The Two Questions Every Board Should Ask a CEO Candidate

Published 09 June 2026 | 4 min read

Hiring a CEO is arguably the most important decision a board will make.

The appointment will influence strategy, culture, performance, stakeholder confidence, and ultimately organisational value. Yet despite the significance of the decision, many CEO interviews follow a predictable script. Candidates are asked about growth, leadership style, strategic priorities, and past achievements. Unsurprisingly, most arrive well-prepared with compelling stories and polished responses.

The challenge for boards is that success leaves clues, but so do failure and self-awareness.

A strong CEO is not defined solely by what they have achieved. They are defined by how they respond when things go wrong and by how well they understand the impact they have on others.

If I were advising a board on selecting a CEO, there are two questions I would insist on asking.

1. What is the most expensive mistake you've ever made?

Not the biggest challenge. Not the toughest project. Not a disguised success story.

A genuine mistake.

Every experienced executive has made one. The question is whether they have the courage to talk about it honestly.

Perhaps it was a poor acquisition, a failed market expansion, the wrong senior appointment, or a strategic decision that delivered disappointing results. Whatever the answer, the board should listen carefully to how the candidate describes the experience.

Do they take ownership, or do they explain it away?

Do they focus on who was to blame, or what they learned?

Most importantly, what happened next?

A supplementary question should always follow:

"How did that experience change the way you make decisions today?"

This is where the real value lies.

Mistakes themselves are not the issue. Repeating them is.

The best leaders emerge from difficult experiences with sharper judgement, greater humility, and a more disciplined approach to decision-making. They become better at testing assumptions, seeking diverse perspectives, and recognising risks before they become problems.

The board is not assessing the mistake. It is assessing the learning.

2. Who are the people that won't like working for you?

At first glance, this question can feel uncomfortable. That's precisely why it works.

Most CEO candidates can articulate their strengths. Far fewer can describe the unintended consequences of those strengths.

Every leadership style creates tension somewhere.

A highly accountable leader may frustrate those who avoid difficult conversations. A CEO who moves quickly may test the patience of people who prefer consensus. A leader focused on transformation may create discomfort for those who value stability.

Self-aware leaders understand these dynamics.

They know not everyone will enjoy working with them, and they can explain why.

The supplementary question is equally revealing:

"What feedback do you hear repeatedly that you know is true, but still have to work on?"

This question often separates confident leaders from genuinely self-aware ones.

At CEO level, honest feedback becomes increasingly rare. People are less likely to challenge authority, meaning blind spots can grow larger over time. Leaders who actively acknowledge their weaknesses and work to address them are often more effective than those who believe they have few.

The answer reveals humility, coachability, and emotional intelligence—qualities that become critical when leading large organisations through complexity and change.

Looking Beyond the CV

Boards often spend considerable time assessing competence. That is understandable. Experience, capability, and track record matter.

However, competence alone rarely determines whether a CEO succeeds.

Judgement does.

Self-awareness does.

Character does.

A candidate's achievements tell you what they have done. Their mistakes and blind spots tell you who they are.

When the stakes are as high as a CEO appointment, that distinction may be the most important insight a board can gain.