Tax planning questionnaire: what to ask clients before year end

By Arthur Teboul, DokuTrak · Published

In brief

A tax planning questionnaire asks a client about the rest of this year and the next one, before the year closes, while choices can still change the tax. It covers expected income, retirement contributions, gifts, life events and payments made so far, and names the statement each answer needs.

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The organizer: Year-end tax planning questionnaire

Answer with your best estimate for the full year. Round numbers are fine.

Income for the rest of the year

Based on: Publication 505, Worksheet 2-1

  1. Do you expect a bonus, commission or raise before year end?If yes, send: Latest pay stub; Offer or bonus letter
  2. Will you change jobs, stop working or retire this year or next?If yes, send: Separation or retirement date; Final pay stub when available
  3. Do you hold stock options, restricted stock units or an employee stock purchase plan?If yes, send: Grant and vesting statements; Planned exercise or sale dates
  4. Do you own a business or have side income?If yes, send: Year-to-date profit and loss report
  5. Did you receive tips, or overtime that federal law requires your employer to pay?If yes, send: Pay stubs showing tips and overtime

Withholding and estimated payments

Based on: Publication 505; Form 1040-ES

  1. Federal and state tax withheld so far this year
  2. Have you made estimated tax payments this year?If yes, send: Date and amount of each payment
  3. Was your adjusted gross income last year above the higher-income safe harbor level?If yes, send: Last year’s federal return
  4. Do you expect a large one-time item, such as a property sale or a lump-sum payout?

Investments

Based on: Schedule D (Form 1040); Form 8949

  1. Have you sold investments at a gain or loss this year?If yes, send: Year-to-date brokerage statement with realized gains
  2. Do you hold any position you would consider selling at a loss?If yes, send: Unrealized gain and loss report
  3. Did you buy, sell or exchange digital assets?If yes, send: Exchange transaction history

Retirement and health accounts

Based on: IRS contribution limits; Publication 590-A and 590-B

  1. Are you contributing to a 401(k), 403(b) or similar plan?If yes, send: Pay stub with year-to-date deferrals
  2. Do you plan an IRA contribution or a Roth conversion?If yes, send: IRA account statements
  3. Must you take a required minimum distribution this year?If yes, send: Account statement showing the distribution so far
  4. Do you have a health savings account?If yes, send: HSA statement with year-to-date contributions

Charity and family gifts

Based on: Publication 526; Form 709 instructions

  1. Do you plan cash gifts to charity before year end?If yes, send: Receipts for gifts made so far
  2. Would you donate appreciated stock or use a donor-advised fund?If yes, send: Statement showing the shares and their cost
  3. Will you give more than the annual exclusion amount to any one person?If yes, send: List of gifts, recipients and dates
  4. Have you updated beneficiaries or your will in the last three years?

Life events, home and vehicle

Based on: Publication 501; Publication 523; Publication 505

  1. Did you marry, divorce, have or adopt a child this year, or expect to?If yes, send: Marriage certificate, decree or birth certificate
  2. Do you plan to buy, sell or refinance a home?If yes, send: Purchase or sale contract; Closing statement when available
  3. Will you move to another state?If yes, send: Planned move date and new address
  4. Did you buy a new car for personal use with a loan?If yes, send: Loan statement with interest paid; VIN, or the label showing final assembly in the United States
  5. Will you or your spouse be 65 or older by year end?If yes, send: Birth dates
  6. Will a child start college or pay tuition next year?If yes, send: 529 plan statement; Tuition bill

Business owners(if it applies)

Based on: Schedule C; Form 1120-S; Form 4562

  1. Do you plan to buy equipment, vehicles or software for the business before year end?If yes, send: Quotes or invoices
  2. Does the business have a retirement plan, or do you want to start one?If yes, send: Plan documents or provider statement
  3. Do family members work in the business?If yes, send: Payroll records for each family member
  4. Owner salary and distributions taken so far this year

Planning questions look forward, organizer questions look back

An organizer collects facts about a year that is already over. By contrast, a tax planning questionnaire is sent in the fall and asks what the client expects to happen before the year closes. The answers drive actions such as a bonus deferral, a Roth conversion or a fourth estimated payment.

Send the individual tax organizer in January for the return itself. Send this questionnaire in September or October, with a reply date that leaves time to act. Many questions ask for a year-to-date figure, so the most useful attachments are the latest pay stub and the latest account statements.

Income outlook and the safe harbor check

Start with what will be earned. Ask for expected wages, bonuses and commissions, any change of job or retirement date, and projected business profit. Then compare withholding and estimated payments so far against the safe harbor.

