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Questions You Should Ask Your Potential Bookkeeper


You’ve finally realized it’s time to hire a bookkeeper for your business. 


You start looking around and setting up some calls with potential bookkeepers. 


But now, what questions do you ask the bookkeeper when you actually get on the phone with them? Or do you let the potential bookkeeper run the entire call? 


When you get on a call with me, I do have my own set of questions to ask you, but I also leave it open for you to ask me as many questions as you want to as well. I want to make sure that we are a good fit to work together before any contracts are signed or money is exchanged. 


So what questions should you be asking your potential bookkeeper? 

What is your education? How did you become a bookkeeper? 


There are courses out there that will teach someone to become a bookkeeper so they can start their own business and work from home. But you want to make sure they have a decent education and know what they are doing. 


Get their credentials. Find a way to understand what they know about the bookkeeping process and how it will work for you business. 


How familiar are they with your specific industry? 


Are you a coach? Are you a virtual assistant? Are you a speaker? And how familiar are they with your specific industry? 


Yes, there are bookkeepers out there that will work with all kinds of different industries. But they also need to be able to fully understand your industry to really work with you and do your bookkeeping to the best of their abilities. 


If they are unfamiliar with your industry, how long is it going to take them to understand your industry? 


What is the scope of the bookkeeping work they are going to do for you? 


Some bookkeepers are limited to just doing the actual data entry type work of bookkeeping. Others are more management level and can do much more than the bookkeeping. 


What you need your bookkeeper to do can depend on what your accountant does for your business, as well as what you want to do for your business’s accounting as well. 


The more your bookkeeper will do for your business, the better off you will be. 


Consider someone who will do more of the following: 

  • Reconciliation of bank transactions
  • Coding transactions correctly in the bookkeeping software to teh correct account for tax treatment
  • Assists with estimated tax payments and sales tax payments
  • Prepares your monthly financial reports like the profit and loss statement and the balance sheet
  • Can help you interpret the reports and even what stories they tell you
  • Helps to prepare a budget and monitor that budget
  • Helps with the cash flow plan
  • Can pay your suppliers
  • Can prepare invoices

You just need to make sure you know what you want the bookkeeper to do before you are read to hire one. Not all bookkeepers are created equal. 


What can you expect around delivery times and response times?


Make sure you ask how long it takes for your bookkeeper to get back to you when you have a question. 


And how long it takes your bookkeeper to ask you a question when they have questions about your transactions. 


Some people take a while to respond to emails. Others respond quickly. Get a feel for this ahead of time. 


How does this bookkeeper communicate with their clients? 


Your time is very valuable as a business owner. So you want to be able to have someone who communicates with you in an efficient manner. 


Do they send one question at a time? Do they create an email that has all of their questions for the day in it? 


Do you prefer to have phone/video conversations with your bookkeeper? Or do you want it to be kept to email or another chat platform (i.e. slack, messenger, voxer, etc.)?


You also need to convey to your bookkeeper which method you prefer. 


While looking for a bookkeeper, you may be interviewing with firms who have multiple people on their staff. Figure out who will be doing the conversing with you. Will it be someone else on the staff, or will it be the person you are interviewing? 


How often does this bookkeeper process your daily transactions? 


Some bookkeepers will log in to your bookkeeping software once a day, some will log in once a week and some may even only log in once a month. 


Get a feel for how often they log in. But also make sure you have your own expectations. How often do you want your transactions to be logged and looked at? 


For me, that’s a question I always ask. How often do you want your bookkeeping to be processed?


Who is responsible for the cost of the bookkeeping program? 


Some bookkeepers will pay for the cost of the bookkeeping program that you use with them (i.e. Quickbooks, Freshbooks, Xero, etc.). 


With others, you are responsible for the cost of the program. 


Make sure you understand who is paying for the program. 


And if your bookkeeper is paying for it, then what happens when you no longer work with this bookkeeper? How do you get your data? And do you have access to your program while they are working with you? (You should always have access to the program, whether your bookkeeper is paying for the program or not.)


How do they price their services? 


Are you paying a flat fee for the month/quarter/year? 


Are there a la carte products that are added on to the base fee of the program? 


Do they charge hourly fees? So the amount of time they are working for your business, gets an hourly invoice each month. 


Many more bookkeepers are now going with a flat monthly fee. Just make sure that you fully understand what is included in this package. 


How do they protect their clients? 


You are sharing financial information with your bookkeeper. Not only do you need to feel like you can trust them before you hire them, you need to know that your information is safe with them. 


I personally have an ethics clause and a nonsharing clause in my contract that you sign when we work together. I have my own money and would never do anything with yours, but do my job. But I have multiple stories from my job as an auditor where I have found accountants and bookkeepers stealing money from their clients and the clients had no idea. 


But you need to get a feel for this when you are talking to your potential new bookkeeper. The more professional and educated your bookkeeper is, the better off you will be. But always make sure to trust your gut instinct. That guy instinct doesn’t lie. 


How do you get copies of your receipts and other documents to your bookkeeper? 


This is financial information you are sharing with your bookkeeper. You need to know that it is being kept safe and secure. 


There are file sharing places out there to share your documents in the cloud. But make sure that your information is staying secure and not easily accessed by many people. 


Your bookkeeper may also help organize it for you for tax purposes. This is another question you can ask. 


Do they help you analyze the data? 


Bookkeeping isn’t just coding and sorting the transactions to the right accounts for tax purposes. It is also looking at the transactions that have occurred and seeing the stories and patterns that they tell. 


Does your prospective bookkeeper look at this data? Can they help you find these stories and patterns in your business? 


Should you outsource your bookkeeping tasks? 


I know that you really don’t want to do your bookkeeping. That’s why you are looking for a bookkeeper in the first place. 


Yes it’s private financial information that you need to share with someone else and you need to be able to trust them. And that may take a lot for you to do. 


But as your business is continuing to grow, you need to make sure the bookkeeping is done correctly for your business and can also end up saving you both time and money. 


Find someone who can really work with you in your business. Someone who understands your industry and your business. Someone who can share your mission as well. 


Interview more than one person. And make sure you follow your gut instinct. 


Go into your interview with your potential bookkeeper knowing what you want to ask and what you expect from your bookkeeper. 

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