“Stories and lessons from an unexpected journey in finance.”

Someone asked a good question on my last post. Before taking a CFO seat, shouldn’t you just ask them what they’re not telling you?

Right instinct. Useless question.

Anyone willing to conceal something will conceal it, and a direct question just tells them what to prepare for. But that isn’t the real problem with it.

The real problem is that it assumes someone knows.

In most of the situations I’ve walked into, nothing was hidden. Nobody lied to me. The uncomfortable facts were sitting in plain sight, in a system somebody had stopped looking at.

I once evaluated a business whose revenue was presented as subscription ARR. Everyone said so. The deck said so. It took pulling fifty-four months of customer-level sales history to establish that the revenue was actually consumption-based — booked as billed. That single correction changed the retention math, the bookings framework, and how the business should be valued.

Nobody misled anyone. Nobody had looked.

So I don’t ask what they’re hiding. I ask questions that test whether anyone has been looking.

Who has left the finance team in the last year, and did anyone ask them why? Finance turnover is the loudest signal available and the one most often explained away. People who close the books every month know exactly where the bodies are. When several of them leave in a short window, that is the answer to your question.

When was the last close you’d describe as clean? Watch what happens in the pause. If nobody can name one, there’s no standard to fall short of — which means nothing has been measured against anything.

What does the board come back to every single meeting? Whatever they keep circling is the thing nobody has fixed. It has survived multiple quarters of attention from the most powerful people in the company. By month two it will be yours.

None of these ask anyone to confess.

They just reveal how long it’s been since the organization asked itself a hard question.

What’s the one question you always ask before you say yes?

#TheAccidentalCFO #CFO #InterimCFO #DueDiligence #INERSEC