How to Choose a Financial Advisor for Roth Conversion Strategy

If you're a pre-retiree with a $1M+ traditional IRA trying to decide how much to convert, when to convert, and how to avoid IRMAA surcharges — you need a specialist. Not your existing brokerage rep who mentions Roth conversions as an afterthought, and not a generalist CFP who runs a one-year snapshot. Multi-year Roth conversion planning is a distinct skill that sits at the intersection of tax law, Social Security timing, Medicare planning, and investment sequencing.

Here's how to find an advisor who actually does this well — and the questions that separate specialists from generalists.

Why Roth conversion requires a specialist — not any advisor

A typical financial advisor manages a portfolio. A Roth conversion specialist does something different: they run multi-year tax projections that model your federal bracket, IRMAA exposure, Social Security taxation, capital gains interaction, and state taxes — simultaneously — and optimize the conversion amount across 10+ years to minimize lifetime taxes, not just this year's bill.

These are different skills. Here's why the generalist approach leaves money on the table:

• IRMAA is a two-year-delayed trap. A conversion in 2026 doesn't affect your 2026 Medicare premiums — it affects your 2028 premiums (when SSA looks back at 2026 MAGI). A generalist running a single-year model won't see this coming. For a couple, one over-large conversion can cost $2,296–$13,872 per year in Medicare surcharges for two years, erasing much of the bracket savings.
• Social Security taxation multiplies the effective rate. In the phase-in zone, each $1 of conversion income makes $0.85 more of Social Security taxable — raising the effective marginal rate from 22% to as high as 40.7%. An advisor running a simple 22% bracket calculation is missing a 18-point difference in true cost.
• The pro-rata rule can blow up a plan. If you have after-tax contributions mixed into traditional IRAs, the taxable fraction isn't the whole conversion — it's your total IRA pre-tax balance divided by total IRA balance. Many advisors don't catch this until tax time.
• The right answer changes every year. Tax brackets adjust, IRMAA tiers shift, Social Security timing changes the calculation. A one-time analysis done in year 1 isn't a conversion plan — it's a snapshot that goes stale.

Fee structure: why fee-only matters here

Financial advisors charge in three basic ways:

For Roth conversion planning specifically, the fee conflict matters because conversions don't generate product commissions. A commission-based advisor has a structural disincentive to prioritize a conversion strategy — there's nothing to sell. A fee-only advisor's incentive is to do the analysis right, since their fee depends on your continued satisfaction, not a one-time transaction.

The NAPFA (National Association of Personal Financial Advisors) and Garrett Planning Network maintain directories of fee-only advisors. All advisors in the Roth Conversion Advisor Match network are fee-only fiduciaries.

Credentials to look for

Credentials alone don't make someone a Roth conversion specialist — but they're a filter. These are the relevant designations:

• CFP (Certified Financial Planner) — The standard foundation credential. Broad financial planning education. Necessary but not sufficient; roughly 95,000 CFPs in the US, most are generalists.
• CPA-PFS (Personal Financial Specialist) — A CPA who has added the PFS financial planning credential. Usually the strongest combination for tax-heavy planning, since the CPA background gives deep tax literacy. An ideal combination for Roth conversion work.
• RICP (Retirement Income Certified Professional) — American College of Financial Services credential focused specifically on retirement income distribution, Social Security, Medicare, and withdrawal sequencing. Highly relevant for conversion planning.
• EA (Enrolled Agent) — IRS credential for tax practitioners. Not a financial planning credential, but signals tax depth. An EA who also has financial planning training is worth noting.

No single credential guarantees specialization. A CFP who has done 200 Roth conversion plans is more valuable than a CPA-PFS who has done two. The diagnostic questions below matter more than the letters.

10 diagnostic questions — and what the right answers sound like

Use these in your first 30-minute conversation or meeting. You don't need to know the right answers beforehand — you're listening for depth, specificity, and whether they can speak concretely without referencing materials.

1. "Walk me through how you model the Roth conversion decision."

