Tax planning consultation questions that lead to a paid engagement

The best tax planning consultation questions each open a decision with a date on it. Ask what changed in the business, what the owner paid last year and when, how they pay themselves, how the business is taxed, what goes into retirement, and what they expect over the next three years.

A good consultation question has an answer you can act on. "Tell me about your business" doesn't. "What did you pay the IRS in April, and did you expect it?" does. The questions below are grouped by the decision each one opens, with the 2026 IRS figures that make them concrete.

If you need the short list to check fit before you book, see questions to qualify a prospect before the meeting.

Start with the change, then the cost

"What's different in the business this year compared with last year?" New staff, a new location, a big contract, a second owner, a bad quarter. Planning is about change, so start there.

"What did that change cost you, or what could it cost you, if nothing else changes?" This is the cost question. Let the owner put a number on it. You are not estimating savings. You're asking them what staying the same looks like.

"What would you want to be different by this time next year?" The answer becomes the goal in your engagement letter.

Tax planning consultation questions about what they paid

"What did you pay at filing in April, and did you expect it?" A surprise April bill is one of the clearest reasons to plan. Get the amount.

"Did you make estimated payments this year? How did you pick the amounts?" The IRS divides the year into four payment periods, with payments due April 15, June 15, September 15 and January 15 of the following year (IRS, estimated tax due dates). It also says most taxpayers avoid the underpayment penalty if they owe less than $1,000 after withholding and credits, or paid at least 90% of this year's tax or 100% of last year's, whichever is smaller (IRS, estimated taxes). An owner who guessed has a problem the plan can solve.

Questions about owner pay

"How do you pay yourself today, and how did you decide the amount?" For S corporation owners, the IRS expects reasonable compensation for services before non-wage distributions (IRS, S corporation compensation). "My last accountant told me" or "I just picked a number" both tell you there's work to do.

"Does anyone else in your family work in the business?" Family payroll changes the picture for wages, benefits and retirement.

Questions about the entity

"How is the business taxed, and when was that decided?" If they're thinking about an S corporation election, timing matters. Form 2553 must be filed no more than 2 months and 15 days after the beginning of the tax year the election is to take effect, or during the preceding tax year (IRS, instructions for Form 2553). An owner who wants the election for next year has a real deadline.

"Who owns what, and is that written down?" Ownership splits drive partnership and S corporation work. Missing agreements are a scope item.

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Questions about retirement

"What did you put into retirement last year, and through what plan?" The 2026 limits give you anchors. The IRS raised the 401(k) employee contribution limit to $24,500 for 2026, the IRA limit to $7,500, and the SIMPLE limit to $17,000. The general catch-up for workers 50 and over in most 401(k) plans is $8,000, and a higher catch-up of $11,250 applies at ages 60 to 63 (IRS, 2026 limits).

"Do you have employees who'd be covered by a plan?" Employees change which plans fit and what they cost. Ask before you suggest anything.

Questions about the next three years

"Are you planning to buy, sell, hire or bring in a partner?" Big moves are where planning pays the most, and they need lead time.

"Is there a date you're working toward, such as a sale or retirement?" A date turns a vague plan into a timeline.

Questions that get straight answers

Owners round numbers, forget things and sometimes say what they think you want to hear. A few habits help.

Ask for the document, later. "Roughly what did you pay?" in the meeting, then "I'll confirm that from the return" once they're engaged.
Ask one question at a time. Stacked questions get one answer.
Ask what they tried. "What have you already looked into?" tells you what they've read online and what their last adviser said.
Write down gaps. If an answer doesn't fit with something else they said, note it and ask again.

That last habit has a rule behind it. Circular 230 section 10.34(d) says a practitioner may generally rely in good faith on information the client gives, but must make reasonable inquiries if it "appears to be incorrect, inconsistent with an important fact or another factual assumption, or incomplete" (31 CFR 10.34). Good consultation questions are also good diligence.

Close with the decision questions

"Of what we've talked about, what matters most to you?" Let the owner rank it. That's your scope.

"If we put this in a plan, when would you want to start?" Get a date on the calendar.

Then state the fee and scope, and send the engagement letter the same day. Our guide on running the consultation covers the full agenda.

What our marketing has taught us about the first meeting

We run marketing that fills tax firms' calendars with qualified planning meetings. Before an owner is booked, they're checked against the firm's written criteria, including entity type, a revenue or profit floor and whether they want proactive planning during the year. So the firm walks in already knowing the basics, and can spend the hour on the questions above instead of on whether the owner fits.

The firm runs the meeting and gives any tax advice. We don't.

Where to start this week

Print the question groups above as a one-page meeting sheet.
Add the 2026 retirement limits and the four estimated payment dates to the sheet.
Ask the "what did that change cost you" question in your next three meetings.
Note every inconsistent answer and follow up once engaged.
End each meeting with the two decision questions.

Questions firm owners ask

What tax planning consultation questions should I ask a business owner? Ask what changed in the business, what the owner paid at filing and through estimates, how they pay themselves, how the business is taxed, what they put into retirement and what they plan over the next three years. Each question should open a decision with a date.

What are the 2026 retirement contribution limits I should know for planning meetings? The IRS set the 2026 401(k) employee limit at $24,500, the IRA limit at $7,500 and the SIMPLE limit at $17,000. The general 401(k) catch-up for ages 50 and over is $8,000, with a higher $11,250 catch-up at ages 60 to 63.

When must an S corporation election be filed? The Form 2553 instructions say no more than 2 months and 15 days after the beginning of the tax year the election is to take effect, or during the preceding tax year. Check the instructions for exceptions and late election relief.

How do I get accurate numbers from a prospect? Ask for rough figures in the meeting and confirm them from returns once engaged. Ask one question at a time and follow up on any answer that doesn't fit with the rest.

Sources

General information from the official sources listed below, checked 25 Oct 2026. Not tax or legal advice.

If you'd rather have qualified owners booked for you

Financial Sales Insider is a marketing company for US CPA and EA-led tax firms. We fill your calendar with qualified tax planning meetings. Our marketing finds business owners who fit your criteria, qualifies them, and books them with you.

20 qualified tax planning meetings in 90 days, guaranteed.

If you have fewer than 20 qualified meetings after 90 days, we keep booking with no further monthly fee until you reach 20.

A qualified meeting is one where a business owner we've qualified books onto your calendar and shows up.

See if your firm is a fit Form not loading? Book here.

Johnny Logan, Founder, Financial Sales Insider.

Financial Sales Insider · Florida · (305) 513-1710