Have They Done This Before?

The most common question in executive hiring is also the one that misleads most often: have they done this before?

The logic behind it is straightforward. Past performance predicts future performance. If you need someone to scale a sales organization, hire someone who has scaled a sales organization. If you need a CFO to manage a transition, hire a CFO who has managed one. The experience is evidence; the absence of it is risk.

This logic is not wrong. It is incomplete. And the incompleteness produces a specific, repeatable failure mode.

What experience actually predicts

Experience predicts performance reliably when the new context is substantially similar to the context in which the experience was acquired.

When the contexts differ significantly — different stage, different market, different organizational culture, different resource environment, different problem structure — the predictive value of experience degrades. Sometimes it degrades dramatically.

The VP of Sales who scaled a Series D SaaS company is not automatically equipped to build a sales function at a Series A. The contexts share a category — sales leadership — but differ in almost every meaningful dimension: available resources, team size, product maturity, customer segment knowledge, expectation management, tolerance for ambiguity. The skills required to succeed are genuinely different, and experience in one context may not transfer to the other.

What predicts performance across contexts is something more abstract — the argument I make in full in intelligence hiring: the underlying quality of someone's thinking, their capacity to diagnose new situations accurately, their ability to build and sustain trust under pressure, their judgment about what matters most when not everything can be prioritized. These qualities are visible in how someone has navigated experience, but they are not identical with having had the experience.

The failure mode

The failure mode that follows from over-relying on credential experience — and why so many executive hires fail because of it is a specific one: you hire someone who has done exactly what you need, and they struggle in ways you did not anticipate.

They struggle because the new context demands something the old context did not develop. Or because the thing they are good at — which was exactly what the previous role required — is not actually what the new role requires, despite the titles matching. Or because they are importing the pattern from the previous context and applying it to a situation that looks similar but is not.

I have seen this failure repeatedly in executive search. The most common version: a company hires a senior executive with an impressive resume in the exact domain they need, and six months later the relationship is failing — not because the person lacks capability, but because the specific capabilities they have are mismatched with the specific capabilities the role actually demands.

The better question

The better question is not "have they done this before?" but "what does this role actually require, and does this person have the underlying qualities that generate those requirements?"

This question is harder. It requires being precise about what the role demands beyond the job title. It requires evaluating qualities that are harder to verify than credentials — judgment, adaptability, the ability to build trust across different kinds of people, the capacity to diagnose a complex situation accurately without the benefit of prior pattern-matching.

It requires resisting the comfort of the credential. There is something reassuring about hiring someone who has done it before. It distributes the risk — if they have done it before and they fail here, the failure is more interpretable. If you hired for underlying qualities rather than credentials and they fail, the hiring judgment is harder to defend.

But the goal is not defensible hiring. The goal is the best outcome. And the best outcome comes from asking the harder question, not the comfortable one.