Choosing the Right Bookkeeper: A Business Owner’s Checklist

Jireh Gibson
May 27
2 min read

Updated: Jun 6

image of hand holding a pen next to a pad with a checklist

Hiring the wrong bookkeeper will quietly drain your profits.

Bookkeeping isn’t just data entry — it’s the foundation of every major financial decision your business makes. Whether you’re a solopreneur or scaling fast, the right bookkeeper will keep you compliant, confident, and cash-flow positive. Here’s how to choose the right one without second-guessing yourself.

What to Look for when Choosing the Right Bookkeeper

Experience with businesses like yours
Look for industry familiarity — whether that’s retail, service-based, or virtual operations.
Up-to-date software skills
QuickBooks, Wave, Xero, or FreshBooks? Your bookkeeper should not only be familiar but certified or highly proficient in your platform of choice.
Communication style
Do they explain things clearly? Are they available for questions? Communication gaps lead to costly misunderstandings.

10 Must-Ask Questions Before Hiring

What experience do you have with businesses like mine?
What bookkeeping software do you use?
How often will I receive reports or updates?
Do you offer catch-up or cleanup bookkeeping?
What’s your policy on data security?
Will I work with you directly or a team?
How do you charge (hourly, flat rate, monthly)?
What happens if I have questions outside our normal schedule?
Could you assist with cash flow forecasting?
Do you have any client testimonials or references to review?

📝 Want a downloadable version of this checklist?

Get the complete PDF here

Red Flags That Signal Trouble

Vague answers regarding experience
No client references or reviews
Delayed responses or poor communication
Lack of clarity around pricing
No formal contract or engagement agreement

Comparing Pricing Models

Hourly: Good for one-off tasks or audits, but may surprise you later.
Flat-Rate: Predictable billing and ideal for ongoing services.
Monthly Retainers: Best if you’re looking for a long-term partner and predictable costs.

🧠 Pro Tip: Ask exactly what’s included — and what’s not.

Industry-Specific Knowledge Matters

Choosing the right bookkeeper doesn’t mean finding an expert in your field, but they should understand the basics. For example:

Contractors might require job-costing reports.
Coaches and consultants need Cash-basis profit-and-loss statements.
Ecommerce businesses will need help to reconcile Stripe or Shopify data.

Outsource or Hire In-House?

Situation	Best Option
Startup or growing business	Outsource
Needing flexibility & expertise	Outsource
High transaction volume daily	In-House (if budget allows)

Final Thoughts

Selecting a bookkeeper needn't be a risky process. A stress-free, growth-focused choice is achievable by asking relevant questions, identifying your needs, and using a checklist.