Questions to Ask the CFO
Questions for talking with the CFO at your own company, whether in a skip level, an all hands, or a project conversation, covering constraints, cash timing, how to build a spending case, and where the risk sits.
20 questions, each with the reason to ask it · includes a conversation guide
The questions
Open any question to see why it works.
- 1
Which numbers do you look at every week?
Distills a long metrics list down to what actually drives decisions. Whatever is named here is what your own work will eventually be measured against.
- 2
What's the constraint on us right now: cash, people, or demand?
Three very different worlds, and most teams guess wrong. A clear answer gives you a way to frame every request you make for the next year.
- 3
How does money move through a typical quarter for us?
Ask about timing rather than totals. Knowing when cash arrives explains hiring pauses and spending freezes that otherwise look arbitrary from the inside.
- 4
What does the board push hardest on?
Explains pressure that reaches you as sudden new priorities, and it tells you which kind of evidence carries weight when it travels upward.
- 5
Which line item surprised you this year?
Concrete and easy to answer, and it often surfaces something teams can directly influence, like cloud spend, contractor costs, or unused software.
- 6
How should I build a case when I want to spend money?
You get the format they actually want: a payback period, a comparison against the alternative, or a named risk of doing nothing. Most rejected requests fail on format.
- 7
What kinds of requests do you turn down most often?
Saves you from making one. The reason is usually unclear ownership or bad timing rather than the size of the number.
- 8
How do you decide between funding a new bet and protecting the core?
Shows the company's real appetite for risk. Watch whether the answer describes a rule or a case by case judgment, because the two behave differently under pressure.
- 9
What did we learn from last year's plan against what actually happened?
The variance story is where strategy shows. A CFO who cannot name a miss is either unusually lucky or not looking closely.
- 10
How concentrated are we in a few customers or suppliers?
Concentration is often the quietest risk in a business. The useful follow up is what would happen in the quarter after the largest one left.
- 11
What's the plan if revenue drops for two quarters?
Asked calmly, this is a fair question and often already answered internally. The reply tells you whether cuts are pre planned and roughly where they would land.
- 12
How do you decide what to share internally and what to hold?
Explains the pattern of what you do and do not hear. Most CFOs have a clear line around legally sensitive and market sensitive information.
- 13
What does your calendar look like, and when should I not bring you things?
Close weeks, audit periods, and board preparation are real constraints. Knowing them makes you noticeably easier to work with.
- 14
Where are we paying for something we no longer use?
Dormant licenses, auto renewing contracts, and duplicate tools come up constantly, and teams are usually better placed to find them than finance is.
- 15
How do you think about the cost of a hire beyond salary?
Loaded cost, ramp time, and management overhead are the pieces most headcount arguments leave out, and hearing the real numbers changes how you ask.
- 16
What financial term should everyone here understand and mostly doesn't?
Gets a short useful lesson on something like contribution margin, deferred revenue, or working capital. CFOs generally enjoy being asked this.
- 17
What do people outside finance most often misunderstand about your team?
Usually the difference between having budget and having cash, or why an approval takes a week. Worth knowing before your next request.
- 18
What would you change about how we plan?
Invites criticism of a process they own, which is why the answer tends to be specific and honest rather than defensive.
- 19
What made you take this job?
Personal without being intrusive. An answer about a specific turnaround, product, or person tells you what they came here to do.
- 20
What could a team like mine do that would make your job easier?
Ends with an offer rather than a request. The answer is usually small and repeatable: earlier notice, cleaner forecasts, fewer surprises in the last week of the quarter.
Talking to Your Own CFO
Practical guidance for the conversation itself.
Match the Question to the Room
Match the Question to the Room
A skip level or one to one
This is where the questions about constraints, planning, and what finance wishes teams did belong. Send one in advance if you want a considered answer instead of an improvised one.
An all hands
Everything you ask is heard by the whole company. Questions about concentration risk or a downturn plan are reasonable but land better if phrased as wanting to understand rather than wanting reassurance.
In the middle of a project
Keep it narrow: what format the case should take, what threshold needs approval, when in the cycle to bring it. Broad strategy questions waste a slot you needed for a decision.
Bringing a Spending Request
Bringing a Spending Request
- 1State the number, the timing, and who owns it in the first two sentences. Finance conversations that begin with context usually run out of time before the ask.
- 2Give the alternative you rejected and why. A single option looks like a preference; two options look like analysis.
- 3Say what happens if the answer is no, in plain terms. That is usually the part that decides it.
- 4Bring the assumption you are least sure about rather than hiding it. A CFO will find it anyway, and finding it themselves costs you credibility.
What Goes Wrong
What Goes Wrong
Asking questions that are really complaints
"Why can't we ever hire" gets a defensive answer. Asking what the constraint is, and what would change it, gets an explanation you can work with.
Asking about compensation or another person's budget
Neither is a CFO conversation, and both make the rest of the exchange guarded. Take pay questions to your manager or HR.
Bringing a number you cannot support
One unverifiable figure will get picked up and the whole request slows down. Round honestly and say which parts are estimates.