Five Client Conversations Every Tax Practitioner Should Have Before Year-End

Tax planning should not be treated like pumpkin spice: something saved for fall. The longer practitioners wait to begin planning conversations, the fewer options clients may have. By November or December, clients often have already made decisions that limit their choices, leaving practitioners to respond rather than plan proactively.

A third-quarter check-in, whether during the late-summer lull or after the October filing deadline, can help practitioners identify issues and uncover planning opportunities while clients still have time to act.

Start Planning While Clients Still Have Options

1. Discuss Life Changes

A lot can happen in a short amount of time. Clients may have gotten married, divorced, or welcomed a new child into their family— all things that can have a tax impact.

For clients who got married or divorced…

• • Remind them to report any name changes to the Social Security Administration
  • Provide instructions for updating their mailing address with the IRS, state tax authorities, and employers
  • Advise on any necessary updates to tax withholding settings
  • Let your divorced clients know they will likely need to file a joint or married filing separate tax return until the divorce is finalized and that considerations like itemized deductions and claiming dependents will need to be discussed with their spouse.

For clients who welcomed a new child…

• • Discuss potential tax credits like the child tax credit, adoption credit, or child and dependent care credit. For the child and cependent care credit, mention the earned income/actively looking for work requirement and what they need to track for childcare expenses.
  • Discuss tax advantages of Trump and §529 accounts

For clients with a death in the family…

• • Inform them of filing requirements in the year of death
  • Discuss qualifying surviving spouse filing status and changes to filing status for the period after

For clients who moved…

• • Discuss state filing requirements and review residency changes. Some states, like New York and California, are strict about tax residency and may scrutinize a taxpayer’s ties to the state. Review the old and new state’s residency requirements and make sure your clients are aware of things they may need to update, like the address on their license, vehicle registration, or voter registration to substantiate their state tax residency position.

2. Review Income, Estimated Payments, and Withholding

It’s much easier to explain to a taxpayer in September, before they’ve spent their entire bonus, why they owe additional tax than it is in April when it’s already gone. That’s why one of the best ways to help taxpayers prepare is with estimated tax calculations. They give taxpayers a gauge of where they stand and help minimize surprises in April.

As part of the estimated tax calculation, practitioners should:

• • Review income
    • Identify possible payments that may be under-withheld due to supplemental rates like bonuses or stock awards
    • Make updates to prior-period calculations for wage increases
    • Ask about any self-employment income or investment income without withholding
  • Estimate liabilities
    • Calculate estimated tax liabilities so taxpayers are aware of where they stand and can prepare for payments before April
    • Recommend quarterly estimated payments or adjustments to withholdings based on the projected liabilities
    • Identify income items for potential tax savings, like large gains that can be offset by losses before year-end
  • Discuss other considerations
    • Premium tax credit (PTC): prepare taxpayers who purchase their health insurance through the Marketplace that they may need to repay a portion of their PTC
    • Have conversations with self-employed taxpayers who receive both the PTC and the IRC § 162(l) deduction now before open enrollment so they can decide on a plan that works best for their family

3. Evaluate Filing Status and Family Tax Planning

While our tax system encourages joint tax filings in many ways, a joint tax return is not always the tax-advantageous option for some couples.

• • Liability considerations: in some cases, especially for high earners with similar incomes, filing separately is more tax-advantageous. Calculating tax liabilities under both joint and separate scenarios can help save clients’ money and present an out-of-scope billing opportunity
  • Deduction and credit considerations: filing a separate return may preclude taxpayers from some deductions and credits like the student loan deduction
  • Retirement account contributions: filing separately may preclude taxpayers from contributing to Roth IRAs and taking deductions for traditional IRA contributions. Discussing this before clients make contributions can save time correcting excess contributions.

Married taxpayers also need to consider factors beyond filing status.

• • IRC § 162(l) deduction considerations: inform married self-employed taxpayers that they do not qualify for the deduction if they’re eligible to participate in their spouse’s plan even if the Marketplace option makes more economic sense for the family.
  • Retirement account contributions: the availability of a taxpayer’s spouse’s employer-sponsored retirement plan impacts a spouse’s IRA deduction even if they don’t have an employer-sponsored retirement plan

4. Identify Remaining Tax Saving Opportunities

Proactively discussing tax-saving opportunities with clients throughout the year gives them time to implement options so they aren’t rushed in the last two months of the year.

Tax savings opportunities to present to clients include:

• • Retirement contributions: discuss contribution/deduction limits which were touched on above
  • HSA contributions
  • Charitable donations: encourage taxpayers to save receipts and maintain records for non-cash contributions, including a description of the property and its fair market value

• • • Starting in 2026, non-itemizers are eligible to deduct cash charitable contributions up to $1,000

5. Review Business or Self-Employment Activity

It’s especially worthwhile to check in with self-employed taxpayers during the year to ensure they make necessary quarterly estimated tax payments and follow best practices.

• • Review income and expense trends to see whether quarterly payments need to be adjusted
  • Expense tracking: encourage self-employed taxpayers to proactively keep track of their expenses so they aren’t scrambling at the beginning of next year to get organized
  • S corporation owners: check in with any S corps to ensure they are running payroll to meet the reasonable salary requirement

Conclusion

Waiting until December to conduct check-ins with clients makes things more stressful for both tax practitioners and taxpayers. A third quarter review gives tax practitioners time to discuss tax opportunities and pitfalls with clients, so they have time to plan and make decisions. As a bonus, these conversations will help strengthen your client relationship and minimize surprises once tax season rolls around.

By Ashley Akin, CPA

Sources:

Types of major life events and how they can affect filing | Internal Revenue Service

Topic no. 456, Student loan interest deduction | Internal Revenue Service

Publication 590-A (2025), Contributions to Individual Retirement Arrangements (IRAs) | Internal Revenue Service

Topic no. 506, Charitable contributions | Internal Revenue Service

Tips for tracking charitable donations | Internal Revenue Service