How To Put Together A Professional Team For Your Small Business

When my husband and I opened our law firm, we were confident. We had a name, a business plan, office space, and a website. We had thought of everything—except paperwork. And more paperwork. We had not considered how much time we would spend sorting through canceled checks, bank statements, payroll stubs, and letters from various tax authorities regarding regulations.

While, as a tax lawyer, I well understood that taxes needed to be filed quarterly, I hadn’t done the math: quarterly filings for federal, state, and local taxes meant 12 separate submissions a year, just for income taxes. We also had to file federal, state, and local payroll taxes (typically also filed quarterly), unemployment taxes, and business development taxes. We were required to register with the state and submit annual reports. When we changed the sign out front, we had to obtain approval from our local authorities and pay a fee. There was even a separate annual fee for having a private alarm company. We needed to maintain business liability insurance, professional insurance, workers’ compensation insurance, and health insurance.

Did I mention that there were only two of us at the time?

Running a business involves more than just flipping the lights on, especially if you want to do things the right way (and trust me, you do). This reality often conflicts with the amount of time you have to spend actually managing your business.

What’s the solution? Surround yourself with good people. Not just capable employees, but a professional team dedicated to handling all the compliance issues so that you can focus on what you wanted to do in the first place: run your business.

It’s true that a professional team costs money, something that startups and small businesses are often short on. But consider this:

1. Many matters, including bookkeeping and tax preparation, don’t have to be surprises. You can budget those costs in advance.
2. Time is money. Every hour that you spend sorting through your own banking statements or trying to figure out the nuances of Form 941, is taking time away from the business of making money.

Who Should Be On Your Small Business’ Team?

A good tax preparer. The IRS reports that business taxpayers spend an average of 24 hours completing their federal income tax return. This includes 11 hours devoted to record-keeping, five hours for tax planning, and eight hours for completing and submitting forms. That’s more than half of one work week—on one form.

Taxpayers who sell or perform services across state or local lines face even more complexity, including computing and remitting sales tax. U.S. sales tax rates not only vary by state but also by city and county—according to tax compliance software company Avalara, there are more than 13,000 sales tax jurisdictions in the U.S. And those rates? They are constantly changing.

There’s also a learning curve. The recent House passed tax bill (now officially named the “One Big Beautiful Bill Act”) weighed in at over 1,000 pages (it’s still being worked on). Four years ago, the American Rescue Plan Act of 2021 made changes to Form 1099-K reporting requirements for third-party payment networks (like PayPal, Venmo, etc.) and online marketplaces, impacting small businesses. Since then, the IRS has walked back implementation, leaving some taxpayers confused. Processing all of those changes—and the changes to the changes—can be time-consuming and frustrating.

So, you could do your own taxes, but chances are you’re too busy with other things.

A tax preparer does not need a specific credential to be competent. However, by law, anyone paid to prepare or assist in preparing federal tax returns must have a valid Preparer Tax Identification Number (PTIN). Paid tax preparers are required to sign and include their PTIN on the taxpayer’s return.

Fortunately, for business taxpayers, it’s all tax-deductible. Additionally, a good tax preparer can also flag potential audit issues and point out areas where you might be wasting deductions or credits (you’re not still depreciating items that might be expensed, are you?).

A good bookkeeper. Bookkeeping, at its most basic, is the recording of financial transactions. However, Nicole Davis, the founder and CEO of Georgia-based Butler-Davis Tax & Accounting, warns that it is more than simply balancing a checkbook, especially for small businesses. It includes recording receipts and expenditures, tracking accounts receivable and accounts payable, as well as potentially managing inventory and loans.

That’s why every business needs a competent person to manage the books. This might be the same person as your tax preparer, or it could be someone different. Today, there are in-house, fractional, and virtual bookkeeping options, making it easy to find someone to fit your model, timeframe, and budget. No matter how you arrange it, solid record-keeping is important.

The most obvious reason to have routine bookkeeping is that it helps you at tax time. If you’re organized all year, there’s no last-minute scramble. Plus, regularly reviewing the books means you’re less likely to miss something.

