Professional Ethics Shared Interest Group

The 5 Questions Every Business Owner Should Ask About Their Numbers

How to spot financial risk early—and protect yourself from ethical drift

Your financials can look completely fine—and still mislead you.

Not because anyone is doing something wrong intentionally.

But because of how the numbers are built—through assumptions, estimates, and judgment calls made every month under pressure to hit targets.

Individually, those decisions can make sense. Over time, they shape the story your numbers are telling you.

And you're using that story to make real decisions:

• Hiring

• Investing

• Expanding

• Borrowing

Your CFO owns the numbers. You own what happens if those numbers are off—or if they're built on compromises.

You don't need to audit the books to protect yourself.

You need to ask questions that surface what's usually left unsaid. Questions that reveal not just what your numbers are, but how they got built and why.

Question 1: "What's the most aggressive assumption we're currently making—and if it were off by 10%, what would that mean for me?"

Every business relies on assumptions.

The risk isn't that they exist.

It's that you don't know which ones matter most—or whether they're aggressive because they're realistic, or because there's pressure to hit a target.

If a small change in an estimate meaningfully impacts your results, your decisions are more exposed than they appear.

You're not looking for perfect accuracy. You're looking to understand:

• How much your numbers depend on being right

• Who made the call

• What data backed it up

• Whether anyone internally questioned it

What to listen for:

✓ "Here's the assumption. Here's the data. The controller questioned it, but here's why we landed here."

⚠ "We're confident in this number" (with no data) or "We need this assumption to hit our targets."

Question 2: "Is there anything in our numbers that would surprise me if I fully understood it?"

Most financial risks aren't hidden—they're just not discussed.

This question creates space for things to surface:

• Areas that are more complex than they seem

• Assumptions that aren't obvious

• Decisions that haven't been fully explained

• Places where pressure to hit targets influenced the estimates

If nothing comes up, that's worth noticing. It might mean your team feels safe being honest. Or it might mean they don't feel safe bringing up concerns.

What to listen for:

✓ "Yes, actually. Here's something we've been watching..." or honest acknowledgment of gray areas

⚠ "No, everything is straightforward" when you know the business is complex, or silence that suggests people are uncomfortable speaking up

Question 3: "If we had to explain our numbers to an investor or buyer tomorrow, where would we feel uncomfortable?"

You may not be planning to sell—but this question forces clarity.

It highlights:

• Areas that rely heavily on judgment

• Decisions that are technically acceptable but hard to defend

• Parts of the business that wouldn't hold up well under scrutiny

• Estimates that benefited from "flexibility" in accounting rules

What feels uncomfortable in that scenario is exactly what deserves your attention now.

What to listen for:

✓ "We'd be fine. Here's how we'd explain it..." or honest acknowledgment of one or two gray areas with clear documentation

⚠ "That's not something we worry about" or hedging language, or they list multiple areas that feel unclear even to them

Question 4: "How much pressure is there to hit certain numbers, and how does that influence our estimates?"

This is the ethics question most CEOs don't ask directly.

But it's critical.

There's a difference between:

• Making aggressive but defensible estimates based on business judgment

• Making estimates based on what you need the numbers to be

The second one is where drifting starts. It's usually not fraud. It's usually rationalization.

"The auditor approved it." "It's technically within GAAP." "Everyone does this." "We'll fix it next quarter."

But once you accept one shortcut, the next one is easier. Once the CFO makes one aggressive call to hit a target, the culture shifts. Once your team sees targets matter more than accuracy, they adjust accordingly.

What to listen for:

✓ "We have targets, but we never compromise estimates to hit them. If the numbers don't support the target, we adjust the target or our strategy."

⚠ "We do what we need to do to hit targets" or "The auditor accepts it, so it's fine" or vague answers about how much pressure exists

Question 5: "If you were in my position, what would you want to look into more closely?"

This is the question most people don't ask—and the one that often reveals the most.

