September 2, 2026

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Hi Everyone,

In early 2021, HubSpot co-founder and CEO Brian Halligan was badly hurt in a snowmobile accident. Yamini Rangan, hired a year earlier as Chief Customer Officer, ran the company while he recovered – board meetings, earnings calls, all of it.

Six months later, Halligan gave her the CEO job. He later wrote that he hoped no CEO would need "a near death experience" to think about stepping back, and that most wait too long.

Halligan could step back because someone was ready. Today we're making the selfish case for building that person yourself.

Why building a successor helps you first

Building a successor sounds like something you do for the company. But mostly, you do it for yourself.

If nobody can properly cover for you, you can't step into a bigger opportunity when it opens. That could be leading a new market entry, selling the business at a good price - or even more simply, just taking a real vacation.

And then, of course, there is stepping into a new role entirely.

Whatever you want next, someone will ask who takes your place.

Companies prefer to promote from within, and the data shows why. Wharton professor Matthew Bidwell studied seven years of personnel records at a large financial firm and found that external hires were paid about 18% more, performed worse for their first two years, and were 61% more likely to be let go.

And if you're the founder, the same logic shows up at exit. A buyer pays less for a company that stops working when you leave.

Name your replacement before asking for a promotion

Go into your next conversation about a bigger role able to say who takes your current one. You're presenting a move the company can say yes to, instead of handing your manager or board a staffing problem.

Have two or three names at different stages of readiness rather than one favorite. If your only name resigns, you'll be starting over.

Give away a decision you own

To get ready for your job, your candidate has to make some of your decisions.

Pick one you make every week, like the pricing exception, the hiring sign-off for one team, or the call on what ships this month. Hand it over completely, so they decide and then tell you what they chose and why.

Then let the people above you see them work. Rangan ran HubSpot in front of the board and the investors, so by the time the CEO decision came, they'd already seen her do the job.

Won't this make me easy to replace?

It works the other way. A leader whose team performs without them gets trusted with more. The leader who can't leave their seat doesn't get considered for the next one, because moving them would break what they run.

Start this week

If a name comes to mind, hand that person one decision this week and tell your manager you're doing it.

If no name comes, that's the finding – pick the person closest to ready and give them the first decision anyway.

Go deeper

👉 Sequoia Capital: A Startup Founder to Scaleup CEO's Journey (Halliganisms) — read Halligan's full list of lessons from 15 years running HubSpot, including why most CEOs wait too long to hand over.

👉 Knowledge at Wharton: Why External Hires Get Paid More, and Perform Worse, than Internal Staff — the research behind the 18% number, useful the next time someone pushes to fill a senior role from outside.

👉 Scarlet Ink: If You Can't Be Replaced, You Can't Be Promoted — a former Amazon leader on what "ready" looks like in practice.

👉 WittKieffer: Succeeding as a Successor: 5 Tips — worth forwarding to the person you're developing, so they know what to do from their side.

Coming up tomorrow

Tomorrow, we're covering the missing step in "let me sleep on it," backed by a study where it doubled problem-solving.