Start with industry experience. A bookkeeper who has worked with trade and service businesses will know what matters for your books. They’ll understand job costing, how to handle subcontractor payments, progress billing, materials tracking, and the deductions that apply to your type of work. A generalist can enter transactions but they won’t set up your chart of accounts in a way that actually tells you how each job performed.

Ask what accounting software they use and whether they have experience with your current setup. Most bookkeepers work in QuickBooks Online these days, but the important part is whether they know how to use it properly for your industry. A bookkeeper who just dumps everything into generic categories isn’t giving you useful information.

Find out exactly what’s included in the monthly fee. Some providers include bank reconciliation, financial statements, and bill tracking. Others charge extra for anything beyond basic transaction entry. Get a clear picture of what you’re paying for so there are no surprises. Ask about their pricing structure too. Is it flat rate or hourly? Does it go up as your transaction volume grows?

Ask how often you’ll hear from them and through what channels. If you want someone you can call with a question about a purchase or a tax issue, you need to know that upfront. Some bookkeepers work on a hands-off model where they do the books and send a report. Others take more of an advisory role where they’ll flag things, answer questions, and help you make decisions. Know which type you’re getting.

Ask what reports you’ll receive and how often. At minimum you should get a profit and loss statement and balance sheet monthly. For contractors and trades, you should also be getting job cost reports so you can see which projects are making money. If a bookkeeper can’t tell you what reports they provide, that’s a red flag.

Ask whether they handle tax preparation or coordinate with a CPA. Having your bookkeeper and tax preparer on the same page saves you money and headaches. When those two are disconnected, things fall through the cracks and you end up overpaying or missing deductions. Working with a CPA who specializes in construction and trade businesses means the books are built with tax time in mind from the start.

Finally, ask what they need from you. Good full-service bookkeeping should require minimal effort on your end, but every bookkeeper needs some level of cooperation. Knowing upfront whether they need weekly receipt uploads, access to your bank feeds, or a monthly check-in helps you decide if the arrangement is realistic for how you actually run your day-to-day.

The right bookkeeper will answer these questions clearly and without hesitation. If someone gets vague or defensive when you ask basic questions about their process, keep looking.