What you want to hear: Multi-year projections, not single-year snapshots. Specifically: tax bracket filling year by year, IRMAA tier checks, Social Security taxation interaction, RMD projections for what happens if you don't convert, and comparison of lifetime tax under multiple conversion schedules. They should mention software (Holistiplan, RightCapital, eMoney, or similar). A hand-wave about "running the numbers" with no specifics is a red flag.

2. "How do you handle IRMAA in a conversion plan?"

What you want to hear: The two-year lookback — a 2026 conversion affects 2028 Medicare premiums. They should be able to name the 2026 Tier 1 thresholds ($109K single / $218K married filing jointly) without looking them up. Bonus: they mention the distinction between IRMAA as a cliff (not a phase-in) and know the per-person vs. per-couple math.

3. "What's the bracket ceiling for a couple doing conversions in 2026 before hitting the 24% bracket?"

What you want to hear: $201,050 of taxable income for MFJ filers in 2026 is the 22%/24% boundary. Below that, you're in the 22% bracket. An advisor who does this regularly should know this number cold — or pull it up immediately from software.

4. "When do RMDs begin for someone born in 1963?"

What you want to hear: Age 75, per SECURE 2.0 § 107. The law changed the RMD age from 70½ → 72 → 73 (for those born 1951–1959) → 75 (for those born 1960 or later). A specialist knows this distinction; a generalist may still be quoting 72 or 73 for everyone.

5. "How do you handle the pro-rata rule if I have both pre-tax and after-tax IRA contributions?"

What you want to hear: The pro-rata rule (IRC § 408(d)(2)) treats all your traditional IRAs as one pool — so if you have $1M pre-tax and $50K after-tax (basis), 95% of each conversion is taxable. They should mention the 401(k) rollover workaround: roll pre-tax IRA money into a current employer's 401(k), leaving only basis in the IRA, so a subsequent conversion is mostly tax-free. Form 8606 basis tracking should come up.

6. "How do Roth conversions interact with Social Security taxation?"

What you want to hear: In the combined income phase-in zone, each $1 of conversion adds $1 of income but also makes $0.85 more of Social Security benefits taxable. In the 22% bracket inside the phase-in zone, the effective marginal rate on a Roth conversion is 22% + (0.85 × 22%) ≈ 40.7%. They should know the IRC § 86 combined income thresholds ($32K–$44K MFJ for the 85% zone).

7. "If I'm selling appreciated stock in the same year as a conversion, does that affect anything?"

What you want to hear: Yes — conversions push up taxable income and can shift long-term capital gains from the 0% bracket into the 15% bracket. The 0% LTCG threshold for MFJ in 2026 is $96,700; if a conversion moves your taxable income above that, gains that would have been tax-free get taxed at 15%. Also NIIT (3.8%) kicks in above $250K MAGI. A specialist coordinates gain harvesting and conversions deliberately, not independently.

8. "What does your ongoing conversion planning engagement look like — is this a one-time analysis or annual?"

What you want to hear: Annual revisits, because the inputs change: tax law adjustments, IRMAA tier shifts, investment account balances, Social Security claiming decisions, one-time income events. A good advisor rebuilds the projection each year, not once at retirement. An advisor who offers only a one-time plan is selling you a snapshot, not a strategy.

9. "What happens to my Roth accounts when I die, and how does that affect the conversion math?"

What you want to hear: Inherited Roth IRAs are not subject to annual RMDs during the 10-year distribution period (T.D. 10001 applies to inherited traditional IRAs, not Roth). Heirs can let the Roth grow for 10 years and withdraw everything in year 10, tax-free. Inherited traditional IRAs under the SECURE Act's 10-year rule require annual distributions when the decedent was past their Required Beginning Date — and those RMDs hit heirs at their marginal rate (often 32–37%). The math: converting at 22% today can save heirs paying 32–37% on the same dollars in forced distributions.

10. "Can you give me a specific example of a Roth conversion plan you've done for a client with similar assets?"

What you want to hear: A concrete example — ages, IRA balance, annual conversion amounts, how they handled IRMAA, what the projected lifetime savings were. Not a hypothetical or a generic description of the process. If they can walk you through a real (anonymized) client scenario with specific numbers, they've done this before. If they pivot to process descriptions without numbers, push for specifics.

