This article was originally written for my column for Inc.
Tax season can be stressful—but much of that stress can be avoided with proper preparation and communication. Part of my role as a fractional CFO is to liaise between my clients and their tax accountants and help keep stress levels low. Over the years, I’ve worked with countless accounting firms, collaborated with my clients’ accountants, and discussed this topic with tax professionals on TaxTwitter. Here are five key tips that I picked up along the way to make this tax season smoother for you and your accountant.
1. Send clear, organized documents in a consistent format.
Every year, accountants receive a flood of tax documents in every possible format—scanned images, blurry photos, scattered emails, and even physical drop-offs. This slows down the process and increases the risk of errors.
Instead, keep things simple and send PDFs, and name your files correctly (2024 W2 – JohnDoe.pdf instead of Scan1234.pdf). This will keep things organized and clear for all parties.
You don’t have to use PDFs, but I suggest you choose one method and stick to it. Your accountant will appreciate it, and your return will be processed faster.
2. Respect deadlines.
Tax professionals juggle hundreds of clients, each with different levels of complexity. You are not their only client. If your accountant gives you a deadline, treat it seriously. Waiting until the last minute or ghosting them when they ask for missing documents causes only frustration and potential delays. Typically, the earlier you can provide documents the better and if you can’t meet a deadline, communicate that.
Don’t assume your accountant can “squeeze you in” at the last second. Filing a return isn’t instant—it requires careful review. And if your accountant suggests an extension, don’t panic. Extensions are a common tool to ensure accuracy and reduce filing-season stress. No, they don’t automatically increase your audit risk (despite what your golf buddy might say).
3. Stop taking tax advice from unqualified sources.
Every tax season, accountants hear, “Well, my friend at the gym said…” or “I saw a TikTok that said I don’t have to pay taxes if I…”—and most of the time, that information is dangerously wrong. Always ask your accountant before making big financial moves that impact your taxes. And definitely don’t base tax decisions on social media influencers, neighbors, or relatives who aren’t trained professionals.
Bad tax advice can cost you thousands of dollars—or worse, trigger an IRS audit. Trust the experts.
4. Be proactive and communicate thoughtfully.
Want to avoid surprises at tax time? Check-in with your accountant before the year ends. A mid-year or Q4 meeting can help you plan ahead and avoid last-minute scrambles. I suggest you schedule meetings instead of randomly calling or randomly showing up at their office. You can even see if they’ll schedule one a quarter at the start of the year. But remember, the acountability goes both ways.
Don’t disappear when your accountant asks for information. If you’re unsure how to answer a question, say so—don’t ignore them. And don’t constantly ask for status updates on your return. Trust me, they have internal systems to track progress, and if they need something from you, they’ll let you know. Repeatedly checking in only slows them down.
Tax planning is a year-round process. The more proactive you are, the more money you’ll save.
5. Respect your accountant’s time and expertise
Many business owners think their return is “easy.” But tax laws are increasingly complex, and even a simple-looking return can have hidden complications. Pay for the right level of expertise—cheaper services can often mean less diligence.
Once you have the right accountant, trust their experience. They’ve spent years training and staying updated on ever-changing tax laws. And definitely don’t devalue their work by saying, “My neighbor’s granddaughter can do my books.” Would you say that to your doctor or lawyer?
Above all, be kind. Accountants work long hours during tax season, and a little appreciation goes a long way.
Tax season doesn’t have to be stressful. By organizing your documents, respecting deadlines, seeking advice from the right sources, planning ahead, and treating your accountant as the professional they are, you’ll make the process easier for everyone involved.
Here’s something to remember: The accounting industry faces a talent shortage. There are far fewer accountants today than five years ago, and demand for their expertise is higher than ever. Good accountants have no problem firing difficult clients who don’t respect their time, follow deadlines, or communicate effectively. If you want to keep working with a top-tier professional, be the kind of client they want to work with.
Also, a little appreciation goes a long way. Whether it’s a box of cookies, a bag of high-quality coffee, a nice bottle of whiskey, or a set of golf balls, a thoughtful gesture at the end of tax season can go a long way in building goodwill. After all, they just helped you navigate one of the most stressful financial tasks of the year—showing gratitude never hurts.
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