Chief of Staff 101

I’ve lived many lifetimes over the course of my career—I’ve been a programmer, a lawyer, a political strategist, an Executive Director, a Diversity, Equity, and Inclusion leader. I’ve worked in government, finance, boardrooms, and tech.

Today, as Chief of Staff to the CEO of GitHub, the question I get most often—three times today alone—is this:

“How do I become a Chief of Staff?” 

The thing is, there’s no linear path to the role—no one singular way to become Chief of Staff, or even one singular definition of what the role is and does. To help amplify what I think it takes to become a Chief of Staff, I looked back over the twists and turns of my career to compile a few lessons, in case it helps you—or someone you know—chart their path.

The first thing to know is that leaders hire Chiefs to solve a problem. I’ve served as a Chief of Staff three times in my career. The problems I’ve been hired to solve have spanned across a multitude of areas, including communications, customer engagement, fundraising, staff management, operations and beyond. And in most cases, the leader is looking for someone to solve cross-functional issues that don’t have a straightforward solution elsewhere on the org. chart—someone with a certain skillset that alleviates the problem they face. 

For example, if the leader needs assistance with communication, they might hire someone with a comms background. If they need to shore up their team with a specific technical skillset, they might seek out a former director, VP, or subject matter expert in that particular technical area. Of course, they might also just need someone to help them get sh!t done all over the place—in which case, they might look for a former executive assistant or business operations expert. But from my experience, the most sought after Chiefs of Staff are those that have a breadth of knowledge across a wide-variety of business needs. It’s a swiss army knife type role, if you will.

So if you want to become a Chief of Staff, you have to start by identifying your organization’s problem. And then show leadership that you’re the solution. If you’re interviewing for a role as a Chief of Staff at another company, a few useful questions to ask are: “What are the business’ biggest pain points?” and “What keeps you up at night?” The answers will help you hone your sense of the problem.

So that’s the what. Then there’s the how. When it comes to their approach to the role, Chiefs typically exist on a spectrum. On one end, you have those who are very service-oriented. They take direction from the leader—and then execute. These are the swiss army knife people I mentioned above. 

On the other end, you have those who are consultative. They approach the role as senior advisors, lending insight to strategy and decision making. Those are typically the ones with a deep substantive or technical background. 

Part of preparing to become a Chief of Staff is finding where on the spectrum you’ll operate and more importantly, where you would like to operate, so you know where to aim—and what skills to refine. In my experience, a few transferable ones include:

• Good communication.

• Good collaboration.

• Ability to wield influence and relationship-build. 

• Ability to keep the 30,000 foot view in perspective while also executing on the ground. 

• Ability to bring down the hammer when needed. Someone referred to me as a "friendly hammer" recently and I realized I like it!

• Ability to discern what needs to "hit the leader's ear" (I call this being a good BS blocker). 

• Capacity to prepare and advise others—and anticipate problems before they escalate.

• Everything, everywhere, all at once—inside the company and externally (remember, breadth, rather than depth, at all times).

This is not an exhaustive list—your mileage may vary. Because ultimately, the most important prerequisite for becoming a Chief of Staff is to hone your own intuition: become the leading expert in your own team and what it takes to serve.

If you’re looking for additional resources, I’d recommend: the Chief of Staff Association, this piece from the Harvard Business Review, the Chief of Staff Journal, and this recent piece from The Information. I’m currently reading The Gatekeepers: How the White House Chief of Staff Define Every Presidency. For those of you who have worked with a Chief of Staff or seen one in action, what advice would you add?