Good bookkeeping also helps you understand the financial health of your business. Just because you’re paying your bills doesn’t mean your business is on track for success. When we first started our business, our local banker would chirp, “Cash flow!” We knew it was important, but we didn’t realize how crucial it was until a major client, who had incurred a very large bill, was unable to pay due to unfortunate circumstances (a nice way of saying he was sent to prison). Suddenly, those accounts receivable weren’t as meaningful because they didn’t translate into cash flow.

Bookkeepers can generate a lot of reports. Jenny Groberg, CEO of BookSmarts Accounting and Bookkeeping in Utah, recommends that businesses focus on one type of statement: a profit and loss statement (or P&L statement. This is a financial report summarizing your income and losses during a specific period, like a quarter or fiscal year. In short, it shows how much money you’re making or losing.

As a business owner, I don’t want to have to beg clients for money. I’m terrible at it, and I find it awkward to ask for money in one breath and offer legal advice in the next. Bookkeepers can prepare and send invoices and issue dunning letters when clients haven’t paid. I know who has paid and who hasn’t (and I intervene when necessary), but having a bookkeeper make those requests allows me to maintain a professional relationship with clients.

I don’t want to spend all of my time in the financial weeds when I need to be building and growing my business. Neither do you. Having someone help keep the books organized is well worth the cost.

(You can find more on hiring a bookkeeper here.)

Lawyers. I know, people hate lawyers. But you need them. Trust me. And you need lawyers (plural) as part of your team.

Think of lawyers as you do doctors: If you’re healthy, you don’t need to see your doctor every month, but you will require an occasional check-up. Checking in at least once a year with a knowledgeable business lawyer to ensure that you’re complying with corporate formalities (like minute books and annual meetings) will help keep your business healthy.

Of course, when you get sick, you see a doctor. The same analysis applies to a lawyer. When you have a problem, pick up the phone. Don’t wait for it to fester; chances are, like an infection, a legal issue will only get worse without attention.

And what about when you have a specific ache? Like a pain in your chest? You see a cardiologist. You don’t go to the dermatologist. Ditto for legal services. Your divorce attorney typically shouldn’t be handling your trademark issues. Your tax attorney shouldn’t be handling your criminal law matter. While it’s true that some areas of the law overlap (like tax and business), most lawyers are not one-size-fits-all. The law is vast and complicated. No one knows everything.

Lawyers can do more than help you fix what goes wrong—they can help you stay compliant with changing rules and regulations, so that things don’t go wrong. For example, during much of 2024, the Treasury Department touted registration under the Corporate Transparency Act (CTA). This year, under the new Trump Administration, Treasury walked back most of the CTA, limiting its scope to foreign companies. Before the revision, however, an estimated 32.6 million companies were potentially subject to reporting requirements, with significant penalties for noncompliance. Having a lawyer stay on top of those kinds of matters as they relate to your business can help you avoid problems down the road.

When you’re just getting started, it’s wise to know a good corporate lawyer, a good tax lawyer, and a good intellectual property lawyer. They might be at the same firm or they might not be; the size of the firm doesn’t always correlate to the quality of the work (the best hamburgers are not found at McDonald’s). You don’t have to pay lawyers to have them in your speed dial, but you do want to be able to call when you need help.

Insurance Brokers. I had no idea how much insurance I needed until I started my own business. There was general liability insurance, business premises insurance, professional (malpractice) insurance, health insurance, life insurance, and disability insurance. I began, like many businesses, by making a few phone calls and obtaining coverage in small pieces on my own. But then things changed. We hired more people, bought a building, and moved. I couldn’t figure out whether I was overinsured, underinsured, or just right. So, I went to the experts.

It’s the job of insurance brokers to explain and coordinate different kinds of insurance. They’ll work with you to figure out exactly what you need and offer different solutions based on industry, geography, and cost. What about that cost? Ed MacConnell, president of Total Benefit Solutions in Pennsylvania, says that brokers are paid differently depending on the client. When it comes to health insurance, brokers are typically paid a commission by the insurer, which means that it costs you, as the business owner, nothing out of pocket since that cost was already included in the premium expense. Brokers may also be paid on a fee basis, depending on the services.

