Start by asking what industries they work with. A bookkeeper who handles trucking companies understands IFTA reporting and fuel tax credits. One who works with restaurants knows food cost percentages. General bookkeeping skills matter, but industry experience means fewer explanations from you and fewer costly mistakes from them.

Ask what accounting software they use and whether they hold any certifications. If you’re on QuickBooks and they only work in Xero, someone has to switch. A certified QuickBooks ProAdvisor has demonstrated knowledge of the platform and stays current on updates.

Get specific about what’s included in their pricing. Some bookkeepers include bank reconciliation, financial statements, and reasonable questions in their monthly fee. Others charge separately for every service and every phone call. Understand the full cost before you commit so you can compare options fairly and avoid surprise invoices.

Ask how often you’ll communicate and in what format. Do they send monthly reports? Schedule quarterly calls? Only reach out when something’s wrong? Some business owners want regular updates. Others prefer hands-off service where they only hear about problems. Make sure your expectations align with their standard process.

Find out how they handle mistakes. Everyone makes errors occasionally. Good bookkeepers catch them quickly, fix them without prompting, and let you know what happened. Ask what their process looks like when something goes wrong. A vague or defensive answer tells you more than the words themselves.

Ask if they can provide references from current clients. Someone who’s been doing this work for any length of time should have happy clients willing to speak on their behalf. Reluctance to provide references is worth noting.

Question what happens when you need answers outside of scheduled communication. Can you email and expect a response within a business day? Is there a charge for phone calls? Knowing the boundaries upfront prevents frustration when you need a quick answer during a busy week.

Ask about their onboarding process for new clients. Do they review your existing books first? Set up systems for document sharing? Walk you through their expectations? A bookkeeper near Gentry with a clear onboarding process has thought through what it takes to serve clients well from day one.

Get clarity on what they need from you and how often. Some bookkeepers want receipts sent daily. Others want bank access and handle everything without much involvement from you. Neither approach is wrong, but you need to know what’s expected so you can hold up your end of the arrangement.

The questions matter less than paying attention to how they answer. A good bookkeeper explains things clearly, asks questions about your business, and seems genuinely interested in helping you succeed. Someone who’s vague about pricing, dismissive of your concerns, or can’t explain their process probably won’t improve once you’re paying them.

Monthly bookkeeping works best when there’s mutual trust and clear communication from the start. Take time to interview at least two or three candidates before deciding. The extra effort upfront saves you from switching bookkeepers six months later when the fit turns out to be wrong.