“What would you like to do when you retire?”
It’s a reasonable question. And it often produces familiar answers: travel, play golf, spend time with family.
We write those answers down, build them into the plan, and refer to them in future meetings. But how much have we actually learned?
Two clients can say they want to play golf three times a week and be describing very different retirements. One wants quiet mornings outdoors. Another wants competition. A third wants a standing appointment with friends.
The activity is the same. The meaning behind it is different.
That meaning matters because it gives us a better understanding of the life our clients want their money to support. It also gives us something more personal to discuss when uncertainty threatens to pull their attention away from their plan.
A client’s first answer opens the conversation. The next question helps us understand what actually matters. For more insights into investor psychology and better client conversations, explore behavioral advisor resources, including free resources and opportunities for deeper learning.
Find the Meaning Behind the Activity
Suppose a client tells you, “I want to play golf a couple of times a week when I retire.”
Before moving on to the next goal, ask:
“What do you enjoy most about golf?”
The client might say, “I like getting out by myself, clearing my head, and having a few hours where nobody needs anything from me.”
Now you know something you didn’t know a moment ago. Golf provides relief from demands and room to think. That is a much richer understanding than “likes golf.”
You could follow up with:
“What makes that time especially valuable to you?”
Perhaps the client has spent decades managing employees, responding to customers, or living by someone else’s schedule. Retirement represents the freedom to decide how to spend a morning.
You don’t need a long list of probing questions. You need curiosity and a willingness to stay with the answer for another moment.
Useful follow-up questions include:
- What part of that are you most looking forward to?
- What would make that experience especially meaningful?
- Can you tell me about a time when you enjoyed that most?
- What would you miss if you could no longer do it?
Ask one question, listen, and let the response guide the next question. The conversation should seem natural, with room for the client to discover something too.
A Deeper Understanding Creates More Possibilities
Defining a future life can be difficult. Clients may reach for activities they already know because imagining every possible way to spend retirement is overwhelming.
Understanding the appeal of an activity can help them see additional possibilities.
If golf provides quiet time outdoors, perhaps walking, gardening, or fishing would offer something similar. If the appeal is friendship, the client might also enjoy volunteering with friends or joining a local group. If it is the challenge of improving, learning a new skill could be rewarding.
This is an opportunity to ask, “What else gives you that same sense of enjoyment?”
The client may love golf for the rest of their life. But interests, health, and circumstances can change. A broader understanding of what brings satisfaction gives them more ways to create a fulfilling retirement.
It also helps us avoid building a picture of their future around an activity without understanding the purpose it serves.
Ask About Anti-Goals, Too
Alongside what clients want to experience, I like to explore what I call anti-goals: experiences or circumstances they want to avoid.
Sometimes those are easier to describe. A client may struggle to picture an ideal Tuesday in retirement but have no trouble saying, “I never want to sit in rush-hour traffic again.”
That answer comes from experience. They know what it cost them in time, energy, and frustration.
You might ask:
“What part of your current routine would you be happiest to leave behind?”
Or:
“When you think about retirement, what would you be disappointed to find yourself still doing?”
Answers might include being tied to a rigid schedule, having too little time for family, or spending every day alone.
Those responses add useful context. A client who values solitude on the golf course may still want regular social connection. Someone eager to stop working may want to preserve the sense of purpose their work provides.
Exploring both sides helps clients describe a future that fits them more fully.
Bring That Understanding Into Financial Conversations
The value of these conversations extends beyond retirement planning. What you learn can help clients evaluate decisions when emotions run high.
Consider a client who wants to move everything to cash during a market decline.
A discussion about allocation, uncertainty, and the consequences of changing course is necessary. But the client may be focused on obtaining immediate relief. Your explanation will be more relevant if you connect the decision to the life they have described.
For example:
“I understand why this decline concerns you. You’ve told me how much you look forward to having control over your time and leaving the commute behind. Before we make a change, let’s look at what it would mean for the plan supporting that retirement.”
Then examine the proposed change together. How would it affect their income needs, spending flexibility, and longer-term objectives? Have their circumstances changed, or has the decline changed how comfortable they are with uncertainty?
The purpose is to help the client consider the decision in the context of their own priorities. Any connection you draw should be supported by their plan. Moving to cash does not automatically mean someone must work longer or give up a favorite activity.
Their goals and anti-goals provide context for evaluating the tradeoffs. They should never become pressure points for getting the answer you want.
Leave Room for the Answers to Change
Once you understand what matters to a client, record it in their words.
“Wants to golf” is useful. “Wants quiet mornings outdoors and freedom from other people’s schedules” tells you much more.
Revisit that understanding over time:
“Last year, you said having more control over your time was what you most looked forward to. Is that still what matters most?”
Clients change. Their plans should reflect the people they are becoming as well as the people they were when you first met.
At your next meeting, take one familiar goal and ask one additional question about it. Then ask what the client hopes to leave behind.
You may discover that an answer you’ve had in your notes for years was only the beginning of the conversation.
JAY