Tax planning meeting checklist

By Tom, CPA · Updated October 27, 2026

Part of: Easy Tax Strategies

TL;DR: A tax planning meeting is worth the most in October or November, while there is still time to act before December 31. Bring last year's return, year-to-date pay stubs and gain/loss reports, account balances, and a list of life changes. Ask about your marginal bracket, Roth conversion room, capital gain timing, retirement contributions, estimated payments and benefit cliffs like IRMAA. Leave with a written action list with dates and amounts.

Educational only, not tax, legal, or investment advice. Examples are illustrations, not predictions. Rules and limits change; verify current figures and talk to a qualified professional about your situation.

Tax preparation is history class: it reports what already happened. Tax planning is the only part where you can still change the ending. Yet most people show up to a planning meeting (with a CPA, enrolled agent, financial planner, or just their spouse at the kitchen table) carrying a vague feeling and a shoebox. Then they get vague advice.

Here's how to prepare so the meeting produces specific moves with dates and dollar amounts. It works just as well for a do-it-yourself planning session. 2026 figures are as of October 2026. For the full framework, see the tax planning guide.

CPA Warning Label: Planning advice is only as good as the numbers you bring. A projection built on a guess about your bonus, a missing K-1 or last year's capital gains can recommend exactly the wrong move.

When to schedule it

• October to early December: the sweet spot. Most of the year's income is known, and there's time for Roth conversions, gain harvesting, retirement contributions and charitable gifts, which mostly must be done by December 31.
• After a big event: sale of a business or rental, inheritance, marriage, divorce, retirement or a move to a new state. Plan before the transaction if you can; many choices are locked in at closing.
• Early in the year: to set withholding and estimated payments, and to decide on prior-year IRA and HSA contributions (allowed until the filing deadline).

Documents to bring

• Last year's full federal and state returns, including all schedules.
• Year-to-date pay stubs for each earner, with expected bonuses and equity vesting.
• Brokerage year-to-date realized gain/loss reports and an estimate of fund distributions.
• Business or rental profit and loss for the year so far.
• Account balances: traditional, Roth, HSA, taxable, and basis in any nondeductible IRA (Form 8606).
• Estimated tax payments and withholding to date.
• Social Security, pension and Medicare information if you're near or in retirement.
• A list of life changes and upcoming plans: a home purchase, college, a job change, a move.

If you'll have K-1s from partnerships, bring last year's and any estimates from the general partner.

Questions to ask

Income and brackets

• What is my projected marginal bracket for 2026, and how close am I to the next one? (Joint 12% ends at $100,800 of taxable income, 22% at $211,400, 24% at $403,550.)
• Should I defer or accelerate income or deductions between 2026 and 2027?
• Do I qualify for the new deductions for tips, overtime, car loan interest or the $6,000 senior deduction, and am I near a phase-out?

Retirement accounts

• Am I maxing the right accounts? For 2026: $24,500 401(k), $8,000 catch-up at 50+, $11,250 at ages 60 to 63, $7,500 IRA, $4,400 or $8,750 HSA.
• How much Roth conversion room do I have? See the December conversion checklist.
• Traditional or Roth for next year's contributions?

Investments

• Should I harvest losses, or gains in the 0% bracket (up to $98,900 of joint taxable income)?
• Am I near the 3.8% NIIT threshold ($250,000 joint, $200,000 single)? See capital gains tax planning.

Real estate and business

• Are passive losses usable, or suspended? What would cost segregation or bonus depreciation do, and what is the recapture risk? Real estate tax planning checklist.
• Would an S corporation or retirement plan make sense for my self-employment income?

Benefits cliffs

• Does my income affect ACA credits, Medicare IRMAA (based on income two years earlier) or Social Security taxation? See IRMAA planning.

Estate and family

• Are beneficiary designations current? Should we use the $19,000 annual gift exclusion? Is there a plan for long-term care costs? See estate planning basics and long-term care planning.

What a good meeting produces

You should leave with a written list, not a vibe. Each item gets an owner, an amount and a deadline.

Illustration

Chris and Robin, both 61, retired in May. Projection: $68,000 of joint taxable income for 2026, including Chris's salary through May and $9,000 of qualified dividends. Action list from the meeting:

1. Convert about $30,900 from Robin's IRA to a Roth by December 12, bringing taxable income to $98,900 so the dividends stay in the 0% bracket. The 12% bracket runs to $100,800, but going past $98,900 would start taxing dividends at 15%. Tax about $3,710, paid from savings.
2. Pay a fourth-quarter estimate by January 15, 2027, using the 110%-of-prior-year safe harbor because 2025 AGI was over $150,000.
3. Robin, under the 401(k) plan until December: use the age 60 to 63 catch-up of $11,250 on the last paychecks (not applicable for Chris, who has left).
4. Health insurance check: they're on COBRA through 2027, so the ACA credit isn't in play this year, and Medicare is four years away. Next year, when they move to marketplace coverage, conversion sizing changes completely: income above 400% of poverty ($84,600 for two for 2026 coverage) means no premium credit at all.

See how item 4 changes next year's item 1? That's why you plan with real numbers, every year.

Red flags in planning advice

• No projection: advice that doesn't start from your actual numbers is generic.
• Only one year: good planning compares this year to the next few, especially around retirement, Medicare and RMDs.
• Product first: if every answer is an insurance policy, an annuity or a fund, the meeting was a sales pitch.
• Too-good strategies: deductions that exceed what you spend, "tax-free" setups with captive insurance or easements, or anything promising to eliminate tax. The IRS publishes its Dirty Dozen list every year for a reason.
• No caveats: aggressive real estate moves like cost segregation or short-term rental losses need documentation, and some create recapture later. A planner who skips that part is skipping the bill.

After the meeting

• Put every deadline in your calendar the same day.
• Recheck in December with final pay stubs before executing irreversible moves like conversions.
• Save the projection; it becomes next year's starting point and helps your preparer in the spring.
• Schedule next year's meeting now. Annual planning is boring, and boring is profitable.

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