10 Hard Questions To Ask About Your Business

Running a business isn’t just about numbers—it’s about decisions, risks, and sacrifices. As business owners, we often find ourselves grappling with tough questions we’re not sure how to answer, let alone ask.

In this post, we’ll tackle 10 difficult yet essential questions that every entrepreneur should ask themselves about their business.

1. Where did all my cash go, and is my business actually profitable?

Why It’s Important: A profitable business doesn’t always mean healthy cash flow. If cash is constantly tight, it’s time to dig deeper.

Starting Point: Review your financial statements regularly and identify areas of leakage—overspending, uncollected receivables, or low-margin products.

2. What is my business worth?

Why It’s Important: Your business’s value isn’t just about today; it’s about planning for the future—whether for selling, raising capital, or strategic growth.

Starting Point: Begin with a valuation that factors in revenue, profitability, and industry benchmarks.

3. Is owning a business even worth it? (Considering financial risk, long hours, and time away from family.)

Why It’s Important: It’s easy to get lost in the grind. Reassessing your “why” ensures that your business aligns with your personal and financial goals.

Starting Point: Reflect on the trade-offs you’re making and whether they bring you closer to the life you want.

4. Is my business protected against the next COVID-like event or an economic downturn? 

Why It’s Important: Resilience is key. Building a plan for disruptions ensures your business can survive and thrive during uncertain times.

Starting Point: Evaluate your current savings, insurance, and risk mitigation strategies.

5. Can my business run without me, and what happens to it if something happens to me? 

Why It’s Important: A business that depends on you for everything can become a liability, both personally and financially.

Starting Point: Start delegating and document key processes. Consider succession planning.

6. Am I paying myself the right amount? (Too much? Too little? Not at all?)

Why It’s Important: Paying yourself fairly is essential for both personal and business financial health.

Starting Point: Determine a balance between reinvesting in the business and meeting your personal needs.

7. What’s my exit strategy? (Retirement? Selling the business?)

Why It’s Important: Every business owner needs an endgame—whether it’s scaling down, selling, or passing it on.

Starting Point: Define what “success” looks like for your exit and create a step-by-step plan to achieve it.

8. Should I reinvest in the business or take profits out, and how do I handle debt?

Why It’s Important: Striking the right balance between reinvestment, profit-taking, and debt management is critical for long-term stability.

Starting Point: Assess the ROI on reinvestments and weigh it against your current debt obligations.

9. Can I afford to hire more staff, or is that too risky?

Why It’s Important: Hiring can fuel growth, but it’s a big commitment. Knowing when the time is right helps you scale sustainably.

Starting Point: Review your revenue projections and cost structure to see if your business can absorb the added expense.

10. Why did I start the business in the first place?

Why It’s Important: Over time, it’s easy to lose sight of the original dream that inspired you to start your business. Reconnecting with your “why” can reignite your passion, guide your decisions, and ensure your business aligns with your core values and goals.

Starting Point: Reflect on what motivated you when you first began. Was it freedom, creativity, financial independence, or making a difference? Compare your current reality to those original aspirations and identify where you may have drifted.

How We Can Help With Our Fractional CFO Services:

At Think Accounting, we specialize in helping business owners navigate tough questions with clarity and confidence. Whether it’s understanding your cash flow, valuing your business, planning for growth, or preparing for the unexpected, we’re here to provide actionable insights and tailored strategies.

Through our Fractional CFO services, we act as your trusted partner—guiding you through financial decision-making, improving profitability, and aligning your business with your goals. From contingency planning to cash flow optimization, we help you tackle the big questions so you can focus on what truly matters.

Let’s Talk: If you’re ready to explore how Fractional CFO services can transform your business, get in touch today. Together, we’ll help you build a roadmap for success.

Thank You For Reading. See You Next Time!

Think Team🙏

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