Tax-Smart Retirement

10 Questions to Ask an Advisor About Roth Conversions, RMDs, and Brackets

The IRS just raised most retirement account limits for 2025, and the tax cuts from 2017 are set to expire after this year. If your advisor isn’t talking about both of those things right now, that’s a problem worth knowing about before it costs you.

Most financial advisors will tell you they “consider taxes.” Fewer than you’d think actually do anything about it. There’s a meaningful difference between an advisor who mentions your tax bracket once a year and one who builds a multi-year conversion strategy around it. The questions below are designed to help you find out which kind you have.

The timing matters more than usual right now. For 2025, the IRS increased the 401(k) contribution limit to $23,500, with a $7,500 catch-up for those 50 and older. Workers aged 60 to 63 get an even larger catch-up of $11,250 under SECURE 2.0, bringing their annual total to $34,750. These numbers matter because every pre-tax dollar you sock away today may be taxed tomorrow at rates you don’t control.

And there’s the other side of the clock: the Tax Cuts and Jobs Act of 2017 expires after December 31, 2025, unless Congress acts. If the provisions lapse, the 22% and 24% brackets widen back to 25% and 28%, the standard deduction drops by roughly half, and upper-income households face steeper marginal rates. That window between now and a potential rate reset is exactly where thoughtful Roth conversion planning lives.

These 10 questions to ask your advisor about Roth conversions, RMDs, and bracket management will tell you quickly whether you’re sitting across from someone who does real tax planning or someone who defers all of it to April.

Why Tax Strategy Belongs in the Advisor Conversation

Investment returns get a lot of attention. Tax drag gets far less. But for a pre-retiree with $1 million or more in tax-deferred accounts, the difference between a good tax strategy and no tax strategy can easily run into six figures over a 20-year retirement. That’s not a projection pulled from thin air. It’s basic math: a traditional IRA that grows to $2 million and gets liquidated in the 22% bracket generates roughly $440,000 in federal tax. The same balance in a Roth generates nothing.

The point isn’t that Roth conversions are always the answer. It’s that the question deserves a real analysis, not a shrug. Here’s how to find out if you’re getting one.

Questions About Roth Conversion Strategy

Roth conversions are the most powerful and most misunderstood tax lever available to pre-retirees. The following questions cut straight to whether your advisor has a systematic approach or is just improvising.

1. How do you determine whether I should convert, and how much?

This is the foundational question. A solid answer involves at least three variables: your current marginal rate, your projected rate in retirement, and the number of years a converted dollar has to grow tax-free. An advisor who simply says “it depends” or “Roth is usually better for younger clients” is not doing the analysis. You want to hear about specific bracket thresholds, the impact on your overall tax picture in the conversion year, and how they weigh the cost of paying taxes now against the benefit of avoiding them later.

2. Do you model the impact on Medicare premiums before recommending a conversion?

This one trips people up. Medicare Part B and Part D premiums are tied to your income two years prior through a system called IRMAA (Income-Related Monthly Adjustment Amount). In 2025, a married couple with modified adjusted gross income above $212,000 pays a Part B surcharge that starts at an extra $744 per person per year and climbs steeply from there. A Roth conversion that pushes you $20,000 over an IRMAA threshold can cost you more in Medicare surcharges than you might expect. Your advisor should be modeling this before recommending a conversion amount.

3. How does the TCJA sunset affect your conversion recommendations for me right now?

The current 22% and 24% brackets are scheduled to revert to 25% and 28% after 2025 unless Congress extends them. That makes the next several months potentially the lowest-rate window many pre-retirees will see for a long time. Your advisor should have a clear opinion on whether that changes their conversion strategy for you this year, and they should be able to explain why in plain language.

4. Will you show me a multi-year tax projection before we convert anything?

This is a process question as much as a strategy question. Some advisors use dedicated planning software like Holistiplan, Boldin, or similar tools to model how a conversion affects your tax liability in the year of conversion, in years when RMDs kick in, and in the year a surviving spouse files as a single taxpayer at higher rates. If your advisor can’t produce that kind of projection, or relies entirely on your CPA to run the numbers, the coordination between investment strategy and tax planning probably isn’t happening.

