The Post-Tax Season Window: 5 Ways RIAs Can Help Clients Pay Less Before Year-End
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I have seen this scenario play out more times than I can count: A client opens an IRS notice in September and calls his advisor in a panic. The notice shows a five-figure liability, the kind that could have been largely avoided.
Nobody did anything wrong during tax season. The return was accurate. The problem is what happened after tax season: nothing. No planning conversation, no review of the return for what it might reveal about next year, no discussion of what could still be fixed before December 31. By the time the notice arrives, the best options, including repositioning assets and maximizing tax-advantaged accounts, are already off the table.
As a CPA and the co-founder of a tax platform used by more than 7,200 CPAs and 150 CPA firms nationwide, I watch the calendar shape client behavior in a way that works against their interests. Tax season ends, everyone exhales, and the conversation about taxes goes quiet until the next return is due. That quiet period — roughly April through December — is exactly when the real tax reduction work should happen. Once December 31 passes, most of the year's levers are gone.
Here are five moves I encourage advisors to walk clients through now, while there is still time to act.
1. Reevaluate Asset Location & Tax-Loss Harvesting
The first is a midyear look at asset location, not just allocation. A client with a fresh capital gain, bonus, or business sale needs to know before autumn whether harvesting losses elsewhere in the portfolio, or shifting income-producing assets into tax-deferred accounts, still makes sense this year. Waiting until the return is filed the following spring often means paying tax on gains that a few trades in October would have offset.
2. Evaluate Entity Structures Early
The second is entity structure. Clients running a business or a side practice as a sole proprietor often do not find out that an S corporation would save real money until a CPA reviews the prior year's return in March — long after the cleanest window to elect S status for the current year has closed. Raising this in June, rather than February, gives the client an actual choice.
3. Audit Deductible Expense Tracking
The third is deductible expense tracking. This sounds basic, but many advisors assume their clients are keeping records that most are not. Home office costs, mileage, health insurance premiums for the self-employed, and retirement plan contributions all need documentation that is built up over the year, not reconstructed from memory in March. A short check-in now, asking what a client has actually tracked, catches gaps while there is still time to fill them.
4. Frame Everyday Financial Decisions as Tax Strategies
The fourth is turning ordinary financial activity into an intentional tax strategy. A client refinancing a mortgage, changing jobs, or receiving equity compensation is making decisions with tax consequences, whether or not anyone frames them that way. Asking about these events as they happen, rather than learning about them from a return, can allow the same transaction to save meaningfully more.
5. Maximize Tax-Advantaged Contributions Before Year-End
The fifth is taking a hard look at tax-advantaged accounts before the year closes. Health savings accounts and 401(k) contributions have hard year-end deadlines.
Backdoor Roth conversions do not share that exact cutoff, since the conversion itself can happen anytime, but leaving them until December compresses steps that are easier to manage earlier in the year.
Doing a five-minute review of current-year contributions against the annual limit in October, rather than making assumptions in April, is one of the simplest ways an advisor can put money back in a client's pocket.
Building a Year-Round Tax Planning Habit
None of these requires a client to do anything dramatic. They do require an advisor to have the conversation before the window closes, not after. Advisors who build a third-quarter planning call into their process, built around these five steps, tend to see fewer IRS notices land on their clients' desks.
Tax season teaches clients to think about taxes once a year. The advisors who win their trust are the ones who think about taxes all year round.
Richard Lavina, CPA, is co-founder and CEO of Taxfyle, an AI-powered tax preparation and planning platform used by more than 7,200 licensed CPAs and 150 CPA firms nationwide. He is a member of the IRS Electronic Tax Administration Advisory Committee (ETAAC). He began his career at PwC. Richard can be reached at [email protected].
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