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Ask This One Question To Help Clients Plan Their Best Lives


Executive Summary

Prospective clients often approach a financial advisor because they have a problem. Perhaps they are approaching retirement and do not know whether their current path is financially sustainable, or maybe they have a complicated equity compensation problem to sort through. But after this initial problem is solved, long-term goals are discussed, and a financial plan is implemented, what comes next? Sometimes the advisor and their client can fall into a complacent routine, with annual check-ins that confirm that the client is on track to meet their long-term goals. However, advisors can add further value by helping them explore new goals to help them not just survive, but also thrive!

One method for getting clients out of their comfort zone to think about goals they might find exciting but were unsure about being realistic is for the advisor to ask the question, “What’s possible now?”. This question can have several benefits, from spurring clients to think about options they might not have previously considered, to energizing the client and giving them ideas for new goals to chase. For example, in conjunction with their advisor, a client might have created a long-term retirement goal but might not have thought much about potential near-term goals such as a sabbatical from work or a major vacation. Furthermore, framing the conversation as an exploration of potential outcomes that are meaningful to the client can be a good way for advisors to strengthen the bond they have with clients; not only does it let the advisor serve as a problem solver, but it also positions them as a confidant who the client can trust with sharing their big (and even not-so-big) dreams!

In terms of implementation, an advisor can choose to ask their client, “What’s possible now?” either by giving the client advance notice or by spontaneously bringing the discussion up during a meeting. One way the advisor can naturally introduce the question is to note how far the client has come since they started working with the advisor and, now that their financial plan is in order and they are on track with what has been put in place, how they now have the flexibility to consider new possibilities. And while additional goals or plans might come easily to some clients, others might respond that everything is going well and they have no other ideas; at this point, the advisor can ask follow-up questions (e.g., What have you not done, but have always wanted to do?) to help them explore new options and keep the conversation moving forward.

Ultimately, the key point is that financial planning is not just about solving problems but also about exploring new opportunities that are meaningful to clients. And given that many clients might not regularly think about new experiences they might want to pursue or goals they want to achieve, financial advisors can add value and reinforce their bond with their clients by helping them explore what’s possible!

Meghaan Lurtz

Author: Meghaan Lurtz, Ph.D., FBS

Team Kitces

Advisor Value Can Take Many Forms

Problem-solving skills (e.g., helping clients navigate to – and through – retirement) and process-oriented planning (e.g., implementing a routine year-end tax review) are perhaps the values most commonly associated with financial advisors. Yet, relationship skills – especially those that provide support and encouragement for clients – can also be a highly valuable asset for advisors. This is because many clients value advisors who recognize their progress and help them to set (and stick to) goals, especially when they may not have realized initially that those goals were even possible. The style of planning that helps clients explore possibilities and shape goals on an ongoing basis, instead of planning for long-term, one-time goals that aren’t expected to change over time, is called possibilities-based planning. Importantly, a possibilities-based planning approach can serve as a framework to help clients dream bigger, providing an ongoing value driver.

Flourish Book CoverThe notion of fostering deeper relationships and pushing clients past just ‘surviving’ to actually ‘thriving’ is a powerful one with connections to positive psychology, sports psychology, and even relationship psychology. For instance, Dr. John Gottman, renowned couples’ psychologist and relationship researcher, established the idea of love maps, which consist of all the things we know about our partners and close friends (e.g., favorite foods, flowers, activities, dreams, and goals). We can expand these love maps by continually re-engaging with and learning about the other person’s interests or ideas as they develop and change over time.

The fact that we can repeatedly engage and re-engage with others to deepen our relationships and knowledge is also reflected in coaching psychology and sports psychology. For example, when a coach first meets an athlete, the coach will often spend time learning about the athlete’s strengths and weaknesses. Yet, as the coach and athlete continue to work together and the athlete’s abilities develop and change – new strengths and weaknesses can be identified. The coach and the athlete are constantly re-engaging and learning about working with each other. Moreover, gaining new perspectives about a person’s abilities and challenges are powerful ways to deepen relationships. And when it comes to advisors and clients, the point is the same – there is a very special and somewhat untapped value that comes from exploring a client’s values, priorities, and challenges, all of which can greatly add to the relationship value that advisors offer clients.

Ask, “What’s Possible Now?” To Deepen Relationships And Increase Value In Calm Times

When it comes to adding relationship value that advisors offer to clients, advisors can leverage the fact that, barring a crisis, clients generally won’t push themselves without a bit of support or prompting. This is because when people are comfortable, it is very easy to simply stay where they are. Which means that when advisors can encourage and support clients to go from good to great, helping clients go past their comfort zone and accomplish new goals as part of a team, they provide tremendous value to the relationship.

