How to Evaluate a Firm's Social Security and Tax Strategy

The clearest test of a firm's Social Security and tax work is what it produces on paper: a year by year projection that shows claiming ages, withdrawal sources and taxable income in the same view, and that gets updated when the rules or your circumstances change.

Why these two are evaluated together

Social Security timing and withdrawal sequencing are usually presented as separate topics. In practice each one changes the answer to the other. Delaying a claim raises the eventual monthly benefit, but the gap years have to be funded from somewhere, and where that money comes from determines the tax bill. Filling those years from a tax-deferred account raises taxable income. Filling them from a Roth account generally does not. The same dollar of spending has a different tax consequence depending on which account it leaves.

A firm that handles these separately will give you two reasonable-sounding answers that do not fit together. A firm that handles them together will show you both on the same page. That is the difference you are testing for, and it shows up quickly when you ask to see the output.

What competent Social Security modeling looks like

For a single person the claiming question is comparatively simple. For a married couple it is not, because each spouse has a claiming age, the benefits interact, and one of the two will eventually be a survivor living on a single benefit.

• Both spouses, modeled together. Claiming ages should be evaluated as a pair rather than one at a time, because the combination is what determines household income across both lifetimes.
• Survivor consequences stated explicitly. When one spouse dies, the household moves from two benefits to one. The higher earner's claiming age is what sets the floor the survivor eventually lives on, which is why that decision usually carries the most weight.
• Longevity treated as a range. A single breakeven age is a starting point, not an answer. The useful version shows how the comparison shifts across different assumptions about how long each spouse lives.
• Rule changes reflected. The Social Security Fairness Act, signed in January 2025, repealed the Windfall Elimination Provision and the Government Pension Offset. If you or your spouse have earnings from work not covered by Social Security, ask how that repeal affects your projection, and confirm your own figures with the Social Security Administration.

Benefit taxation belongs in the same conversation. The portion of your benefit that is federally taxable depends on provisional income, which combines half your Social Security benefits with your other income and any tax-exempt interest. Above certain federal thresholds, part of the benefit becomes taxable. Those thresholds are set by federal rule, so confirm current figures with the Social Security Administration or your CPA rather than relying on a number in an article. Our Social Security planning work starts with why you are making the decision before it addresses when.

What competent withdrawal sequencing looks like

The familiar rule is to spend taxable accounts first, then tax-deferred, then Roth. It is a reasonable default and a poor plan, because it ignores what happens in the years after the one you are currently in.

The more deliberate approach blends withdrawals across account types each year, drawing enough from tax-deferred accounts to use up lower tax brackets intentionally and taking the remainder of what you need from Roth or taxable accounts. The point is not to minimize this year's tax bill. It is to avoid a pattern where several very low-income years are followed by a permanent jump once required minimum distributions begin.

Under current law, required minimum distributions start at age 73 for most people approaching retirement now, and at 75 for those born in 1960 or later. Large tax-deferred balances produce large mandatory withdrawals, and those withdrawals arrive whether or not you need the money. The years between retiring and the first required distribution are usually the lowest-income years a household will have, which is why they get so much attention in planning. Our tax-efficient retirement planning work is built around that window.

This is not tax or legal advice. Tax rules change, and the right approach depends on facts a general article cannot know. Consult your CPA or attorney about your own situation.

Roth conversions and the surcharge cliffs

Converting tax-deferred money to Roth in a low-income year moves future growth out of the required distribution system. It also raises your income in the year you do it, and that has knock-on effects worth understanding before anyone recommends one.

Medicare Part B and Part D premiums include income-related surcharges that are based on modified adjusted gross income from a prior tax year. The tiers work as thresholds rather than gradual slopes, so income that crosses a line by a small amount can move you into a higher premium tier for a full year. A conversion sized without reference to those thresholds can create a surcharge that was avoidable. A conversion sized with them in view usually cannot.

Ask a firm how it sizes a conversion, whether it looks at more than one year at a time, and how it handles the lag between the tax year and the premium year. Ask what happens if a conversion turns out to have been too large. Those questions are hard to answer well without having done the work.

What the written output should contain

Descriptions of process are easy. Output is harder to fake. Ask to see a sample plan with the names removed and look for these elements.

None of this requires proprietary software or a large team. It requires that someone has actually done the modeling for households like yours and can walk you through why each year looks the way it does.

Credentials, registrations and capacity

Designations tell you what someone has studied. Registrations tell you what they are licensed to do and who supervises them. Both are worth checking, and neither substitutes for the other.

You will encounter a range of professional designations in this market, including the CFP and RICP marks and the Enrolled Agent credential for tax matters. Each has its own education, examination and continuing-education requirements, and each is verifiable through the body that issues it. Registrations are verifiable through FINRA BrokerCheck and the SEC Investment Adviser Public Disclosure database.

The more practical question is capacity. Many representatives are registered to act in an advisory capacity, a brokerage capacity, and as an insurance producer. Advisory recommendations carry a fiduciary duty under the Investment Advisers Act of 1940. Brokerage recommendations are governed by Regulation Best Interest. Insurance placements are a separate line of business. Ask which capacity applies to any specific recommendation and how the firm is compensated for it, and expect the answer in writing. Our page on fee-only versus comprehensive retirement planning covers the compensation side in more depth.

LaMont Chandler holds FINRA Series 7, 24 and NASAA Series 63, 65 registrations, CRD 2794744, and has been registered in the securities industry since 1996, and is registered in Kansas, Missouri, Texas and Idaho. He is involved directly in client meetings and reviews at CFG Wealth Management. Securities and advisory services are offered through Madison Avenue Securities, LLC, member FINRA and SIPC, and a registered investment advisor. CFG Wealth Management Inc. and Madison Avenue Securities are not affiliated companies. His record is available on FINRA BrokerCheck.

Questions worth asking

• How do you model claiming ages for a married couple, and can you show me the survivor income under each scenario
• How do you decide which accounts a given year's withdrawals come from
• How do you approach Roth conversions between retirement and the first required minimum distribution
• How do you keep a conversion from pushing us into a higher Medicare premium tier
• What does your written plan look like, and how often is it rebuilt
• How do you test the plan against poor returns in the first several years of retirement
• How do you coordinate with my CPA, and what do you send them
• In which capacity are you acting on this recommendation, and how are you paid for it

Common questions

Where this connects

• Social Security planning covers claiming timing in detail
• Tax-efficient retirement planning covers conversions, distributions and withdrawal order
• Retirement income planning is the plan these decisions sit inside
• Comparing retirement planning firms in Prairie Village and Overland Park
• More retirement planning insights