Finding the right bookkeeper or accountant can feel like looking for a needle in a haystack—especially if you’re not sure what to ask or where to start. Over the years, I’ve learned that the questions you ask are as important as the answers you get. And with tools like ChatGPT at your fingertips, you can craft interview questions that cut through the fluff and get to what really matters: finding someone who will treat your numbers with the care and accuracy they deserve.
Here’s how to create the best prompts in ChatGPT to help you dig deeper and get the information you need to make the right decision.
- Start with Your Must-Haves
Before you even think about crafting prompts, get crystal clear on what you want in a bookkeeper or accountant. Do you need someone to keep your books squeaky clean month after month? Someone who can help you plan for taxes? Or maybe someone who’s already worked with businesses like yours?
Once you know your must-haves, you can ask ChatGPT to create prompts that align with your needs. For example:
“Create a list of 5 different interview questions for a bookkeeper who has experience with service-based businesses and can handle monthly reconciliations and year-end tax prep.”
This prompt gives ChatGPT a clear focus, so it can help you build questions that get straight to the point.
- Get Specific About the Role
The more specific your prompts, the more tailored the questions will be. Here are some ideas:
- “Generate 5 interview questions to assess a bookkeeper’s ability to catch errors and reconcile accounts.”
- “Create 5 questions to find out how an accountant would handle financial reporting for a business that sells both services and products.”
These prompts tell ChatGPT exactly what kind of questions you’re looking for. No more generic, one-size-fits-all lists!
- Dig Into Their Process
You don’t just want someone who knows the numbers—you want someone who owns them. Use prompts that ask about their process and how they think:
“Create 5 questions that uncover how a bookkeeper ensures accuracy in monthly reports and tracks down discrepancies.”
Or:
“Make a list of 10 interview questions that reveal an accountant’s approach to proactive business growth planning and communication.”
This helps you find out if they’re the type of person who will just crunch the numbers, or if they’ll also partner with you to help your business grow.
- Test for Communication and Fit
Skills matter, but so does how they communicate. You want someone who can explain what’s going on in plain English—not in a jumble of accounting jargon. Try prompts like:
“Generate 5 questions to find out if a bookkeeper can explain financial reports in simple terms to a business owner.”
Or:
“Write 5 interview questions that explore how an accountant manages expectations and handles tough conversations with clients.”
These questions will help you find someone who fits with your style and can talk to you about your numbers in a way that builds trust.
- Add a Few Curveballs
Sometimes, the best way to see if someone’s the right fit is to ask questions that go beyond the usual “tell me about your experience.” ChatGPT can help with that too:
“Create some unconventional interview questions to see if a bookkeeper has a proactive mindset and can handle the unexpected.”
Or:
“Generate a few ‘what if’ scenario questions to test how an accountant would respond to a tricky financial situation.”
These curveball questions can be surprisingly revealing.
Putting It All Together
Here’s a quick example of how you could use these prompts in practice:
“ChatGPT, create a list of 4 interview questions for a bookkeeper who has experience with law firms, is detail-oriented, and can communicate financial information clearly to non-accounting folks.”
ChatGPT will then give you a set of questions that’s actually useful—not just generic questions you could find with a quick Google search.
Final Thoughts
At the end of the day, your goal isn’t just to find someone who can reconcile your books or file your taxes. It’s to find a partner who will help you understand your numbers and use them as a tool to grow your business.
By using these targeted prompts in ChatGPT, you can craft questions that go deeper, help you see past the resume, and find someone who truly gets what your business needs.
If you’re in the market for a bookkeeper or accountant, I hope this guide gives you the confidence to ask the right questions—and find the right person for your team.
Want to learn more about how to turn your numbers into powerful decision-making tools?
Let’s chat! Pick out a time on my calendar —I’d love to hear about your business and your goals.
