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7 Secrets to a Successful “First Date” with Your Tax Professional

CPA for Freelancers NYC Taxes

There’s no avoiding it this week—the mushy cards and candy-filled aisles of every grocery and drug store aisle remind you that if you’re not coupled off in a romantic relationship already, you “should” be. In stark contrast, there are very few public reminders that if you want to build a productive relationship with a Certified Public Accountant (CPA) or tax professional this tax filing season (and beyond), you’d better do so quickly before all the good ones are “taken.”

The truth is, you can always wait a little longer for Mr. or Mrs. Right, but if want your taxes professionally filed, now’s the time to get serious. (Friendly reminder: Tax Day is April 18 this year). If you’ve never engaged the services of a professional tax preparer or CPA, at first the process may feel as awkward as, well, a first date—but it doesn’t have to be if you keep the following in mind:

  1. Choose your preparer wisely. In any good relationship, romantic or otherwise, picking the right partner is paramount to achieving a successful outcome. The relationship you have with your CPA or tax preparer is an important one (after all, they will be handling some of your most personal information) so if the chemistry just isn’t there or you don’t get a good vibe, trust your gut and ask around for a referral from your inner circle. Be sure to do your own homework, too, making sure that the tax preparer you partner with has legitimate credentials such as being a CPA, an Enrolled Agent or an accountant.
  1. Don’t stand them up. Your time is precious—and so is that of a tax professional, especially during tax season. Don’t just bail if you decide to go it alone on your taxes or you find a better fit. Be the professional that you are and cancel your appointment. Or, if some legitimate issue comes up, call with as much advance warning as possible and reschedule.
  2. Prepare to pick up the tab. When you engage the services of a professional (just like when a client hires you) there will be an invoice at the end of the transaction. Be prepared to pay for the time and expertise of a tax professional—but remember, unlike the dinner you buy for your main squeeze—this expense is tax deductible. And, just like bringing your own food to a restaurant, asking a tax preparer to “help” you with your DIY tax return is really bad form. So just don’t.
  1. Make the most of your time together. Once you have an appointment set with your CPA or tax preparer, it’s time to get prepared. In most relationships the more you put in, the more you get in return. This rule applies to your relationship with your tax professional. If they send you a document to gather key information before your appointment, try to complete it as fully as possible. Don’t have all of your info together? Then do the best you can before your appointment so that you can make the most of your with your tax preparer.
  2.  Fuel up before you go. While many first dates involve dining of some kind, this one should not. Many a tax appointment has been waylaid and wasted when a tax professional becomes the unwitting dining companion of their client who brings takeout to their appointment (strange but true!). If you’re tempted to get some to-go treat on your way to your tax appointment, eat it before your meeting—or better yet, save it for after your appointment as a reward for being such a proactive tax filer. This will make the process will be more efficient and you won’t risk any “special sauce” soiling your key documents.
  1. Avoid distractions. Just like eating, there are many other distractions that are best left until after your tax appointment. As you might guess, just like when you are on a first date, attending to phone calls/social media/personal hygiene and other ancillary activities while you’re in the tax prep zone of your accountant’s office is not only in poor taste…it’s a waste of the time you are paying for—yikes!
  2. Be honest. While it’s pretty harmless to stretch the truth a little on a first date with a potential love interest (maybe you didn’t run a six-minute mile in high school—who cares?!), it can be downright dangerous if you do so on your tax return. When you meet with your tax preparer, just be honest. If you haven’t kept good financial records to this point or you didn’t pay taxes when you should have, don’t create inaccurate numbers for the sake of it. Let your tax professional know. They can help you determine the best way to handle sensitive situations—that’s part of the value you are paying for, and why having good chemistry and trust in this relationship is so important.

Starting a relationship with a CPA or other tax professional is an important step and one that can have far-reaching consequences on your future financial happiness, but there’s no need to feel “first-date nervous” about it. A good and reputable tax preparer is there to help and advise you, so do your homework and find a professional who fits your needs, then keep these “secrets” in mind as you work with them to successfully file your taxes this year, and hopefully for many years to come.

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Jonathan Medows, CPA

Jonathan Medows is a certified public accountant licensed in New York, New Jersey, Maryland, and Pennsylvania. He is also a recognized expert in taxation for freelancers and the self-employed—often tapped for his expert knowledge and perspective on self-employment taxation by national and regional publications such as The New York Post, BusinessWeek, Forbes taxation blog, WebCPA, CPA Practice Advisor, and others. You can read some of Jonathan’s press coverage here.

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