20 Questions

Questions to Ask Bookkeeper Interview

Essential questions to evaluate a bookkeeper's qualifications, experience, and approach to financial record-keeping for your business.

1

What accounting software are you most experienced with, and how do you stay current with updates?

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Why this works

Ensures they have the technical skills needed for your systems and demonstrates their commitment to staying current with industry tools.

2

How do you approach reconciling accounts and what's your process for catching discrepancies?

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Why this works

Reveals their attention to detail and systematic approach to maintaining accurate financial records, which is crucial for bookkeeping accuracy.

3

What experience do you have with our industry, and how do you handle industry-specific accounting requirements?

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Why this works

Shows whether they understand the unique financial needs and regulations of your business sector.

4

How do you handle month-end and year-end closing procedures?

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Why this works

Demonstrates their understanding of critical accounting cycles and their ability to manage complex financial reporting requirements.

5

What's your approach to managing accounts payable and receivable?

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Why this works

Reveals their cash flow management skills and understanding of how to maintain healthy business relationships with vendors and customers.

6

How do you ensure compliance with tax regulations and what's your experience with tax preparation?

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Why this works

Critical for avoiding penalties and ensuring your business meets all regulatory requirements.

7

What's your process for handling payroll and employee-related financial matters?

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Why this works

Shows their ability to manage complex employee financial obligations and maintain accurate payroll records.

8

How do you organize and maintain financial records for easy access and audit purposes?

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Why this works

Demonstrates their organizational skills and understanding of the importance of record-keeping for business operations and compliance.

9

What experience do you have with financial reporting and creating management reports?

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Why this works

Shows their ability to provide valuable financial insights that can help guide business decisions.

10

How do you handle confidential financial information and what security measures do you implement?

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Why this works

Critical for protecting sensitive business data and ensuring compliance with privacy regulations.

11

What's your approach to working with external accountants or auditors?

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Why this works

Shows their ability to collaborate with other financial professionals and maintain records that meet professional standards.

12

How do you stay current with changes in accounting standards and regulations?

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Why this works

Demonstrates their commitment to professional development and ensures they can adapt to changing regulatory requirements.

13

What's your experience with budgeting and financial forecasting?

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Why this works

Shows their ability to contribute to business planning and provide forward-looking financial insights.

14

How do you handle discrepancies or errors when you find them?

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Why this works

Reveals their problem-solving approach and integrity in dealing with financial mistakes or irregularities.

15

What's your preferred method of communication and reporting to business owners?

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Why this works

Ensures their communication style matches your needs and that you'll receive the financial information you need in a useful format.

16

How do you prioritize tasks when you have multiple deadlines to meet?

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Why this works

Shows their time management skills and ability to handle the varied demands of bookkeeping work.

17

What experience do you have with different business structures (LLC, Corporation, etc.)?

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Why this works

Ensures they understand the specific accounting requirements for your business structure.

18

How do you handle seasonal fluctuations in business activity?

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Why this works

Shows their ability to adapt to varying workloads and maintain consistent service quality throughout the year.

19

What's your approach to training and knowledge transfer if you need to bring someone else up to speed?

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Why this works

Important for business continuity and ensuring your financial processes are well-documented and transferable.

20

What questions do you have about our business and its financial needs?

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Why this works

Shows their interest in understanding your specific situation and their proactive approach to providing tailored service.

Finding the Right Bookkeeper for Your Business

Expert tips and techniques for getting the most out of these questions.

Best Practices

Check References Thoroughly

Ask for references from similar businesses and follow up to understand their experience with the bookkeeper's work quality and reliability.

Assess Technical Skills

Ensure they're proficient with the accounting software you use and can demonstrate their ability to handle your specific accounting needs.

Evaluate Communication Style

Choose someone who can explain financial concepts clearly and provide reports in a format that's useful for your decision-making.

Question Sequences

The Technical Assessment

1
What accounting software are you most experienced with?
2
How do you handle data backup and security?
3
What's your process for reconciling accounts?
4
How do you ensure accuracy in financial records?

The Business Fit Evaluation

1
What experience do you have with our industry?
2
How do you handle our specific business needs?
3
What's your approach to working with business owners?
4
How do you prioritize tasks and meet deadlines?

Common Pitfalls

Don't Focus Only on Cost

While budget is important, prioritize quality and reliability. A good bookkeeper can save you money by preventing errors and ensuring compliance.

Avoid Hiring Without Industry Experience

Industry-specific knowledge is valuable. A bookkeeper familiar with your sector will understand your unique accounting needs and regulations.

Don't Skip the Reference Check

Always check references to verify their work quality, reliability, and ability to meet deadlines consistently.

Conversation Templates

The Capability Explorer

1
Step 1: Start with: "What's your experience with [specific accounting software]?"
2
Step 2: Follow with: "How do you handle [specific business need]?"
3
Step 3: Deepen with: "What's your process for [specific task]?"
4
Step 4: Verify with: "Can you walk me through how you would handle [specific scenario]?"

The Fit Assessment

1
Step 1: Begin with: "What experience do you have with businesses like ours?"
2
Step 2: Explore with: "How do you typically work with business owners?"
3
Step 3: Investigate with: "What's your approach to [specific challenge]?"
4
Step 4: Assess with: "How would you handle [specific situation]?"

Further Reading

"Small Business Bookkeeping" by Greg Shields
"Accounting for Small Business" by Michael Badger
"The Bookkeeper's Guide to QuickBooks" by Bonnie Biafore

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