What happens when your star performer decides to quit?

If you’re like most managers you congratulate them, ask if you can get them to stay, and then get straight to planning their handover.

Most companies I’ve worked at have elaborate systems for this exact situation. Most of them work very well — until they don’t. In my experience, no matter how elaborate, even the best ones work only 50% of the time. Pretty soon you run into the biggest weakness of any handover process: edge cases.

An edge case is a problem that carries meaningful impact but happens infrequently. Easy to miss, but impossible to skip when it’s staring right at you.

Now before you judge the documentation process or suggest using AI, let me tell you this: expert knowledge is hard to capture even with the best tools and processes.

Here’s why.

A philosopher named Hubert Dreyfus¹ spent years studying how humans develop skill. What he found was unexpected. Experts don’t just accumulate knowledge, they reorganise it into heuristics, recognisable patterns, and perception.

Simply put, expertise is as much learning through lived experience as it is acquiring deeper knowledge.

Here’s how we know this.

In the 1940s, a Dutch chess player and psychologist named Adriaan de Groot wanted to understand what separated great chess players from good ones. The obvious assumption was that grandmasters were simply smarter.

And their intelligence gave them the edge to think further ahead, consider more moves, and process more combinations. That assumption, ironically, is still how many organisations treat expertise today: as innate ability rather than accumulated experience.

So de Groot ran an experiment. He showed chess positions to players of different skill levels and asked them to think aloud as they analysed the board. What he found changed the was unexpected.

The grandmasters weren’t thinking more. In many cases they were thinking less. They considered fewer moves than intermediate players but the moves they considered were almost always the right ones.

De Groot couldn’t fully explain the mechanism. That came later, when Herbert Simon and William Chase picked up the work in the 1970s. They discovered that grandmasters had memorised somewhere between 50,000 and 100,000 meaningful board patterns or chunks, as they called them, accumulated over years of play. When a grandmaster looks at a board they aren’t seeing 32 pieces. They’re recognising configurations, the way you recognise a face without consciously processing each individual feature.

Dreyfus took this further and made it philosophical. While a novice follows rules. For the grandmaster, decades of pattern recognition have dissolved into instinct.

That’s the first clue to our handover problem.

When you ask as expert to explain their thinking, what you get is a reconstruction built after the fact. The reasoning is plausible, often technically accurate, but it isn’t the actual cognitive process. It’s a story told to explain something that happened faster than language.

This is what makes handovers structurally impossible to fix after the fact.

Most handover documents contain reasonable questions about the job, the projects, the clients, the processes. Experts can answer them accurately. But the knowledge that handles edge cases isn’t organised as answers to questions, it’s organised as responses to situations.

Like the grandmaster reading the position of pieces on a board, it only becomes accessible when the right situation activates it.

Michael Polanyi captured this with a phrase that has stayed with me:

‘We know more than we can tell.’

But even that undersells it. It’s not just that expert knowledge is hard to articulate.

It’s that the very process of becoming expert reorganises knowledge into forms that are faster, more contextually sensitive, and more integrated than language allows.

The next clue comes from Herbert Simon, the same Simon who helped explain the grandmaster’s chunking.

Studying how people make decisions under complexity, in organisations, in economics, in everyday life, he found that nobody optimises. Not really…

He wanted to understand how any mind, human or machine, navigates a world too complex to fully process. His answer was bounded rationality: the idea that minds don’t optimise, they satisfice.

We search until we find something good enough, using the categories and heuristics available to us, and we stop. This is the only viable strategy for a finite mind operating in an infinitely complex world.

The implication for expertise is precise: when you sit down to document your knowledge, you would find it much easier to write down what’s prompted and what’s top of mind. Easy peasy.

But you won’t be able to consciously thing of every edge case unless you’re actively prompted. They knowledge exists in your experience but it’s never stored as something a finite mind could retrieve on demand.

So what do you do?

The answer isn’t a better offboarding process. It’s a different relationship with expertise altogether.

One that doesn’t wait for the resignation letter. Expert knowledge needs to be treated as something you harvest continuously, while the expert is still performing, while the knowledge is still alive and activated in real situations.

The most underused tool for this is reflection and managers can facilitate it in regular 1-2-1s.

When your star performer has a great quarter, don’t just celebrate and move on. Help them contextualise it by asking them to walk you through exactly the specifics: What did they choose to do? What did they choose not to do, and why? Where did they make a judgment call that isn’t in any playbook?

Be mindful that is not an interrogation. it is a way to contextualise knowledge that’s as valuable for the expert as it is for the organisation. Repeated over months and years, it builds something no exit interview ever could.

One of my favourite experts on the subject is Peter Senge. He spent years studying why some organisations learn and others don’t. His conclusion was that the unit of capability in any organisation isn’t the individual — it’s the team.

Top performers matter, but an organisation that depends on them is fragile by design. What makes organisations genuinely capable is the degree to which knowledge circulates, gets tested, gets refined.

The handover problem is really a symptom of this: organisations that treat expertise as individually owned discover what they’ve lost only when the individual leaves.

Most organisations have many people, each carrying expertise that is partially tacit, partially compiled, partially invisible even to themselves. The moment you try to build systems that run on shared expertise, this stops being an offboarding problem and becomes a competitive advantage.

¹Hubert Dreyfus: https://en.wikipedia.org/wiki/Hubert_Dreyfus