Have They Done This Before?

In 2020, I presented a shortlist for a VP of Sales role that included someone who had never carried the title. She had run sales at a firm where the VP title was reserved for people who had been there fifteen years. Her actual function was identical to what the role required. The hiring manager's first response: "She hasn't done this before." She got the role. She was the best performer on the shortlist.

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 it is one of the most common reasons executive hires fail, 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.

A specific case that changed how I think about this, with details changed to protect confidentiality: an early-stage technology company hired a VP of Operations from a well-regarded supply chain company where they had built robust operational systems at scale. His credential was precisely what the CEO was looking for. He struggled significantly in the first eight months, not because he wasn't excellent, but because this company's core challenge was building operational clarity in a product environment that was still shifting. His deep experience was in scaling an established operational model. He had never had to build clarity while the underlying model was still being defined. These are different problems. They weren't visible as different from the outside of his resume.

He was eventually successful, but only after a genuinely difficult period that cost the company more than a better-matched hire would have. The credential matched. The underlying requirement did not.

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.

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.

What this looks like in practice

In a search where I am doing it well, I spend more time understanding the role than I spend reviewing candidate profiles. What is the specific challenge this person will face in the first six months? What organizational dynamics will they need to navigate? What does success actually look like at twelve months, and what capabilities produce that success?

Only after I have that picture do I start assessing candidates against it, not against the job description, which is typically written around the idealized credential match, but against the actual requirements of the actual situation.

The candidates who match on credentials and on the underlying requirements are the easiest cases. When I have to choose between a strong credential match with uncertain underlying qualities versus a weaker credential match with strong underlying qualities, I almost always favor the latter in my recommendation. The credential is a signal. The underlying quality is the thing.

The CEOs who get the best outcomes from retained search are the ones who engage seriously with this question before the search begins, who are willing to examine their assumptions about what "done this before" actually means for their specific situation. The ones who are locked into a specific credential profile from the outset tend to get the profile they asked for, which is not always the hire they needed.

See also: How to Make Decisions When You Don't Have Enough Information, How I Think About People, Active Waiting

Sources

McKinsey: The Real Secret to Retaining Talent

HBR: Hiring for Cultural Fit Doesn't Have to Undermine Diversity

LinkedIn: Global Talent Trends Report