TrustFile > Blog > Accounting > Business Owner Seeking Dreamy Accountant: 10 First-Date Questions to ask a Potential CPA

Business Owner Seeking Dreamy Accountant: 10 First-Date Questions to ask a Potential CPA


It happens to nearly everyone at some point. The loneliness. The indecision. Then, the mustering of a steely-eyed resolve (and maybe a glass of wine) to take action, immediately followed by more nervousness, questions, and anxiety. “Where do I find that one special person? How do I know who is the right one for me? Where do I look?”

When you’re seeking a meaningful relationship with an accountant, says Avalara’s Brandon Houk, “It’s not unlike being on a dating game. The same anxieties apply. Picking a CPA is like going out on a first date, having a few conversations, then trying to predict their level of commitment. Scary stuff. But it doesn’t have to be.”

Three Avalara tax experts—Christine Martin, John Sallese, and Brandon Houk—offer these questions for you to ask your potential CPA when you’re ready to take the plunge.

#1. How would your closest friends describe you?

Most accountants will say they’re detail oriented and organized. Others may add that they’re on time, respect schedules, and don’t miss meetings. Laudable traits all. However, what’s most important is that they can clearly demonstrate that they have the experience you need. “State and local taxes are incredibly nuanced, so their prior book of business becomes really important,” says John. “If they say, ‘Well, I’ve never done it but how hard can it be?’ that’s not good enough. You need someone who really understands your business, which becomes even more important the more complex and sophisticated your company and supply chain are.”

#2. Do you value long-term relationships or prefer a fling?

Some accountants work full time, others part time. There’s a difference. Small companies might simply need part time help with compliance or income and/or business taxes for a limited number of states; larger, more complex national companies will most likely need full time help. Regardless, “There’s getting it done, and there’s getting it done right,” says Brandon. “Part time and winging it and sort of getting it kind of right and then dealing with the audit is, unfortunately, one way some companies do business. And it’s not always their fault alone: many clients feel that just having it done feels good enough, which is a recipe for failure.”

#3. You really are single, correct?

You’re putting yourself out there solo, and the expectation is that your potential accountant is doing the same, but sometimes that isn’t the case. Make it very clear if you will or won’t be exclusive, says Christine. “Ask them point blank: will I be working with you, or with a partner, or a CPA, or a staff accountant? Mutual performance expectations are very important.”

#4. If I checked you out online, what would I see?

Like dating, it’s a basic move today to prescreen potential CPAs online. For professionals, LinkedIn is a great way to see their resume, verify their skill sets, and check out their connections. If they’re listed on tax professional websites (ITT and IET, for example), even better, “but the big bonus points come when they can send a link to their blog to show that they’re actively researching and publishing their thoughts and analytics on various sales tax topics, actively pursuing research on behalf of their clients, and looking for opportunities to promote their knowledge. That shows engagement in the process,” says Brandon. Facebook snooping? That’s up to you.

#5. What are your hobbies?

“Sales tax laws and rates change ALL the time, so having an accountant who eats, sleeps, and breathes it is important. They don’t necessarily need to know everything the second something changes, but they certainly need to know more than their client,” says John. In addition to basic MS Office skills, make sure your CPA is well-versed in Excel.

#6. Do you like travel?

Some businesses operate in and out of a single state. But what if your business has nexus in five states? Or ten? Or forty or more? According to Christine, “You know what states you do business in, but will your accountant know what to do in each of them? Are they multi-state and/or multi-tax proficient on income, property, payroll, and sales tax and can they manage your filing and remittance?”

#7. Are you on the rebound?

“We hear from people all the time: ‘I have QuickBooks but I’m not so great at it. Should I just get an accountant?’ The answer is yes. Tools like QuickBooks and TrustFile supplement the advice of an accountant—they don’t replace one,” states John. “At the end of the day, you can have all the tools but you can’t build the house if you don’t know how.”

#8. When can we meet in person?

Of course, having an introductory chat online or through e-mail is a great first step, but most business owners like to eventually meet the person they’re hiring. Set up a time, dress the part, and show up. Both of you. Of course, some larger firms—for example, international tax firms—don’t necessarily see new clients face to face. Don’t take it personally.

#9. My friends’ opinions are very important to me.

How do you feel about meeting them? If you already have a great working relationship with an accountant who is helping you in other matters, ask their opinion of this new suitor and/or for recommendations or referrals. If you don’t want an exclusive relationship, ask the new person if they’re willing to work with both of you.

#10. Who pays for dinner?

Billing and rates are important and most business owners don’t choose an accountant based on price point alone, says John. “What you want is value. Being really upfront, clear and transparent about the process and the pricing is where most firms differentiate themselves. Today, many firms look at sales and use tax projects based on value-based billing and pricing, meaning the firm will say, ‘This is X dollars for this project, rather than my rates are X per hour for this project.’”

Yes, it’s a big world out there but, like mom said, there’s someone for everyone. Think of these questions as a helpful starting point to find your own CPA LTR (long-term relationship, for those of you who haven’t dated since the Eisenhower era). But unlike in romance, this is strictly business—if it doesn’t work, neither of you have to decide who gets the stupid, Roy Rogers wagon wheel, garage sale coffee table.


Avalara Author
Ryan O'Donnell
Avalara Author Ryan O'Donnell