Is Your Financial Advisor Still the Right Fit as Retirement Gets Closer?

You may have worked with the same financial advisor for years. The relationship helped while paychecks were still arriving and retirement remained somewhere in the future. Now a target date is on the calendar, and the questions are becoming more immediate.

The first withdrawals need a plan. Social Security has a starting date. Health coverage can have enrollment deadlines tied to when work ends. [1]

A familiar relationship can still deserve a fresh look when the work changes. That review is not a verdict on past advice. It is a way to see whether the relationship still fits the decisions ahead.

What changes when retirement gets closer?

During your working years, the plan may have emphasized regular saving and investing. Progress was measured against a future retirement goal. Those responsibilities do not disappear. Retirement adds a different job: showing how the resources you built can support life after the paycheck stops.

Withdrawals may affect both taxes and the investment plan. A Medicare decision may depend on when employer coverage ends. Social Security timing can change the income available later. A retirement number can still be useful. The plan also needs to show how decisions will function over time.

These questions do not prove that your advisor is unprepared. They do change what the relationship may need to explain. They also affect which decisions need to be considered together and revisited.

Does the current relationship cover the work ahead?

Start with the written scope rather than assumptions. Which retirement decisions are included? Who is responsible for the work? What remains outside the relationship?

Form CRS summarizes a firm’s services and costs. It also addresses conflicts and disciplinary history. The form also explains the required conduct standard. It is intended to help someone decide whether to begin or continue a professional relationship. [2]

Form ADV Part 2A provides more detail about an investment adviser’s business practices. It also describes fees and conflicts. Part 2B addresses the background of people who provide advice. [3]

Those documents can confirm what a firm says it provides. They cannot show how clearly the work will be explained in your situation. That part requires a conversation.

Ask whether your current service includes retirement income planning. Clarify how tax questions will be addressed. Then ask how Medicare and Social Security decisions enter the planning process. An advisor does not need to perform every professional role, but you should be able to understand how an issue outside the advisor’s role will be handled.

How will the advice be explained and revisited?

A useful review examines both the process and the list of services. Ask your advisor to walk through one retirement decision that is relevant to you. What information would be needed? Which tradeoffs would be discussed? What would cause the advice to be reviewed?

CFP Board’s standards illustrate why scope and follow-through matter. They require a CFP® professional to provide financial planning to determine whether monitoring and updating are part of the engagement. When they are, the professional must explain what will be monitored and how updates will occur. [4]

CFP Board’s consumer guidance suggests asking about services and team roles. [5] NAPFA’s guidance emphasizes compensation and conflicts. [6] AARP’s advisor-interview resource begins with credentials and compensation. It then directs the conversation toward the person’s needs. [7]

Investment performance can be part of the review. It does not show whether the agreed planning work is being completed. It also cannot tell you whether advice is understandable when a decision has real consequences for your life.

Dovetail Principle: When Life Changes, the Plan Can Change Without Starting Over

A retirement reassessment does not erase what has worked. It asks whether the earlier work remains useful and what needs to be added for the next stage. Some parts of the relationship may continue unchanged. Other parts may need a clearer scope or a different review schedule.

What should you clarify with your current advisor?

You can begin with a direct conversation:

• As retirement gets closer, how will our work together change?
• Which retirement decisions will you help me evaluate?
• What work is outside our agreement?
• Who will remain my regular contact?
• How often will we revisit the plan after I retire?

Compare the answers with your agreement, Form CRS, and Form ADV. Use FINRA’s BrokerCheck if you need to confirm an investment professional’s background. [8]

If the answers are clear and the work fits, the reassessment may confirm the relationship you already have. If a gap appears, you can name it before deciding what it means. The next step may be one follow-up question. It may also be a change in scope or more time to evaluate the relationship.

What would a useful reassessment tell you?

A useful reassessment does not need a score. Its purpose is to determine whether the relationship can support the retirement work now coming into view.

Before you finish, see whether you can answer three questions in your own words:

1. What retirement work will this relationship provide?
2. How will important decisions be explained and reviewed?
3. What remains outside the advisor’s role?

Your answers may support continuing the relationship as it is. They may show that one part of the agreement needs clarification. Either result can make the next conversation more useful without presuming that you should change advisors.

To see how Dovetail describes the work involved in preparing for and living through retirement, visit Retirement Planning.

Related Reading: How to Compare Financial Advisors: What to Ask and What to Verify

About the author

Ross Marino, CFP®, CeFT®, is the Founder & CEO of Dovetail Financial and creator of Human-First Financial Guidance®. He helps people nearing or living in retirement connect their lives and wealth so that financial decisions become clearer, more personal, and easier to navigate.

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Notes

1. When Can I Sign Up for Medicare?, Medicare.gov.
2. Form CRS, Investor.gov, U.S. Securities and Exchange Commission.
3. Investor Bulletin: Form ADV – Investment Adviser Brochure and Brochure Supplement, Investor.gov, U.S. Securities and Exchange Commission, updated August 27, 2020.
4. Code of Ethics and Standards of Conduct, CFP Board.
5. 10 Questions to Ask Your Financial Advisor, CFP Board’s Let’s Make a Plan.
6. Working With a NAPFA Registered Financial Advisor, National Association of Personal Financial Advisors.
7. What to Ask a Financial Advisor – Be Prepared With AARP, AARP.
8. About BrokerCheck, FINRA.

Disclosure

This content is provided by Dovetail Financial Group LLC (“Dovetail Financial”) for informational and educational purposes only. It is not intended as, and should not be construed as, individualized investment, tax, legal, or accounting advice; a recommendation to buy or sell any security; or a recommendation to adopt any investment strategy. Because each person’s situation is unique, readers should consult their own financial, tax, and legal professionals before taking action based on this content. Information contained herein is believed to be reliable, but its accuracy or completeness is not guaranteed. Any opinions expressed are current as of the date of publication and are subject to change without notice. All investing involves risk, including the possible loss of principal. Asset allocation and diversification do not guarantee profits or protect against losses in declining markets. Past performance is not a guarantee of future results.

Dovetail Financial Group LLC is a registered investment adviser. Registration does not imply a certain level of skill or training. Additional information about Dovetail Financial Group LLC, including Form ADV Part 2A and Form CRS, is available at adviserinfo.sec.gov. © 2026 Dovetail Financial Group LLC. All rights reserved.