09/01/2026
Here’s how asking a CFO one question can lead to better ones.
Picture this: you’re sitting at your desk, thinking about hiring someone.
The question you might be asking is:
“Can I afford another employee?”
It’s a reasonable question.
But if you were sitting across the table from me, I probably wouldn’t answer it right away.
Instead, I’d dig deeper and ask:
What problem are we trying to solve with this hire?
What will this person actually allow the business to do?
What will the hire cost—not just in salary, but in payroll taxes, benefits, training, and the time it takes to get them productive?
What would need to happen financially for this investment to make sense?
And what happens to cash while we’re getting there?
If you really think about it… “Can I afford to hire?” may not actually be the question we need to answer.
The better question might be:
“What would need to be true financially for this hire to be a good decision?”
That’s a different conversation. A different lens. Even though it’s related to the initial question at hand!
Have you ever noticed how sometimes having another perspective changes the entire conversation and decision?
That’s one of the things I love about looking at a business through a CFO lens.
It’s not always about having the answer.
Sometimes it’s about asking a better question first before making a decision.
