10 Cash Questions. Most CEOs Answer Four.
THE SHORT ANSWER
Most CEOs can state revenue, gross margin, and EBITDA without hesitating, and cannot state their true available cash, their days sales outstanding trend, or their runway. The ten questions below are the standard diagnostic for cash visibility. Answer each without looking at a report, and score one point for each yes.
A CFO in Paul Whitley's book asks every new CEO she works with the same ten questions in their first working session. Not to test them. To calibrate, so she knows which parts of the financial picture the CEO holds clearly and which parts are, in her words, held by faith.
The CEO in the story answered four of them with confidence, three with approximation, two with "Dana should know that," and one, number seven, with a long pause followed by the admission that he had never thought about it before.
"That's not unusual," she told him. "Most CEOs have three or four of these cold. The goal is to have all ten."
These are not a quiz. They are a map of where the blind spots are.
1. What is your current cash balance, and what do you expect it to be in 30 days?
Not yesterday's balance. A forward-looking projection. CEOs who operate from a forward cash picture make different decisions than those working from the last bank statement they happened to check. Start with your true available cash, which is rarely the number in the banking app.
2. What is your days sales outstanding, and is it trending up or down?
Days sales outstanding lives in the CFO's world. Sales celebrates the close. The CEO who owns this number has the conversation before the cash impact lands rather than after.
3. What are your three largest open receivables, and what is the status of each?
A company with $600,000 in total receivables looks diversified until you see that $410,000 is owed by one client who is 72 days past due. Concentration hides inside the summary.
This is the one question on the list that is supposed to require a report, because the names and amounts change every week. The other nine should be instinct.
4. What is your cash conversion cycle, and what is one thing you could do to shorten it?
The CEO who can answer this starts to see billing frequency, payment terms, and inventory levels as cash management decisions rather than operations decisions. That reframe is worth more than the metric.
5. What would a 20% revenue shortfall in the next 90 days do to your cash position?
The CEO with a playbook for this scenario is not surprised when it arrives. The CEO without one works it out in real time, under pressure, with fewer options than they had a quarter earlier.
6. What is your current gross margin, and what are the two biggest levers that could improve it?
Revenue is the number CEOs watch. Gross margin is the number CFOs watch. The gap between those two habits is where the real cash conversation lives.
7. How much of your cash flow comes from operations versus financing?
This is the question the CEO in the book paused longest on, and it is the one most likely to stop a reader here. It distinguishes between generating cash and borrowing it, two situations that look similar on the income statement and very different on the cash flow statement.
8. What is the largest single decision you could make in the next 90 days that would meaningfully improve your cash position?
When a CEO can answer this, cash management becomes a leadership conversation rather than something approved on the way to the next meeting.
9. How long would your business survive if revenue stopped tomorrow?
Current cash plus available credit, divided by monthly cash burn. The question feels catastrophic and has a precise, calculable answer. Every CEO should know it before the revenue stops.
10. What is the one financial conversation you have been avoiding with your CFO?
The avoided conversation is almost always about a risk that is known but not acknowledged. Naming it is almost always the beginning of the solution.
How should I score myself?
Eight to ten is genuine cash visibility. Five to seven is partial visibility, with specific gaps worth naming. Zero to four means you have reports but you do not yet have intelligence, and the gap is wide enough to allow a significant surprise through.
Most CEOs have three or four cold on the first pass. That is not unusual and it is not a judgment. The goal is all ten, built through repetition rather than memorization.
These ten questions are not a quiz. They are a map of where your blind spots are.
Why do the answers matter more than the numbers?
Because there is a difference between a CEO who reads a cash flow statement and one who understands it.
The CEO who reads it can recite the numbers. Ending cash. Operating cash flow. Ask them what drove it, ask why cash from operations dropped even though revenue was up, and they start reaching. They look at the CFO. Or they offer something general, like we had some timing issues with receivables. It sounds informed. It is surface. They are reading the weather report without understanding the pressure systems.
The CEO who understands it does not recite numbers. They tell you a story.
Something like this: we collected less this month because we closed three large deals late in the quarter and the invoicing did not go out until week four, which pushed about $600,000 into next month's collections, and meanwhile we prepaid for the equipment build-out on the east coast facility, a one-time hit of $400,000, so operationally we are fine, the cash timing just got compressed.
That is a completely different conversation. That person is not reading a document. They are narrating the cash life of their business.
And when a crisis comes, and it always comes, the second CEO already knows which levers to pull. They do not panic and they do not freeze. They act, because they have been living inside those numbers rather than looking at them once a month.
How long does it take to get there?
About twelve months of consistent practice, and the pattern is fairly predictable.
Months one to three, foundation. The weekly cash report is established. The CEO is reading it and still deferring to the CFO on most interpretations.
Months four to six, language. The CEO starts asking questions before receiving answers, and begins noticing when profit performance and cash position diverge.
Months seven to nine, habit. The CEO anticipates the weekly meeting rather than preparing for it, and knows the shape of the 13-week cash flow forecast before opening the document.
Months ten to twelve, integration. The CEO connects operational decisions to cash consequences automatically, and asks what this does to our 13-week before approving initiatives. The CFO shifts from presenting to the CEO to thinking alongside them.
It is not linear, and setbacks are normal. A busy quarter. A distraction. A stretch where the weekly meeting gets deprioritized. What matters is that the practice is maintained, not that it is perfect.
What is the fastest way to start?
Ask your CFO to walk you through your 13-week cash forecast this week, and pay attention to how they explain it. If they have to simplify it for you, that is your starting point. If you already understand it, you are further along than most.
Then ask question ten, out loud, in a room where the answer can go somewhere.
The CEO in the book kept the list in the top drawer of his desk for eleven months. By the end of those eleven months he could answer nine of the ten without looking at a document.
The one he still had to check was number three, and that one is supposed to require a report.
Frequently asked questions
What financial metrics should a CEO review weekly?
Three at minimum: true available cash net of committed outflows, receivables due in the next fourteen days, and payables due in the next fourteen days. Add days sales outstanding and the 13-week forecast summary as the habit establishes.
Should a CEO understand accounting?
No. A CEO needs to understand cash, which is a different skill. The useful test is whether you can explain the difference between your profit and loss statement and your cash flow statement in plain language without a prompt from your CFO.
What if I score low on this list?
It is a common starting point, including among CEOs running profitable, well-regarded companies. The gap is usually a systems and habit gap rather than an ability gap, and it typically closes within two to three quarters of a disciplined weekly cash rhythm.
Call to action
Get the book. Every one of these ten questions has a chapter behind it in Profitable and Broke: What Your Cash Flow Reveals About Your Leadership. If you scored below eight, the book is the cheapest way to close the gap, and it is built to be finished.
If you would rather walk the ten with a CFO who has answered them at $1.5 million and at $5 billion, book a strategy call with Paul Whitley.
About the author
Paul Whitley is the Founder and CEO of C-Suite Support, a Texas-based fractional executive firm that provides fractional CFO, COO, and CMO services to owner-led businesses across Dallas-Fort Worth, Houston, Austin, and North Texas. Paul Whitley has spent more than thirty years as a CFO, COO, CMO, and general manager for companies ranging from $1.5 million to $5 billion in revenue, and has helped raise more than $336 million in public debt, private equity, bank debt, and asset-backed financing. He is the author of Profitable and Broke: What Your Cash Flow Reveals About Your Leadership and the host of CEO Talks with Paul Whitley on the C-Suite Network.
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