Tax Preparation Checklist: Five Questions to Ask Before You File
By Joe Cilley, CFP® | Vice President of Financial Planning, Partner, Merit Financial Advisors
Tax season naturally pulls us into the past. We look at last year’s income, expenses, and forms. But the most productive tax conversations don’t stop there. They use what just happened to shape what comes next.
When I sit down with clients, I like to structure the conversation around their “tax story.” It’s a simple way to turn a stack of documents into a clear picture. Before you meet with your CPA and advisor, asking these five questions can help you feel prepared well beyond this year’s return.
1. Who Paid You This Year?
Most tax returns today are filed electronically, which means income has a way of surfacing even if it doesn’t show up neatly in your mailbox. That’s why this question goes beyond a W-2 or a retirement statement.
Think about every place money came from over the year banks paying interest, brokerage accounts generating dividends or sales, rental properties, contract work, or cash and digital payments for side projects and tips.
If you drove for work, invoiced clients, or were paid through an app, those records often live outside the usual year-end forms. Pulling them together yourself even in a simple spreadsheet or a folder labeled “2025 Income” can save you from chasing down details later or having to amend a return after the fact.
2. What Changed in Your Life?
Taxes follow life, not the other way around. Marriage, divorce, new dependents, or a move all shift how your return looks. One detail that often gets overlooked is documentation for dependents. Recent changes to the child tax credit now require valid Social Security numbers in order to qualify for enhanced benefits.
Home purchases and major renovations matter for a different reason. They establish your cost basis, which determines how much of a future home sale may be taxable. Most people can’t remember what they paid for their home years later. Writing it down now and saving it with your tax records is a small step that can make a big difference later.
3. What Happened with Your Health and Insurance?
Every year, millions end up amending their tax returns, mostly because one last form shows up after they’ve already filed. Health and insurance forms are often the ones that arrive just late enough to cause trouble.
Marketplace coverage forms, employer insurance statements, and HSA records don’t always arrive by February. While many households take the standard deduction, high medical expenses can still make detailed records relevant.
This is where patience pays off. Filing before everything arrives is one of the most common reasons people end up amending their returns and paying for additional time from their accountant.
4. What Did You Pay for Your Kids?
Education and care expenses can open the door to meaningful credits, but only if the paperwork is complete. This is one of those areas where a small missing detail can quietly undo a good intention.
That includes college tuition forms, childcare provider information, and records of what you actually paid. Adoption expenses also matter more now, since recent changes allow a portion of the adoption credit to be refundable starting in 2025. This part of the checklist is less about forms and more about having the right names, numbers, and totals in one place.
5. How Much Did You Invest, Save, or Give?
This is where tax preparation starts to blend into tax planning. IRA and HSA contributions, charitable giving, and investment activity don’t just affect what you owe; they influence how flexible your plan can be going forward.
One form that often causes unnecessary anxiety is the IRA Form 5498. It typically arrives after tax season, as contributions can be made up to the filing deadline. The important part is knowing what you contributed, reporting it accurately, and filing the document when it eventually arrives.
Looking ahead, charitable recordkeeping becomes even more relevant in 2026, when a new deduction will allow married couples to deduct up to $2,000 in donations, even if they aren’t itemized.
A Final Note Before You File
One of the most common mistakes I see every year is filing too early and missing late-arriving brokerage or employer statements. Another is not keeping good records for things like tips, overtime, or major purchases that may matter years down the line.
Your CPA and advisor play different roles in this process. Your CPA reviews last year to ensure it was reported correctly. Your advisor looks ahead to help you make better financial decisions moving forward. When those two perspectives connect, the checklist becomes more than a formality; it becomes a planning tool.
If you’d like help connecting your tax strategy with your broader financial plan, Merit Financial Advisors offers complimentary consultations to help bring clarity and structure to your financial life. Let’s start the conversation.