Why Proactive Business Owners Never Scramble at Tax Season (And How You Can Join Them)

Every year, some business owners breeze through tax season while others scramble at the last minute, stressed and overwhelmed. What’s the difference? Smart business owners know that a little preparation goes a long way. Here’s what they do to make tax season easy, including tips on how you can adopt these same strategies.

Close Your Books Properly

The foundation of stress-free tax season starts with clean, closed books. Work with your bookkeeper to complete your annual accounting and properly close your books, whether you use QuickBooks, Xero, Excel, or another system. This annual close process should result in a complete set of financial statements that accurately reflect your business’s performance. When your books are organized and finalized, preparing your tax return becomes significantly simpler.

Get Ahead on 1099 Forms

For businesses that work with independent contractors, issuing 1099 forms is a common pain point. But it doesn’t have to be! Proactive business owners gather W-9 forms as soon as they hire a contractor or vendor. Don’t wait until tax season to track down this information.

Throughout the year, determine how much you’ve paid each contractor. If they meet the reporting threshold, you’ll need to issue them a 1099. Keep in mind that if a contractor mentions a change of address or other contact information changes, you should request an updated W-9 form. This simple habit eliminates the last-minute scramble to locate contractor information when filing deadlines approach.

Communicate Changes Promptly

One of the biggest mistakes business owners make is waiting until tax time to inform their accountant or tax preparer about significant business changes. Smart business owners notify their tax professionals ahead of time about events like bringing on new owners or partners, relocating the business, or other major changes.

Why does timing matter? Your accountant may need to adjust their strategy based on these changes. At minimum, inform them soon after a change occurs—but ideally, let them know beforehand so they can provide proper guidance. This proactive communication prevents unpleasant surprises and ensures you’re positioned for the best tax outcome.

Keep Payroll Filings Organized

If you have employees, staying on top of payroll tax filings is essential. Many businesses work with payroll processors, which makes this relatively seamless. However, you’ll still need to ensure W-2s go out to your employees on time and that you have W-3 forms (which summarize all W-2s) ready for your tax preparer.

Make sure all your payroll tax filings are complete and organized. When these documents are in order, your tax preparation process moves much more smoothly.

The Benefits of Being Proactive

Taking these proactive steps delivers tangible benefits that make the effort worthwhile. When you’re organized and prepared, you’ll get your tax return filed earlier. Your employees and stockholders will receive their necessary tax documents sooner, allowing them to file their personal returns without delay. If you’re expecting a refund, you’ll receive it earlier rather than waiting months for an extended return to process.

Perhaps most importantly, you’ll avoid the stress and chaos that comes with last-minute tax preparation. Instead of scrambling to gather documents and information, you can confidently move through tax season knowing everything is handled.

Partner with CJG Partners

At CJG Partners, we believe in proactive planning that removes obstacles and reduces stress for our clients. Our team provides timely guidance on regulatory changes and works with you throughout the year to ensure tax season is smooth and efficient.

Whether you need help closing your books, managing contractor documentation, or developing a year-round tax strategy, we’re here to support you.

Contact CJG Partners today to discuss how we can help you join the ranks of proactive business owners who never scramble at tax season.