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

Ross Marino |

You may have worked with the same financial advisor for years. The relationship supported saving and investing while retirement remained in the future. Now a date is on the calendar, and the work is changing.

A familiar advisor can remain the right fit. The useful question is whether the relationship now covers the decisions that begin when paychecks stop, including withdrawals, Social Security, and health coverage. A fresh review can confirm the fit or reveal a gap before that gap affects a real decision.

What changes as retirement gets closer?

During your working years, the plan may have emphasized regular saving, investment allocation, and progress toward a future retirement date. Retirement adds a different assignment. The resources you built must begin supporting spending after the paycheck ends.

That shift connects decisions that may once have been discussed separately. A withdrawal can affect taxes and the portfolio. The end of employer coverage can start a Medicare enrollment window.[1] Social Security timing changes when one source of lifetime income begins. Each choice also affects how much the household may need from savings.

These connections do not prove that your advisor is unprepared. They show what the relationship now needs to explain, coordinate, and revisit.

What should the relationship cover now?

Begin with the written scope. Form CRS summarizes a firm’s services and costs. It also addresses conflicts, disciplinary history, and the required standard of conduct.[2] Form ADV Part 2A provides more detail about an investment adviser’s business practices, fees, and conflicts. Part 2B describes the background of people who provide advice.[3]

Those documents can confirm what the firm offers. The next conversation should connect that scope to your retirement. Ask whether retirement income planning is included. Clarify how tax questions enter the work. Then ask how Medicare and Social Security decisions will be evaluated.

An advisor does not need to perform every professional role. You should be able to see who handles an issue outside the advisor’s role, how information will move between professionals, and who will help you understand the combined effect.

Where does the work need to shift?

Decision area

While paychecks continue

As retirement begins

Cash flow

Saving from earned income

Coordinating income sources and withdrawals

Benefits

Using employer coverage

Coordinating work exit, Medicare, and Social Security

Investments

Building toward a future goal

Supporting withdrawals while preserving an investment role

Review

Measuring progress toward retirement

Revisiting decisions as spending, health, and life change

The advisor-fit question changes when the relationship must support use, coordination, and adaptation as well as accumulation.

How should the advice be explained and revisited?

Ask your advisor to walk through one decision that is relevant to your retirement. What information would be needed? Which tradeoffs would be discussed? What could change the recommendation later?

CFP Board’s standards require a CFP® professional providing financial planning to determine whether monitoring and updating are part of the engagement. When they are included, the professional must explain what will be monitored and how updates will occur.[4] CFP Board encourages questions about services and team roles.[5] NAPFA emphasizes compensation and conflicts.[6] AARP begins with credentials and compensation before directing the conversation toward the person’s needs.[7]

Investment performance can be one part of the review. It cannot show whether the agreed planning work is being completed. It also cannot show whether you understand the choices well enough to decide how they fit your life.

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

Reassessing an advisory relationship preserves the work that still serves you. It also makes room to add the decisions, coordination, and review rhythm that retirement requires. The result may be continuity, a clearer scope, or a different relationship.

What should your reassessment tell you?

A useful reassessment should let you answer three questions in your own words:

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

Compare the answers with your agreement, Form CRS, and Form ADV. FINRA’s BrokerCheck can help confirm an investment professional’s background.[8] Clear answers may support continuing the relationship as it is. A gap may lead to a follow-up question, a change in scope, or a broader comparison.

To see how Dovetail connects the financial and personal decisions involved in preparing for 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.

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.