Questions About Required Minimum Distributions

RMDs start at age 73 under current law (rising to 75 in 2033 under SECURE 2.0). For anyone with significant assets in pre-tax accounts, they’re not just an inconvenience, they’re a tax bill that compounds in size every year you wait. Planning around them well before they start is the whole game.

5. At what point should we start planning around RMDs, and how do you calculate the future hit?

The answer should be: now, if you’re within 10 to 15 years of age 73. RMD amounts are calculated by dividing the prior year-end account balance by an IRS life expectancy factor. For a 73-year-old, that factor is 26.5, so a $1.5 million IRA produces a roughly $56,600 mandatory distribution in year one. A $3 million IRA produces $113,200. That’s ordinary income whether you need it or not. An advisor doing this right will run forward projections of your account balance at 73 and show you what those forced distributions look like against your Social Security income and any pension, so there are no surprises.

6. Do you use Qualified Charitable Distributions as part of an RMD strategy?

QCDs are one of the cleaner tax tools available once you turn 70½. They allow you to send up to $105,000 directly from an IRA to a qualified charity in 2025. That amount counts toward your RMD but never touches your adjusted gross income, which means it doesn’t affect your IRMAA calculation, doesn’t inflate your taxable Social Security, and reduces your state income tax in most states. If you give to charity and you’re over 70½ with an IRA, and your advisor has never mentioned QCDs, that’s a gap.

7. How do you coordinate RMDs with Social Security timing?

This is where planning gets genuinely complicated. If you delay Social Security to 70 to maximize your benefit, you may face a window between ages 65 and 70 where your income is low, making it ideal for Roth conversions. But delaying Social Security also means a larger check that, combined with RMDs after 73, could push you into a higher bracket. Up to 85% of Social Security benefits are taxable once combined income exceeds $44,000 for a married couple. Your advisor should be able to show how the Social Security start date interacts with your projected RMDs in a single tax picture.

Questions About Tax Bracket Management

Bracket management sounds technical but it’s a practical concept: systematically pulling income into lower brackets before you’re forced to take it in higher ones. Good advisors do this deliberately. Here’s how to tell.

8. Which bracket are you targeting for me, and where is the ceiling?

In 2025, the 22% bracket for a married couple filing jointly runs from roughly $96,951 to $206,700. The 24% bracket extends to $394,600. There’s a meaningful gap between those thresholds, and many pre-retirees could convert substantial IRA balances within the 24% bracket before things get expensive. A good advisor will know exactly where you sit relative to those ceilings and use that figure to size any conversions, capital gains harvesting, or other income events each year.

9. How do you handle capital gains harvesting alongside ordinary income?

Long-term capital gains are taxed at 0%, 15%, or 20% depending on your income level. The 0% rate applies to married couples with taxable income up to $96,700 in 2025. If you have appreciated securities in a taxable account, a year with lower ordinary income may be the right time to realize some of those gains at no federal tax cost. An advisor doing proactive planning will think about capital gains and Roth conversions in the same breath, because they compete for the same bracket space. If yours treats them as entirely separate conversations, ask why.

10. How does your strategy change if the TCJA brackets revert after 2025?

This is the planning question of the moment. If current rates expire, the 12% bracket shrinks, the 22% and 24% brackets become 25% and 28%, and several deductions change in ways that affect pre-retirees specifically. Your advisor doesn’t need to have a crystal ball. But they should have two plans: one that assumes an extension, and one that assumes a reversion. If they’ve thought about it seriously, they’ll have an opinion and a contingency.

All 10 Questions to Ask Your Advisor

Bring this list to your next meeting. The quality of the answers will tell you what you need to know.

