How to Interview a CFO
Or: The numbers don't lie, and neither should your finance leader.
This is the next post in the How to CEO series, a collection of tactical guides for leading high-growth companies. If you’re just joining, start with the series welcome post, or check out How to Write a Job Description for a Senior Exec and How to Interview a Product Leader.
Hiring a CFO is different from every other exec role, and it should be. This is the one part of the business where there’s zero room for gray. Zero room for half-truths, improv, or “we’ll fix it later.”
Finance has to be bulletproof. The numbers have to be right. The books have to be closed. The story has to hold up to investors, auditors, the board, and you.
“A great CFO doesn’t just report the numbers, they understand what’s behind them and help you make the hard calls because of them.”
There’s no room for creativity here. No innovation points. You want a CFO who tells you the truth, every time, with no spin. You want transparency, accuracy, and maturity. And you want someone who sees their job as keeping the company safe and helping it grow.
The One Axis That Matters Most
Controller-Strong vs. FP&A-Strong
Most CFOs come up through one of two paths: Accounting and Controller, or Financial Planning and Analysis (FP&A).
A Controller-strong CFO knows the numbers cold. Payroll, compliance, cash flow, audit, taxes, board-ready reporting, they don’t miss. You can hand them to any board member, investor, or auditor, and know they’ll have the answer.
An FP&A-strong CFO is a strategic thinker. They model scenarios, analyze risk, and help you see around corners. They’re your partner in planning growth, managing burn, funding investments, and preparing for acquisitions, yours or theirs.
You need both. But know which one they default to, and which one your company can’t afford to be weak in.
And One Non-Negotiable Expectation
A CFO must be your truth-teller and your steady hand.
This isn’t optional. The best CFOs tell the CEO the truth, always. But they know when and where to do it.
With you: brutally honest. Private, clear, no spin.
With the team: calm, confident, protective of the company’s stability.
This is about trust and maturity, not background.
The 5 Questions That Reveal Who They Really Are
1. “Walk me through your experience running finance and accounting. How do you make sure the numbers are bulletproof?”
How do you ensure accuracy in reporting, compliance, payroll, and cash flow?
Show me: what does a finance team you’ve led look like, how many people, what roles, what systems?
2. “What are your go-to benchmarks and operating ratios? How do you evaluate the health of a company financially and operationally?”
Sales and Marketing vs. Engineering spend?
CAC to LTV?
Sales comp, quota attainment?
How do you know when the business is performing, or not?
3. “Tell me about a time you helped a company raise money or prepared for an acquisition. How did you support the CEO and the process?”
What was your role in fundraising or M&A?
How do you think about capital strategy, debt, equity, dilution?
4. “If I talked to your last CEO, how would they describe your relationship? How did you disagree, and how did you support them publicly?”
When did you have to deliver hard truths privately?
How did you manage alignment with them, and confidence with the team?
5. “Let’s talk about our business. What do you want to know, and what would you look at first?”
What would you ask me about our financials?
What would you want to understand about our business model?
What jumps out to you as key risks or levers?
Closing Set (Always):
What’s your long-term ambition?
What’s your superpower—what do people rely on you for?
What’s something you’re not great at, or still working on?
If I talked to your last manager, what would they say your biggest growth area is?
CFO Interview Scorecard
Want a version you can actually use in interviews?
Grab the CFO Interview Scorecard here
Make a copy and take it into your next CFO interview.
Final Gut Check:
Do I trust this person with every number in the business, and am I hiring a partner or a scorekeeper? Do I want them at the table helping shape the future, or just keeping the books straight?
“You don’t want someone who just tracks your business. You want someone who helps build it.”
The CEO Move
Decide if you want a partner, or just someone to keep score. Then hire accordingly.
The biggest mistake CEOs make is hiring a CFO for what they think they need, when they haven’t been honest about what they actually want. You can hire someone to give you the truth, help shape strategy, and challenge your thinking. Or you can hire someone to keep the books tight and the reports clean. Both matter. But you can’t confuse them.
And don’t forget, the kind of business you’re running changes everything. A CFO who knows SaaS might not know marketplaces. A PLG business isn’t the same as sales-led enterprise. Hire someone who knows how to manage and grow this kind of company, not just any company.
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#leadership #howtoceo #executivehiring #cfo #startups #RealTalk