How I Think About People

Fifteen years of placing people in senior roles — of evaluating what they are capable of, what they will do under pressure, whether they will stay or go, whether the client who hired them will be glad they did — produces a set of observations that are more specific than "judge people by their actions" and less systematic than a psychological framework.

What follows is what I actually believe, derived from the specific kind of attention that executive search requires you to pay.

Past behaviour under similar conditions is the most reliable predictor

The question that matters most in any assessment of what a person will do is not "what would you do if..." It is "what have you done when..."

The hypothetical is answerable by anyone with decent pattern recognition and enough intelligence to identify the expected answer. The historical is harder to fabricate, more specific, and far more predictive of actual future behaviour.

I have learned to weight heavily what someone has done in conditions similar to the ones they're being placed in. Not what they've done at their best, under ideal conditions — what they've done when the project was failing, when the resources weren't there, when the team wasn't performing, when the outcome mattered and wasn't guaranteed. Those are the conditions that reveal character rather than capacity.

This sounds obvious. It is resisted in practice, because past behaviour in difficult conditions is often uncomfortable to discuss, and the conversation naturally drifts toward the highlights. The discipline is to bring it back to the specifics.

Most people are better at understanding than executing

A large portion of the gap between where people are and where they aspire to be is not a gap in understanding. It is a gap between understanding and execution — between knowing what to do and consistently doing it under conditions that make it uncomfortable.

This is true at the individual level and at the organisational level. Organisations where everyone knows what's wrong but nothing changes. Individuals who can articulate exactly what their problem is but keep producing the same outcomes. The knowledge is not the constraint.

The distinction matters practically because the interventions are different. If the gap is knowledge, the solution is information. If the gap is execution, the solution is structure, accountability, and the kind of support that makes execution easier. These are different and the wrong diagnosis leads to the wrong intervention.

Confidence calibration is more telling than confidence level

I have learned to pay less attention to how confident someone is and more attention to whether their confidence is calibrated to the evidence.

The person who is highly confident in areas where they have deep, validated experience and appropriately uncertain in areas where they don't is someone I can work with. Their confidence is information. The person who is uniformly confident — who brings the same assurance to what they know deeply and what they are guessing — is harder to use, because their confidence is no longer informative about the underlying quality of the judgment.

Overconfidence in the specific form of insufficient uncertainty about the future is the most common professional failure mode I observe in senior leaders. Not incompetence — overconfidence. The plan that doesn't account for what could go wrong. The hiring decision made with certainty about a person who turns out to be different than assessed. The market call made without acknowledgment of the range of outcomes.

Calibration is learnable. It improves with feedback — with seeing how your predictions match outcomes over time and adjusting. People who have that feedback loop and pay attention to it are more calibrated than those who don't. The people who are most overconfident are often those who have been in environments where their predictions weren't tracked against outcomes, so they never had to update.

People tell you what they care about when they're not trying to

The conversations that are most revealing about what a person values are the ones that aren't about values. The casual comment about a past colleague. The way they describe a decision that didn't work out — who they blame, what they take responsibility for, what they edit out. The speed at which they move from their own experience to the broader principle, or the reverse. What they find funny.

People manage the signals they send when they know they're being evaluated. They are less managed in the margins — in the small moments that don't feel assessment-relevant. Those moments tend to tell the truth.

I pay attention in the margins. It is one of the habits that executive search has built that I cannot turn off.

The people I trust most have a short list of things they actually know

There is a strong correlation between intellectual honesty and competence, in my experience. The people who are clearest about what they know versus what they are guessing at tend to be more right when it matters than the people who speak with equal certainty about everything.

The honest intellectual moves — "I don't know," "I could be wrong about this," "this is what the evidence suggests but the evidence is limited" — are not hedges that undermine credibility. They are markers of calibration that, over time, build more trust than the appearance of comprehensive certainty.

The corollary is that I am immediately more cautious with people who have no uncertainty. Not because uncertainty is inherently virtuous but because its complete absence suggests either that the person hasn't been tested by enough situations where they were wrong, or that they've been in environments where admitting uncertainty was penalised and they learned to suppress it. Neither is a pattern I want to depend on.

Most people are more similar than different

After seeing a lot of people in a lot of contexts, I have come to believe that the similarities across people outweigh the differences more than is usually assumed. The surface differences — in background, culture, approach, style — are real and matter in some contexts. The underlying concerns — security, respect, meaningful work, the welfare of people they care about — are far more consistent.

This is not a feel-good observation. It is a working tool. When I am trying to understand what someone wants or why they are behaving in a way that doesn't make sense to me, the most useful starting assumption is that they are trying to solve the same problems I would be trying to solve in their situation, with the information and incentives available to them. Usually this reframe makes the behaviour more legible.

When behaviour is still illegible after that reframe, I pay attention. It usually means I am missing something important about the situation they are in or the information they have.