Imagine an advisor with a client who is happy and satisfied with how their life is going. Nothing is wrong, but the advisor recognizes that the client may be capable of achieving a deeper level of fulfillment and thinks they can help them go from good to great. Clients enjoying financial stability, who are not worried or feeling threatened by scarcity, will tend to have the emotional energy to explore how adding new goals to their financial plan might bring more satisfaction to their lives. These are the clients that can be especially good candidates for advisors to connect with on a deeper level by encouraging them to strive to thrive instead of just survive… to consider things they may have never seen or imagined before. These are the clients who are primed to benefit most from their advisor asking the question, “Given what we know, what is possible now?”

Importantly, asking the question will ideally circle back to problem-solving and planning for potential outcomes, which, for many clients and advisors, can be the most enjoyable part of the financial planning relationship. This is because many people tend to enjoy the process of accomplishing a goal even more than actually reaching the final outcome – a phenomenon called “arrival fallacy”.

Arrival Fallacy – Why We Love Chasing Dreams Even More Than Achieving Them

Arrival fallacy is a concept developed by Harvard Psychologist Tal Ben-Shahar and describes the tendency for an individual to believe that arriving at a solution to a particular problem will bring them happiness. For example, a person might think that once they have a certain dollar amount saved up, they’ll never have to worry about money anymore and that they will finally be happy. Yet, for many individuals, once they get to that place, they often realize the happiness of achievement is fleeting; it is not lasting.

But many clients who are content with their current situation may question why setting another goal might be worthwhile. Why start pushing toward something else when they are happy with where they are?

The reality is that many people actually enjoy strategizing and taking action to pursue their dreams… more than they enjoy achieving a particular goal. Furthermore, setting new goals can encourage clients to push themselves further than they ever thought possible, which can serve not only to strengthen the bond between the advisor and client but also raises new opportunities to strategize and take action on new goals – the type of opportunities that can be so enjoyable for both clients and advisors!

Why does this happen? As difficult as working toward important goals might be, individuals often feel focused and satisfied with the sense of making progress toward something meaningful, especially when there’s just enough stress to feel motivated without becoming overwhelmed and shutting down. Making progress on goals in this manner can often be described as achieving a state of ‘flow’, in which engaging in some activity – such as practicing a talent or working toward a goal – is challenging enough to hold one’s attention and focus, but not so difficult as to feel overwhelming.

In a financial planning scenario, these types of progressions can be explored by having a discussion around the question, “What’s possible now?” as the question allows advisors and clients to reflect on how far they have come together and can be taken one step further by incorporating positive scenario planning, which can reinvigorate and excite clients (and at the same time, underscore the value provided by the advisor).

Yet, identifying new goals and scenario planning aren’t the only things that matter when asking clients, “Given what we know, what’s possible now?” Another valuable benefit for the advisor is the expanded understanding of what’s important to the client. Much like Gottman’s love map used with partners, close friends, and family, building out new goals and taking a second look at values and ideas expands the understanding and relationship between the advisor and the client.

Understanding How Clients Change Can Strengthen Trust And Pave The Way For Deeper Conversations

Clients change, just like anyone else, over the course of a relationship. And actively seeking to understand those changes, which can be subtle and even difficult for the client to discuss (as they may not be accustomed to having these personal conversations with their advisor), can help the advisor establish new, stronger bonds with the client.

Of course, having conversations delving into these areas may not be practical during times when major life events and transitions necessitate more of the advisor’s time and attention to focus on dealing with immediate planning needs, but when critical planning issues have been addressed, advisors can consider exploring these facets of the client’s own ‘love map’.

Example 1: Bill originally hired Tom, his financial advisor, 6 years ago for tax issues related to some RSUs.

As Tom walked Bill through the process of explaining how his RSU benefits were structured, he not only mapped out Bill’s vesting schedules, but he also had many conversations throughout the first year of the service engagement, getting to know his client Bill better and understanding his financial goals.

Through these early conversations, Bill grew to trust his advisor Tom, revealing more of his priorities and retirement ideas. Tom helped Bill clarify his goals, and they crafted a practical retirement plan that also included saving up for a house on the lake and a boat.

Since then, Bill and Tom have been meeting every year to discuss how things are going and to check in with each other. Each year, Tom asks Bill if he has had any big changes or if he has any concerns about his portfolio that he wants to discuss. And each year, Tom says that everything is going well and that he has no concerns.

Admittedly, this is a very good place to be – Bill is satisfied with his financial situation and is very comfortable with his financial plan. He appreciates that Tom has helped him cover all the relevant bases, and Tom is satisfied that his client is happy.

