I interviewed Chiefs of Staff from Google, Lyft, Twilio, Uber, Chime & more. Here’s what I learned.

Gillian O'Brien

Dec 8, 2020·13 min read

• I shut down my company in response to COVID & have been documenting my work experiences since — including my journey to determine my post-founder career.
• I ended up taking a Chief of Staff role at Dover & wrote about that decision here.
• Since starting, I’ve gotten tons of questions about being a CoS. I’m writing this article to address them — but since I’ve only been in the role for a few months I interviewed 14 CoS from various companies to learn more (names of interviewees at the bottom).

Before I dive in…

I’ve come to this conclusion in the last few months that I’ve been interviewing people:

The Chief of Staff role is a hot one. Every week I see another connection looking for a CoS to join their company, or someone pings to ask me about what being a CoS is like.

“Chief of Staff” started as a government role, then became commonplace for big tech companies. Now, the role is bleeding into smaller companies and startups. Articles about Chiefs of Staff get hundreds of thousands of views, there’s an entire online network for CoS, and every year, Chiefs of Staff get paid more and more.

What makes the Chief of Staff role so hot? What I’ve realized:

1. 🌙 It’s mysterious. The whole reason I decided to conduct these interviews is because when people were asking me about Chief of Staff-ing, I continued to fall back on answering with “it depends.” I knew I couldn’t speak on behalf of CoS as a whole; the role is too varied. As I sought clarity, asking other CoS about their experiences, I was surprised to get similarly wide ranging answers to the ones I had been giving. They, too, knew they couldn’t speak on behalf of the broader community, only for themselves because of how case by case the role is. It’s truly defined between the CoS & the executive they support. Because of the variability, CoS is mysterious. No one (except maybe the exec they work with) has a window into the scope of what they are doing. Often, the work a Chief of Staff does is sensitive and shouldn’t be shared with the broader team, which only adds to this phenomenon.
2. ⚖️ It’s influential. “Execs have power, and Chiefs of Staff have influence” is a quote that stands out to me from my interviews. Mysterious though the CoS role may be — something that is visible to everyone is the CoS right-hand relationship to the CEO. The CoS has a level of access to the exec that no one else in the company has. There’s an underlying level of influence, then, that they have on this person. The Chief of Staff has an opportunity to see how decisions are made from up close, & be aligned with execs about higher level company information. I think it’s the combination of mystery & influence that makes the role appear so attractive from the outside looking in.
3. 🦸 A kick-ass side-kick. For an executive considering hiring a CoS, the role can be attractive because of the way it’s often framed. Chiefs of Staff are seen as these super capable, yet super humble people who will do whatever needs to be done for the success of the business, while also staying out of the spotlight. It’s someone who the exec can throw at any task, who will jump in with no hesitation. Someone who can be trusted, and someone who exists to make the executive better: whether that’s freeing up time, up-leveling skills, rounding out weaknesses, or being an ear piece. This person is the Robin to their Batman, and that idea is appealing to anyone at any level. Who would say no to an arrangement like that?

But assumptions and appearances aside: what does the role actually look like and feel like on a day to day basis? Here are a few realities to balance the above:

1. ❓ It’s mysterious. This aspect of mystery can work against someone in a company. With so little visibility and consensus around the role, people may not realize everything that this person is doing. It’s easy for a CoS to get slammed with an overwhelming number of tasks.
2. 📝 To a certain degree, it’s administrative. Every single CoS, no matter their level, has had administrative work as part of their role. Whether that’s a shipping and logistics issue, paperwork, or running errands: a portion of the time the CoS will do the unglamorous work, because if they don’t, a founder/exec has to — and the CoS is all about protecting the executives time.
3. 🤷 It’s dependent on leadership. Something that came up with many of the CoS I spoke to was the sense of imposter syndrome. CoS & Execs both have the romantic notion of instantly onboarding their Robin — but in reality, those kinds of relationships take time and nurturing.

At the end of the day, there’s of lot of mystery and intrigue around this role. So let’s de-mystify it below. :)

💡 PART 1: What is a Chief of Staff?

Okay, so a Chief of Staff is a partner in crime. Someone who has access & influence, someone who works across “all parts” of the organization. But what does that actually mean and look like on a tactical level? After these 14 interviews I was able to distill it into the following responsibilities:

1. Filling in Gaps

Chiefs of Staff often fill in gaps where their executives might have weak spots. Perhaps the CEO is particularly visionary, but not good at operationalizing his or her ideas. Perhaps the CEO is a strong executor, but is weak with internal and external communications. No person is perfectly well-rounded. When a CoS whose strengths and weakness are compatible to the CEO comes in, the CoS can fill in the gaps and help develop perspectives.

