Succession Planning: The Conversation We Keep Putting Off

Aug 11

4 min read

The Conversation We Circle Around

Ask a leader about their vision for the next five years, and they'll talk with real confidence. Ask who takes over if they left tomorrow, and watch the room go quiet. Succession planning sits on every leadership checklist, right near the bottom, filed under "important but not this quarter." Most of us treat it as a formality, something that gets schedules once a year and everyone quietly hopes gets postponed. Underneath the paperwork, though, it's one of the most personal conversations a leader can have. It asks a question most of us would rather not answer out loud: what happens to this thing I've built, when I'm no longer the one building it?

What We're Actually Protecting

Naming a successor can feel uncomfortably close to naming your own expiry date. That's rarely said out loud, but it sits underneath a lot of the hesitation I've watched leaders carry. Ego plays a part, though it's quieter than the word suggests. Few leaders think "I refuse to be replaced." Most think "they're not quite ready yet," a line that can hold true for years without ever being properly tested. Identity plays an even bigger part than we tend to admit. When a role has shaped how you see yourself for a decade or more, handing it over can feel like losing something more than a job title, closer to losing a piece of who you are. Kishimi and Koga's writing on separating our tasks from other people's judgements is useful here. A leader's job is to build capability in whoever comes next. What that person does with it afterwards, and how they choose to lead, isn't the leader's task to control. Fear of comparison sits close by, rarely spoken but easy to recognise once you know what to look for. Nobody enjoys watching their replacement do the job differently, especially when different starts to look like better. That fear is understandable, even reasonable. It's also one of the clearest signs the conversation has quietly become about the leader, rather than about the team they're meant to be serving.

The Short-Termism Trap

Succession planning competes with everything urgent sitting on a leader's desk, and urgent nearly always wins in the moment. There's always a deadline closer than five years out, a fire more immediate than a hypothetical departure. Covey's distinction between what's urgent and what's genuinely important applies directly here. Succession stays important without ever feeling urgent, right up until the moment it suddenly is. A resignation lands unexpectedly. An illness changes everything overnight. A departure nobody saw coming leaves a gap the leader always meant to close and somehow never did. Short-termism isn't usually a conscious choice, and it rarely feels like negligence from the inside. It's simply what happens when a genuinely important conversation keeps losing to whatever's loudest that particular week, month after month, until years have quietly passed.

What Avoidance Actually Costs

The cost of avoiding succession planning rarely shows up as one dramatic failure. It shows up as drift, the kind that's hard to point to until you look back and notice how far things have moved. Talented people leave because they can't see a path upward, and no one ever told them one existed. Knowledge stays locked inside one person's head instead of being shared deliberately across the team. People sense the uncertainty even when nobody names it directly, and that uncertainty erodes confidence slowly, the way a stream wears down stone over years rather than days. Duhigg's research into habits offers a useful way to think about this. Avoidance is rarely a single decision made once and left behind. It's a loop that repeats quietly until something external forces it to break. The longer succession planning gets deferred, the more entrenched the avoidance becomes, and the harder it gets to start the conversation without it feeling like an emergency rather than a choice.

Leaning In: Trust, Resilience, and Growth

Something shifts the moment a leader chooses to open this conversation early, before anyone's forcing their hand. It signals to the team that their growth genuinely matters, more than the leader's own comfort or sense of control. That single act builds trust in a way few other decisions can match. It builds resilience too, because an organisation that knows how to develop its next leaders can absorb shocks that would otherwise knock it sideways for months. There's a personal benefit as well, one most leaders don't expect until they actually feel it land. Letting go of the idea that you're irreplaceable is uncomfortable at first, sometimes genuinely painful. Most leaders who've done it, myself included, describe what follows as relief rather than loss. The role gets lighter the moment it stops being the only thing holding the organisation up.

Starting the Conversation

None of this needs to begin as a formal process, complete with forms and five-year timelines. It can start much smaller, with a single honest question put to someone on your team: what would you need, to be ready to do more? That question does more work than any succession framework I've come across. It shifts the conversation away from replacement and towards development, which is where it should have lived from the start. The leaders I respect most aren't the ones who never think about who comes next. They're the ones who think about it early, often long before anyone's asking, and treat it as an act of care rather than a threat to guard against.

"It's what you do. Not what you're called."

Published by The Everyday Leader

Written by Craig Bromage

www.theeverydayleader.online