20 questions a CFO would ask about your business

Hire a CFO and the first meeting is mostly questions. Not exotic ones — almost embarrassingly plain ones. That's the trick: the CFO mind isn't a bigger spreadsheet, it's a short loop running on repeat. Where's the cash, what's the trend, what breaks first. Every question below is one of those three wearing different clothes.

Here are the twenty, grouped the way a CFO works through them. Read them against your own business — the ones that sting a little are where the money is.

Money coming in

1. Is revenue growing, or just moving? New customers and repeat orders are growth. The same dollars arriving from different names is churn with good manners. And always compare to the same month last year, not last month — otherwise you're mostly measuring the seasons.

2. Who are your five biggest customers, and what share of revenue is that? If one name is a third of your revenue, their bad quarter is your bad quarter. Concentration isn't a flaw — most businesses are built on a few good relationships — but it should be a number you know, not a feeling.

3. What do you actually make on each sale? Gross margin, by product or service line. Almost every business has an offering that quietly subsidizes another. You can't fix the freeloader until you can name it.

4. If you raised prices 5% tomorrow, who would actually leave? Usually fewer than you fear. A 5% price move falls almost entirely to the bottom line — it's the highest-leverage, lowest-effort number in the whole business, which is exactly why a CFO pokes at it early.

Money staying in

5. Which costs grew faster than revenue last year? Anything outpacing revenue is taking a bigger slice of every dollar than it used to. Some of that is deliberate (you hired ahead of growth). The rest is drift — and drift compounds.

6. What does a month cost if you sell nothing? Rent, payroll, insurance, software — the fixed base. This is the number payroll anxiety is made of, and knowing it precisely is calming in both directions.

7. What are you paying for that you stopped using? Software seats for people who left, subscriptions nobody opens, the storage unit from two offices ago. Vendor creep is boring, which is why it survives.

8. How far into the month do you break even? If the doors open on the 1st and your fixed costs are covered by the 19th, every sale after that is the profitable part of the month. When that date drifts later year over year, the business is getting heavier.

Cash

9. How many payrolls are in the bank? CFOs don't count runway in vague months — they count it in payrolls, because payroll is the obligation that can't slip. "Four and a half payrolls" is a number that changes how you sleep.

10. Why is profit up while cash is down? The most-asked question in small-company finance, and the answer is almost always growth: more receivables, more inventory. Profit is an opinion about the period; cash is a fact about the bank account. A CFO never lets one stand in for the other.

11. Who owes you money, and how late are they? A past-due invoice isn't revenue being slow — it's an interest-free loan you're extending, involuntarily, to your customer. Age your receivables and the polite version of the question becomes: which loans would you like to call in?

12. Whose money is funding the gap — yours, your suppliers', or the bank's? Stretched payables, a drawn credit line, and your own cash are the three answers. All three are legitimate. Only one of them was usually chosen on purpose.

The cycle

13. How long does a dollar take to come home? Pay a supplier today; sell the thing weeks later; collect weeks after that. That round trip is the cash conversion cycle, and it's the single best one-number summary of how hard your working capital is working.

14. How many days does inventory sit on the shelf? Put it in days, not dollars — "119 days" lands differently than "$240k." Every day you shave frees real cash without selling a single extra unit, which is often more cash, faster, than next month's profit.

15. What happens to cash if you grow 30% next year? Growth soaks up cash before it pays out — more inventory bought ahead, more receivables outstanding. The CFO question isn't "can we grow" but "who funds the growing." A three-statement model answers it on your own numbers — better to pick the answer in January than discover it in August.

What breaks first

16. Which customer, supplier, or person would hurt most to lose? Every business has single points of failure. Naming them out loud is most of the protection — backup suppliers get sourced and processes get written down only after someone admits the exposure exists.

17. If revenue dropped 20% tomorrow, what gets cut, and in what order? Decide calmly now or decide panicked later — those are the options. A cut list written in good times is shorter, smarter, and kinder than one written in a bad week.

18. What's coming due in the next twelve months? Loan maturities, lease renewals, equipment that's due, tax payments. These are known dates that businesses routinely treat as surprises. A CFO keeps them on one page, in date order.

The forward look

19. How did the year compare to the plan — and was there a plan? Budget vs. actual is how numbers learn to mean something. Even a one-page plan turns every month's results into feedback instead of weather.

20. What would you do with an extra $100k? Whatever you just answered is your strategy, written down or not. More inventory, a hire, an acquisition, paying down the line — and if nothing came to mind, that's information too.

The loop, one more time

Notice that none of these require a CFO's salary. They require statements you already have and an honest hour a month. Where's the cash, what's the trend, what breaks first — ask it monthly, on repeat, and you're running the loop. That's the CFO mind.