Chiefs of Staff also fill in gaps where the broader organization is “weak” or underdeveloped. When a project doesn’t have a clear owner, it usually goes to the CoS. This can be across Marketing, Sales, HR, Fundraising, CS, Product, Legal… depending on a given day or week, the CoS may be acting as a functional player for burning business needs. Jumping into operational vacuums as required is a big part of the job.

Does the CoS knock it out of the park on everything? Definitely not. They’re a generalist and a strong utility player. The CoS should be someone who can jump into anything and learn quickly as they go.

2. Connecting the dots

Because the CoS floats around and plugs into multiple parts of the company; they’re often able to connect the dots where people may otherwise be too deep in their silos.

The CoS can look at the team and see how it’s operating; figuring out what needs to happen to keep supporting the team and get things done. They can be a resource to people & then relay information back to the exec and other partners across the company. Ensuring the right people are looped into conversations, people are speaking to who they need to, processes and systems are operating as they should — and understanding where people are coming from. By connecting dots, the CoS creates cross team collaboration and alignment.

The CoS is also a dot connector between the executive and the broader team. Things are often tested first with the CoS, in both directions. Executives will test communications with the CoS before putting it out to other employees, and employees will test communications out with the CoS before bringing them to the executive.

3. Amplifying the team

The CoS will come up with comms plans, create talk tracks, prep for meetings, and orchestrate who and what needs to be brought in on various levels so that the exec can focus. The CoS is like a stage manager and producer to the company in many ways while the executive is like a director.

A lot of visionary leaders need to be able to keep their brainpower for thinking, so having someone whose primary job is structure helps.

This can mean running his or her meetings, defining the agenda & driving actions and accountability. The CoS works on the questions: “how do we run better meetings? how are we more effective?” They create the processes and tools to effectively grow.

The CoS is constantly stewarding and ensuring the success of the CEOs primary objectives, and making sure the right players are aware of and plugged in to a vision.

4. Acting as a sounding board

Execs aren’t immune to emotion. Whether they’re looking for advice or just venting: a Chief of Staff is a trusted person that the executive can talk things through with. With a Chief of Staff, there is an invitation for vulnerability and openness with the pure intent to improve the organization, and the executive will often share things with the CoS that they can’t share with others.

The CoS can be a sounding board to help keep the exec in check with his or her priorities. They can be a release valve, where the exec can speak honestly and drop the diplomatic facade. The CoS can then use their enhanced understanding of the executive to help them become a more effective leader, and keep their focus on what matters.

Executives have different ways of establishing this relationship with their CoS: for some, that means the CoS is in every single meeting alongside him or her, including board & executive meetings. Chiefs of Staff can then know everything that’s going on and their knowledge is second to none after the CEO. This helps to build the level of familiarity, trust, and context that is necessary for this aspect of the role to develop.

💡 PART 2: What is the skillset?

Now that we know the “what” of the role, the next question is “who”? Who is right for this role? Is there a through-line in terms of background, experience, and skills?

Many CoS come from consulting, People, Ops & Strategy backgrounds (ex: they may have been a COO or Biz Ops Lead) Others are former founders, like me.

As covered above, the desirable dynamic is: your superpowers are the weakness of your CEO. Assuming that’s there, here are the other main skills a CoS should have:

1. Discretion

It’s extremely important that a CoS be discreet, mature, and reliable. The CoS is exposed to a lot because what is sensitive information to the broader org will not be sensitive to the CoS. It’s natural for others on the team to try to get information from the CoS to understand what’s going on at a higher level. The CoS needs to understand when and where to communicate. Once you say too much, it’s hard to go back. The CoS needs to treat confidential matters and private opinions as such.

2. Low ego

This term gets thrown around a lot — I don’t mean that a CoS shouldn’t be confident or strong, or that you need to be a “low ego” person all around to succeed in this role. What I mean is that a Chief of Staff should be able to execute, and do so with a level of humility.

It’s important that a CoS have a willingness to get their hands dirty. Leadership will inevitably need help on tedious things. Being willing and able to do the unglamorous stuff is what builds trust and reliability among leadership. There should be no work that is “beneath” you. The CoS role is about helping the exec with absolutely anything in order to get them operating on a higher level.

The other important thing here is that the CoS needs to stay humble and know they are not number 1. The CoS will never be the CEO, nor should they try to be. They stay out of the spotlight, and they don’t always get recognition for their work. Most of what they do is about enabling someone or something else to shine. The question many CoS ask themselves is “How do we make it feel like we have 125–175% of him or her (the executive)?” but they are never trying to replicate the CEO.

3. A fluency in business fundamentals and a generalist skillset

In terms of core business skills, it’s very important that the CoS have a fluency with core business fundamentals and operations. They should be a strong generalist. There should be few things where the CoS isn’t able to make a decent effort when needed and operate effectively across a range of roles. Being tasked with any and everything across the org means knowing how to show up and figure it out. They should have empathy to the segments of the team that they service.

The functional peer role to a CoS would be strategy and Biz Ops.

