if you look at it in reverse. I started my career in the Navy as a Special Operations Officer — also called Explosive Ordnance Disposal — which is where I really cut my teeth. I have a theory that where you cut your teeth trains you how to think about the world. For me, bomb diffusers are problem solvers. Defusing bombs with the military, deploying overseas, doing special missions…it’s a radical place to start a career.

When I left, I had no idea what I wanted to do. I always thought of going to Harvard Business School and then I heard about the Schwarzman Scholar program in China, so instead of getting an MBA I got a Master’s in Management there, which in a sense, couldn’t have been more different than an MBA given the focus on Chinese culture, history, and language.

Even after the Schwarzman program, I still had no idea what I was going to do. But I knew what I was trying to avoid, and that was finance, tech, and San Francisco. Finance sounded a lot like the military — a little “bro culture-y”, very intense — and I had just come out of an extremely intense and universally masculine culture. I didn’t want that. And tech felt like vaporware.

And boom. I get a call from basically all three of those things, which is, hey, we got a job for you, it's running an investment firm for tech royalty out in San Francisco, and we want you to be the CEO. When I interviewed with them, they asked me “what can you do?”, and I said, well, I'm a MacGyver — you can just send me into any problem and I’ll fix it. So I got through to the rest of the interviews, we had a good mind meld there, and before I knew it, I was moving to San Francisco. So I had found my way to both tech and finance IN San Francisco — all the things that I was trying to avoid! After that, I had the opportunity to join a sustainable fintech company, so I went from being CEO to Chief of Staff. It’s a career trajectory that doesn’t make sense.

Z: What kind of career path would have made sense?

D: It should have been in reverse. It should have been: join a startup where you’d hopefully have some measure of success, then go to a bigger company that’s growing like crazy, and then have some type of exit and get into a family office in a leadership role. That would make sense to me. It’s been the opposite of 1, 2, 3, but maybe 3, 2, 1 is what leads to blast off.

Z: So you’ve been the Chief of Staff to the CEO at GoodLeap for a few years now. What’s your take on the role? What should aspiring Chiefs of Staff know about being a Chief of Staff before getting into it?

D: Chief of Staff is a crazy role. There are so many categories of a Chief of Staff, so many styles, like everything from the air traffic controller who’s preventing things from crashing all day long, or an EA+ that’s more focused on logistics and calendaring. But they're a master of all these moving things.

EA+ is the starting point of what a Chief of Staff can be and then it kind of moves up from there. You can be this project manager where you are in on major initiatives where you're helping plan, you're helping be the connective tissue in between all the different executives, and then you start getting up into a “mini-me” or CEO-in-training where you can channel the CEO or founder’s voice, finally moving up into almost an avatar of your CEO. At that point the CEO can zig and their Chief of Staff can zag.

Ultimately, I love the chaos of the position. It is deeply, deeply chaotic. You're constantly trying to pull yourself out of reactivity and get to proactivity so that you can actually do some planning. But it’s false to believe that you're ever going to be fully proactive. Because as we used to say in the military, the enemy has a vote — they get to shoot their guns, too.

You’re proactive until a competitor introduces a new product into the market, or a collaborator decides that they’re going to do something differently, or the candidate that you’ve been recruiting for six months has another offer. And then the Chief of Staff becomes head firefighter because the CEO has five meetings and we can cancel two of them, but we can't cancel the other three because they're so high priority. Well, who's fighting this fire? The Chief of Staff is the one who’s really coordinating the firefighting efforts.

Z: Would you say that firefighting is a core aspect of the Chief of Staff role then?

D: Yes, there are three main categories of work. The first is this administrative function, which is a constant. The calendar is constantly changing so there’s this coordination element to the work and I probably spend up to a third of the time helping other admin folks manage that.

The second is what I call being both a Chief Firefighter and Chief Rubik’s Cube Officer. As a company grows and expands, the problems that get handed up to the CEO are different than they used to be. Sometimes these problems are fires that need immediate attention, and the Chief of Staff can put on their cape and go save the day. Then there’s another version of that problem which is that it isn't necessarily a fire, but somebody comes in and drops a Rubik's cube on their desk — it’s not urgent, but it’s a problem to solve. Eventually, all the easy Rubik's Cubes are handled a few layers down and only the hardest ones land on the CEO’s desk.

