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October 30, 2026 Top Stories
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What to discuss during the first retirement planning meeting

Image shows a meeting note for 9 a.m.
A first meeting needs to establish what retirement looks like for the client. (AI-generated image)
By Anna Baluch

Meeting with a client for the first time to discuss their retirement is exciting, but helping them envision the future requires more than crunching numbers. To start, focus on who they are and what they hope to accomplish.

“Some people struggle to convey their retirement goals, but they can tell you about their family,” said Salvatore “Tory” Milazzo, senior vice president and regional trust and investment manager at Farmers and Merchants Trust Co.

Asking a client what a good week looks like five, 10, or 20 years from now, as well as who is in it, usually gets the conversation moving in the right direction.

“Those questions get people talking about grandchildren or a family property they hope to keep, and that’s usually where the real vision and goals come out,” Milazzo explained.

A strong discovery process helps clients organize information they may never have assembled in one place before. It also lays the groundwork for a personalized, realistic plan and meaningful, long-term relationship.

First, help clients picture a longer retirement

At the initial meeting, clarify the difference between lifespan and healthspan.

“Explain that lifespan is how long you live. Healthspan is how long you live well, before illness may begin to debilitate you,” said Salvatore Capizzi, executive vice president and chief sales and marketing officer at Dunham & Associates Investment Counsel and Trust.

Then, ask the client to describe what they picture as an ordinary day in retirement.

“Where are you living, what are you doing, and who are you spending time with?” Capizzi said.

Next, ask: “What worries you most about retirement, and how would your plans change if you lived 20 years longer than you expected?”

Instead of planning around a single retirement age or life expectancy estimate, this approach can help clients explore multiple scenarios. It may give them an idea of how their plan may hold up if they live longer and remain healthier than they anticipated.

Capizzi reinforces the fact that advancements in medicine and longer healthspans can create a multi-generation retirement, where clients must fund their own retirement while helping parents or even grandparents who have outlived their assets.

Before discussing products, advisors need to understand how much money may be needed to support how many people for how long, and how inflation could erode that ability.

Then, focus on lifestyle

Every client has their own vision for retirement. To determine what that may look like, take a close look at the client's current lifestyle and priorities.

For example, those with children living nearby may not anticipate significant travel expenses, while clients with family spread across the country may expect travel to become a meaningful part of retirement spending.

Likewise, if clients don't enjoy traveling now, they likely won't start traveling just because they are retired.

“The goal is not to tell clients what retirement should look like, but to help them articulate what a fulfilling retirement looks like for them,” said Nicole Schelkopf, financial advisor at Edward Jones.

Don’t forget to assess risk

A client's risk tolerance, guaranteed-income needs, liquidity requirements and comfort with market fluctuations can reveal a lot about the types of strategies and products that might work for them.

“I always begin with a risk tolerance questionnaire to learn about their appetite for risk,” Schelkopf said.

She also inquires about cash reserves, including checking, savings and CDs, to understand any liquidity issues.

“Equally important is understanding whether the client will need guaranteed income to support essential expenses during retirement,” Schelkopf explained.

Before recommending products right off the bat, take the time to understand how these factors work together and whether a particular strategy aligns with the client's financial needs, retirement timeline, and risk tolerance.

© Entire contents copyright 2026 by InsuranceNewsNet.com Inc. All rights reserved. No part of this article may be reprinted without the expressed written consent from InsuranceNewsNet.com.

Anna Baluch

Anna Baluch is a finance reporter and writer with more than a decade of experience. Contact her at anna.baluch@innfeedback.com

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