In 2020, Reforge was 30 to 40 people and growing extremely fast. While I was hiring an Executive Team and functional level leaders, eventually projects would bubble up that didn’t neatly fit into any current function, leaving them on my plate. Ultimately it became too much for me to handle on my own and I was encouraged by other founders to hire a Chief of Staff. 

I had never hired a Chief of Staff before, and from my initial research everybody seemed to have a different definition of the role. Like many CEOs, I’d previously hired for many roles and functions that I’d never hired before, so I had a process for this new task. 

First, I talk to a variety of people who have been in that role, not a recruiting conversation, but a research conversation.

I interviewed current and former Chiefs of Staff to learn what makes a great candidate in that role, what are the different archetypes for that role, and why did they personally take their roles. Ultimately I want to know how to attract excellent candidates, avoid an expensive mis-hire, and I’m speeding up the recruitment process because I’m learning what I need to be looking for instead of figuring it out as I go.

To find interviewees for my research I looked on LinkedIn for people in Chief of Staff roles and asked for a 30-minute informational interview. I got a pretty good conversion rate.

Quickly I learned there was a very clear set of archetypes. Even though there were many different types of Chief of Staff, they lived on this spectrum. With this understanding, I could start to think of what I specifically wanted, which was somebody who was a Strategic Owner. Next I found the backgrounds that would make for this person.

Through my research it was clear that the Full Surrogate was a very powerful asset, but far less common because it requires so much trust. This would typically look like building somebody who wants to be in that role as a career versus a temporary position.

In the interview process I oriented more towards people with functional backgrounds, even though I actually ended up with somebody who had more of a generalist background, but with an entrepreneurial focus.

While interviewing people I realized there is a trade-off in the Chief of Staff role that you have to be super upfront with people about. The Chief of Staff is going to have to take on not exciting projects that are actually really important. In exchange they tend to get broader executive exposure, see inside parts of the company that they would never see before, and sit alongside you as the executive or the CEO. You've got to be upfront about that because you need somebody who is going to proactively take those types of projects off your plate without you having to sell it to them.

In my interviews a lot of people talked about how you as the executive or CEO spend more time with this person than anybody else in the company by a long shot. It was really, really important that you enjoy spending time with this person, so much so that you could even envision being a friend with them outside of work.

Something I found that was super cool is that the Chief of Staff system you create can be an effective pipeline of leaders within the organization. For example, Sheryl Sandberg essentially has two Chiefs Of Staff at the same time and they overlap for a six to nine month period. The more tenured Chief Of Staff recruits and trains the second so that there's constant continuity. The whole purpose is for Sheryl to bring in folks, have them learn how she thinks, and get broad context and experience. Eventually Sheryl spins that person back out into the company to lead a new kind of initiative or new function.

Brian Balfour

As Reforge grew to the size where I needed a Chief of Staff, I began my search by holding informational interviews with Chiefs of Staff at other companies. I used these learnings to inform the job description and interview activities. 

What are the different ways Chief of Staff spend their time?

What is the difference between Chief of Staff and hiring an operations leader or team?

What are the different types of Chief of Staff?

What attracted them to the Chief of Staff role (use as selling points in recruiting)?

What makes someone successful in the role?

What does a typical week look like in the role?

Found that the roles lived on a spectrum:

 Helps prioritize, organize, and run your schedule/initiatives.

 Takes on projects that require your voice, but you are the decider.

 Takes on projects that require your voice, and they are mostly the decider.

 They fully replace you on some projects. Represent you and makes decisions when you aren’t there. This model is where the CoS commonly has a team. They can be a full stand in for the CEO or executive and make decisions before they even get to the executive. Think Chief of Staff in White House. This is someone who is in the Chief of Staff role for a long time.

 Person has a generalist background. Commonly an operations, management consulting, or similar background. More versatile but less helpful when comes to functional specific stuff.

 Person as a functional background like Product Management. Helpful when Chief of Staff to a functional executive like Chief Product Officer since they understand the function well.

Effective setup when a pipeline of leaders. They spend 12 to 18 months with the CEO or exec. Get a ton of business context they otherwise wouldn’t. Learn how the CEO thinks. Spin out to lead some other strategic project. Rinse and repeat. Other companies solve this with rotational leadership programs.

Often great at turning a generalist with no functional or tech background into a more effective employee within a technology company.

Main selling point is to get executive exposure and learn more general business context. Tradeoff is that you often work on important but not exciting topics.

Relationship and how well you personally connect with the person is everything. You spend more time with this person than anyone else in the company. You need to enjoy spending that much time with them.

Those with functional backgrounds seem to do better. They come with the functional background, and get the broad context/learnings. Where as someone with management consulting background go from being a generalist to more generalist context.

She found there were two different models:

Supportive CoS - In the meetings with you, working to be the gatekeeper for work on the desk, coordinating the work below us. Not a lot of decision making power, not to fill your shoes. Not take work off the plate.

Surrogate CoS - Like the white house. They run their own staff, they are there to make decisions before they get on your plate. Way more impactful, but harder to hire for. Building that trust and getting to that point is pretty hard. Only seen it work when someone up from within.

The 2nd model is far less popular in Silicon Valley. Sheryl’s was the first model. Called business leads at Facebook. Commit to 2 years. 2 CoS typically at the same time. One is training the other so there is constant continuity.