And the last third of my time was spent on strategic planning, a big part of which was keeping people inspired and morale high, but also talking to them about where we’re going. The constant tension here was that you want to spend time on strategy but you’re constantly getting pulled down into the minutiae of the day-to-day.

Z: What was it like stepping into the role? How did you find your rhythm?

D: There is a right way to step into the Chief of Staff role, and almost no Chief of Staff will ever have that luxury. I was thrown into the fire. I found my flow by trying to grab as many things as possible, and this gets into my philosophy as to what makes a good Chief of Staff — it’s the ability to say to your executives “that's already done”. That's the highest form of a Chief of Staff. That's when people are like, “Wow, we got a Chief of Staff here”. You're taking friction away and you're anticipating needs. The second highest form is “let me take care of that” and then the lowest form is, “wait, what do you need me to do?”.

Z: Do you think there are common misconceptions that executives have about the role?

D: As with all things, you get out of a Chief of Staff what you put into a Chief of Staff. There there needs to be investment. One of the things that I see consistently is that the executive sees the Chief of Staff as quite static, and they aren’t. The Chief of Staff ramps up in the first six months and find their stride at the 12-month mark, and then by 18 months they’re at full power.

It's a shame that the 18-month mark is often the end of a Chief of Staff’s time at the company in that role, right at the time when the role has become the highest form of itself. The Chief of Staff has this very short shelf life of ideally 18 to 36 months, and almost nobody sticks around that long. A big part of the reason why is because it's so intense. And what’s funny is that the real rewards don’t come for the first 12-18 months anyway. If only there was a way to make this rule more survivable. Perhaps mentorship can help that.

It’s a real challenge stepping into this role. In many cases, you’re dropped into a team where people have been there since the inception of the company and are industry veterans, and you go “hey guys, I'm 10-15 years younger than all of you. I'm inexperienced in this industry, and I'm even more inexperienced in your specific discipline and all the tactical and operational bits that you obsess over every day” but you need to be smart and dynamic enough to be helpful to these people. That is crazy hard! Crazy hard. Who would sign up for that? That's dumb.

Z: And yet people are chomping at the bit to get into the Chief of Staff seat.

D: Yes, because there are people who are young, scrappy, hungry, really talented, and they know that the Chief of Staff pathway is a secret pathway. It's a massive step forward. It's an accelerator that can launch a career and launch it way, way faster because of the access you get. Because you are tap dancing onstage in front of the heavy hitters and the people who decide who is going to be in charge of what next.

Z: What tips would you give aspiring Chiefs of Staff?

D: I would say to aspiring Chiefs of Staff “you're right”. You are correct in thinking that the Chief of Staff role is where you want to be. Now buckle up. Because it's going to be way more than you thought it was. It is crazy intense. It is wildly challenging. It's a lot of fun. There are incredible rewards for those that are strong enough, swift enough, and smart enough and who can endure, but it is not for the faint of heart.

Z: On top of all that, it can be a “lone wolf” kind of role that lacks natural mentors. What are your thoughts on mentorship?

D: If you don’t have it, you will fail. You need to find it internally and externally. Otherwise you will not be successful, I think, full stock.

External mentors probably already exist in your network. Who are the wise sages that you can call for help? You need to develop them within the company as well once you get in. I could not have been successful in any of my roles if I didn’t have executives that were willing to spend time with me and on me, and then external advisors that I turned to multiple times a week in both formal and informal ways.

I would not have been able to learn the industry or understand the business fast enough, nor be an impactful player without them investing in me, which is what mentorship is. I was fortunate because mentorship was part of the culture that already existed, but relationships are something you need to develop yourself. You need to be able to reach out to somebody who's 10 or 20 or 30 years your senior and say “I need help”.

And a good mentor will protect you from so many own goals. They will protect you from yourself because ultimately, this game is not played against other people: it's played in front of a mirror.

How to Learn More

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