Most business owners decide to start to interview bookkeepers because they've reached a point where either:

1. their time is more valuable in selling and generating income for the business or
2. they recognize that bookkeeping and the financial related stuff is not their forte and would rather leave it to the experts or
3. they want to ensure that an expert is involved at the early stages of the business to ensure that the business is on the right track with accurate reporting and creating financial processes early on.

But it's important to remember when interviewing that not just anyone should be involved in the business books. These financials are for YOUR business, it's a very personal decision to bring someone into your circle and turn over things like logins, bank account information, all of your transactions, inevitable employee drama, or the emotional times like an employee leaving, or a family member falling ill. The relationship with a bookkeeper usually starts with just the books, but they can become one of your closest associates in business, that isn't another owner, that you end up relying on for various other business-related tasks.

Your business can only be as efficient as your bookkeeping. Bookkeeping is how you identify successes and opportunities for growth when assessing the financial health of your business.

Here are some attributes that you should consider when evaluating and interviewing bookkeepers.

TRUST

Trust is a huge factor in the decision as to whether or not a bookkeeper is the right fit for you, and your business. You have to make sure that when you're talking to that person, you feel that you can trust them and ask them questions and provide answers without any uncomfortable feelings. You'll be communicating with this person at least once a month. So take the time to have a phone call or video call with them at first and ask them a few questions to try and gauge whether or not you can trust them. How do they present themselves? Are they in the car in the parking lot of the grocery store? Or are they in a dedicated office space in their house, dressed nicely? Or are they hiding in the bathroom of their 9-5 job because bookkeeping is a nights and weekends gig for them? You can tell a lot about someone when you see where they're taking a video call from. So even if you can't get together in person because they're out of state or for any other reason, try to avoid phone interviews only. Have them turn their video on so that you can see them. Eye contact helps to build trust.

KNOWLEDGE

Knowledge is very important for a bookkeeper. They need to understand the difference between an overhead expense and a cost of goods sold expense. They need to understand the difference between meals and entertainment, travel meals, and a personal meal. They need to understand how a business like yours operates, whether that's dealing with tips, accrual basis revenue recognition, flipping houses, or knowing how you should pay yourself based on your entity setup. It's not only important to identify with someone who is smart and current on all updated information. But they also need to be familiar with your industry. Preferably even within your area of the country, so that they understand all reporting requirements and any other taxes that are involved in the business. After all, you're not hiring a robot to just categorize transactions, you need your bookkeeper to be looking out for your interests.

Also, try to understand the accounting systems they have worked with in the past and what they're comfortable working with. Make sure you are comfortable using the accounting software they're most familiar with. Not all accounting systems are made equal and it's a good idea to use a bookkeeper that is familiar with a particular system. And if you're not already on an accounting platform like QuickBooks, then you should just use whichever software the bookkeeper recommends. As long as you're able to log in and access your transactions, run reports, run comparison budget vs actual reports, and any other functions, that's most important. Make sure you retain access to your books at all times.

Besides accounting software, the rest of your tech stack is different for every business. But a pain point for many retailers either in person or online is their Point of Sale (POS) system. And it's a pain point for bookkeepers and accountants as well. As convenient as they are to accept payments and track inventory, because there is so much involved in a daily deposit, sales less discounts plus sales tax less returns less merchant fees less cash received. And then you have to account for the inventory being sold and a cost being recognized against that sale. And that needs to happen every day of the year, and for some reason, the connections between POS systems and accounting systems still STINKS. Most of them are really really bad, which usually means more manual work for the bookkeeper, either to record the entire month and reconcile what came through the bank or to adjust what was posted to make it match what was recorded in the POS system. It's can be a lot of extra work. Depending on the functions the bookkeeper is doing, it might require them to access the POS system when doing the books. So if you're set up on a POS or plan to be, ask the bookkeeper if they have experience with that system talking to the books and records. If the bookkeeper has never worked with Shopify's POS system before, which is what you're set up on, you might want to reconsider hiring them.

If it's something easy to learn, you might not have a problem. But from our experience, the reporting from POS systems are quite complicated and there are often multiple reports that need to be run each month to get various totals for gift cards sold, sales tax collected, merchant processing fees, inventory sold, etc.

Technology changes rapidly and it can be helpful in a lot of ways. But it often takes accounting systems a while to catch up to those changes. In the meantime, as a workaround, books require manual entries, and the only way to gather the information needed to make those entries is to have knowledge of the other software systems. So you want to make sure you have someone on your team that will be able to keep up.

EXPECTATIONS AND TIMELINESS

Make sure you fully understand what functions the bookkeeper will do for you. Understand if they're going to present you with financials every month, every quarter, every year, or what the process for reports and data will be. Obviously one of the main goals is to have accurate financials for tax reporting purposes but you should have access to current data, whenever you need it. This will allow you to make decisions quickly as opposed to waiting nine months to a year before implementing a change or changing the structure of your schedule to save on payroll costs.

And when you begin to work with someone, hold them to those deadlines. If they didn't hit the deadlines that they agreed to, understand why. Was there something you could have done differently, did you not respond fast enough for them to be able to turn the workaround and present financial statements? Hold them accountable in the beginning so that they know you're invested in the business and you need to have your financial data in a timely manner. Some business owners couldn't care less about the numbers and financials, as long as they can still generate income they don't care to see how they're doing it or what it's costing, so the bookkeeper likely has some of those clients. Make sure that you set yourself apart from those types of business owners in the bookkeeper's mind, right off the bat.

COMMUNICATION

Unfortunately, hiring a bookkeeper doesn't mean that you never have to think about financial stuff again. It also doesn't exonerate you from any financial-related work. You will have to answer questions that the bookkeeper has. Because the bookkeeper won't know if what you bought on eBay was for an event you're doing, or for a gift for your nephew. And checks will probably cause some confusion as well. Remember, the bookkeeper's job is to keep the books in order. But they're only as good as the information they have about each transaction. And a COGS or an Overhead Expense or a personal expense are treated very differently and lead to different calculations that you're going to use to make business decisions. So the goal is to give you accurate data. So expect that the bookkeeper will want to talk to you at least every month, depending on the scope of work they're doing for you.

Ask them their preferred method of communication, see if it matches with yours. Do you like to do video chats, if you can't meet in person? Or would you rather just do a phone call to answer questions that they have? Ask the bookkeeper what arrangements they have with other clients, in terms of meetings. Monthly, weekly, never? My suggestion is that you should have a standing meeting or a standing form of communication (phone call, email, Instagram Live) with your bookkeeper every month. Even if that's just to discuss open items that they have for 15 minutes.

A good rapport with your bookkeeper will allow you to feel comfortable asking them questions and asking for their input or analysis of your business. They see a lot of other businesses books and likely have an idea of what it takes to be a successful business owner. So use them as a resource. The bookkeeper can also give you their input on the taxes you're paying since they see lots of books and records for various businesses and will have a good sense of the types of taxes your business might be subject to besides the commonly known personal income taxes and sales taxes.