20 Must Ask Bookkeeping Interview Questions (With Answers)


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We find that many business owners struggle with bookkeeping interview questions. Most business owners are not financial experts, to begin with. Many will not even know enough about bookkeeping to know where to begin.


A man talking to a happy man on a video call asking bookkeeping interview questions


In this post, we’ll give you 20 of our favorite interview questions to ask bookkeeping candidates. We borrowed these from the Outsource School founders. They curated these golden nuggets through their many years of hiring experience. 


Let’s dig in!


Importance of Asking the Right Questions


Pay close attention to both bookkeeping interview questions and answers. A big part of your winning hiring strategy is the right questions. They won’t work, though, if you are not keenly attuned to the answers you get. You also need to be ready to ask follow-up questions on the fly. If you don’t get a satisfying response, you need to know how to squeeze a candidate a bit to get the good juice out.



Experience and Red Flags


This set of questions is where we like to start. They get some good background on the candidate. They also establish the basics so you can know right away if this potential bookkeeping virtual assistant will not work out. This way, you don’t waste a lot of time interviewing someone you’ll never hire.


The word "caution" written on the ground in dark yellow chalk.


1. Tell me a little bit about yourself. Where are you from? What are your hobbies outside of work? What’s something interesting about you?


Developing rapport straight off the bat is essential to a successful interview. It puts candidates at ease, because, let’s face it, interviews can be really stressful! When you help them keep calm, you get better answers. More than getting comfortable, asking these personal questions also gives you important information. For example, living in a small town can indicate poor internet service. An expensive hobby for a beginner-level candidate can indicate a strong drive to level-up. (It can also be a red flag since entry-level work does not pay as much. Stay alert and ask those follow-up questions!)


2. How long have you been working as a bookkeeper?


I like to say, go straight for the core as soon as you’ve built rapport. Experience should be a key factor in your hiring decisions. Get the low-down before you go any further because you’ll likely want more than just the bookkeeping basics. If they don’t meet this requirement, you may want to move on. That is, if you indicated it on your job post. Alternatively, you may be willing to work with someone who has less experience. Ideally, they will have the rarer qualities of integrity and willingness to learn.


3. Can you please describe your bookkeeping experience with past clients? What specific software do you use? What tasks do you handle for them?


Dive deeper into the candidate’s experience by going into quality, not just the number of years they’ve been working. For all you know, they’ve worked for 12 years but never leveled-up. That’s not good. Asking about specific experience will qualify what they’re sharing. Then, following up with specific tools and tasks will round out the picture for you.


4. What’s your greatest strength as a bookkeeper? What have you had the most experience with?


Asking these bookkeeping interview questions will give you insight into their confidence levels. This will also reveal whether they have true confidence from experience, or empty arrogance. You want to bring people into your team who know what they’re doing. But you want to avoid people who have boastful attitudes. That’s not going to be good for your culture.


A man and woman hi-fiving and smiling. bookkeeping interview questions


5. Do you have any experience working with a client that has a similar business to mine? (Explain your business model so they can answer off that).


Again, getting more details about who they have worked with can be very useful. This question can also get into how they worked with that client. Ask them open-ended follow-ups like, “Can you explain more?” will allow them to speak freely and reveal more about their values and attitudes.


6. How many clients do you currently have? How many hours are you currently working for them?


Now we transition into the new position with your company. Many bookkeepers, freelance or otherwise, have several clients. That’s just the nature of the work. Only huge businesses would need a bookkeeper to work a 40-hour week for them. So, you’ll need to get clear on how many other clients they serve and how many hours they spend with these clients. This way, you can gauge whether they have enough quality time to take care of you.


7. We’re looking for someone that can work <<insert schedule>>, does that work for you?


Be very clear upfront with the times and days you want them to work. This is more important when you’re hiring overseas. Mainly, you will want to be able to reach out to them during a convenient time for you. This is in case you need something from them or want to check in. You may also want to monitor them here and there for accountability. The overlap in working times also makes it convenient when you need to share authentication codes. (We highly recommend maintaining this extra level of control when dealing with financials.) 


8. We’re looking to hire this role at <<insert rate per hour>>. Are you good with that rate?


This is the last of all the interview questions to ask bookkeeping candidates in this first section. We like to end here because it deemphasizes rate as the main concern. While rate is important, we don’t want candidates to think it’s a make or break point. They will likely know the rate range you are willing to pay before they apply. This just confirms that they are happy with it. It also gives them a chance to negotiate within your range based on your requirements and the value they can offer. A space for negotiation is good for them and for you.


Culture and Attitude


If you’re happy with the candidate thus far, you can move on. This next set of bookkeeping interview questions gets into the heart of the matter. You’ll be leaving hard skills for a bit and poking around the softer side of work.


A group of people smiling at something on a laptop screen.


9. Why did you choose bookkeeping as a profession? Is it something that you are passionate about? Why?


Many people, unfortunately, are in professional fields that they aren’t happy with. If you’re hiring in Asia, this is likely because their parents chose their career path for them. We start the culture and attitude section with this because job happiness level is vital to performance. Simply put, any candidate who expresses that they are unhappy with being a bookkeeper should not be one. You don’t need the kind of negativity that can produce to get into your company. 


