6 Questions to Ask Before Filing Your Taxes
By Joe Dowdall, CFP®, RICP®, CRPC®, CCFC, TPCP®
You work hard all year, make the right decisions, and file your tax return on time—yet the result still feels disappointing. A larger tax bill than expected or a refund that simply confirms you overpaid can leave retirees wondering what they missed. Filing a tax return checks a box. Reviewing it through the lens of retirement planning can potentially reduce lifetime tax bills. For retirees and those nearing retirement, asking the right questions before your return is finalized can uncover opportunities that software and even experienced tax preparers may overlook.
These six questions to ask before filing are especially important once your income shifts from paychecks to Social Security, pensions, and investment withdrawals.
Question #1: Did I withhold too much or too little from my retirement income?
Retirees don’t always realize they’re overpaying (or underpaying) taxes throughout the year.
If you took distributions from an IRA or pension, it’s a good idea to review how much you had withheld. Too much? That’s money you didn’t need to send to the IRS just yet. Too little? You could be facing a penalty.
For example, a retiree who had 25% withheld from an IRA distribution might find that their actual effective tax rate is closer to 12–18%, depending on other income and deductions. In that case, the excess withholding would create a refund that could have stayed invested or been used for living expenses throughout the year.
On the other hand, someone who took distributions with little or no withholding might be surprised by a tax bill at filing time, simply because the withholding wasn’t adjusted during the year.
Even if your tax software doesn’t flag it, a quick projection from your financial advisor can help you fine-tune your withholding for the year ahead.
Question #2: Am I eligible to use a qualified charitable distribution (QCD)?
If you’re 70½ or older and give to charity, a QCD might let you donate directly from your IRA while reducing your taxable income.
This is especially helpful if you’re taking required minimum distributions (RMDs) and don’t itemize your deductions. But if your return doesn’t show a QCD correctly—or if no one mentioned it at all—you could be missing out on a simple tax benefit.
Question #3: Should I have itemized deductions this year?
With today’s higher standard deduction, fewer retirees itemize. But if you’re close to the threshold, it may make sense to bunch charitable donations or medical expenses into one year.
Ask your tax preparer to show you both scenarios. Sometimes a small timing change can create a bigger deduction, especially if you’re facing large medical bills or property tax payments.
Question #4: Did I convert any IRA assets to a Roth, and was it reported correctly?
If you complete a Roth conversion during 2025, it’s reported as taxable income on your 2025 tax return.
For example, a retiree who converts $50,000 from a traditional IRA to a Roth in 2025 should expect that $50,000 to appear as taxable income on their 2025 return.
If you didn’t convert previously, this is a good time to talk with your advisor about whether a conversion makes sense in the year ahead, especially before tax rates potentially shift again down the road.
Question #5: Where does my income land relative to Medicare thresholds?
Your 2025 tax return determines what you’ll pay for Medicare in 2027. If your income was larger than usual, even by a few thousand dollars, you could be bumped into a higher IRMAA bracket.
It’s worth reviewing where you landed and whether you might want to appeal your premium if your income has since dropped.
Question #6: Has my financial advisor reviewed this return?
This one’s often missed. Your financial advisor should have a copy of your return, not just your CPA.
Here’s why: income, deductions, withholdings, IRMAA brackets, and RMDs all tie directly into your financial plan. If your advisor doesn’t see your return, they can’t help you make smart decisions for the year ahead.
A collaborative advisory relationship means your advisor and tax preparer are aligned. That coordination helps prevent missed opportunities and supports smarter tax planning beyond filing season.
Review the Key Questions to Ask Before Filing Your Return
If you haven’t walked through your return with an advisor, now is a good time. Thoughtful questions to ask before filing can uncover planning opportunities, identify risks, and support a smoother year ahead.
At Worth Asset Management, I take a personalized, hands-on approach. We sit down together, review your return line by line, and connect it directly to your retirement plan.
If you’d like a second set of eyes before your return is finalized, schedule a review. We’ll walk through it together so you can move forward with a plan that supports your retirement goals and helps reduce lifetime tax bills.
Get started today with a 15-minute introductory call. I can be reached at (469) 423-1989 or by email at joe@worthassetmgmt.com.
About Joe
Joe Dowdall is a CERTIFIED FINANCIAL PLANNER® professional at Worth Asset Management, a financial services company in Dallas, TX, that provides a wide range of wealth management services. With over 20 years in the financial services industry, Joe is a fiduciary who creates tax-focused financial plans for people nearing or in retirement—to help them build and safeguard their wealth through all life stages. He desires to offer clients the best financial planning experience while developing a friendship based on mutual respect. Joe’s philosophy as a financial planner is rooted in his experience as a teacher, where he learned the importance of explaining complicated concepts in understandable terms. He’s passionate about working with a select group of clients to help them achieve their financial goals with confidence and clarity.
Joe has an education degree from the State University of New York and an MBA in finance from Saint Joseph’s University. In addition, he has obtained the CERTIFIED FINANCIAL PLANNER®, Retirement Income Certified Professional®, Chartered Retirement Planning Counselor℠, Certified College Financial Consultant (CCFC), and Tax Planning Certified Professional® (TPCP®) designations. Joe resides in Frisco, TX, with his wife, Leila, and their two daughters. During his free time, he enjoys traveling with family, exercising, and hiking the national parks. To learn more about Joe, connect with him on LinkedIn.
The information provided is for educational and informational purposes only. Please consult with a qualified financial and tax professional for advice tailored to your specific financial situation.