Year-End Tax Checklist: What to Ask Your CPA Before Dec 31st

The final quarter of the year is a critical time for business owners. While you’re focused on hitting annual goals and planning for the holidays, it’s easy to let strategic tax planning slip through the cracks. But a proactive meeting with your CPA before December 31 can be one of the most profitable moves you make all year. It’s your chance to not just wrap up the current year cleanly, but to strategically position your business for greater success and efficiency in the next.

As a business owner wearing multiple hats, you know the value of your time. You’ve worked hard to build your company beyond the million-dollar mark, but now you’re looking for ways to scale without adding more hours to your already long week. Effective tax strategy is a key lever for achieving that. This meeting is about more than compliance; it’s about uncovering opportunities to optimize cash flow, reduce your tax burden, and make informed decisions that support your long-term growth.

This checklist will guide you through preparing for that crucial year-end conversation with your CPA. We’ll cover the essential documents you need to gather and the key questions you should be asking to ensure you’re not leaving money on the table.

Why a Year-End Meeting with Your CPA Matters
For many successful business owners, the relationship with their CPA is often reactive—focused on filing taxes once the year has already closed. Shifting this to a proactive, strategic partnership is a hallmark of a business that runs efficiently without its owner chained to the desk.

A year-end review allows you and your CPA to analyze your financial standing while there’s still time to make adjustments. It’s an opportunity to look at the big picture—where your business has been and where it’s going—and align your tax strategy with your growth objectives. You can identify potential issues before they become costly problems and implement strategies that will pay dividends for years to come. This is how you move from simply running a business to intelligently guiding its financial future.

As one of our clients, the owner of a thriving logistics company, shared: “Before we started year-end planning with Cobb CPA, tax season was a stressful scramble. Now, our December meeting is one of our most important strategic sessions. We’ve been able to reinvest thousands back into the business, all because we asked the right questions at the right time. It gave me the confidence to delegate more and focus on expansion.”

Key Documents to Gather for Your Meeting
To make your meeting as productive as possible, you need to arrive prepared. Having your financial documents organized allows your CPA to quickly assess your situation and provide targeted advice. This preparation also empowers you to have a more meaningful conversation, moving beyond simple data review to strategic planning.

Gather the following key reports:

• • Profit & Loss (P&L) Statement: This is the most straightforward report of your profitability. Your CPA will use it to see your revenues and expenses, providing a baseline for tax liability estimates.
  • Balance Sheet: This snapshot of your assets, liabilities, and equity helps your CPA understand the overall financial health of your business. It’s essential for discussions about debt, assets, and potential structural changes.
  • Statement of Cash Flows: Profit doesn’t always equal cash in the bank. This statement shows how cash is moving in and out of your business, which is critical for planning major expenses or investments.
  • Depreciation Schedules: If you’ve invested in significant assets like equipment, vehicles, or property, your depreciation schedule is crucial. Your CPA can identify opportunities to accelerate depreciation and maximize your deductions.
  • Receipts for Major Purchases: Have documentation ready for any large or unusual expenses made during the year. This includes equipment, software, professional services, or significant travel costs.

7 Questions to Ask Your CPA Before Year-End
With your documents in hand, you’re ready to dig into strategy. Your goal is to uncover every opportunity available. Don’t leave money on the table—these seven checks are often overlooked but can have a major impact on your bottom line.

1. Are There Any Unclaimed Deductions I Can Still Take?
As you review your P&L, ask your CPA to help you spot any missed opportunities. Were there home office expenses, vehicle mileage, or professional development costs you forgot to track? Sometimes, expenses that seem minor can add up to significant deductions. Your CPA can also advise on whether it makes sense to make certain purchases before the year closes.
2. Should I Prepay Expenses to Shift Deductions?
One common year-end strategy is to prepay expenses for the upcoming year to accelerate your deductions into the current tax year. This could include items like rent for January, insurance premiums, or annual software subscriptions. Ask your CPA if this strategy, known as the 12-month rule, makes sense for your business based on your current and projected income.
3. Should I Delay Receiving Income?
If your cash flow allows, you might consider delaying the invoicing for a large project until January. This defers the income—and the tax liability on it—into the next tax year. This can be a powerful tool, especially if you expect to be in a lower tax bracket next year or need to manage your income thresholds for certain tax credits or deductions.
4. Is It Time to Re-evaluate My Business Entity?
As your business grows past the million-dollar mark, the entity structure that served you in the beginning may no longer be the most tax-efficient. Ask your CPA to analyze whether a change of entity, such as making an S-Corp election for 2026, could save you significant money on self-employment taxes. This is a complex decision with long-term implications, making expert advice essential.
5. Do I Have Any Carryforwards I Can Use?
If your business experienced a net operating loss (NOL) in a prior year, you may be able to “carry forward” that loss to offset income in the current year. The same applies to certain tax credits. These are easily missed but can provide a substantial tax benefit. Your CPA can review your past returns to ensure you’re taking full advantage of any available carryforwards.
6. Are My Retirement Contributions Maximized?
For many business owners, their company is their primary vehicle for retirement savings. A year-end review is the perfect time to ensure you are maximizing your contributions to plans like a SEP IRA, SIMPLE IRA, or Solo 401(k). Your CPA can help you determine the maximum allowable contribution based on your income and advise on the best plan for your goals.
7. What Do My Financials Tell You About My Operational Efficiency?
This question moves beyond taxes and into strategic advisory. Ask your CPA for their perspective on your financial health. Are there areas where your expenses seem high? Are your margins in line with industry benchmarks? An experienced CPA can offer insights that help you streamline operations, improve profitability, and build a more resilient business that can thrive without your constant oversight.

Your Next Step: Put This Checklist into Action
A year-end tax planning session is your opportunity to work on your business, not just in it. By preparing your documents and asking these strategic questions, you transform a routine meeting into a powerful tool for growth. You’ll not only optimize your tax position for this year but also lay the groundwork for a more automated, efficient, and profitable year ahead.

At Cobb CPA, our role is to serve as your expert guide. We help you connect the dots between your tax strategy and your larger business ambitions.

Ready to get started? We’ll walk through it live and help you build a concrete plan for year-end success.