1. How do you decide whether I should convert to a Roth, and how do you determine how much each year?
2. Do you model IRMAA surcharges before recommending a conversion amount, and do you show me the numbers?
3. How does the potential TCJA sunset change your Roth conversion advice for me in 2025?
4. Can you produce a multi-year tax projection that shows me the before and after of any conversion you recommend?
5. How much will my RMDs be at 73, 78, and 83 based on realistic growth assumptions, and how does that affect my tax bracket?
6. Am I a candidate for Qualified Charitable Distributions, and are we using them as part of the RMD strategy?
7. How does my Social Security start date interact with my projected RMDs in terms of total taxable income?
8. Which tax bracket ceiling are you targeting, and how do you size income events to stay inside it?
9. Are you looking at capital gains harvesting in the same planning conversation as Roth conversions?
10. Do you have a contingency plan ready if Congress lets the TCJA provisions expire at year-end?

2025 Federal Tax Bracket Reference (Married Filing Jointly)

Use these as a reference when your advisor discusses conversion amounts. The 22% and 24% brackets are the sweet spots most pre-retirees are working within.

Rate	2025 Income Range (MFJ)	Planning Use Case
10%	Up to $23,850	Rarely a conversion target; small balances only
12%	$23,851 – $96,950	Excellent for conversions; low-income years post-retirement
22%	$96,951 – $206,700	Primary conversion zone for most pre-retirees
24%	$206,701 – $394,600	Extended conversion zone before TCJA potential reversion
32%	$394,601 – $501,050	Generally avoid as a conversion target
35%	$501,051 – $751,600	Avoid for conversions; other strategies apply
37%	Over $751,600	Focus shifts to deduction strategies and estate planning

Source: IRS Rev. Proc. 2024-40. Standard deduction for MFJ in 2025: $30,000. Figures apply to taxable income after deductions.

Red Flags That Tax Planning Isn’t Happening

Some warning signs are obvious in hindsight but easy to miss in the moment. Watch for these.

• Your advisor has never mentioned the TCJA sunset or how it might affect your Roth conversion strategy, despite it being the single largest scheduled tax change in years.
• All tax questions are deferred to your CPA, and your advisor and CPA have never spoken to each other or coordinated on your plan.
• Roth conversion recommendations come without a projection showing the before-and-after on your tax liability or the impact on Social Security taxability.
• Your advisor has never brought up IRMAA, even though you’re in your mid-50s or older with a significant IRA balance.
• You’ve never been shown what your RMDs will look like at various ages based on a reasonable return assumption.
• The advisor recommends the same conversion amount every year regardless of changes to your income, account balances, or the tax code.
• Capital gains harvesting is never discussed, even in years when your income is lower than usual.

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Who Should Push Harder on These Questions

• Pre-retirees aged 55 to 70 with $500,000 or more in traditional IRAs or 401(k)s
• Anyone currently in the 22% or 24% bracket who expects to stay there or climb in retirement
• Couples where one spouse will predecease the other and face single-filer tax rates on RMDs
• Retirees who give regularly to charity and are over age 70½
• Anyone who has never seen a multi-year tax projection from their advisor
• People within five years of Medicare enrollment who don’t know their IRMAA threshold

Who May Have Less Urgency Right Now

• Those under 50 with most assets in Roth accounts already
• Retirees already deep into RMDs with limited pre-tax balances remaining
• Individuals in the 10% or 12% bracket with minimal projected income growth
• Those whose estates plan to leave traditional IRAs to charities, which pay no income tax on them
• Anyone with a pension that already fills their bracket in retirement, leaving little room to convert efficiently

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The Bottom Line

Tax planning isn’t a specialty that belongs only to CPAs. For pre-retirees, it’s one of the most direct levers an advisor can pull on your behalf. The difference between a thoughtful multi-year Roth conversion strategy and none at all can represent a significant portion of your retirement income.

The 10 questions above aren’t designed to catch your advisor off guard. They’re designed to have a real conversation. A good advisor will welcome them. One who struggles to answer specifically, who defers everything to your CPA, or who has never modeled an IRMAA surcharge is showing you something useful about the limits of what they do.

With the TCJA potentially expiring after 2025, the planning window is narrower than it’s been in years. If you’ve been meaning to revisit your tax strategy with an advisor, that conversation belongs in 2025, not 2026.

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This content is for informational purposes only and does not constitute financial, tax, or legal advice. Consult a qualified fiduciary advisor before making significant financial decisions.