Insurance brokers just don’t collect a check for premiums. They can assist with compliance issues, advise on best practices, and help with healthcare reimbursements and settling benefits issues.

Retirement Plan Administrators. One of the most challenging aspects of running your own business can be giving up the benefits you once enjoyed. One often-overlooked benefit of a small business is a retirement plan. It can feel like a luxury—one of my fellow small business owners once burst into laughter when I mentioned setting up a 401k (“With what?” she cracked)—and it can be complicated by a host of rules and regulations.

While small businesses used to be limited to one or two options, there are now many different kinds of retirement plans for small businesses to choose from. A retirement plan administrator can explain your options (as well as what you’re not allowed to do), walk you through the process, and keep you on top of what you need for compliance purposes. That might include flagging due dates for returns, figuring limits and caps for plans, and assisting with filling out annual reports. Retirement plan administrators can also advise on whether plans are subject to the Employee Retirement Income Security Act of 1974 (ERISA), a federal law that governs retirement and health plans, including whether you need to provide certain kinds of notices to your employees.

Like insurance brokers, many retirement plan administrators operate on a commission or fee-for-service basis—ask upfront.

Payroll Services. Throughout my years of practice, one mistake made by small businesses stands out the most: failing to manage payroll effectively.

For wage earners, Social Security and Medicare taxes are called FICA (Federal Insurance Contributions Act) and are taken out of your paycheck. Taxes on self-employment income are sometimes called SECA (Self-Employment Contributions Act) taxes since self-employed persons pay both the employee and employer contributions.

If you’re a wage earner, your employer collects your Social Security and Medicare payments and remits both their portion and your share to the government (self-employed persons pay the IRS directly).

Employers, including small business owners, have a legal obligation to make the remittance. If that doesn’t happen on time, there can be serious consequences. For example, a trust fund recovery penalty may apply. The penalty is 100% of the unpaid trust fund tax and may be imposed on those the IRS deems responsible for collecting or paying the tax. That means that the liability becomes personal (as opposed to a business liability) and isn’t easily discharged. Even more serious? Those employers and responsible persons who fail to pay over trust fund taxes may be subject to criminal charges. Sentences can result in restitution and jail time.

Payroll taxes, including withholding, should be immediately set aside to be paid over to the tax authorities—I always recommend maintaining a separate account for this purpose. However, it can be tempting for some business owners to dip into those funds when cash is low. They often figure that they’ll just “borrow” the money now and put it back later. For many business owners, later never comes. Instead, tax liabilities multiply.

The solution for most businesses? Hire a payroll company. Outsourcing payroll to a payroll company can be a significant time-saver for small businesses. Payroll companies will figure out how much is owed for federal, state, and local purposes and can remit payments straight from your checking account. They can also create reports and coordinate with your bookkeeper or tax preparer to help ensure that you, your employees, and the tax authorities get paid on time.

What’s Next?

Now that you know whom you need, how do you go about assembling your team? Here are some tips:

• Ask your friends and colleagues who they use: as in any service-based business, referrals are still the best way to find a good fit.
• Do your homework. Check credentials online and explore networking sites like LinkedIn for potential leads.
• Ask other professionals for recommendations, since most are happy to pass along a few names.
• Check out lists, like the Forbes Best In-State CPAs. While you should take some accolades with a grain of salt (people may pay to be mentioned on some lists–this isn’t the case for our Forbes list), peer-recommended or vetted lists are a good place to start.

When you identify someone who might be a good fit, set up a time to ask questions about their background, work processes, timelines, and style .

As you add members, remember that you’re building a team, not a group of strangers. While your team doesn’t have to be best friends, you should make sure that the folks you choose feel comfortable communicating with each other. If your bookkeeper won’t schedule time to talk to your tax preparer, it creates more work for everyone. And if your tax attorney crafts a great benefits plan for your business but fails to communicate the specifics to your retirement broker, the plan is meaningless. Don’t be afraid to explain that you’re not happy or let someone go if they’re not working out—if they’re not willing to be part of your team, they’re not useful to you.