Help clients get better organized for a less stressful tax season

Research shows that three in four (75%) senior accountants describe tax season as “somewhat” or “extremely” stressful. It doesn’t need to be this way.

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We have worked with over 1,000 businesses since 2012. I’ve found the clients with the smoothest tax seasons do four things consistently well:

1. They maintain clean books throughout the year. This isn’t just about recording transactions; it’s about categorizing them correctly as they occur. When your client’s bookkeeping is current, they’re not scrambling in January to remember what an isolated expense from the previous March was for. It was recorded properly in March, and that dramatically reduces their tax prep time.

2. They establish a year-round relationship with their CPA rather than treating tax preparation as an annual event. When you’re familiar with your client’s business structure, industry, revenue streams and growth trajectory, you can spot opportunities and issues well before Dec. 31 — when there’s still time to address them.

3. They use technology to their advantage. New mobile apps now allow clients to upload documents as they receive them, answer questions about transactions in real time, and track their financial performance throughout the year. This eliminates the frantic document hunt that happens every January. Tax organizers can also be built directly into client portals that will help clients track exactly which documents they’ve submitted and which are still outstanding.

4. They set aside money for estimated taxes throughout the year rather than facing a surprise bill. Whether paying quarterly estimated taxes or just setting aside funds monthly, having ready cash available at tax time eliminates one of the biggest sources of taxpayer stress. Help clients calculate the right amount to set aside based on their income and tax situation.

Tip: Have all of your clients set up a dedicated folder (digital or physical) in January and add tax documents as they arrive. W-2s, 1099s, K-1s, charitable receipts, business expense receipts — everything goes in that folder the day they receive it. It’s simple, but clients who do this consistently report far less stress come filing time.

Handling late-arriving forms

One of the biggest frustrations for both taxpayers and tax preparers is not having all the forms they need well in advance of their March 15/April 15 tax deadline. While W-2s and 1099-NECs have a hard Jan. 31 deadline, the reality is more complicated for K-1s, 1099-DIV, 1099-INT and 1099-MISC.

K-1s (Schedule K-1) don’t have to be issued until March 15 for partnerships and S corps, with extensions pushing out delivery as far as Sept. 15. That’s because partnerships and S corps need to complete their own returns before they can issue K-1s to partners and shareholders.

Other 1099 forms (like 1099-DIV and 1099-INT) technically have a Jan. 31 deadline for mailing to recipients, but financial institutions often wait until mid-February to issue corrected versions because they’re consolidating information from multiple sources. Most prefer to send a single accurate form than to issue corrections.

1099-MISC forms for royalties, rents or other miscellaneous income often arrive late because the payers are smaller entities without sophisticated accounting departments. Real estate partnerships are notorious for this.

Foreign income documentation (Forms 1099-INT from foreign banks, or documentation for foreign tax credits) can be delayed significantly due to international reporting differences and currency conversions.

Solution

For late K-1s: If your client has ownership stakes in multiple businesses, reach out to each entity’s tax preparer in November or December. Ask when they expect to complete their returns and issue K-1s. Some businesses prioritize getting K-1s out early because they know it helps their partners. If you’re dealing with consistently late K-1s, factor this into your planning and file an extension.

Another strategy: Ask if the partnership can provide draft K-1s or estimated figures in January or early February. Many partnerships now issue preliminary K-1s marked as “draft” for planning purposes. While you can’t file with these estimates, they allow you to begin preparation and help clients plan for tax liability. When the final K-1 arrives, you’re simply updating numbers rather than starting from scratch.

For late investment forms: Contact your client’s brokerage in early January and ask if they have a history of issuing corrected forms. If they do, you might want to wait until late February to gather everything. Most brokerages now post preliminary forms online that you can review, with updates flagged clearly.

Start working with clients in November to create a personalized checklist that lists every form and document they’ll need based on their specific situation from the prior year. Instead of having clients wonder: “Am I missing anything?”, they have a concrete to-do list that they can work through methodically.

Here are some tactics that work well for us:

Make it easier for clients

Send a brief video tutorial (with the tax organizer) before tax season.
Use client portals with drag-and-drop upload functionality — the easier the process, the more likely they’ll do it.
Build tax organizers into client portals. At our firm, for instance, we’re rolling out a tax organizer directly in our client portal for the 2025 tax season. If we’re asking for a 2025 1099 statement and a client uploads their 2024 version by mistake, our AI will catch it immediately and prompt them to upload the correct year. This kind of intelligent document validation eliminates a huge source of back-and-forth during tax season.
Assign a staff member to help older clients get comfortable using the portal.
Send personalized checklists of exactly what each client needs (not generic lists).
Offer to accept documents in batches as clients find them, rather than requiring everything at once.
Provide mobile-friendly options since many people manage tasks from their phones.

Create meaningful incentives

Offer early-bird discounts (typically 10-15% off) for documents received by specific deadlines such as Dec. 31 or Jan. 31.
Implement tiered pricing in which fees increase as filing season progresses.
Consider priority scheduling for early submitters — they get their returns done first and get refunds sooner.

Start communicating much earlier

Begin outreach in October or November; don’t wait until January.
Send multiple reminders through different channels (email, text, portal notifications).
Frame deadlines around getting refunds faster rather than just avoiding penalties.

Set firm internal deadlines

Establish a “last acceptance date” for new clients or complex returns (e.g., March 1).
Communicate clearly that documents received after certain dates may incur a rush fee or require extensions.
Follow through on your stated policies — clients will learn you’re serious.

Use year-round touchpoints

Quarterly check-ins keep you top of mind.
Send reminders when W-2s and 1099s typically arrive (late January).
Build relationships so clients want to help you, not just see you as a vendor.

Move clients to a year-round advisory relationship

Building a year-round relationship with clients transforms your practice from transactional to truly valuable.

Start with education, not sales: After completing a tax return, include a brief writeup or video telling the client: “Based on your return, here are three tax planning opportunities for next year.” Point out missed deductions, timing strategies or entity structure considerations. This costs nothing, provides immediate value, and plants the seed that you’re thinking about their taxes year-round.

Identify natural trigger points: When clients mention hiring employees, selling assets, receiving a big contract or facing an unexpectedly large tax bill, remind them: “These have significant tax implications. Would you like a planning session to minimize your liability?'” These moments create natural openings for ongoing tax advisory conversations.

Offer year-end tax planning sessions: In November, reach out to tax clients with a message like this: “‘Let’s review your year-to-date situation and identify opportunities before Dec. 31.” Even a one-hour paid consultation can uncover strategies worth thousands in tax savings. After their first year-end session, most clients want them every year. You can also offer the sessions quarterly or at mid-year.

Bundle with bookkeeping: When you’re already handling monthly bookkeeping, adding quarterly tax planning feels natural. You’re already reviewing a client’s financials, adding tax strategy is a logical extension. Our most successful tax advisory relationships started with bookkeeping clients asking simply, “What are the tax implications of this?”

Show the alternative: A full-time tax director costs $100,000 to over $150,000. Year-round tax advisory at a fraction of that cost gives clients proactive tax strategy without the overhead. Frame your advisory work as expertise that would otherwise be way too expensive for clients to afford in-house.

Tax preparation looks backward at what already happened. Tax advisory looks forward to what you can control. Moving clients from annual compliance to ongoing advisory means they stop reacting to tax surprises and start planning to minimize them. When clients see how much less stressful tax season is when they’re proactive and well organized, they’ll readily jump onboard. A carrot always works better than a stick.