It shifts the conversation from:

• Reporting → Perspective

• Defense → Honesty

It gives your team permission to tell you what they see but may not say directly.

If the answer is "nothing," it's worth asking again. Sometimes twice.

What to listen for:

✓ Direct, specific concerns. Even if they're uncomfortable. Even if they challenge something you thought was fine.

⚠ "Nothing" or "Ask the CFO" or deflection. These suggest your team doesn't feel safe speaking up.

What These Answers Reveal

Over time, the way your team answers these questions will tell you more than the numbers themselves.

🟢 You Have a Disciplined, Ethical Environment If:

• Answers are direct and specific

• Assumptions are openly discussed

• People acknowledge discomfort rather than hiding it

• Team members are willing to challenge each other—and you

• Estimates are made based on data, not targets

• When pressure exists, people say so

• Concerns surface before they become problems

What this means for you:

You're making decisions based on something real—not just something that looks right. Your numbers are reliable. Your team won't compromise ethics to hit targets because the culture doesn't allow it. If problems emerge, you'll hear about them early.

🟡 You May Be Drifting If:

• Answers feel vague or overly confident without clear data

• A few people control most of the narrative, and no one pushes back

• Small concerns exist but don't get fully explored

• Pressure to hit targets is acknowledged but brushed aside

• "The auditor accepted it" is used as justification rather than explanation

• The same accounting questions come up every year

What this means for you:

This is where most problems start. Nothing is broken yet—but you're relying more on trust than visibility. Your CFO might be making aggressive calls that are technically acceptable but ethically questionable. Your team may be learning that targets matter more than accuracy. The culture is slowly shifting.

Why this is dangerous: Drifting is how scandals start. It's not one big lie. It's a series of small compromises that become normal. By the time you realize you have a real problem, it's systemic.

🔴 You're in a High-Risk, Ethically Compromised Environment If:

• It's hard to get a straight answer

• Discomfort is avoided, dismissed, or explained away

• The same concerns come up repeatedly—or people have stopped raising them

• Estimates are openly tied to hitting targets

• "Everyone does this" is used to justify borderline decisions

• Your team shows signs of fear rather than engagement

• Corrections happen quietly every quarter as "adjustments"

What this means for you:

The risk isn't obvious in your numbers. It's in what's not being said about them. Your finance team has accepted a culture where targets drive estimates. The ethical lines have shifted. Corrections are being hidden. This doesn't feel like fraud because no one framed it that way—but it is. And it will blow up.

Why This Matters

Most businesses don't go from "fine" to "problem" overnight.

They drift.

Quietly. Gradually. With each small compromise feeling reasonable at the time.

The CFO makes an aggressive call to hit a target. It works. Next quarter, it's easier. By year two, it's normal. By year three, it's the culture.

And one day—a new auditor questions it. A shareholder lawsuit surfaces it. An SEC inquiry forces disclosure. And you have to explain why you didn't ask these questions.

The companies that avoid this aren't the ones with perfect numbers. They're the ones with honest conversations about how those numbers are built.

What You Should Do Next

At your next meeting with your finance team:

• Ask 2–3 of these questions

• Pay attention to how people respond—not just what they say

• Notice what gets explained clearly… and what doesn't

• Notice who speaks up and who stays silent

• Ask follow-up questions if something feels vague

After the meeting, ask yourself:

• Which culture do I have?

• Are my team's answers consistent?

• Did anyone seem uncomfortable?

• Did I learn something I didn't know?

If you're in 🟡 or 🔴:

Don't wait. This doesn't fix itself. Start with a direct conversation with your CFO about pressure, targets, and how estimates are actually made. If you don't like the answers, you may need to make changes.

If you're in 🟢:

Protect it. These cultures are rare. Don't let pressure or growth compromise what you've built.

The hard truth: You own the consequences of your numbers. Whether they're accurate, whether they're ethically built, whether they'll hold up under scrutiny—that's on you. Asking these five questions is how you stay ahead of it.