You need to decide if you want this to be a tour of duty or long term. That fundamentally changes how you sell the role and the candidates you go after. Most CoS to Sheryl have 10 to 12 years of work experience, mostly consulting/strategy/ops.

There is an immediate notice to day to day. A lot of it is clearing time, shuffling things around, becoming first line of defense. But they don’t materially take away quantity of work unless they become a surrogate CoS.

The difference between an EA and CoS for us was that CoS would take on discrete project work where as EA’s typically didn’t. Additive to what the exec is doing. Goal is to get the project to where it needs a full time person and you hire that person or transition it internally.

Wish they had a trial period. Really hard to evaluate the relationship when it’s going to be that close of relationship. Next best is to spend a day or two working together.

We had a daily operating cadence. Would have a daily call at 7am and then would send out the next day’s schedule at 10pm. Would then do weekly briefs, summaries of key meetings and outcomes, updates and status on the most important projects. Things shifted so much that all this needed to be daily.

Former Chief of Staff to Head of Eng at Airbnb

Viewed the different types of CoS on a spectrum: 

Helps prioritize, organize, and run your schedule/initiatives.

Takes on projects that require your voice, but you are the decider.

Takes on projects that require your voice, and they are mostly the decider.

They fully replace you on some projects. Represent you and makes decisions when you aren’t there.

Airbnb didn’t officially have the title even though there were a few across the org. The role was super specific to a team and leader. Very varied.

Originally worked on more org related things for t he leader. Projects that needed the leader to driver but they didn’t have bandwidth for. An example was at one point there was a lot of Senior Engineer attrition and needed to figure out why.

Then worked on creating an onboarding program for those working on the Homes team. Making the team more effective, score cards, operating system for the team.

Another was taking on leading 2020 planning. Gathering inputs from teams, etc.

Former Chief of Staff to President of Airbnb Homes

Views CoS role can be anywhere on the spectrum of Exec Assistant to COO of a Company

Tailor the role to what you need. Main goal should be to get leverage on your time but also groom the person to take on a leadership role. Create a pipeline of people who can take on these roles who are well versed to take on these roles.

At Amazon they were called Tech Advisors. 6 to 18 month period, works directly with exec, in every meeting, takes on projects, then when they are in the role they take on something else. Increase the leverage and capacity of the person you are supporting.

Much more program management, keeping track of loose ends. Major projects to get done and don't have the capacity.

Commonly two types of background The mold of a pure operator and program manager...not most strategic end to end owner. But great at keeping house in order. Other is strategic and owns things ends to end.

Operating System and Cadence - how is the leadership team, what are the meetings we have across all the different teams. What is the content we are covering in each of these. Partner with finance and biz ops to put that together. For the year what are the highest level priorities. How are we tracking those. Operations and program management aspect.

Strategic Growth Focus - Growth sprint, what are the main levers for the business, then make sure we have initiatives across every team to make sure they are tied to them, then looking out 6 to 12 months and what strategic areas do we need to get ahead of. Business reviews. Wrote strategic plan, 5 year plans, getting input from the boss.

Ad Hoc Strategy Initiatives - Working on a loyalty program, this is my highest priority. As they spend more time they know what you are going to think, look for pitfalls. Help guide projects to be more successful.

Their motivation to do it. Decided to do it for two reasons.

Timing. Needed to find a new role as was filling for someone on maternity leave. Needed to find a new role, this came up at the same time.

Learning. Really good for someone broad exposure and want to get more perspective on things. Opportunity to learn from someone you want to learn from.

Agreed upfront of the 12 to 18 month role.

The advantage of the PE/Management Consulting background is someone who has worked with exec teams and is polished on communication. However they’ve typically never been in the guts of how something is built.

Company was 800 Employees, exec team was 15 people.

Org 70% - Help the cadence, leadership, all hands, to make sure the information flows through the meetings, across a cross functional cadence. Worked with finance. Run company all hands, and the planning process of OKR's. Make sure we are marrying the right things.

20% Leadership - Every week 90 minute meeting. Making sure working on the most urgent issues. Decision making framework. Need one or two meetings to make a decision. Preparing for the meeting takes a lot of time. Also led exec onboarding.

10% CEO - Work closely with CEO, direct reports, templates for 1:1's, was a sounding board for him for strategic thinking partner, leadership offsite structure. Projects that don't have a natural home.

My recommendation for the person is to develop an exit plan on the role. Too easy to stay in the CoS. Every week and every month is different. 18 Months is a healthy tenure. You need 6 months to understand the team, the CEO you are supporting, and historical knowledge of the org.

Huge advantage if you hire some internal. Offer to someone high performance in the org. Gets them up to speed much faster.

If you hire a consultant, you hire a generalist, hard to grow into a role that leads a business unit with out the functional experience. People who are a specialist previously, they get the broader context, then go back and are able to be more effective.

One advantage of a CoS is that they tend to be in a more neutral position vs other execs and can make sure the conversation is balanced. CEO can’t be in all the meetings. CoS can provide a neutral perspective.

If you hire internally need to be able to speak a lot of the different functions. They need to be well respected of the person on the team. It’s a person that if an employee has an issue they feel comfortable to go to the CoS. Try to hire someone who fills holes and coach you on feedback.

Chief of Staff Role Research at Reforge

Chief of Staff Role Research

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