9 Questions To Ask When Hiring A Bookkeeper

You’ve decided to delegate a few piles off your desk – this is a big step for ANY business owner. To add to the stressful decision, it’s pretty intimidating conducting your first employee interviews. Take a deep breath, repeat 3 times in your head: This is my business and I need people who will help me take care of it. Trust us, skills are important, but never overlook the importance of hiring people who have the same core values and behaviors as you do.

Learn More

Discover the 9 Questions to ask when Hiring a Bookkeeper!

Skills can be learned, but good character, not so much. Before you trust someone with your books, you need to find out if their principles are gold or tin in nature. Here are some of our favorite interview questions we use when looking at potential bookkeepers. Because we’re cool sometimes, we’ve also given tips on what to look for within answers.

So let’s get started!

1. Tell me about a time when you pulled a report and nothing matched? What did you do?

Bookkeepers are problem solvers. They take a mess of papers and numbers and produce a work product that helps you navigate the complexities of your decision making. You want a bookkeeper who is willing to dig into the numbers, analyze trends, and help you solve problems – not add to them.

2. Tell me about your payroll experience and the platforms you are familiar with?

If you need someone with payroll experience and they don’t have it, this question will help you determine if you need to continue the discussion. If they do have experience, even on a platform that you currently don’t use, their perspective could be very helpful. Chance are, the similarities between systems will be enough to help with any learning curve.

3. Tell me about your bookkeeping experience? In what industries have you done bookkeeping?

Depending on the size of your business, you may want to determine what kind of parameters you need. For example, anyone with only Fortune 500 experience may not know the ins and outs for what a non-profit needs.

4. What would you consider to be your top 3 greatest strengths?

No one really likes asking (or answering) this question. A helpful tip would be to jot down some of the attributes you think you need for someone to “win” in this role with your business. Are you someone who misses details? A candidate that can explain how their attention to details helped a previous organization would be a thing to listen for in their response.

5. Is there anything that I have missed that you would like for me to know about you or your experience?

Our recruiting team likes to throw this question in at the end as a wrap up question. You know the feeling after you’ve led a discussion or presentation and later wished you’d remembered that one last thing. This is that opportunity for the candidate to share if their nerves had them distracted at the beginning of the interview.

6. What is your experience working remotely or collaborating with a team who isn’t at your office?

With this question, you are looking for someone who can show they take the initiative. They err on the side of over-communicating to be sure that there are no gaps in understanding. They are proactive and have no moss (get it… they aren’t idly waiting on others). You are also looking that they communicate in an effective way with all team members and have no qualms about leaning into others and being leaned into as well.

7. Tell me about a time a mistake was made due to broken communication lines and what you did to move forward.

You are waiting to hear if they own their mistakes. You want someone who can own their shortcomings, and who can show how they work for improvement. Listen for if they blame others. Overly suggesting that they absorb all the blame for things not their fault is also something to watch for in this response. You want someone who takes feedback well, owns their mistakes, but doesn’t advertise they are the office scapegoat.

8. Tell me about a time when you hit the ball out of the park. How’d it feel? Did you like the way you were shown recognition?

The “Me Monster” loves this question. If you hear a lot of “this was all my idea and I worked on it on the side…” There is NOTHING wrong with having a great idea, but an idea can grow if giving the chance to flourish with the knowledge and experience of others. While you are looking that they don’t gloat about their achievements, you want to know they own them. That is humble as shown in The Ideal Team Player – you want them to take credit but to also acknowledge the the contributions of others.

9. Describe the perfect day.

Here, you will get an idea of who they are, what their hobbies are, and what they find to be important. You’ll also be about to see if you have anything in common or similar interests. This question can give you an idea of how they will fit with the culture of your organization.

Does the very idea of finding, interviewing and training a new bookkeeper make you break out in hives? Then you’re in the right place. We’ve been helping organizations find the right bookkeeper for over 10 years.