The Questions You’re Not Asking Your Bookkeeper (But Should Be)

The Questions You’re Not Asking Your Bookkeeper (But Should Be)

When most business owners think about bookkeeping, they picture receipts, reconciliations, and reports they barely glance at before tax time. But a good bookkeeper does so much more than keep your records clean. The real magic happens when you start asking better questions.

And not just about what happened, but about what’s possible.

If you’ve ever felt stuck in survival mode, unsure whether you’re “doing it right,” or wondering why your numbers never seem to match your bank balance, this post is for you.

First, Here’s What Most People Ask:

Let’s start with the usuals, the questions we hear all the time:

• Can I write this off?

• How much did I make last year?

• What do I owe in taxes?

• When do I send my 1099s?

These are valid. They matter. But they’re just the tip of the iceberg. If you want real growth, real clarity, and real control, you have to dig deeper.

Now, Let’s Talk About the Questions That Actually Change Things

These are the ones we wish more clients would ask, because they open the door to financial transformation.

❓ How much can I safely pay myself?

Too many business owners either pay themselves nothing or pull from the business without knowing the impact. Asking this question lets us look at your actual cash flow, upcoming expenses, and income trends, so we can give you a number that feels safe and sustainable.

❓ Am I charging enough?

Your pricing is directly tied to your financial health. If you’re always stressed about money but booked solid, this is a sign it’s time to review your rates. We can show you how much you need to earn per service or product to cover costs and grow with confidence.

❓ What’s my profit margin, and is it good?

Revenue is great, but it doesn’t mean much if your expenses are eating it all up. Knowing your profit margin tells you whether your business model is actually working. If it’s low, we can help you course correct.

❓ Where am I overspending?

This question is gold. We can help you spot subscriptions you forgot about, expenses that no longer make sense, or areas where a little tightening could create breathing room.

❓ What should I be planning for next?

Whether it’s taxes, a slow season, or a big equipment upgrade, the earlier we know your plans, the better we can help you prep for them. There’s power in planning ahead, and peace, too.

What I Wish Every New Business Owner Knew About Money

Now for the real talk.

I wish every new business owner knew that they don’t have to figure it all out alone.

That the goal isn’t to do it perfectly, it’s to stay in motion, ask questions, and be open to learning. That your numbers are not a report card. They are a story. And when you learn how to read it, you can start writing better chapters. That ignoring your books does not make the fear go away. It multiplies it. But facing your finances head-on? That builds confidence you can feel. That bookkeeping is not just a task. It is a tool for clarity, confidence, and control, and yes, even peace.

Ready to Ask Better Questions?

We’re not just here to organize receipts and send reports. We’re here to support you, strategize with you, and walk beside you as you build something incredible.

If you're ready for more than just number crunching, let’s talk. We’ll answer your questions, and help you ask the right ones.

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