As your small business grows, outsourcing your bookkeeping to an experienced provider can be a strategic choice. But finding the right partner requires asking the right questions upfront.

Over the years, I’ve made mistakes choosing the wrong outsourced bookkeeper, resulting in headaches down the road. I’m here to help you avoid similar pitfalls! In this article, I’ll share key questions to ask potential bookkeepers to select the best fit for your needs.

Vet Credentials and Experience

First, verify credentials, education, and expertise:

• Are you a certified bookkeeper? Do you have specific credentials like the Certified Bookkeeper (CB) designation?
• How many years of professional bookkeeping experience do you have? What types of business clients have you served?
• What accounting training or education have you completed?
• What accounting software and tools are you highly proficient in?
• Are you familiar with bookkeeping best practices in my industry?

Strong credentials and experience handling books for similar businesses are ideal.

Understand Their Process

Next, gain insight into their bookkeeping process:

• Walk me through your typical workflow for key tasks like accounts payable/receivable.
• How do you prefer to track billable time and communicate with clients?
• What methods do you use for reconciling accounts?
• How do you keep organized records of documentation?
• What tools do you use? Are you comfortable with cloud-based apps?
• How do you maintain accuracy and handle errors?

Detailed responses build confidence in their skills.

Confirm a Good Personality/Culture Fit

Since you’ll work closely together, assess compatibility:

• How would you describe your work style and personality?
• What do you enjoy most about your job?
• How have you built trust and strong relationships with clients in the past?
• How do you prefer to communicate with clients and team members?
• How do you stay focused on meticulous details while meeting deadlines?

Ensure they’ll align well with your company culture.

Discuss Expectations Upfront

Finally, be clear on scope of work, availability, and other expectations:

• What hours/days are you available? Can you accommodate our schedule?
• What bookkeeping tasks require my involvement vs. what you can own independently?
• How often can we meet to review financials and metrics?
• Can you provide tax preparation support?
• What does your onboarding process look like?
• How are you compensated? What are your rates?

Discussing details early prevents future issues. Finding the ideal outsourced bookkeeping partner takes diligence. But asking the right questions upfront lays the groundwork for a relationship built on qualifications, transparency, and trust. Don’t settle – invest time into finding the perfect fit! And if you need guidance navigating your bookkeeping options, the team at Pittroe is here to help. Reach out anytime!