Your RSUs Vested in June. Your Preparer Won't Call Until March.

She is a senior director of product at a company you have heard of. Eight years in. Her Q2 RSUs just vested, about $150,000 in shares hitting her brokerage account in late June. Her company withheld 22% for federal taxes, same as it always has. Same as it always will, unless she changes something.

She knows the withholding is short. She ran a rough calculation over the weekend and came up with a number that made her close the spreadsheet. So she emailed her preparer. The reply came back the next day, polite and predictable: "We will sort it out on the return."

That sentence is the whole problem in miniature. Because by the time her preparer opens her file in February, every decision that could have changed the outcome will already be behind her.

The June Vesting

Here is how a routine Q2 vest looks for a senior tech executive with a concentrated position. The shares appear in the brokerage account. The company withholds 22% for federal taxes, plus state withholding if she is in California. The rest lands as shares she now owns. At her income level -- a director-level base salary plus bonus, the RSUs on top -- her actual federal rate is higher than 22%. How much higher depends on the full picture: her total income for the year, her filing status, how much she has already earned in the first half, whether she sold any shares from previous grants.

The gap between what was withheld and what she will actually owe is the quiet story of RSU tax planning. And in August, six weeks after the vest, that gap is still fixable. By February, it is just a number on a form.

What the Preparer Sees

To be clear about how most firms work: a once-a-year preparer collects your documents in late February or March. Your W-2, your brokerage statements, your prior year return. They plug the numbers into their software. They run the calculation. They file the return.

That is a perfectly good process for someone whose taxes are straightforward. But for a tech executive holding a seven-figure concentrated stock position with quarterly RSU vestings, it leaves a lot on the table. Because the preparer is working in the past tense. The year is over. The vesting happened. The withholding happened. The sales happened. The return is a report of what already occurred, not a design for what could have.

The preparer has no reason to call you in August. Your file is not open until February. The gap between those two points -- nine months -- is where all the leverage lives.

What a Strategist Sees in August

A year-round strategist looks at the same June vesting and sees a set of decisions with deadlines attached. August is the last practical window before the end of the year to act on most of them. This is what year-round tax planning looks like for someone with a concentrated position: you model the full picture, then adjust before the window closes.

The first decision is the simplest: adjusting estimated tax payments before the September 15 deadline. If the 22% withholding left a gap for the first two quarters, the Q3 payment is the chance to close it. A strategist models the full-year picture in mid-year -- total income, expected vestings, capital gains, deductions -- and sets the Q3 payment to cover the shortfall. A preparer who does not look at your file until March has already missed three quarterly payment deadlines.

The second decision is about the shares themselves. Holding shares after they vest means you own the stock outright. Selling some creates a tax event. Selling none means the position grows. The question is not whether one choice is right. The question is which one fits the full-year picture you want. August is when you can still choose.

The third decision is about the longer arc. A 10b5-1 plan for systematic sales (more on how a 10b5-1 plan decides the tax bill), a donor-advised fund for charitable giving with appreciated shares, a plan to diversify a single-stock position across multiple tax years (a full walkthrough here). These are not things a preparer brings up in March, because by March there is nothing to plan. Filing an extension extends the deadline. It does not extend the options.

The Nine-Month Gap That Decides the Outcome

Between June of one year and March of the next, a lot of things happen that matter to your taxes. Your RSUs vest again in September and December. The stock price moves. Your income crosses into a higher bracket. You make decisions about what to sell and when. And none of it gets reviewed by the person who will eventually file your return.

The nine-month gap is a feature of how most firms operate, not a flaw in your personal approach. They batch work by filing season. They staff for volume in March and April, not for mid-year reviews. That model works for millions of taxpayers. But for someone whose single largest asset is tied to one stock and whose tax bill depends on decisions made throughout the year, the gap is expensive in ways that do not show up on a preparer's invoice.

Same Compensation, Different Design

Consider two executives with the same role, same company, same RSU grants. Both have their shares vest in June at $150,000. Both are in the same tax bracket. Neither changed anything about their withholding.

Executive A emails her preparer in June. Her preparer says they will sort it on the return. In February she sends over her documents. In March her preparer files her return and she owes, because the gap between 22% withholding and her actual rate was larger than she expected. She writes the check. The preparer closes her file. Next year, same thing.

Executive B works with a tax strategist. In late July, the strategist models her full-year income: salary, bonus, four quarterly RSU vestings, some shares she plans to sell from an earlier grant. The strategist identifies the gap in withholding, adjusts her Q3 estimated tax payment accordingly, and sets up a 10b5-1 plan to sell a portion of each future vest systematically. In November, they review again. By the time her return is filed in April, there are no surprises. She knew the number, chose the timing, and designed the outcome instead of reacting to it.

Both paid the legal tax they owed. One chose how. The other found out after it was done.

The Question a Preparer Never Asks

The difference between a preparer and a strategist comes down to one question. A preparer asks: "What were your taxes this year?" A strategist asks: "What do you want your tax outcome to look like?"

One question is retrospective. The other is design-oriented. And a design-oriented approach requires someone who knows your full picture before the year closes, not after.

If your Q2 RSUs vested two months ago, and you are reading this in August, there is still time to look at the full picture before the next estimated tax deadline. The question is whether anyone is looking at it now.

Book a free 15-minute discovery call with Roadmap Tax at (619) 280-2700 or info@RoadmapTax.com. The paid strategy session is where you get a real deliverable with specific insights on your situation. The free call is the first step, not the whole thing.

FAQ

What is the difference between a tax preparer and a tax strategist?

A tax preparer collects your documents after the year ends and files a return reporting what happened. A tax strategist works with you during the year to model outcomes and make decisions before the tax year closes, designing the result rather than reporting it.

How much should I adjust my estimated tax after an RSU vest?

The adjustment depends on your full-year income, the size of the vest, and the gap between the 22% default withholding and your actual tax bracket. A mid-year review can model this and set your Q3 payment to cover the shortfall before the September 15 deadline.

When is the best time to review my RSU tax situation during the year?

July and August are the most valuable windows, because you have half a year of data and enough time left to adjust estimated payments and make strategic decisions before the year closes. A second review in late November catches any changes from Q3 vesting.

Can my CPA set up a 10b5-1 plan for me?

Most preparers do not design or coordinate 10b5-1 plans, because those are forward-looking trading arrangements that intersect with tax strategy, not returns preparation. A tax strategist who works with equity compensation is more likely to coordinate this with your company's legal team.

Does California tax my RSUs differently depending on when I sell?

California taxes RSU income based on where you lived when the shares vested, not when you sell. The sale itself is a separate capital gains event sourced to your state of residence at the time of sale. A strategist tracks both layers; a preparer usually reports them as received.