When I set out to recruit my own successor as CEO of Operio Group, I was the one asking the questions, and I noticed something quickly: the questions that actually separated candidates were not the ones on any standard interview list. Anyone credible can talk about leadership philosophy. Almost nobody gets asked the questions that predict whether they'll run your business well for eighteen months and then hand it back better than they found it. Now that I'm on the other side of that table, offering interim work myself, my view hasn't changed. If anything it's hardened, because a candidate who is uncomfortable with the questions below is telling you something, and a candidate who welcomes them is telling you something too.

You are about to give a stranger the keys to a business you may have spent decades building, or one that landed in your lap without warning: a death in the family, a diagnosis, a falling-out that left the company without anyone at the wheel. However you came to be the person making this decision, here is what I would ask them, and the answers a good candidate should be able to give.

1. Have you run a business of this size, with a real P&L?

Not advised one. Not consulted for one. Run one, with the revenue responsibility, the headcount, and the sleepless nights that come with the seat. The gap between advising and operating is enormous and it shows up in the first crisis. A good candidate answers with specifics: the size of the business, what happened to it on their watch, and at least one thing that went wrong and what it cost. Just as critically, they should demonstrate a genuine command of the numbers: the P&L, the balance sheet, the cash flow statement, and the discipline of a 13-week cash flow forecast. Any CEO who can't dig into the numbers of their own business is not worth their salt. Be suspicious of a track record with no scar tissue. In seventeen years of building businesses I have accumulated plenty, and I'd trust nobody in this role who hasn't.

2. Have you ever handed a business over, and can I speak to the person you handed it to?

This is the single most revealing question on the list, because the interim job ends in a handover by definition, and the only evidence that someone can do it is that they have. In 2025 I recruited my own replacement at Operio, managed the transition, and moved to a different seat in the same business; the person I handed it to still runs it, and anyone considering me is welcome to that reference. Whatever the equivalent is for your candidate, ask for it. A candidate whose engagements all ended ambiguously, or who can't produce a successor willing to take the call, has shown you the ending of your own engagement in advance.

3. What will you do in your first thirty days?

The wrong answer is a detailed plan, because a detailed plan formed before meeting your team is fiction. The right answer is a listening structure: who they'll meet, what they'll read, which numbers they'll want, and roughly when you can expect their honest assessment. You're listening for humility about what they don't yet know, paired with evidence they know exactly how to find out.

4. How will you handle my existing leadership team?

An interim CEO inherits a team they didn't choose, containing people who wanted the job, people loyal to the last regime, and usually one person quietly holding the place together. A good candidate has a considered answer: assess quickly, communicate directly, make no symbolic firings to establish authority, and tell the owner the truth about what they find even when it's awkward. If they talk mainly about replacing people, be careful. Churn is easy; judgment about who to keep is the actual skill.

5. What authority do you need in writing, and what happens when we disagree?

A CEO who has to phone home before acting is an expensive observer, so a serious candidate will ask for real authority: over the team, the operating decisions, and spending within agreed limits. Just as importantly, they should volunteer where your authority continues: the things owners and boards rightly keep, like major transactions, and the mechanism for resolving a genuine disagreement. My recommendation is to write this up as a short document that clearly lists the decisions reserved for the board, so there is no ambiguity on either side. We did exactly that when I handed over at Operio, and it meant nobody ever had to guess where the CEO's authority ended. A candidate who wants unlimited authority is as concerning as one who doesn't ask for any.

6. How will we both know it's working by day ninety?

Insist on numbers and dates. A good candidate proposes a small set of measures, agreed before they start, reviewed at a fixed cadence, and is comfortable with the corollary: that if the measures aren't moving, you'll both say so out loud. Vague answers here become vague accountability later, at which point you have hired a very senior person you cannot evaluate.

7. What would make you tell us this isn't working?

Few owners ask this, and it's a shame, because the answer reveals whether the candidate thinks of the engagement as a service to the business or a billing arrangement. The best answer names real conditions: if the authority we agreed isn't honoured, if the business needs skills I don't have, if the situation turns out to need a permanent hire faster than planned. Someone willing to argue themselves out of a paying engagement is exactly the person you want in one. The role is an oxymoron, after all: the ultimate goal of an interim CEO is to make themselves redundant, and the candidates who have genuinely accepted that find this question easy to answer.

8. How does this end?

The engagement should end in succession, planned from the first month rather than the last. A good candidate talks unprompted about developing internal candidates, defining what the permanent hire needs to look like, running or supporting that search, and staying long enough to make the handover real rather than ceremonial. I think of this as succession by design: the ending is not an interruption of the job, it is the job. A really well-structured engagement puts money behind that principle, with some form of bonus around a successful handover, so the incentives point at the exit rather than away from it. Any candidate who seems to prefer engagements that quietly extend forever is optimising for the wrong outcome, namely theirs.

9. Who else are you committed to right now?

Interim work is full-time, so the answer should be short. Other board seats and modest advisory commitments are normal and often useful; another operating role is not. You're entitled to know exactly where their attention will be, and a professional will tell you without being offended by the question.

10. Why this engagement?

The good answers are specific to your situation: the sector, the problem, the stage, something in the business they find worth eighteen months of their life. The bad answer is any version of "I'm between things." An interim CEO who is running toward your problem will behave differently, for the entire engagement, than one who is running away from an empty calendar.

A closing thought on how to read the conversation as a whole. Every question above is really the same question wearing different clothes: does this person treat the seat as theirs to occupy, or yours to hand back? The candidates you want are the ones who talk more about the ending than the beginning, and who answer hard questions with specifics rather than reassurance. Confidence with the questions is the pitch, and any candidate worth hiring, myself included, should be glad you asked. If you're facing this decision and want to put these questions to someone who has sat on both sides of the table, you'll find me via my leadership and consulting page.