The Financial Questions Every Owner Should Ask—Every Month

Simple questions to keep you grounded, focused, and leading from your numbers

Running a business is never static. No matter what industry you’re in, there are pressures—economic, competitive, operational, and personal—that shift constantly. And in the midst of that change, it’s easy to slip into reacting instead of leading.

That’s where a disciplined rhythm of monthly financial questions becomes one of your best leadership tools.

When business owners stay engaged with a few key financial questions every month, they stay grounded in the numbers that matter most. These questions aren't just about reviewing reports—they’re about using your financials to lead, strategize, and make confident decisions. They're the framework that helps owners rise above the weeds, refocus on outcomes, and stay aligned with long-term goals.

Let’s walk through the questions every business owner should be asking—month after month—and why each one matters.

1. Are My Margins Holding Steady—or Slipping?

Margin erosion is one of the most dangerous trends in business because it usually creeps up slowly. If your revenue is growing but your gross profit margin is shrinking, you might not notice right away—but it can have a significant impact on cash flow and profitability down the road.

Every month, ask:

• What was my gross margin percentage this month?

• How does that compare to last month and the same month last year?

• If margins have changed, do I understand why?

Margins should always be trended. Look at them in a horizontal format—months across columns, margins as percentages. This trend view is what helps you see early warning signs, such as a supplier cost increase, discount creep, or team inefficiency in service delivery.

2. Do I Understand What’s Driving the P&L?

It’s not enough to just look at whether you made money this month. The deeper question is: What’s driving the numbers?

• What changed from last month, and why?

• Are any expense lines unusually high or low?

• Were there any one-time events?

You don’t need to be a trained accountant to spot unusual patterns. You just need your reports to be structured in a clear and consistent way—and you need to take the time to compare, question, and understand. The best business owners look at their financials the way a coach looks at game footage: to learn and improve.

3. Is My Cash Position Strengthening or Weakening?

You can be profitable and still run out of cash. That’s why you need to evaluate cash flow separately from your income statement.

Ask each month:

• What was my ending cash balance?

• Did cash go up or down this month?

• Why?

You don’t need a complex cash flow statement to answer this at a basic level. You just need to track whether your total cash on hand is trending up or down—and be able to tie that to operational activity. If cash dropped, was it because of a big tax payment? A drop in collections? A slow month in sales?

Understanding your cash movements is essential for short-term decisions like timing payroll, inventory purchases, or owner distributions.

4. Are My Receivables and Payables in Good Shape?

Accounts receivable (A/R) and accounts payable (A/P) are like the arteries of your cash flow. If you’re not monitoring them, your business might be healthy on paper but struggling in real life.

Ask:

• How much am I owed, and by whom?

• How old are those outstanding invoices?

• Do I have any bills I haven’t paid that I need to plan for?

Good bookkeeping will give you clear A/R and A/P aging reports. Great bookkeeping will summarize that data and help you act on it. If customers are paying slower than usual, or if you’ve let vendor balances build up, you need to catch it before it turns into a cash crunch.

5. Am I Forecasting Forward—or Only Looking Back?

This is where good accounting becomes great leadership. Looking at the past helps you understand what’s happened—but looking forward is how you make better decisions.

Ask yourself:

• What is my best-guess forecast for the next few months?

• Do I expect to hit my goals?

• Am I being proactive with staffing, pricing, and spending based on what’s coming?

The best-run businesses maintain a monthly rolling forecast—an expected P&L for the next 6–12 months. And they revise it every month, using their most recent actual results and what they know now.

You don’t need to get every forecast perfectly right. But you do need to build the muscle of looking forward—because that’s what gives you the time and space to course-correct before problems get big.

6. Is My Reporting Set Up to Help Me Lead?

Even the best questions won’t help if your financials aren’t structured clearly. If your reports are cluttered, inconsistent, or hard to understand, you’ll avoid looking at them—and miss critical insights.

Take a moment to evaluate:

• Do my reports give me trends, not just one-month snapshots?

• Are they structured the same way every month?

• Do I understand what’s being shown?

• Is there a summary page that highlights the key takeaways?

If not, talk to your accounting team. Great reporting is about communication. It should help you lead better conversations—with your team, your partners, and yourself.

The Monthly Review That Builds a Better Business

These questions don’t require a finance degree. They just require consistency. A rhythm. A habit.

That’s why we encourage our clients to build a monthly financial review process into their business cadence. Whether you take an hour on the first Monday of the month or set a quarterly finance meeting with your leadership team, the key is to make these questions part of how you lead.

You’ll be surprised how often these simple questions lead to smarter decisions. Clearer priorities. Healthier cash flow. And a better understanding of what’s working—and what’s not.

Because at the end of the day, your numbers are telling a story. When you ask the right questions, you’ll finally hear what they’re saying.