Alternatively, if a candidate loves bookkeeping, that’s amazing. Bookkeeping is not the most loved of professions, after all. Asking why they are passionate about it will confirm if they’re telling the truth. Giving them some time to glow about their passion will also help the interview go more smoothly. 


10. Are you detail oriented? Please rate yourself on a 1-10 scale and explain why.


Being highly detail oriented is vital for a bookkeeper. Keeping accurate records is their entire job description. You may be ok accepting a score of 8 or even 7 in other areas. Here, however, we recommend accepting only a 9 or 10. Again, accuracy is a non-negotiable in bookkeeping.


11. Are you organized? Please rate yourself on a 1-10 scale and explain why.


Organization is somewhat related to benign detail oriented. All other things being equal, you definitely should prefer an organized candidate. This just means that they will take better care of all the files they have access to. They may even systematize things to make it convenient for everyone else, too. Organizational skills are always a bonus in my book.


12. When you run into issues within your work, how do you handle them?


This is the start of a string of our other favorite bookkeeping interview questions. Here you get even deeper into how they work. Asking about specific trouble spots will tell you how they will behave when they face problems at your company. Can you depend on them to push through? Will they complain when they can’t have the perfect tool or will they adjust? These are the kinds of things you can find out with this line of questioning.


People with laptops and documents working together at a large table. bookkeeping interview questions


13. Do you like working with others? Are you a team player?


Continuing from the above, many issues arise out of interpersonal relations. Conflict is unavoidable, so you need to know that they will be mature about it. They might cover an issue with a co-worker in the previous question. In that case, you can follow-up with a question about a work issue. This will show you if they can handle both situations well. 


14. What are your best practices for communicating with your clients?


Communication is key, even if it’s #14 on our list. That doesn’t mean it’s not one of the most vital interview questions to ask bookkeeping candidates. Communication is super important to us because it can solve most problems within a company before they even become problems. It can also solve existing issues before they cause real damage. If a candidate doesn’t have the best communication practices, don’t write them off. You need to know this not to eliminate them. This is to know how much you need to focus on this key element during their onboarding. 


15. What motivates you most in life? Why?


This is actually a precursor to the next question, just so they don’t get startled by the sudden shift. In any case, it’s another opportunity to learn about their core values. Then you can see how that aligns with your core values.


16. Money or stability/flexibility? Which is more important to you?


This is the real question. We like to hire people with a more entrepreneurial mindset. This means leaning towards candidates who value money less than the other benefits a position can offer. We mention stability and flexibility here specifically. Really, though, it can be anything that the position in your company offers. The point is to determine whether they are interested for the sake of a mere paycheck. The best hires will know that money comes regardless when you have the right goals.


17. What do you see yourself doing 5 years from now?


This is a great follow-up to the above because it will show the truth in their answer. Whatever they say, it will reveal a bend towards either lasting personal and professional value or bare finances.


Final Questions


If your candidate has managed to impress you until now, you may have a winner. We just have a few final bookkeeping interview questions before you sign that bookkeeping engagement letter.


Two men shaking hands over some documents. bookkeeping interview questions


18. Are you 100% sure that you’re good with the rate and schedule that we’ve discussed for this role?


Rate has now been considered at least twice and personally discussed at least once. Asking about all this again is intentional. This is because most issues with hires stem from disagreements over pay. You want to be as clear as you possibly can about it. You also want to get the candidate to verbally agree more than once. This can avoid issues down the road. 


Schedule has also been considered and personally discussed at least once. You need to confirm this to secure quality time. This is especially true when hiring from a different time zone. 


19. If you were hired, how soon could you start?


The candidate should already have some expectation of when you will need them, but it’s always good to confirm. Also, a candidate who is available right away is usually a more interested candidate. Even if they have some other project to finish up, a slight delay shows that they are diligent and respectful. They sought a new client before the last minute and are honest with you about needing time to finish the job properly.


20. Do you have any questions for me?


Do not skip this one. You may be tired after talking for this long already. You may have other interviews to conduct today. Still, do not skip this question. It can be the most important question of all because it targets exactly what’s on the candidate’s heart and mind. You must give them the opportunity to be perfectly open with you. Spend a few minutes now and save yourself more potential losses in time, money and stress later on.


What Is EcomBalance? 



EcomBalance is a monthly bookkeeping service specialized for eCommerce companies selling on Amazon, Shopify, Ebay, Etsy, WooCommerce, & other eCommerce channels.


We take monthly bookkeeping off your plate and deliver you your financial statements by the 15th or 20th of each month.


You’ll have your Profit and Loss Statement, Balance Sheet, and Cash Flow Statement ready for analysis each month so you and your business partners can make better business decisions.


Interested in learning more? Schedule a call with our CEO, Nathan Hirsch.


And here’s some free resources:




These are our favorite bookkeeping interview questions. You may have other ones that you’d like to use. That’s great! It’s important that you are completely comfortable with the questions you are using. We love these because they get us results. Your experience could be different. We just hope that these ones can help you round out your approach so you can find and hire the best fits for your bookkeeping needs.


Want bookkeeping off your plate? We’ve got you! Get started, Speak w/ a Founder, or Schedule a Callback

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Julia Valdez

Julia Valdez is Freelance Writer and Agency Owner. She regularly writes on topics related to Business Finances, Growth, Hiring, Entrepreneurship, and more.

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