Before you hire a bookkeeper, ask questions that reveal whether they can actually handle your business. A few targeted questions during the initial conversation will tell you more than a polished website or sales pitch.

Start with industry experience. Ask what types of businesses they currently work with and whether they’ve worked with companies in your industry. A bookkeeper who understands restaurant food costs, construction job costing, or professional services billing will get your books right faster than one learning your industry on your time. General bookkeeping skills matter, but industry knowledge means fewer mistakes and more useful financial information.

Ask about their process and timeline. When will your books be closed each month? How do they handle questions that come up? What do you need to provide on your end, and when? A vague answer like “we’ll figure it out as we go” suggests they don’t have a reliable system. You want specifics. Books closed by the 15th, questions answered within 24 hours, bank access and receipts needed by the 5th.

Clarify what’s included in the price. Monthly bookkeeping can mean transaction entry and reconciliation only, or it can include financial statements, sales tax prep, bill pay support, and more. Ask exactly what you’re getting. If the quote seems low, find out what’s excluded. If it seems high, understand what additional value you’re receiving. Comparing prices without comparing scope is meaningless.

Ask how they communicate. Some bookkeepers send a monthly email with your reports. Others schedule monthly calls to review the numbers. Some respond to texts within hours, others take days. Neither approach is wrong, but you should know what to expect and whether it matches how you like to work.

Find out what software they use. Most bookkeepers work in QuickBooks Online, but some prefer Xero or other platforms. If you already have a system you like, confirm they’ll work in it. If you’re starting fresh, understand what they recommend and why. The software itself matters less than whether they’re proficient in it.

Ask for references. A good bookkeeping service should be able to connect you with current clients who can speak to their reliability and accuracy. If they hesitate or can’t provide references, that’s worth noting. The clients don’t need to be in your exact industry, but they should have similar complexity or needs.

Ask what happens if something goes wrong. Mistakes happen. What matters is how they handle them. Do they have a process for catching and correcting errors? Do they carry professional liability insurance? A bookkeeper who gets defensive about this question might be harder to work with when issues arise.

Finally, trust your gut. If the initial conversation feels disorganized or the answers are vague, that probably reflects how they’ll handle your books. A competent bookkeeper should be able to answer these questions clearly because they’ve thought through how they serve clients.