Founder Q&A: 5 Money Questions Every Owner Should Ask Quarterly

Every founder knows that running a business is different from growing a business. Growth requires clarity, discipline, and the courage to ask tough financial questions regularly. The problem is, many owners only ask them once a year often at tax time when it is too late to course-correct.

A quarterly financial check-in is your chance to hit pause, look at the numbers that matter, and make decisions from a place of insight rather than guesswork. Here are the five questions I recommend every CEO ask themselves and what to do with the answers.

Question 1: Are we profitable and why (or why not)?

Why it matters:

Profits is not just about the bottom line; it is about what is driving that number. Many businesses assume all sales are good sales, but often 20% of products or clients produce 80% of profit.

Common blind spot:

Business owners often mistake revenue growth for profitability. A new client may increase top-line sales but add hidden costs in labor, materials, or support.

Action step:

Break down profit by product line, client segment or service.

• Compare margins quarter-over-quarter.

• Drop or reprice the offerings that drain resources without returns.

  
  

Question 2: Is our cash flow predictable?

Why it matters:

Cash flow is the lifeblood of any small business. A company can be profitable on paper but run out of cash if collections lag or expenses spike. Predictability matters more than size when it comes to cash flow.

Common blind spot:

Many founders track revenue but do not track the timing of cash inflows and outflows. They are shocked when payroll or tax deadlines hit harder than expected.

Action step:

Prepare a 13-week rolling cash flow forecast every quarter.

• Flag clients who consistently pay late and adjust terms or incentives.

• Identify large expenses coming up (taxes, equipment, bonuses) and plan reserves now.

  
  

Question 3: Are we aligned with our budget?

Why it matters:

Your budget is not just a spreadsheet; it is a commitment to how your business will allocate resources. Reviewing actual performance against your budget helps you spot waste, prioritize spending, and keep control.

Common blind spot:

Owners set budgets at the start of the year, then never revisit them. By the time the CFO (or accountant) points out overruns, thousands have already been lost.

Action step:

Compare actual results to budget quarterly, not yearly.

• Focus on big variances (positive or negative) to understand what’s driving them.

• Update your forecast for the rest of the year based on what you’ve learned.

Question 4: What risk are we carrying right now?

Why it matters:

Financial risk is not always obvious until it is too late. Client concentration, rising costs, market shifts, or regulatory changes can hit hard if you’re not monitoring them.

Common blind spot:

Many CEOs only think of risk as debt. But dependence on one large client, underpricing services, or ignoring rising costs are just as dangerous.

Action step:

Identify your top 3 risks each quarter.

• Run 'what if' scenarios: What if my largest client leaves? What if interest rates rise another 2%?

• Build contingency reserves or adjust strategy proactively.

Question 5: Do we have the right financial support in place?

Why it matters:

Strong businesses eventually outgrow DIY accounting or part-time bookkeeping. Having access to fractional CFO or interim CFO services can mean the difference between reacting and planning.

Common blind spot:

Owners often wait until they are overwhelmed or facing a crisis (cash crunch, bank loan request, investor pitch) to bring in financial expertise.

Action step:

Ask yourself: Do I understand my numbers enough to make confident decisions?

• Consider whether your current financial partner provides analysis or just reporting.

• Explore outside support if you want proactive insights on profitability, cash flow, and growth strategy.

Closing Takeaway

Your numbers are speaking to you every quarter. The question is: are you listening?

Founders who regularly ask and act on these five questions build healthier, more profitable, and more resilient companies.

If these questions raised uncertainty, that’s a signal it is time to go deeper.

• Free Template: CEO Financial Self Assessment Journal

Before you chase growth, test your model with this tool. It helps small business owners and executives apply structured corporate finance thinking without needing a full-time CFO.

You got this. One step at a time.

✅ Ready for Strategic Financial Planning? Let’s get eyes on your numbers and build your roadmap to profit.

👉 Book a Discovery Call Now : (630) 670-3989

📥 Or forward this to someone who needs a second set of eyes on their finances.