Deputy CEO Interview Questions: What a Board Tests

Deputy CEO interview questions are asked by a board about a role that sits close to the top job without being it. The board wants to find out whether you can be a real number two to the chief executive, standing in for them and speaking for them, without acting as though you are the successor in waiting. It is a narrower test than a chief executive interview, and a harder one to pass. JOH Partners, which has closed more than 1,000 senior mandates since 2014, sees the pattern often in Gulf family groups. JOH's own research, The succession gap, found that forty-seven of sixty Gulf-listed family companies face a succession event within five years, and only fourteen have a documented internal successor.

This guide is for senior leaders being considered as deputy to a chief executive. It sits alongside the other board-level interview guides and draws two boundaries. The CEO interview covers the top job itself. The COO interview covers the operating mandate. This guide covers a role that is defined by its relationship to the chief executive, and by the question of who comes next.

What are deputy CEO interview questions really asking?

Three things, none of which will be said out loud. Can the chief executive trust you? Can the board trust you to tell it the truth about the chief executive? And will you still be here in three years?

Those pull in different directions. A candidate who is very loyal to the chief executive will look like a courtier to the board. A candidate who is very open with the board will look like a spy to the chief executive. The strong answer is plain about both. You will back the chief executive in front of the organisation. You will say what you think in private, early, and to their face. And if you ever had a concern you could not settle with them, you would tell them you were going to the chair before you did it.

Some boards put this to you directly: "How would you describe the relationship between a chief executive and their deputy?" Others come at it sideways, with a question about a time you disagreed with your boss. Either way, they are listening for how you describe the people above you. Candidates who criticise a former chief executive in the interview are telling the board what they will say about this one.

How do you answer the question about wanting the top job?

It will come up. Do you want to be chief executive? The board has two worries and you are caught between them. If you say no, they wonder why you are taking a deputy role and whether you will leave in eighteen months. If you say yes, the chief executive in the room wonders if you are measuring the office.

Say what is true, and say it in a particular order. First, you want to do this job well, and the job is to make the chief executive successful. Second, you would like to be considered for the top role one day, and you would expect to be measured against other candidates, inside and outside. Third, the choice belongs to the board and not to you, and you will not behave in a way that makes the chief executive's life harder in the meantime.

That answer works because it contains both ambition and restraint. A board can hire someone with that mix. It cannot hire someone who has only one of them.

A board does not want a deputy with no ambition, and it does not want one who is waiting. It wants one who will make the chief executive better and be honest about what comes after.

What will the board ask about the line between you and the chief executive?

Boards that have been through a bad number two arrangement ask very concrete questions. Which decisions would be yours alone? Which would you take to the chief executive first? What would you do if the chief executive was travelling, a major customer called, and the call could not wait?

Do not answer these with principles. Say what you would decide, say what you would not, and say how you would tell the chief executive afterwards. The test of a good deputy is that the chief executive is never surprised. They may disagree with a decision you took in their absence, but they will not find out about it from someone else.

Be ready to describe a time you stood in for a senior person, and what happened when they came back. If it went well, say why. If you made a call they would have made differently, say how you handled the conversation. Boards trust the candidate who admits that happened more than the one who says it never did.

This is also the place to explain how you are different from a chief operating officer if the role is close to that one. A deputy often has an operating load. The difference is that you carry the chief executive's authority as well as the operating plan, which means you must know what they would say. JOH's perspective on the chief operating officer role sets out the operating side, and it is worth reading to see where the two roles overlap and where they do not.

Can you work beside a family principal who may be the real heir?

In a Gulf family group the chief executive is often a professional, and the person who decides what happens next is a member of the family. That person may chair the board, or sit behind it as owner. They may have a son or a nephew in the business who is the likely heir. You are being asked to work beside all of them.

A good panel will test this. How would you handle a request from the principal that cut across the chief executive's plan? What would you do if the principal asked you for an opinion on the chief executive's performance? How would you treat an heir who was learning the business and had the right to ask questions?

The honest answers are uncomfortable. You would not go around the chief executive, and you would not lie to the principal. You would say to the principal that the best way to get a straight answer about the chief executive is to ask the chief executive, and that you would be glad to be in the room. You would treat the heir as a future colleague and not as a rival or a client. JOH's perspective on where boards get succession wrong explains why a handover usually fails in the months after the appointment, not at the point of choice, and why the person in the middle is often the first to feel it.

The family context matters for the sector too. Group holdings carry this structure more than any other part of the Gulf market, and a candidate who understands the owner's position will do better than one who treats the owner as another board member.

In a family group the person who decides your future may not be the chief executive. The deputy who understands that, and still serves the chief executive well, is the one worth backing.

What should you ask the chair and the chief executive?

Your questions tell the board how you will behave in the job. Ask what decisions would be yours when the chief executive is away. Ask whether the board has had a conversation about succession and whether you are part of it, or whether you are being asked to be a placeholder. Ask the chief executive how they want to work with you day to day, and what they would want you to do differently from the last person who held the role.

If the role is new, ask why it was created. A deputy appointed because the chief executive is stretched is in a different position from one appointed because the board is quietly preparing for a change. You are entitled to know which you are being offered.

Watch for vagueness on authority. If the chair says the deputy will "support" the chief executive and cannot say what that means in practice, you are being asked to build the role with no one's backing. That can work, but you should know it before you accept.

How should you prepare?

Prepare three real examples. One is a time you stood in for a senior person and decided something they had not. One is a time you disagreed with a chief executive or another senior leader and said so to their face. One is a time you supported a decision you did not agree with, and how you went about it. Then say each aloud to someone who works in a different industry, and cut anything they do not follow.

On the JOH podcast, Santi Rasanayagam on moving from CFO to CEO is a useful listen for how the step to the top looks from the person taking it. JOH's anonymised case study of the first non-family chief executive at a Saudi industrial group shows how much depends on the people around a chief executive, which is where a good deputy earns their place.

AssessYou is the candidate platform from JOH Partners, built on the diagnostics the firm uses on retained search mandates, and it is a sensible way to hear your answers aloud before a board does. Start with the free leading people interview question bank on AssessYou, with example answers, which is built around how you lead people. The wider set of free banks is at assess-you.com/interview-questions and needs no sign-in. When you want practice on your own CV, with candid feedback on every answer, sign up to AssessYou.