Yet, it is important to Tom that his clients live their full potential, and he wants to encourage Bill to explore ideas around what else he might want to pursue and plan for. What else might matter to his client that may not have been on his radar 6 years ago? Perhaps Bill might already have been thinking about new goals that he hasn’t shared with his advisor; unless Tom can have a dialogue with Bill inviting him to share these ideas, nothing new will be added to the relationship.

For some advisors, initiating a conversation at this stage of the relationship to uncover new goals can be challenging. But asking clients, “What’s possible now?” can be a natural way for advisors to broach the conversation and invite the client to share new ideas.

But perhaps most importantly, framing the conversation as an exploration of potential outcomes that are meaningful to the client can be a way for advisors to strengthen the bond they have with clients… not only by serving as a problem solver but also by being a confidant who the client can trust with sharing their big (and even not-so-big) dreams. The connection between the advisor and the client becomes that much more valuable.

Asking, “What’s Possible Now?” To Reveal New Goals During Routine Check-In Meetings

While giving advance warning that a particular question will be asked during the next meeting is crucial for some questions, “What’s possible now?” is not one of them. Advisors can let clients know they are going to ask the question ahead of time, but they can also spring the question on them spontaneously during a meeting.

The question is not necessarily scary or difficult, so it is very safe to use at will. If advisors feel the client may not be enthusiastic about having the discussion when they ask the question, one approach is to ask the client for permission to try something new. If the client has a good level of trust in his advisor, chances are that they will agree to the advisor’s request even without knowing what the advisor has in mind. By giving the advisor permission, the client has also pre-committed themselves to engage in the discussion. And when people pre-commit to take action, they are much more likely to take steps to follow through on their commitment.

Conversely, letting clients know ahead of time that the question will be asked does allow the client to prepare or as a way to organize fun ways to deeply engage the client during their next meeting.

For instance, consider the following email:

Dear Client,

I am looking forward to catching up again with you next week. Things are going really well for you; your situation is financially healthy and secure.

And because you are now in this healthy and secure place, I wanted to let you know that I am going to be asking you this question when we meet next: Given what you know now, what else is possible for you?

We have worked together for a while, and we have accomplished great things. I want to use our next monitoring meeting to explore what might be next; what are we going to do that we have not yet done?

Excited to brainstorm with you.

Sincerely,

Advisor

In the meeting that follows, the advisor can review the things that are going well with the client and then segue into asking about any new goals or possibilities that the client might want to share. Notably, the client may indicate that while they thought about the question, they are really happy with how things currently stand and don’t feel compelled to do anything else.

It’s perfectly fine for clients not to have a response the first time they are asked the question. But advisors can revisit the question again – and again – in future meetings. If clients continually have nothing to share, advisors can consider reviewing some of the initial discovery questions asked early in the relationship to get to know the client better.

For example, consider the following questions that can be revisited to elicit meaningful discussions with long-time clients:

  1. What does money mean to you?
  2. What have you not done, but have always wanted to do?
  3. What were things you enjoyed as a kid that you have not spent a lot of time doing?
  4. Describe your idea of a perfect day for me; how close are we to that ideal day?
  5. What makes you feel inspired?

Conversely, if clients do answer the “What’s possible now?” question with new ideas, goals, or aspirations, advisors can make many meaningful discoveries by asking lots of follow-up questions.

The Impact Of Good Follow-Up Questions

Follow-up questions, in both new and old relationships, can be very valuable. Not only can they help the advisor be more likable, but they are also instrumental in the shared process of social constructionism, which is how new goals, ideas, and dreams are built and planned for together – by both the client and the advisor – establishing a situation that allows the advisor to be an active participant in the client’s goals and plans. This results in clients who tend to be more compelled by the goals that are developed and more motivated to stick to the plan to make those goals happen.

Importantly, follow-up questions can be used to explore situations as much as they can be used to explore emotions. This means that advisors can choose to investigate particular aspects of the client’s situation – perhaps the advisor can review how the client has come a long way and explore other possible outcomes that might appeal to the client. Or the advisor may reflect on the emotions that a client may be experiencing – if the client has noted that they feel great or happy, the advisor might suggest that their emotional energy might help them identify exciting new ideas.

Consider the following exchange between Bill and Tom.

Bill and Tom are having their regular six-month check-in meeting. Tom did not tell Bill ahead of time that he was going to ask him the question, “Given what we know now, what else is possible?” Instead, he has chosen to spring the question at some point during their meeting together.

Tom: Hi, Bill. It’s so good to see you. How are you doing today?

Bill: Good! I’ve no complaints. I’m playing golf later today, so things are looking up.

Tom: Great! Well, I want to run through your portfolio and review our normal check-in points, but before we get into that, I actually wanted to ask you something else first. Would that be alright if we switched up the order of our normal check-in?

