How to Hire a Bookkeeper for a Trades Business: Questions to Ask

There’s no license required to call yourself a bookkeeper, which means the person keeping your books could be excellent or could be learning QuickBooks on your dime. Most owners find out which one they hired about a year in, usually when the CPA calls with questions nobody can answer.

Whether you end up working with us or someone else, these are the questions I’d ask before handing anyone your books, plus how to tell a few months into the relationship whether you picked well. A lot of the lists of bookkeeping questions out there are written for any business. These are for businesses that run crews, trucks, and jobs.

First, Know What You’re Hiring For

Bookkeeping help usually falls into one of two jobs, and it’s worth knowing which one you need before you start interviewing:

• A cleanup or catch-up. The books are behind, messy, or were set up wrong. This is a project with a start and an end, and it’s usually priced separately.
• Monthly bookkeeping. The ongoing work of recording transactions, reconciling accounts, and closing the books each month.

Plenty of businesses need both, cleanup first and then monthly. It also helps to decide whether you want someone in-house, a freelancer, or a firm. An in-house person knows your business day to day, and a firm usually has backup when someone is out sick or leaves.

The Questions to Ask

Do they understand how a trades business works?

• “What other trades or service businesses do you work with?” Experience with your type of work matters more than years in the field.
• “Can you show me a job cost report or a P&L by service line you’ve set up for another client?” With the client’s name removed, of course. If they’ve never built one, they’ll be learning on your books.
• “How do you record field labor versus office payroll?” The answer you want is that field crew wages, their payroll taxes, and their workers’ comp go into cost of goods sold, and the office staff and owner pay don’t. If everything goes into one payroll line, your gross margin won’t be accurate.
• “Can you track revenue and costs by service line or location?” If you run install and service, or lawn care and hardscape, you want to see each one’s margin separately.
• If you do bigger jobs: “Have you worked with progress billing, retainage, or a work-in-progress schedule?”

How will the work get done each month?

• “When will my books be closed each month?” A good answer is a specific day, usually somewhere around the middle of the following month. “When I get to it” is not a good answer.
• “What will I get from you every month?” At a minimum: a P&L, a balance sheet, and a list of who owes you money (the A/R aging). If you run jobs, a job cost report too.
• “Do you reconcile every account every month?” That means every bank account, credit card, and loan, not just the main checking account.
• “What do you do with a transaction you don’t recognize?” You want someone who asks you. A bookkeeper who guesses or parks everything in “Uncategorized” is building a mess you’ll pay to clean up later.
• “How do you work with my CPA at year end?” A good bookkeeper hands your CPA clean books without a lot of back-and-forth, and is willing to jump on a planning call.

Systems and people

• “What software do you use, and can it connect to my field software?” If you run Jobber, Housecall Pro, ServiceTitan, or something similar, ask how invoices and payments will flow into the books. You can also ask whether they usually recommend disconnecting the CRM from QuickBooks and recording only cash sales.
• “Who will actually do my work, and who do I call with a question?” At a firm, the person on the sales call may not be the one doing the work.
• “What happens if that person leaves or is out for a few weeks?”
• “How do you keep my information secure, and who has access?”

Pricing

• “What’s included in the monthly fee, and what costs extra?” Payroll, 1099s, sales tax filings, cleanup work, and extra meetings are common add-ons, and it’s better to know now than on the first invoice.
• “Is it a flat monthly fee or hourly?” Either can work, but with hourly billing you want a rough estimate of the monthly hours.

Bookkeeping Red Flags to Watch For in a Trades Business

• They can’t explain your P&L back to you in plain language.
• They never ask you questions about transactions. Nobody knows your business well enough to categorize every charge without asking once in a while.
• The books are always two or more months behind.
• They seem annoyed when you ask what something means.
• They only talk about the P&L and never look at the balance sheet, which is where loans, credit cards, and customer balances live.
• There are negative numbers on your balance sheet.
• Some of your assets or loans are missing from the balance sheet.
• The P&L has so many categories, or so few, that it’s hard to read and use.

How to Tell If You Have a Good One

A few months in, these three checks take about five minutes and tell you a lot:

Check	What good looks like
Compare the cash balance on your balance sheet to your bank statement for the same month-end date.	They match. If they don’t, the bank reconciliation isn’t getting done.
Compare your loan balances on the balance sheet to your latest lender statements.	They’re close. Loans are one of the most common places books drift, since only the interest shows up on the P&L.
Look for “Uncategorized,” “Ask My Accountant,” or “Suspense” on your reports.	They’re at or near zero.

Beyond those, a good bookkeeper closes on time, sends the reports without you asking, flags things before you notice them (“fuel costs jumped this month, did something change?”), and makes year-end easy for your CPA. If your CPA’s first comment is how clean the books were, you picked well.

If You Need to Switch

There’s a myth that the only good time to switch bookkeepers is at the beginning of a new year. While that timing has some advantages, the benefits of switching to a good bookkeeper today far outweigh the benefits of staying with a mediocre one until the end of the year. Waiting means more months of bad data to run your business on, and more to clean up before you can file taxes. Before you make the change, make sure you have admin access to your own QuickBooks or Xero file, copies of the last few months of reconciliations, and a list of any open items the old bookkeeper was working on. If the books are already in bad shape, plan on a cleanup before the monthly work starts.

Where to Start

If you want one thing to do this week, run the three checks in the table above on last month’s books. Whether you’re hiring someone new or checking the person you already have, it’ll tell you where things stand.

If you’d like help figuring out what your business needs from a bookkeeper, a free 15-minute discovery call is an easy place to start, and we’re happy to help even if you end up hiring someone else.