Why Founders Should Hire a Chief of Staff

Hey y’all — I’m heading back to the US at the end of this weekend and will be back with a fresh deep dive next week.

But first I wanted to revisit the importance of a chief of staff.

When Houck’s Newsletter started generating meaningful revenue last spring one of the first things I did was hire one.

I had actually set out to hire a research analyst (here’s the "JD”) but as I talked to candidates I realized my needs were more broad and rapidly changing than just research.

It’s one of the best decisions I’ve made for the business.

This week I’m (re)sharing why my thoughts on a CoS changed and:

• What is a Chief of Staff?

• Why a CoS is valuable to founders

• A framework for when to hire a CoS (and why I recommend it)

• What qualities to look for when hiring a CoS

Why Founders Should Hire a Chief of Staff

What is a Chief of Staff?

A surprisingly common misconception is that a Chief of Staff is a glorified executive assistant.

I can’t find it now, unfortunately, but I remember seeing a tweet that said giving out the title “Chief of Staff” is how you convince MBAs and management consultants to become executive assistants.

Pretty funny, but not accurate.

Instead a CoS handles high-leverage, often cross-functional projects that the founder(s) doesn’t have bandwidth to take on. The CoS is there to jump in on critical projects and take ownership of them.

Typically a founder will give their CoS a goal and some context on a project, but a good CoS can handle ambiguity.

These are projects that require the creation of new processes or systems, and the CoS can either maintain those themselves or offload them to others on the team once they get things working.

Some examples I’ve asked my CoS to do in the last 6 months:

• Build and manage automated sales and partnerships outreach

• Set up and manage our SEO process

• Manage logistics for our many global founder meetups

Michael Girdley also shared some other good examples here.

Additionally a CoS typically has full business transparency from founders and are aware of all workstreams that are going on. They maintain a tight feedback loop with the founders on their areas of ownership via 1:1s (but are often in many if not all other major meetings as well).

A good working relationship with a CoS is to make it so that whatever you know, they know too. And as a result, the CoS is able to make decisions and operate without needing your input on everything.

Top tier executive assistants are great at many things but have critical core operational tasks and simply don’t have the wide strategic business context required for CoS-style work.

In fact, having a great CoS and a great EA is an incredibly powerful and complimentary combination.

Why a Chief of Staff is Valuable to Founders

Startups are chaotic, of course, and even after prioritizing ruthlessly you’ll still have to cut projects you know you should do. With a CoS acting as a force-multiplier for you, these will actually get done (or at least more of them!).

You can also give your CoS smaller, one-off tasks and trust that they’ll be done at a high level.

But the real benefit of having a CoS is the focus it brings to your own work.

For founders, minimizing switching costs — the mental burden you take on when you go back and forth between different tasks — is essential.

You’re already fighting the biggest fires and pursuing the highest leverage opportunities. You’re probably aware of every bug in the code (even if your cofounder is the technical one) and building up tribal knowledge about how to do sales or marketing for your product by the day… among 100 other things.

Having a CoS to take on the parts you (or your cofounders) either aren’t good at or be able to step in when you get pulled onto something urgent gives you considerably more peace of mind, which leads to more focused work and better outcomes.

Spend your time orienting your CoS on:

• What the most important goals are for the business overall right now

• How any given project fits into that and what it’s goals are, too

• What would and would not be worth looping you in about

Then turn them loose.

A Framework for When to Hire a Chief of Staff

Some founders are generalists who can attack any problem while others are specialists who are the best in the world at the particular area they’re solving a problem in.

Both should approach hiring a CoS differently:

Generalists should hire a CoS when they either notice the quality of their work is suffering due to being spread too thin or they’re having to say no to truly essential opportunities.

It’s incredibly important to be honest about this. One of the most common mistakes founders make is letting themselves get infected by shiny object syndrome. I talked a bit about the risks of that last week. If the projects you’re saying no to aren’t essential, don’t hire a CoS.

On the other hand, specialists should hire a CoS when they find they’re being drawn away from where they can add the most value — driving their main area of the business forward.

An example would be if you’re a brilliant technical founder who’s only spending minimal time building the product or talking to customers because they’re getting roped into other work to keep the business running. Your startup is probably better off if you let a CoS do those things to give you the time back.

For this reason I generally recommend specialists to hire a CoS earlier than generalists. The problems they’re solving with a CoS happen earlier (though both will likely happen relatively early on).

This isn’t universally true. I’m a generalist but hired a CoS before anything else (other than an assistant) because I knew I wanted to remain a solo founder, didn’t have any technical work that needed to be done, and also knew my weak points. As my bandwidth decreased I realized hiring proactively (rather than waiting for the quality of my work to decrease) for those weak points was in my best interest.

What Qualities Make a Good Chief of Staff?

A good CoS will "manage” you. They’ll tell you what they expect and need from you to get their job done and treat you largely like a peer. Here’s some more context from Girdley:

in terms of qualities you should look for when hiring a CoS, look for:

• Resourcefulness → You don’t want your CoS coming to you with problems they could solve themselves. They’re here to solve problems. and to be a swiss-army knife. Make sure they actually are.

• Adaptability → If a founder’s role is chaotic, a CoS is equally so. The difference is that the CoS isn’t in control of the company, so they need to really and truly be ok with constantly shifting priorities.

• Candor → A CoS needs to feel confident being open and honest with you, quickly, when things go wrong. They need to feel comfortable pushing back on you when they think you’re wrong.

• Urgency → A CoS may never care quite as much about the business as you do, but they need to care a lot. They will if you’re providing opportunities for them to learn and being transparent about the business.

• Excellence → You want your CoS to be scrappy, but you don’t want them to cut corners. They need to care about the quality of their work. Otherwise you’ll have to clean things up for them anyway.

• Ambition → Your CoS will probably leave your startup within 3 years. Often even less. The tradeoff of getting a high-achiever in the role is worth it. High-achieving people become a CoS because they want to grow. Maybe they want to be a founder themselves one day, or maybe just an executive. Either way, seek out candidates who have big goals. They’ll work hard.

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