Facilitating Meaningful Retirement Conversations with Older Clients: 3 Key Strategies for Advisors

Do you want to have more substantive discussions about retirement with your older clients? Here are some strategies to help facilitate these important conversations:

1. Use Open-Ended Questions to Encourage Deeper Dialogue

It’s common to start with direct inquiries like, “Have you thought about retirement?” or “What do you envision for your business in the future?” While these are valid, open-ended questions can often spark a more meaningful and informative discussion. Consider asking:

• How are you feeling about your profession these days?
• What’s your long-term perspective on your work?
• Which parts of your job are you still enjoying, and which would you be ready to move on from?
• How do you envision rounding out your career?
• What would an ideal path look like if you decided to stop working?

These types of questions invite clients to reflect more deeply and share their thoughts about the future.

2. Encourage Clients to Express Their Ambivalence

Even clients who are eager to retire may feel some level of ambivalence, which is natural. However, unless these feelings are acknowledged, they can interfere with the retirement planning process or even disrupt the transition itself. You might say something like, “It’s normal to have mixed emotions about retiring. These feelings may not always be front and center, but when they do come up, let’s make sure to talk about them. They can actually inform our planning and highlight areas that are important to you.” By encouraging an open discussion about ambivalence, you can help clients better navigate their feelings and approach retirement with clarity.

3. Acknowledge What They’re Leaving Behind

While it can be tempting to reassure clients that retirement will be great, it’s important to recognize that retirement is a major life transition and not just the beginning of something new—it’s the end of a significant chapter. ?Advisors can certainly help clients plan for a rewarding post-retirement life, but we do clients a disservice if we don’t allow them to talk about what they’re leaving behind. Allowing clients to reflect on this loss can ease their transition into retirement and help them fully embrace what’s next.