Red flags to avoid

• They recommend an insurance product as part of the conversion plan. Annuities and life insurance can be legitimate tools in retirement planning — but if they come up in the first meeting about Roth conversions, ask why. A commission-based product recommendation embedded in a "conversion strategy" is a red flag.
• They can't explain the IRMAA lookback without reading materials. This is fundamental. An advisor who doesn't know the two-year lookback without prompting hasn't been doing conversion planning.
• They propose the maximum possible conversion each year. "Convert as much as you can before the bracket ends" is not a strategy — it ignores IRMAA, SS taxation multipliers, capital gains interactions, and state tax timing. A real specialist optimizes across all these layers, which usually means a more nuanced amount than "fill the bracket."
• They've never worked with clients in the pre-RMD golden window. Roth conversion specialists have built their practice around this niche. If most of their clients are 35-year-old tech workers in accumulation phase, they're a generalist who can talk about conversions, not someone who runs multi-year conversion plans for 60-75 year-olds every week.
• They use the phrase "it depends" as the whole answer to every question. Everything in financial planning "depends" on something — but a specialist should be able to follow that with specific criteria and a concrete example. Pure equivocation without substance signals they haven't modeled this enough times to have real intuition.

Typical fee structures for Roth conversion planning

Expect one of these arrangements from a fee-only specialist:

• AUM-based (0.5–1.0%): Annual fee on assets managed. Common when the advisor is also managing your investments. A $2M IRA generates $10,000–$20,000/year in fees — reasonable for ongoing management + annual conversion plan.
• Flat retainer ($3,000–$10,000/year): Fixed annual fee for planning services, regardless of asset size. Common for planning-focused advisors who don't manage investments. Tends to be cost-effective for larger portfolios.
• Hourly ($250–$500/hour): Per-hour for project-based work. Can work for a one-time conversion analysis, but less ideal for ongoing annual planning where the model needs to be rebuilt each year.
• Project fee ($2,500–$7,500): One-time fee for a comprehensive conversion analysis and multi-year schedule. Appropriate if you want the plan built by a specialist but will execute and update it yourself or with your existing advisor.

Questions to ask about fit — not just credentials

Beyond technical depth, a few fit questions matter:

• "What percentage of your current clients are in the pre-RMD window doing active conversion planning?" — More than 20% suggests real specialization.
• "Do you work with CPAs to implement the plan, or are you handling the tax projection yourself?" — Both can work, but coordination matters. If they're not a CPA, they should have a relationship with one.
• "How do you communicate with clients during the year about conversion opportunities?" — A proactive advisor should be in touch in November/December when income for the year is known and there's still time to act.

Related guides

• The Roth Conversion Golden Window: The 10-15 Years That Matter Most
• IRMAA and Roth Conversions: Complete Strategy Guide
• Roth Conversion Schedule: Lump Sum vs. Multi-Year Plan
• 7 Roth Conversion Mistakes to Avoid
• Is Roth Conversion Worth It? A Decision Framework

1. IRS Rev. Proc. 2025-32 — 2026 tax bracket thresholds including 22%/24% boundary at $201,050 MFJ taxable income and LTCG 0% threshold at $96,700 MFJ.
2. CMS 2026 Medicare IRMAA fact sheet — 2026 Part B/D surcharge tiers, Tier 1 threshold $109,000 single / $218,000 MFJ based on 2024 MAGI. cms.gov
3. SECURE 2.0 Act of 2022, § 107 — RMD age 73 for individuals born 1951–1959; age 75 for individuals born 1960 or later.
4. IRS T.D. 10001 (July 2024) — Finalized annual RMD rules for inherited traditional IRAs when decedent was past Required Beginning Date; inherited Roth IRAs not subject to annual distribution requirement under 10-year rule.

Tax values verified as of May 2026. Tax law changes frequently — confirm current-year values with a qualified tax professional before acting.

Roth Conversion Advisor Match is a referral service, not a licensed advisory firm. We may receive compensation from professionals in our network. Content is for informational purposes only and does not constitute financial, tax, or legal advice.