In most cases, a client must pay estimated tax for 2026 if they expect to owe at least $1,000 after withholding and credits (IRS Publication 505 (2026), Tax Withholding and Estimated Tax). The payments are enough if withholding and credits cover at least 90% of the 2026 tax or 100% of the tax shown on the 2025 return (IRS Publication 505 (2026), Tax Withholding and Estimated Tax). If 2025 adjusted gross income was more than $150,000, the prior-year figure becomes 110% (IRS Publication 505 (2026), Tax Withholding and Estimated Tax).

A safe harbor is a payment level that avoids the underpayment penalty even if more tax is due at filing. That is why the questionnaire asks for last year’s return: the prior-year tax line sets one of the targets.

Planning topicQuestion for the clientRecord to attachRule to check
Withholding and estimatesHow much tax has been withheld or paid so far this year?Latest pay stub, estimated payment confirmations90% of 2026 tax or 100% of 2025 tax, 110% above $150,000 of AGI (IRS Publication 505 (2026), Tax Withholding and Estimated Tax)
Workplace retirement planHow much have you deferred into your workplace plan this year?Plan statement or pay stub with year-to-date deferrals$24,500 elective deferral limit for 2026 (IRS, 401(k) and profit-sharing plan contribution limits)
Gifts to familyDo you plan gifts to any one person above the annual exclusion?List of planned gifts and recipients$19,000 annual exclusion per recipient for 2026 (IRS, What’s new: Estate and gift tax)
Charity, non-itemizerWill you give cash to charity and take the standard deduction?Donation receiptsUp to $1,000, or $2,000 joint, from 2026 (IRS Publication 505 (2026), Tax Withholding and Estimated Tax)

The deductions and limits worth asking about in 2026

The deductions for tips, overtime, car loan interest and seniors began in 2025 and run through 2028 (IRS fact sheet, Tax deductions for working Americans and seniors). Two charity rules are new in 2026 (IRS Publication 505 (2026), Tax Withholding and Estimated Tax). Each depends on a fact the preparer cannot see in January, so ask now while the client can still keep the right record.

Investments, retirement and giving

Investment questions are about timing. Ask for realized gains and losses so far, positions with a loss that could be sold, and any large concentrated holding. Tax-loss harvesting is selling an investment at a loss to offset gains realized in the same year. A year-to-date brokerage statement answers most of it.

For retirement, ask what has gone into each account and what the client plans to add. Ask about Roth conversions, required distributions and an HSA. For equity pay, such as restricted stock units or incentive stock options, ask for the vesting schedule and any planned exercise.

Giving questions cover cash gifts, appreciated stock and a donor-advised fund. For gifts to family, the annual exclusion for 2026 is $19,000 per recipient (IRS, What’s new: Estate and gift tax). Gifts above that amount to any one person call for a conversation about Form 709.

Life events and business owner questions

Life events change filing status, dependents and state returns. Ask about a marriage or divorce, a birth or adoption, a child leaving the household, a parent moving in, a home purchase or sale, and a planned move to another state.

Business owners need their own block. Ask for a year-to-date profit and loss report, planned equipment purchases, owner pay, a retirement plan for the business, and family members on payroll. Bunching is grouping two years of deductible payments into one year so itemizing beats the standard deduction in that year.

Questions people ask

What is the difference between a tax organizer and a tax planning questionnaire?

An organizer collects facts about the year that just ended, so the return can be prepared. A planning questionnaire asks about the months ahead, so the client can still act before year end.

When should a tax planning questionnaire be sent?

Send it in early fall. That leaves time to adjust withholding, make a final estimated payment, or move a contribution before the year ends.

What estimated tax safe harbor applies to 2026?

Payments covering at least 90% of the 2026 tax or 100% of the 2025 tax generally avoid the penalty, and 110% of the 2025 tax applies when 2025 AGI was over $150,000 (IRS Publication 505 (2026), Tax Withholding and Estimated Tax).

Which 2026 law changes should the questionnaire cover?

Ask about tips, overtime, car loan interest and the enhanced senior deduction, which run from 2025 through 2028 (IRS fact sheet, Tax deductions for working Americans and seniors), and about charity, where two rules are new in 2026 (IRS Publication 505 (2026), Tax Withholding and Estimated Tax).

Sources

About the author

Arthur Teboul (Founder, DokuTrak) is building DokuTrak after watching professionals lose hours chasing clients for documents over email. Arthur Teboul.

Editorial standards

How this page was made (methodology): it is built from the primary sources listed under Sources, and every rule and figure on it links to the source it comes from. Last updated October 25, 2026. Spotted an error or a rule that changed? Contact us.

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