[Tom is strategically asking for permission because he knows that Bill might not be very receptive to engaging in an open-ended discussion around the question, “What’s possible now?”. If Bill agrees – which Tom expects he will – he’ll have pre-committed to going along with Tom’s suggestion and will be much more likely to engage in the discussion.]

Bill: Yeah, no problem. Assuming you’re not about to ask me for a loan or something like that… we’re good!

Tom: Ha, no! No loan. I actually want to revisit a question from one of our first meetings together. We’ve come a long way together over these last 6 years. You are now at a completely new vantage point, with a very different perspective on life and what you can do with your available wealth. And so I want to ask, given what you know now, what else is possible?

Bill: What else is possible? Like, what else do I want to do with my life?

Tom: Exactly. When you first came in, we were focused on understanding how your RSUs impacted your tax situation. Now that we’ve cleared that up and have planned for some of your important financial goals, like your lakehouse and boat, what’s possible now?

Bill: I’m not really sure; I haven’t ever thought about it.

Tom: Well, let me ask you this – what does money mean to you, now?

Bill: It still means security, and maybe boats… [laughing], but I could also say that, more generally, it means leisure.

Tom: Leisure… okay. Tell me a bit more about what you’re thinking about when you say “leisure”.

Bill: Well, I’ve actually thought it would be fun to plan a few larger fishing excursions to some remote places. I watch this show where vacationers visit these incredible islands in the South Pacific and Alaska. I would never have thought something like that would be possible, but now that you’re asking, well… maybe that would be possible. It might not have been possible 6 years ago, but now… maybe it doesn’t have to be something I just think would be nice. Maybe I could actually do it.

Tom: Alright! I really like this. I’m hearing you say that fishing in perhaps the Maldives is on your list. When would you go? When is fishing season in some of these areas you’d like to visit?

Bill: ….

The conversation between the men continues, along with their exercise in social constructionism, as Tom helps Bill envision the details of his goal. However, the key that Tom used to unlock the conversation in the first place was getting Bill to pre-commit to having the conversation. When Bill noted that he hadn’t really thought about the answer to the “What’s possible now?” question, Tom revisited some questions used earlier in their relationship as prompts to get Bill to slow down and think through the possibilities.

While it is common for financial planners to ask, “Is there anything new?” or “Have your goals changed?” in routine check-in meetings, recognizing that most clients often respond like Bill – saying, “No, nothing” or “Not really” – can help advisors be prepared to do what Bill’s advisor Tom did, and push the issue.

Bill is comfortable with his financial situation, and that’s good, but Tom wants to push Bill to recognize that he has the capacity to push for more if he wants to… and helping clients realize their broader potential is a powerfully valuable exercise. Because unless financial advisors are very intentional about directly challenging the client to contemplate what is possible for them now, the client is very likely never going to volunteer anything unless a new problem arises that they need help solving.

This is because, for many clients, talking about money can be very stressful. People are often socialized to believe that the only time they should talk about or request help with money is when there is a problem. Which means that encouraging clients to talk about money – and helping them understand that it is okay to have that discussion – can be immensely valuable for them to realize that proactively having conversations about money can make a huge difference in helping them identify and realize meaningful financial planning goals.

Most advisors generally want to help clients with problems, yet advisors know that when there is a problem to be solved – especially when a high level of stress, anxiety, frustration, or fear is involved – clients may not be fully focused on their long-term goals. As such, it is important to ask clients strategically about new goals when they are in a comfortable place and actually have the time and bandwidth to focus on new goals.

Furthermore, when it is time to review the standard check-in points during the check-in meeting (e.g., the portfolio review and other routine housekeeping tasks), the conversation can proceed as an interactive process but in the context of the client’s newly identified possibilities. The advisor can demonstrate how new goals can be funded and what impact they may have on other concurrent or future goals.

For instance, while Tom’s client, Bill, is still working, Tom can show Bill that he can still retire as planned, but also show how Bill might work a fishing trip into his plan sometime before retirement. Tom can help Bill see how the possibilities can actually become a reality in the context of his existing financial plan by modeling scenarios with financial planning software in real-time. By doing so, Tom helps Bill understand the practicality of his ideas and, perhaps more importantly, he is daring him to live a richer life by exploring his most cherished dreams and values.


Financial planning can be an incredibly powerful process. It can save clients from pitfalls, but it can also be the impetus for pushing clients from simply surviving comfortably to thriving and realizing their full potential. Because when we support our clients to be more than what they think they can be or do more than what they imagine is possible, strong bonds based on trust and friendship can be formed, similar to those between coaches and high-performing athletes. Advisors can have these types of close-knit relationships with their clients; all they have to ask is, “What’s possible now?”

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