10 Critical Things to Look for in a Small Business Bookkeeper

If you run a business and are looking for a bookkeeping solution, it’s important to start by understanding the who, what, when, where and how of your ideal scenario. (What is ideal for you may not be ideal for a different business type.)

Below, I’ve outlined 10 of the most important areas to consider when comparing bookkeepers so that you will be able to weigh the pros and cons of each.


Experience comes in many shapes and sizes. You may think that if you have a small business, the experience you need from a bookkeeper can be “small” as well. There is nothing further from the truth. You need as much experience as you can afford, because great bookkeeping and accounting is instrumental in growing your business and maximizing your profits.

Experience does not always equal good fit, either. Someone who has worked for 20 years as a part-time bookkeeper for a landscaping company, although “experienced,” may not have the depth and breadth you need for an early stage startup company. When you start looking for your solution, make sure you create a wish list of level, depth, and type of experience you need.


The person that is doing your bookkeeping should have had some level of formal business and accounting education. A business degree by itself does not qualify someone to be a great bookkeeper. Make sure the education level of your solution matches the needs of your business — today and in the future.

A great bookkeeper is always going to be thinking 10 steps ahead, helping you prevent problems rather than just helping you solve them. Someone who has a formal accounting education will understand policy, procedure, strategy, tactics and ethics. The educated bookkeeper is going to want to grow with you and your business. This desire will keep them sharp, focused, and looking ahead to help your business become a financial success.


You are probably not an accountant yourself and you may not have the resources, knowledge, or desire to oversee and check the work being done by your current bookkeeping solution. You may have a CPA, but paying them for oversight can be costly. You must take oversight into consideration.

Oversight has various levels. If you employ a bookkeeper that does not have formal education or training, your need for oversight will be high. Conversely, if your solution has lots of specific experience and education, oversight will be simpler and less costly.

Working with a bookkeeping service that has built-in oversight is a great way to get the function for a fraction of the cost. Whatever you decide, at the end of the day, you are responsible for the condition and accuracy of your books.

Banking Technology

In the 21st century, being able to conduct commerce over the Internet is not just a luxury, it is a necessity. Working with your bank and other third-party companies to pay bills and receive payments is crucial to remaining competitive and strong. Being able to access your financial data online from anywhere is now a key aspect of running a business. Make sure your bookkeeping and accounting solution is capable of conducting your business online in a safe and secure manner 24/7.

Software and Systems

Are you still writing checks to pay vendors, employees and others? A great 21st-century bookkeeping and accounting solution has the ability to conduct a majority of your financial business electronically. We have been able to do individual parts of this for some time; the problem has been that these “time-saving” technologies have not been tied together.

Fortunately, there are now a few bookkeeping and accounting solutions today that have been able to glue most of this together, creating a streamlined, efficient, and cost-effective means of keeping your books virtually. QuickBooks and Bill.com, in conjunction with online banking systems, now allow for a smooth flow of information and funds from a single point of access, anywhere and anytime, to name one example.

If you are not already set up with systems that work for you, make sure that your bookkeeper can assist you in setting up or transferring your documents.

Accounting Policies and Procedures

You already have accounting policies and procedures in place, whether you know it or not, but they are probably not yet where they need to be. Policies and procedures are the guidelines you establish on how bookkeeping and accounting get done in your business — how items get posted, when bills are paid, when you close the monthly books, who reviews what and when, and so forth.

It is extremely important that no matter what bookkeeping solution you choose, you set up at least simple guidelines. If you are a nonprofit or if you have certain types of government loans, you may have to adhere to policies and procedures specific to loans, grants, and fundraising. Your bookkeeping solution should be able to guide and direct you in establishing policies and procedures and should be savvy enough to adhere to any guidelines.

Data Entry, Reporting and Reconciling

Bookkeeping is not just about entering numbers into the ledger. It is a thoughtful understanding of the business at hand, managing the day to day input of information, outflow and inflow of cash, and much more.

Having accurate financials at your fingertips allows you to react quickly and deftly to situations as they arise. For example, let’s say you have a vehicle or machine that your business depends on, and it unexpectedly dies on you. Unless you have a large pile of cash, you are going to have to borrow money to replace that equipment. You can spend days or weeks trying to catch up the bookkeeping to satisfy the bank or lending institution — or you can just print out up-to-date financials. But those days or weeks could mean the difference between success and failure of your business.

Keeping on top of the data entry, reconciling and reporting also means you head into tax season armed with every expense, depreciation, and deduction you can possibly file, saving you hundreds, if not thousands, of dollars on your tax bill.

Bottom line? Your bookkeeping solution should provide you with the reports and regular updates you need to make good decisions every day of the week.

Cash Flow Management

Cash flow, or lack of it, can make or break any business.

All too often, a small business will sacrifice positive cash flow to meet short-term crisis needs and may never recover. This is one of the biggest reasons small businesses fail. A great bookkeeper will be able to understand your financial needs from day-to-day and month-to-month, help to keep you honest, and keep you walking in financial reality. Even though it is up to the business owner to set the guidelines of what gets paid and when, your accountant should be able to foresee problems and help you make wise financial decisions. Understanding the ramifications of your possible actions is half the battle.

Tax Preparation and Planning

It’s January 15th and you suddenly realize that tax season is here. You call your bookkeeper in a panic, asking him or her to make time to get all the bookkeeping finished and the reports ready for your tax person.

If you had a great bookkeeping solution, December would have already been closed out and year-end reporting would be the push of a button away. You would not have to worry about mistakes, missing expenses because you were in a hurry, or risking an audit.

A great bookkeeping solution will warn you about red flags that might arise in terms of unforeseen tax burdens. When your business is growing, you may not be taking into account that you will be paying higher taxes and/or heading into a new tax bracket. Your bookkeeping solution should be able to see that far ahead and help you plan wisely so that you are ready to meet growing pains and keep the finances under control.

Credit Management and Strategy

Lines of credit are a double-edged sword. If you use credit cards, you should be aware of the risks and costs of maintaining high balances and the ramifications of not paying those balances down. Sometimes, Line of Credit balances must be paid down to zero, depending on the terms of the bank agreement, and are not really revolving lines of credit.

With either instrument, the business must exercise planning, discipline, and consistency to prevent serious business-threatening situations from arising. A good bookkeeping and cash management strategy will ensure that the credit lines remain a priority and don’t get you into trouble. Once you have screwed up your credit rating, it may difficult or impossible to recover.

Enrico Palmerino, a graduate of Babson College, is a serial entrepreneur recognized by Inc., Bloomberg Businessweek, CNN, and USA Today. He was a co-founder founder of ThinkLite, an international lighting company ranked #46 in Inc's 500 Fastest Growing Companies, and is currently Managing Director at SmartBooks, an outsourced bookkeeping & accounting company providing small and midsize companies with a virtual finance department that is better, faster, and more affordable.

The Young Entrepreneur Council (YEC) is an invite-only organization comprised of the world's most promising young entrepreneurs. In partnership with Citi, YEC recently launched StartupCollective, a free virtual mentorship program that helps millions of entrepreneurs start and grow businesses