Why You Should Hire a Chief of Staff Sooner than You Think

I recently hired a Chief of Staff (CoS) to support my unsustainable growing workload. It has been one of my best decisions. Our CoS immediately returned 30 to 40 hours a month while elevating everything she took over.

Since then, other CEOs have asked me what a CoS does and if they should hire one. My answer to the second question is yes! My answer to the first is the detailed explanation below.

Three levels of CoS

When deciding to hire a CoS, I sought someone to do two things:

1. Give me at minimum a day a week back, on average.
2. Level up everything I wanted to improve but didn’t have the capacity or existing people to address.

My first step was to determine which level of CoS I wanted. For guidance, I followed this excellent Harvard Business Review article. It describes three levels of CoS:

• Level 1: A recently promoted executive assistant. This person helps with admin and reporting tasks that you aren’t comfortable giving to a traditional EA. But they won’t take big things off your plate and run with them.
• Level 2: An MBA with a few years of work experience. This person can run with projects and make things happen. You can turn to them for advice and tasks that only you used to do, like preparing board packages, managing staff meetings, and more.
• Level 3: Your surrogate. This person is you when you’re not in the room. They usually focus on strategy and get very involved in M&A activities. They might travel with you and accompany you to every meeting.

I decided to go with level 2.

The role of a CoS at BenchSci

At BenchSci, the CoS works closely with me as a trusted partner, acting as a force multiplier to get twice as much done as I could do alone.

We divide the role in two:

1. Structured work. This includes quarterly OKR planning, board updates, running weekly and monthly leadership meetings, high-impact company-wide communications, and yearly strategy planning.
2. High-priority special projects. These encompass strategic initiatives that I want to drive but for which I lack capacity. For example, redesigning our organizational structure, developing a foundational culture listening tour strategy, and leading executive searches.

In the interest of providing even more detail for those hiring a CoS, here’s a list of everything our CoS does at BenchSci:

Reporting

• Weekly update to company and board
• Monthly update to company and board
• Quarterly board package

Facilitating leadership team (LT) meetings, creating action items, and ensuring their execution:

• Weekly LT meeting
• Monthly LT meeting
• Quarterly LT retro
• Board monthly call
• Quarterly board meeting

Driving strategic planning:

• Facilitating, organizing, and documenting our yearly plan
• Owning the quarterly OKR process

Managing company communication:

• CEO company-wide communication and storytelling
• Monthly all-hands meeting
• Quarterly company-wide presentation
• Yearly retro company-wide presentation
• Yearly kickoff company-wide presentation

Managing culture initiatives:

• Working with me on enhancing BenchSci’s culture and values
• Facilitating our culture working group
• Participating in diversity, equity, and inclusion (DEI) initiatives

Managing the Office of the CEO:

• Managing my executive assistant
• Creating and maintaining internal knowledge base cards related to the Office of the CEO

Leading executive searches and hiring

Leading special projects

Finding ways to improve the company and running with them

Finding their replacement and onboarding them (more on why below)

When to hire a CoS

With so many benefits, you might think that I would recommend a CoS to every CEO as soon as possible. But I don’t think it’s that simple. I hear of founders who hire a CoS when they’re five people. We hired ours when we hit 120. Looking back, I should have done it at about 70.

One key variable to consider is your growth rate. At BenchSci, we’re more than doubling our team each year. A fast growth rate increases the risk of delaying hiring because soon after you realize you need a CoS, you’re well beyond that point.

Who makes a good CoS

Once you’ve decided when to hire a CoS, the next question is who. The answer depends on the type of CEO you are, what you value, and the gaps you need to fill.

I wanted someone creative who takes a people-centric approach, can tackle any problem regardless of prior knowledge, can drive change management, and has a background in DEI and culture. The best candidates we’ve seen like this have an MBA and consulting background — more specifically, business design consulting.

What’s most important, though, is that you fully trust whoever you hire. You need someone to talk with about the most sensitive topics and be an extension of you. Choosing candidates that you know well can address this challenge.

Also, only hire someone who understands the CoS position is time-limited. One of our investors gave me this great advice. Since a CoS role does not have a “career path,” it provides limited growth opportunities. Therefore, we limit the service period to three years. The CoS will then either transition to another senior role in the company or find a leadership position elsewhere with our help. Their last task in the CoS role will be recruiting and onboarding their replacement.

I hope this gives you enough information to decide about hiring a CoS. If you want to learn more, read this great article by the former CoS of Opendoor.