4. A1 Communication Skills

I think it’s easy to forget how hard most employees find it to give feedback to managers and leaders. Most people will never feel 100% comfortable speaking freely with them, even when the company is small. The CoS therefore needs to be able to do that, freely and fearlessly.

Still, the CoS should be able to communicate effectively with more than just execs. Though they should have an executive presence, the CoS also needs to be approachable. They should be equally as fluent with an entry employee as a senior leader. They should be able to talk to anyone about anything and be very receptive to feedback, themselves. It’s a job where you have to be motivated by helping teams run well and helping individuals be successful.

A CoS is the “link between” — so people should feel comfortable coming to them and having candid conversations. The CoS needs to understand how people are feeling, and then filter that up.

They are constantly figuring out how to help people feel like they belong to the team. Driven by the mission, connected to the vision, and keeping the exec connected to what is going on “on the ground”; the CoS job is inherently a relational job.

5. Agility and flexibility

A CoS needs to be extremely good at context switching, and have the ability to move and flow with the executive as they make decisions. Getting attached to an idea of process is not good. The role will likely change as the company changes, and Chiefs of Staff need to be comfortable with that.

💡 PART 3: Career paths

A CoS role is extremely dynamic. So where does one go next? What is the career path of a CoS?

I had an interesting split reaction when asking this question. Half of the people I spoke to were very clear about “getting in and getting out”. There was a sense of urgency about not getting stuck in the role. For others, that was not the case. They had been in the role for more than a year without plans to stop or switch. Some even had plans to be a CoS again for other executives. Here’s what I saw and heard most commonly:

Next steps look like:

1. Business lead or exec. Becoming a COO, Business Operations or Strategy Lead, or generally peeling off to head up another part of the org. You may become a Head of Marketing, a CRO, a Director of Ops…The CoS role can be seen as “learning to do the job you ultimately want to do, while building an executive mindset.”
2. Founder. Many CoS end up leaving orgs to start their own companies. The CoS role lets you see, up close, what it’s like to run a company. You get an understanding of business and financing, board meetings and investor conversations… the things you’d need to be familiar with to go at it on your own.
3. Executive Coach. Depending on what the exec wants from you, and how the role evolves, a lot of the role can have this “executive coaching” aspect already built in. Becoming a coach for others can be a natural next step. You have the exposure and have worked with CEOs before. You saw the challenges up close and advised this person.
4. Chief of Staff again, for others. Some people are CoS for 10 years. In large companies particularly, the CoS role can be a rotation for executives of different departments.

What I heard regardless of next steps, was that the CoS should have their own goals about what they’re going to get out of their time as a CoS.

💡 PART 4: When and how to hire?

What I learned from asking this question is that there is no magic number in terms of headcount or revenue that will tell you when the time is “right” to hire a Chief of Staff. The consensus was: When you can clearly articulate the need, and understand what this person will do and how they will help — you’re ready for a CoS. Phrased differently; When the company is starting to scale, and someone should be thinking through how processes and people are going to scale — you’re ready for a CoS.

There’s also another, newer hiring model in which the thought process goes like: “this is a talented person. We want them. There’s isn’t a specific role for them, but let’s hire them in and as we all develop we’ll grow a role that fits them. Let’s call it a CoS for now, and they’ll do a bunch of things.”

The important thing to consider in all three cases is that the org can inadvertently use the CoS as a crutch instead of developing and investing in areas of the business. It’s a crutch function that delays maturing some processes that should be developed.

So should you hire one? Ask yourself: what are my super powers & how valuable is my time? What are the areas I need to be amplified in or what are the things I’m not good at? If I got a CoS could I be 1.25X more efficient?

💡 Conclusion & other takeaways

In this article, I covered the ways that CoS are consistently the same, no matter the size company they work for, or the executive they support. But this only scratches the surface of what a CoS does. There is a lot of variability to the CoS role, depending on the organization you belong to, and the executive you work with. Depending on who you are, and who they are — there are a bunch of different ways that you can shape it.

I’m now about three months into my role and learning an incredible amount. I’ve been exposed to many different business functions, responsibilities and projects. My primary objective is just to learn what it takes to make a business successful, and how a startup can effectively scale.

If you have more questions for me about CoS, send me a note! & thanks for reading.

Thank you to everyone who allowed me to interview them:

1. Dennis Yu, Chime
2. Arianna Churchill, Uber Elevate
3. Peter Jeffrey, Modern Health
4. Ben Donald, Google
5. Anne Kauth, Lyft
6. Michael Harrison-Ford, Zoox
7. Karn Khunger, Split
8. Eva-Marie Costello, Springboard
9. Brittany Tensfeldt, Dropbox
10. Dara Warner, Fictiv
11. Ali Rohde, Sourceress
12. Lucy Dana, Blue Bottle Coffee
13. Lauren Paul, Common Future
14. Steven Boone, Twilio