Questions great CFOs ask in interviews – and what they reveal about how they think

When companies set out to hire a CFO, the focus is often on preparing the right questions to ask the candidate. What’s your experience with fundraising? How do you lead a finance transformation? What’s your approach to business partnering? All valid questions,  but in our experience working with senior finance professionals, some of the most telling moments in an interview come not from the answers CFOs give, but the questions they ask.

Exceptional CFOs treat the interview as a two way conversation. They’re not just there to talk about themselves or tick boxes. They want to get under the skin of the business, understand its challenges, assess how they can create value, and ultimately, figure out if it’s the right fit for them. Their questions reveal a huge amount about their mindset: how they think, what they prioritise  and how they lead. Below are some of the best questions I’ve heard from CFO candidates - and what those questions tell us.

1. "What keeps the CEO awake at night?"

This one cuts straight to the heart of the business. It’s not about day to day processes or technical capability. It’s about strategy, risk, and alignment.

By asking this, a CFO is signalling that they want to be in lockstep with the CEO. They’re thinking like a business partner, not just a financial gatekeeper. They want to understand where the pressure points are and where finance can make the biggest impact - whether that’s in stabilising cash flow, supporting investment decisions, or modelling different scenarios for growth.

2. "What’s the current finance team structure and where are the gaps?"

This question tells you that the candidate is already thinking like a leader. They’re not simply stepping into a role, they’re assessing how to build capability, drive efficiency, and scale a team that supports the wider business.

It also shows self awareness. A great CFO knows they can’t do it all themselves. They’re interested in the strengths and weaknesses of the existing team, how responsibilities are distributed, and where they might need to invest or restructure.

3. "How frequently do you reforecast and why?"

This one is subtle, but very telling. It’s not about whether the answer is weekly, monthly, or quarterly. It’s about understanding how the business manages change and uncertainty.

A CFO who asks this is looking for insight into how decisions are made. Is the business data driven and agile? Or reactive and disorganised? It also reveals whether finance is seen as a strategic function - or just a reporting one.

4. "What does success look like in 12 months?"

A classic for a reason. Smart CFOs want to align expectations early. They’re looking to understand what the board and leadership team really want from their finance leader.

Is it about securing funding? Improving reporting? Preparing for an exit? Without clarity on what success looks like, it’s hard to prioritise. Great CFOs want to hit the ground running, and this question helps them focus on the outcomes that matter most.

5. "How has the business funded growth to date – and what’s the runway?"

This is particularly relevant in VC/PE-backed or high growth businesses. It tells you that the CFO is already thinking about capital strategy, burn rate, and future funding needs.

They’re assessing risk. They’re thinking about cash. And they want to know how robust the business model is - not just now, but in 12, 24, 36 months’ time.

6. "What do you wish the previous CFO had done differently?"

A bold but brilliant question. It gets straight to the pain points.

Asking this shows courage. It shows curiosity. And most of all, it shows a desire to learn from the past in order to shape the future.

Great CFOs know that leadership is about change, not just continuity. This question helps them identify where they can make a difference and avoid repeating mistakes.

7. "Where is the business going in 3-5 years, and how fixed is that vision?"

This one’s all about strategic alignment. The best CFOs are thinking long term. They want to understand whether the company has a clear vision and whether it’s willing to adapt along the way.

This question also reveals how the CFO approaches uncertainty. Are they rigid in their planning  or comfortable with ambiguity? Do they see finance as a co-pilot to strategy? If they’re asking this, they probably do.

So what’s the takeaway?

Truly great CFOs don’t just give strong answers. They ask smart questions. The kind that show commercial awareness, strategic thinking  and emotional intelligence.

Their questions reveal more than a CV ever could. They show you what kind of leader they’ll be. How they’ll work with the CEO. Where they’ll add value. And how they’ll shape the future of your business.

So next time you're interviewing for a CFO, pay close attention to what they want to know.

Because in many cases, the smartest question in the room doesn’t come from the interviewer - it comes from the candidate.

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