What to Bring to Your Year-End Tax Planning Meeting

Most business owners only think about taxes twice a year: when the return is due, and when the bill shows up. By then, almost every decision that affected the number has already been made.

A year-end tax planning meeting changes that. It happens in the fall, while there are still a few months left in the year, and it looks forward instead of backward. Tax preparation reports what already happened. Tax planning asks what you can still do about it.

The catch is that a planning meeting is only as good as the information on the table. If we spend the first half of the meeting guessing at your numbers, there isn't much time left for actual planning. So here is what I ask business owners to bring.

Why Fall Is the Right Time

Once December 31 passes, most of your options for the year close with it. Timing a large purchase, adjusting how you pay yourself, catching up on estimated payments, or making a retirement contribution all work best when there is still time to act.

Meeting in October or November gives you room to make decisions on purpose instead of in a rush the week before Christmas.

The Year-End Tax Planning Checklist

1. Current, Reconciled Financial Reports

Bring a year-to-date Profit and Loss and a Balance Sheet through the most recent month end. "Reconciled" matters here. It means your bank and credit card accounts in QuickBooks have been checked against your actual statements, so the numbers reflect reality.

Planning off of unreconciled books is like planning a road trip with a map that's missing half the roads. I wrote more about this in how messy bookkeeping can affect your taxes.

2. Last Year's Tax Returns

Bring your prior-year business return, and your personal return too if your business income flows through to it (common for sole proprietors, LLCs, and S corporations). Last year's return is the baseline. It shows how your income was taxed and often points to opportunities that were missed.

3. A Record of Estimated Tax Payments

List every federal and state estimated payment you've made this year, with the date and amount. Business owners usually don't have taxes withheld from a paycheck, so these payments are how you pay as you go. The IRS has a helpful overview of how estimated taxes work.

If you haven't made any, bring that fact too. It's one of the most important things to talk about.

4. Payroll Reports and How You've Paid Yourself

If you run payroll, bring your year-to-date payroll summary. Also bring a clear picture of what you've taken out of the business for yourself, whether that's a salary, owner draws, or distributions. How you pay yourself can affect your taxes more than many owners realize.

5. Your Contractor List

Make a list of everyone you've paid as an independent contractor this year, how much you paid them, and whether you have a current W-9 on file for each one.

This year there's a change worth knowing about. For payments made in 2026, the threshold for filing Form 1099-NEC is $2,000 per contractor, up from the long-standing $600. You can read the details in the IRS instructions for Forms 1099-MISC and 1099-NEC. Collecting W-9s now is much easier than chasing them in January.

6. Big Purchases You've Made or Are Considering

Equipment, vehicles, software, a new hire, a building improvement. Bring a list of what you've bought this year and what you're thinking about for the next six months.

The timing of a large purchase can change which tax year it affects. That said, I never recommend buying something just for the deduction. A deduction reduces your taxable income, but you still spent the money. The purchase should make sense for the business first.

7. Vehicle, Mileage, and Home Office Details

If you use a vehicle for business, bring your mileage log or whatever records you have. If you work from home, bring the square footage of your office space and of your home overall. These details are easy to forget and hard to reconstruct later.

8. Retirement and Health Insurance Information

Bring statements for any retirement accounts you contribute to, and details about how your health insurance is paid. Some of these may have deadlines tied to the calendar year, so it helps to talk about them while there's still time.

9. Changes in Your Business or Your Life

Taxes don't only respond to what happens in the business. Bring a quick list of anything that changed this year, such as:

• A new location, new service line, or a large new client

• A change in how your business is set up (for example, forming an LLC)

• Selling equipment or other business assets

• Marriage, divorce, a new baby, or a dependent leaving the house

• Plans to hire, expand, or slow down next year

10. Your Own List of Questions

This might be the most valuable item on the list. Write down anything you've wondered about this year, even if it feels small.

For example, if you're planning holiday gifts for clients, it's worth knowing that the IRS generally limits the deduction for business gifts to $25 per recipient per year (you can see the details in IRS Publication 463). Questions like that are exactly what a planning meeting is for.

What If Your Books Aren't Ready?

This is more common than you'd think, and it's not a reason to skip the meeting. It is a reason to get started now.

If your accounts haven't been reconciled in a while, or you're not sure your categories are right, the books need attention before any planning conversation will be reliable. That's where cleanup and catch-up bookkeeping comes in. Getting current in October leaves time to plan. Getting current in March only leaves time to file.

Once your numbers are solid, there's a lot more you can do. I covered a few options in 4 ways small business owners can reduce taxes before filing.

Get the Free Tax Planning Meeting Guide

To make this easier, I put together a free Tax Planning Meeting Guide. It walks you through organizing your 2026 numbers so far, noting the changes you expect in 2027, and deciding which questions and goals matter most to you. It also includes a quick check on whether your books are solid enough to plan from.

Walk into your meeting organized, and you'll walk out with decisions instead of guesses. Get your free Tax Planning Meeting Guide here.