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Master Year-Round Tax Prep: How to Stay Ahead of the Stress

Written by Marketing | Sep 24, 2025 12:41:22 PM



If you’ve ever found yourself buried in documents, chasing down W-9s, or scrambling to close the books as tax deadlines loom, you’re not alone. 

Tax season stress is real. But it doesn’t have to be.

Brad Ebenhoeh of BELAY recently sat down with Alex Cram at BILL and industry leader Questian Telka of ReQoncile Financials for the Master Year-Round Tax Prep webinar.

The conversation revealed a simple but powerful truth: The key to stress-free tax preparation is moving from reactive to proactive.

Here’s what you can take away to master tax prep all year long.

Why Reactive Tax Prep Creates Chaos

For most firms, the bottlenecks show up at year-end:

  • Missing or incomplete W-9s.
  • Hours lost chasing clients and vendors for documentation.
  • Catching up on missed bookkeeping and coding transactions.
  • Delayed opportunities to apply smart tax strategies.

Not only does this slow everything down, but it also leaves you and your clients stressed and scrambling. 

As Questian shared during the webinar, the stress of not having vendor paperwork in order is enough to make even seasoned accountants want to quit each year.

Brad added another perspective: Your clients are expecting a seamless experience. When you’re stuck in reactive mode, their experience suffers — and so does your team’s.

Building Proactive Habits

So what’s the alternative? It’s all about building intentional, consistent habits.

1. Close the Books Monthly (or at Least Quarterly)

Keeping your books current isn’t just best practice. It’s a lifeline. 

Instead of cramming an entire year into December and January, spread out the work. 

BELAY recommends setting clear service-level agreements so everyone knows what’s expected and when.

2. Collect W-9s Before Payments Go Out

This one change can save you endless headaches. 

Both Brad and Questian agreed: You should never cut a check before you have the W-9 in hand. 

By baking this requirement into your processes — and reviewing compliance quarterly — you’ll prevent incomplete or incorrect filings later.

3. Set Expectations Early

Don’t wait for problems to surface. 

From onboarding onward, clearly outline both your responsibilities and your clients’ responsibilities. 

As Questian shared, when clients know that delays in providing documentation increase costs and cause bottlenecks, they’re far more likely to stay on track.

4. Standardize Your Tech Stack

Whether it’s QuickBooks Online, BILL, or your preferred payroll platform, using consistent tools across clients creates efficiencies and makes training your team simpler. 

The more consistency you create, the smoother tax season becomes.

The Power of Automation

Automation isn’t about replacing people. It’s about freeing them up to focus on high-value work.

  • Vendor management: BILL automates W-9 collection and validates taxpayer information before payments are released.

  • Expense management: Tools that capture and store receipts automatically reduce audit stress and keep documentation airtight.

  • Workflow visibility: Automation ensures nothing gets lost between team members. Each task seamlessly passes to the next, creating accountability and efficiency.

Of course, automation isn’t perfect. 

As Questian noted, tools like QuickBooks sometimes miscategorize transactions, so human review remains essential. But the right balance of automation plus oversight eliminates hours of manual work.

Why Proactivity Builds Trust

At the end of the day, tax preparation is about more than compliance — it’s about relationships.

Your clients aren’t just buying financial services; they’re trusting you with some of the most sensitive aspects of their business. 

By proactively preparing throughout the year, you create peace of mind, reduce costs, and — most importantly — deliver an exceptional client experience.

As Brad put it, “If you want to have a well-rounded tax service, you cannot be reactive. You have to be proactive.”

Bringing It All Together

When you embrace proactive tax prep, you:

  • Reduce stress for yourself and your team.
  • Protect clients from costly errors.
  • Create efficiencies that scale your firm.
  • Build stronger, lasting client relationships.

And the best part? You don’t have to do it alone. 

BELAY’s team of Financial Experts leverages leading tools like BILL to help you implement proactive practices that save time, reduce stress, and create margin for what matters most.

Tax season doesn’t have to be chaotic. With the right habits, technology, and partner, you can stay ahead — all year long.