What to Ask Before Hiring a Bookkeeper

Hiring a bookkeeper can make your life a whole lot easier, but not all bookkeepers are the same. Whether you're a solo business owner or managing a growing team, asking the right questions upfront helps you find someone who understands your needs and can keep your finances in order.

Here are the most important questions to ask before you hire a bookkeeper.

1. Have you worked with businesses like mine?

Different industries have different bookkeeping needs. A contractor, a retail shop, and a hair salon all handle money and expenses in unique ways.

• Ask if they’ve worked with your industry before
• Make sure they understand the type of expenses and income your business deals with
• See if they’re familiar with your state’s rules or specific requirements

2. What software do you use?

Your bookkeeper should be comfortable using software that fits your business. If you're already using a tool, ask if they’re experienced with it.

• Do they use QuickBooks Online, QuickBooks Desktop, or something else?
• Can they help you get set up if you're starting from scratch?
• Will you still have access to your books anytime?

3. Can you help clean up past records?

If your books are a mess or you’re behind, don’t worry. Many business owners are in the same boat. A good bookkeeper should be able to clean things up and get you on the right track.

• Ask how they handle catch-up work
• Find out if they charge hourly or offer flat-rate cleanup services

4. How will we communicate?

You want someone who keeps you in the loop and makes things clear.

• Will they send monthly reports or check in regularly?
• What reports will you get?
• Can you call, email, or schedule a meeting when you have questions?

5. What services do you offer, and how much do you charge?

Bookkeepers offer a range of services, and every one structures pricing a little differently.

• Do they charge a flat monthly fee or bill by the hour?
• What’s included in their service packages?
• Do they offer tax prep, payroll, or other services?

6. How do you keep up with changes in tax laws or accounting rules?

Things change, and your bookkeeper should be paying attention to those updates.

• Do they stay current on business tax rules?
• Do they work closely with CPAs or tax pros?
• Can they give advice on staying compliant?

7. What happens if there’s a mistake?

Nobody's perfect, but you want to know that your bookkeeper has a process for fixing things quickly and correctly.

• How do they handle errors?
• Are they insured?
• Will they take responsibility for fixing any problems?

Final Thoughts

The right bookkeeper isn’t just someone who handles your numbers. They’re someone who supports your business and helps you feel more confident about where you’re headed. Ask questions, trust your gut, and make sure you feel comfortable.

At The Sassy Bookkeeper, we make it easy. Every new client starts with a free consultation, and we walk through your needs, goals, and how we can help. Whether you're starting out or already running a busy business, we’re here to support you every step of the way.