Announced on Sunday, handed off on Sunday

Photo by Isaque Pereira.

The first time it happened, we were at a conference when we got cornered by a group of small-business owners. The specific problem was that they were nearing retirement age, and they wanted to hand more of the business off to their (now adult) children. But they had no confidence that their (now adult) kids could take the reins.

Is this a management problem? Yes, of a sort. Is it the type of work we do? Not exactly. So we listened and nodded and tried to say soothing things. But, since it was the first time it'd come up, at that point, it was a one-off.

But then COVID happened and a lot of the workforce that had been eyeing retirement as part of their five-year-plan put those plans on hold. Many senior leaders felt like lockdowns and economic precarity were a shitty time to hand off or bring in another leader. Faced with the question "Does it have to be you?" a lot of execs answered "Yeah, it does. At least until we're on more solid ground."

Even though the ground isn't solid, per se, those leaders are five years older. And succession planning discussions are on fire, across every major industry. What started as a weird one-off discussion for family-run small businesses is now so screamingly loud, it's front-page news. Non-profits are shutting down because there's no one to run them. Private equity firms are gobbling up successful businesses because, again, there's no one to run them.

And if you think this is just a problem for non-profits and small businesses, just wait until you find out what's going on with the US presidential race.

Very seasoned, senior person in charge. Who was maybe starting to think about retirement and their professional legacy. But then extended a tour of duty during the pandemic. Because that felt like a time for experienced hands at the helm. And now we're here, several years later. And it's time to hand over the whole thing. Not slowly. Not gradually. But announced on Sunday, handed off on Sunday.

Handing over the whole thing

We have both been execs who had to hand over the whole thing. Like when we left startup roles to co-found together. And we've both been the execs who had to pick the whole thing up on a Sunday night. When the last person at the helm, without a lot of advance notice, suddenly wasn't.

Whether you're on the incoming or outgoing end of a succession, by the time it's being planned and executed within 24 hours, things have gotten tight. Not because execs don't hear about succession planning. And not because orgs and boards can't spot the risk. There's literally a whole section of contracts devoted to key man clauses. And yes, wild as it is, they are actually called that.

The working world has a mental model for shit-is-good on Thursday but shit-hits-fan on Friday. It's just that knowing it and actually planning for it are two very different things.

Succession plans have a brand problem

Despite HBO's valiant attempts, succession planning is not cool. On your personal continuum of leadership satisfaction, succession planning probably doesn't live up at the head end with making job offers, closing incredible deals, or seeing your mission alive and thriving in the world. For most leaders, it sits over at the other end, past audit committee and office seating chart discussions, over by descaling the office coffee maker. Which, you know, you should do (every three months or 100 brew cycles!). But also which, if something's gonna get skipped, well. Maybe next week.

There are a few reasons for that. One is that a lot of bosses we meet find the whole concept sort of morbid. Succession planning sits in roughly the same bucket for them as writing a will (which you should also probably do, btw!). It feels like planning for a far-away time, when you will be gone. And that isn't very fun to think about.

Another reason is the fear. Fear that succession planning means training your replacement. If you crown a successor, goes the argument. Train them up on all the things that right now only you can do. And gradually hand off all your favourite legos. What's left at that point? Won't your employer just realize they have two people doing the same job and get rid of you because you're the more expensive one?

Sometimes these two — avoidance and fear — will wrap themselves up in altruism to throw you off the scent. They'll say, "No no, it's really about the team. My team is fully loaded with their own work. I can't possibly give any of my work to them, so I'll have to bravely carry it all myself."

Carrying load so that your team doesn't have to can be righteous, for sure. It can be the mark of a great boss that you are willing to do what it takes to get barriers out of your people's way, and help them succeed. Or it can be a mark of ego and fear that you let no one else get the opportunity to step into the work that you do.

Want to know how to tell the difference?

A succession plan is not a work-will

The first thing to understand is that the metaphor of a will is totally misleading. A last will and testament is fundamentally a document that sits in a folder somewhere. You can write a new one or edit it when things change, but mostly it just sits, inert, until it's needed.

The idea of a literal, written succession plan that sits inert in a folder until needed is...silly. It would be immediately out of date, for one thing. And the first page of the plan would presumably say things like "start cross-training Rob on a lot of my work in this area," and "bring Deb in more on our board meeting prep sessions." Which are. You know. Not going to happen if you're not there any more.

The word "plan" is part of what messes us up here. People talk about wills and estate planning and they are talking about something deferred, and static — "I'm writing a plan today that you should execute a long time from now." But planning is usually more active than that. A series of objectives and the concrete actions we will take to achieve them. Overlaid and interspersed and evolving with the other things we're trying to get done. In real time. "Can you grab cabbage rolls at the deli on your way home?" is a plan. And so is "let's work towards you presenting our results to the SLT instead of me." Not plan like "death plan," more plan like "monthly savings plan."

Succession planning is an ongoing investment in resilience and growth for your team. It's the name we give to the recognition that organizations and people flow and change. That it is a major risk for any team, department, or organization to have only one senior person who knows how to do a thing. Succession planning isn't about picking one of your direct reports as your favourite, it's about deliberately investing in bench strength and resilience.

The path to better succession planning starts with taking a moment to reflect. We hope you have a nice gentle week, to be clear, but imagine for a moment that you have a shit-hits-the-fan Friday. Something takes you out and suddenly, for a month, or six, or longer, you can't work. What happens to your org? Really truly, if you play it out, do you know who steps in? What important work suffers, or gets dropped?

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That's how you tell the difference, by the way. A great boss carries weight so their team doesn't have to, for sure. But a great boss doesn't leave their team twisting when a surprise hits. Whoever you thought might step in, succession planning is investing in those people now so that they have an easier time if and when. Whatever important work you thought might drop, succession planning is cross-training on that work and distributing it so that it doesn't.

And yes, your people are busy already. But cross-training and support are not burdens for them. And time after time, study after study, they tend to lead to better outcomes and more productivity, not less.

And yes, it's possible that the more they know about your work, the more they'll take off your plate. But in a thousand at-bats, we have just never seen that result in a bad outcome for the boss. People do get cynically asked to train their junior/cheaper/off-shore replacements before a layoff, but that's not what's happening here. You're building a stronger team, and some headroom for yourself. We're pretty confident you'll find something to do with the extra time.

If nothing else, it's probably time to descale the coffee machine.

— Melissa & Johnathan