10 Questions To Ask An Accountant If You Work For Yourself

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From elementary school all the way through college, I was a good student. I earned mostly A's and B's — except in math, which would warrant its own celebration if I brought home anything higher than a C. Math didn’t make sense to me then, and it doesn’t make sense to me now, which is why my finances are the one thing I don't handle by myself in my freelance career.

Everything else is on me. Meeting deadlines? Done. Working on tight turnarounds? No problem. Transcribing my own interviews? Easy peasy. I handle it all, but having a trusted financial expert to rely on makes my life much easier, and if you're going to hire one yourself, there are a few  questions to ask your potential small business accountant.

Below, I've listed the questions I asked my current accountant when I was on the hunt for one, plus a few that I've learned about in hindsight. For example, I had no idea it was so important to find someone who was familiar with small businesses specifically, since there are specialized items that a regular tax person may not know as well. If you're currently finding yourself in the same boat, here are some helpful points that will navigate you through your search:

What Services Do You Provide?

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Financial services can range from payroll to taxes, retirement planning, financial forecasting, education accounts, and much more. You may only want or need basic help like filing taxes, but it never hurts to ask what other services they provide in case you want to expand their role in your business in the future.

Do I Need To File Quarterly Taxes?

As a freelance writer, I’m on the hook for quarterly taxes (and most self-employed business owners are, too). There are plenty of articles on how to file quarterly taxes, but honestly, I still find the process confusing. Plus, there are potential penalties for doing it wrong or late, and even more write-offs that I as a non-accountant just don’t know about. Needless to say, having a professional file my taxes for me has saved me time, probably some money, and definitely kept anxiety at bay.

What Sort Of Business Insurance Should I Have?

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Like health or rental insurance, there are different levels of business insurance coverage. However, some industries don’t need it, and for others it’s an absolute necessity. Having an accountant review your business to recommend a level of protection that suits you and your budget can save you a lot of heartache down the road.

Do I Need To Incorporate (And If So, Into What)?

Sole proprietorships don’t require filing any paperwork, but limited liability companies (LLCs), S corporations, and other corporate structures do. A savvy accountant will be able to review your current business model and estimate future growth to determine the best corporate structure for you.

How Many Small Businesses Do You Work With?

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Self-employment finances are different than finances at large companies. A smaller scale means you’ll need someone familiar with small business accounting specifically. Find out how many small businesses they work with or have worked with to get a sense of their expertise.

Do You Have Any Letters Of Recommendation From Clients?

This isn’t a must, but it can’t hurt! Asking for references is a standard part of the interview process for many companies, so why not with contractors? It’s helpful to get unfiltered insight from people who have been in your shoes to help you decide if this particular person meshes with your business.

How Familiar Are You With My Industry?

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Maybe you own a salon. Perhaps you’re a freelance journalist. It’s possible that you make and sell crafts. Whatever your small business is, it’s nice to have someone who’s worked with others in that field before. If you’re extremely niche, that may not be possible (and it’s certainly not necessary), but it gives financial advisors an edge.

What Is Your Preferred Method Of Contact?

As a parent who works from home, I strongly prefer to correspond via email rather than on the phone, but some people prefer to set firm office hours, and some prefer a quick phone call for an immediate reply. Find out how your potential accountant’s communication syncs with yours.

Is My Business Sustainable?

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Sometimes it helps to have a third-party crucially examine every aspect of your business to identify strengths and areas needing improvement. See what your potential accountant comes up with by setting up a preliminary look at your expenses. Show them cash flow, debt, assets, and hear what they have to say. If they come back with bad news, ask if they're able to provide tangible steps to turn things around.

How Can You Help Me Be Successful?

This is a key question to ask any future accountant. It’s a broad, open-ended question, but requires them to identify tangible steps. If they’re able to answer thoroughly with actionable to-do’s for you to take, that shows they’ve done their due diligence and are committed to your success.