6 Questions to Ask Before Hiring a Bookkeeper
Hiring a bookkeeper means handing over access to your business's financial life, which is a real act of trust. A discovery call is your chance to figure out whether the person you're talking to is actually the right fit, and that goes a lot better when you have specific questions in mind rather than a general "vibes" check.
Here are six questions to bring to your discovery call, what to listen for in the answers, and how I answer each one for context.
1. What experience do you have with businesses like mine?
Industry-specific experience matters more than people realize. A bookkeeper who's worked with massage therapists already knows what Mindbody payouts look like, how to handle tip income, and what a typical chart of accounts looks like for that kind of practice. A bookkeeper coming in cold has to learn all of that on your dime.
What to listen for: specifics, not generalities. "I've worked with service businesses" is a vague claim. "I've worked with three yoga studios and four solo practitioners in the wellness space" tells you something. Ask for concrete examples.
My answer: I work primarily with self-care providers (mental health therapists, yoga studios and teachers, massage therapists, estheticians, holistic practitioners) and working-class people. If your business is in one of those buckets, I'm probably a fit. If it's significantly outside them, I'll tell you and refer you to someone who'd be a better match.
2. Who is actually doing the work?
Some bookkeeping firms are run by one person who does everything. Others have a team. Others outsource the actual bookkeeping to subcontractors, sometimes overseas. None of these is automatically wrong, but you should know which arrangement you're signing up for, and the answer should be consistent with what you're being charged.
What to listen for: a clear answer. "I do all the work myself" is fine. "I have a team of US-based contractors who handle most of the day-to-day, and I review everything before it goes to you" is fine. "It depends" or vague answers are a potential red flag. Also worth asking: if subcontractors are involved, are they being paid fairly?
My answer: Boomtown is a one-person firm. I do all the work myself. In rare cases when I need an extra set of hands, I bring in trusted, US-based colleagues I've worked with before, and they're paid a fair wage. I don't outsource bookkeeping offshore.
3. What's your communication style and turnaround?
Communication mismatches are one of the most common reasons bookkeeping relationships end, and a lot of them are avoidable if you talk about expectations up front. Some bookkeepers are highly responsive and check in often. Others batch communication and respond on a slower cadence.
What to listen for, with sub-questions to ask:
How quickly do they typically respond to client emails or messages?
What's their primary channel (email, phone, client portal, Slack)?
Are their working hours compatible with yours? Especially relevant if you're in a different time zone or work irregular hours.
Can you book a call with them when something complicated comes up, or is communication strictly written?
My answer: Email is my primary channel, and I use a secure client portal for document requests and specific transactional questions. My hours are 9-6 Eastern, weekdays. I aim to respond within two business days and usually I'm faster. Clients can book a virtual call with me anytime through my online scheduler when something needs more conversation than email allows.
4. What will I receive each month, and when?
Vague answers here are common, and they cause problems later. You want to know specifically what reports you'll get, what cadence they'll arrive on, and what they'll show.
What to listen for: a specific list of deliverables and a specific timeline. "Monthly financial reports" is vague. "A P&L, a Balance Sheet, an A/R aging summary, and a brief writeup of anything notable, delivered by the 21st of each month" is specific.
My answer: My standard monthly package includes a Profit & Loss broken out by month for the year-to-date, a Balance Sheet for the current reporting period, and any custom reports we've agreed your business needs. Reports go out by the 21st of each month, assuming you've gotten me your statements and answered any open questions by the 18th.
5. How do you price your services?
Bookkeepers use a few different pricing models, each with tradeoffs:
Hourly rate. You pay for the time spent. Pro: you only pay for what's actually used. Con: your bill varies month to month and can be hard to predict. Some clients also feel like they can't ask questions because the meter is running.
Project-based or fixed monthly fee. A flat fee for an agreed scope of work. Pro: predictable cost, no anxiety about asking questions. Con: scope creep can become a tension point if your business changes.
Value-based pricing. Pricing based on the impact the bookkeeper believes their work has on your business, often the most expensive of the three. Pro: aligns the bookkeeper's incentives with your outcomes. Con: harder to evaluate whether you're getting your money's worth, and harder to compare against other firms.
What to listen for: a clear answer about which model they use and why, plus a clear policy on rate changes. Most bookkeepers adjust rates periodically; you want to know how often and how much warning you'll get.
My answer: Fixed monthly fee, scoped to your specific business. I review scope every six months and adjust if your business has changed (new accounts, new revenue streams, more transactions). I also review rates annually and adjust for inflation, (if necessary) and I give plenty of notice when I do.
6. What's your cancellation policy, and what happens to my records?
Not every bookkeeping relationship works out. You want to know up front how to end the relationship if it isn't a fit, and what happens to your data when you do.
What to listen for on cancellation: a clear, reasonable policy. Most bookkeepers ask for some amount of notice (usually 30 days), which is fair.
What to listen for on records: this part is non-negotiable. You own your records. Your QBO file is yours. Your historical statements, reports, and documents are yours. Any bookkeeper who isn't clear on this, or who tries to make you pay extra to access your own data, is a hard no. Walk away.
My answer: 30 days written notice from either side, and your records belong to you.
A bonus question worth asking
If you're looking for a bookkeeper who shares your values (sliding scale practices, anti-shame approach to financial mistakes, class-aware pricing for your own clients), it's worth asking about this directly. Most bookkeepers won't volunteer it, and a values mismatch can make a working relationship awkward in ways that are hard to repair.
You don't have to ask in those exact words. Something like "what kinds of businesses do you work with, and what do you find interesting about them?" usually gets you the same information.
If you'd like to bring these questions to a call with me
If after all this you want to actually try a call, here's the link to my schedule. The point is to figure out if we're a fit, which is a question that goes both ways.
You can also read more about what working with me actually looks like in this post.