11 Essential Questions to Ask When Hiring a Bookkeeper (Plus a Bonus Tip!)

If you’re thinking about hiring a bookkeeper for your business - first of all, congrats! It means you’re stepping into a new season of growth and want to get your finances organized, which is a huge win and so exciting. 

But how do you know if someone is the right fit to handle your books? 

How do you feel confident sharing sensitive information with someone who’s essentially a stranger? 

How do you even navigate this if you’re not familiar with bookkeeping at all? 

All valid questions and whether you’re hiring your first bookkeeper or looking to switch from someone who just isn’t working out, it’s important to ask the right questions before you commit. A great bookkeeper should make your life easier, not more confusing.

Here are 11 smart, simple questions to help you find someone you can trust (plus a bonus one you might not have thought to ask).  

1. Do you have experience with businesses like mine?

Every industry has its quirks. Whether you’re a service provider, coach, e-commerce seller, or creative entrepreneur, it helps to work with someone who understands the nuances of your type of business. Bonus points if they’ve worked with other clients using similar platforms or payment processors.

2. Are you familiar with the bookkeeping software I use (or want to use)?

A good bookkeeper should be confident using your preferred software (like QuickBooks Online, Xero, or Wave). If you’re not sure about which software you’d like, ask if they can help you choose the best platform that meets your goals (user friendly, budget, app integrations, etc.) 

3. What’s included in your monthly services?

Services vary bookkeeper to bookkeeper. Ask about what's covered (like reconciliations, monthly reports, sales tax tracking, payroll support, or advisory services). It’s also worth asking what’s not included so you’re clear on pricing and expectations.

4. How do you communicate with clients?

Do they prefer email? Loom videos? Scheduled Zoom calls? Text messages? You’ll want someone who communicates in a way that works for you and keeps things clear and collaborative.

5. How quickly do you respond to questions or finish month-end books?

Understanding their average turnaround time (and how they handle urgent requests) can help set expectations and avoid last-minute surprises. 

If you're not sure what a month-end close is, it's the formal process a bookkeeper completes to close the prior month of financial activity. When asking about month-end close, you’re asking how soon they complete the prior month’s bookkeeping. For example, if June just ended, when can they close June? By July 15th? July 20th? End of July? (If you’re looking for a quick monthly close, be upfront with anyone you talk to).  

6. Do you offer clean-up or catch-up services if I’m behind?

If your books are a little (or a lot) messy, it’s okay - life happens! Not every bookkeeper offers clean-up services, so it’s good to ask upfront and find out how they approach getting things back on track. 

7. How do you keep client data safe?

Your bookkeeper will have access to sensitive financial info, so security matters. Look for someone who uses secure platforms, encrypted file-sharing, and strong password protection.

8. Will I have access to my books at all times?

This is your business! You should always have access/visibility into your financials. Ask whether you’ll have your own login and if reports will be shared regularly.

9. Can you help me understand what my numbers mean?

The best bookkeepers don’t just track your numbers, they help you understand them. You deserve to feel confident reading your reports, knowing where your money is going, and using your financials to make smart decisions. 

If it ever sounds like a bookkeeper is speaking a foreign language, don’t be afraid to ask questions. (Personally, I prefer when clients ask for clarification, it helps me communicate better). 

10. What will you need from me each month?

There will be info your bookkeeper needs from you to complete bookkeeping tasks and month-end closes on time. Ask what your role will be (sending receipts, reviewing reports, etc.) so you know what to expect and can keep things running smoothly.

11. Can you help me prepare for tax time (or work with my CPA)?

While most bookkeepers don’t file taxes, a good one should help you stay organized throughout the year so tax season isn’t a nightmare. They might prepare year-end financial reports, 1099 info, or coordinate directly with your CPA to make things easier. It’s worth asking how they support that process.

BONUS QUESTION: What type of team do you work with? 

Okay, so this topic is not talked about often, but it’s important. Many bookkeepers, regardless of their business size, work with offshore teams. While your tax preparer must disclose if your tax return information is shared with anyone outside of the US, bookkeepers don’t have the same obligation. 

I’m not offering an opinion about offshore teams, just making you aware that this is way more common than you may realize. If you’re not comfortable with your financial data (items like bank statements or accounting files) being shared with a team outside the US, this question is worth asking. If you don’t mind, then great! 

Final Thoughts

Hiring a bookkeeper is more than checking off a box, it’s about finding someone who understands your business, keeps things stress-free, and empowers you to grow. Asking these questions upfront can help you feel confident and supported from the start.

The content on this website is for informational purposes only and does not constitute financial, tax, accounting, or legal advice. Reading blog posts or other materials on this site does not form a professional relationship. Services are only provided under a signed engagement agreement. You should consult with a licensed professional before making any decisions based on the information provided.