What to ask when you're hiring accounting help at $3M+

Most of the questions people ask when hiring accounting help are the wrong ones. Is the rate reasonable, are they QuickBooks certified, do they seem responsive? All valid, but none of them tell you whether this person can run the accounting for a $3M company.

A ProAdvisor certification means someone passed an Intuit software exam. It says nothing about whether they can close a month on accrual, build a WIP schedule, or hand your bank a package that doesn't come back with lots of questions. Plenty of certified bookkeepers have never done any of those things, because their clients never needed them.

At your size the job is owning the close and being accountable for what the numbers say. Here's how to tell in an interview whether someone can do that.

First, decide which job you're filling

"Bookkeeper" covers two different jobs, and conflating them is the most expensive hiring mistake at this size.

One job is transaction processing: coding, bank reconciliations, running payroll, entering bills. The other is the controller function: owning the close, reconciling every balance sheet account, handling accruals and cutoff, producing financials someone can make decisions on, and being the person who can explain what the numbers mean.

A $3M company needs both, and they're rarely the same person. Hire a processor and you'll still have no one who owns the close. Hire a controller-level person and put them on data entry, and they'll be bored and overpriced, and gone within a year. Decide which one you're filling before you start, and if the honest answer is both, plan for two people or an outsourced team that covers both.

The questions below are for hiring at the controller level, because that's the gap most companies your size actually have.

The questions that separate the two

"Walk me through how you close a month."

The single most useful question you can ask, and the answer is enlightening. Someone who does the controller job will talk about a close calendar, cutoff, accruals, reconciling balance sheet accounts, and a review step before financials go out. Someone who does the processing job will describe categorizing transactions and reconciling the bank, and then stop, because in their experience that's what closing means.

Both are legitimate answers to two different jobs. You just need to decide whether the answer fits the role you’re hiring for.

"How do you know your balance sheet is right before financials go out?"

Every number on a balance sheet should have a schedule supporting it. Accounts receivable ties to an aging. Fixed assets tie to a depreciation schedule. Loans tie to amortization schedules. The controller-level answer describes that support without hesitation. The processing-level answer treats the balance sheet as whatever QBO generated, which is exactly how the errors we usually find get in.

"How do you give me margin by job?"(or by location, or by product line — whichever runs your business)

If you bid and manage work at the job level, you need financials that report at the job level, and that depends on how the books are structured. Someone who's done this will talk about cost of revenue, labor burden, and using projects or classes to carry the job dimension. Someone who hasn't might offer to build you a spreadsheet, which usually means it'll only get done after the job is complete, if at all.

"A pay period straddles month-end. What do you do?"

A clean tell for whether someone actually closes on accrual. The right answer is that payroll gets accrued so the expense lands in the month the work happened. If the answer is that it hits whenever it clears the bank, you're talking to someone who runs a cash-basis close, and your months won't reflect your months.

"What do you need from me, and when will I have financials?"

A controller-level hire will commit to a date — financials by the 10th, the 15th — and tell you what they need from you to hit it. Vagueness here predicts vagueness every month for as long as they work for you.

The questions about coverage nobody asks until it's too late

If you're hiring one in-house person, ask what happens when they're out.

A single in-house bookkeeper or controller is a single point of failure. When they're on vacation during a close, the close waits. When they leave, they take the undocumented knowledge of how your books work with them, and you get a gap plus a search plus whatever they left on their desktop. This isn't an argument against hiring in-house. It's a question to ask honestly before you do, because the answer shapes whether one person is really enough.

One setup that handles this well is an in-house bookkeeper paired with an outsourced fractional controller. Your bookkeeper is in the building for the daily work — coding, bills, payroll, chasing down the packing slip that doesn't match. The controller function sits outside, running on documented, repeatable procedures rather than living in one employee's head. When your processor is out, the close still happens. When they leave, the way your books close doesn't leave with them. You get daily presence and a close that doesn't depend on a single point of failure, usually for less than a second full-time hire.

Remote or on-site

Whether your accounting is in the building matters less than whether the work is right, but it's worth being clear about the tradeoff.

Virtual gets you access to people who've done accounting for companies like yours, instead of whoever commutes to your zip code. For specialized work like construction, manufacturing, and multi-entity, that reach is often the difference between someone who's built a WIP schedule before and someone who'll learn on your file.

What virtual gives up is physical presence. Nobody walks to the shop floor to ask why a PO doesn't match a packing slip, and nobody's in your Monday operations meeting. If your books need someone on site every day, hire local.

The question worth asking everyone

"When we outgrow you, will you tell me?"

The best accounting partners will name the point at which you should bring the function in-house, and help you make the move when you get there. That answer signals someone thinking about your business rather than their monthly fee.

If you're weighing that decision now, book a call. We'll tell you which one you need, even when it isn't us.