This question shifts the conversation from dollars and cents to what is truly important in a person’s life. Clients typically respond quickly with a general answer. The most common response is ‘family.’ At this point, I get to follow up and probe deeper to understand what aspect of family is important to the client. It’s from this spot that all financial plans should be firmly anchored.

This question uncovers a lot of hidden beliefs and actions that control the clients’ relationship with money. I’ve learned that most people are doing what they witnessed their parents doing with their money or, in some cases, the extreme opposite. Once we uncover some of those attitudes, I have a better idea of how to proceed. To deepen the conversation, I actually created a card game for couples to have those types of discussions around money called ‘For the Love and Money.’

Understanding stress relievers and a person’s motivation is a great way to learn personality traits and values. Also, it provides an opportunity to uncover any potential concerns or problems on the horizon. With this information, I am better able to formulate custom solutions. For example, an elderly couple may desire financial security for their children or grandchildren, and this gives them the most satisfaction or ‘peace of mind.’ The conversation can then shift to legacy and education-planning strategies.

I typically ask this question at the second financial planning meeting with clients. The primary goal of this request is to learn about their parents’ financial and physical well-being. A secondary goal is to learn whether the parents have estate plans set up for themselves and whether the clients (their children) are aware of their potential roles. This is so important because we often find that our clients are in fact named as trustees/executors/DPAs/HCPs without them knowing. I have seen too many times when our clients are left in the dark regarding their roles in their parents’ estate plans. This question invites clients to review documents and ask and resolve the important estate questions.

This question allows clients to consider their priorities in a new way. Then, I ask this follow-up question: ‘Looking at the individual activities, are these things you’d like to do every day, a few times a month or a few times a year?’ This second question gets clients to consider whether they think they’d really like to sit on the beach, or golf or ‘name the activity’ every day. If not, what would they want to be doing instead? The question elicits what, if anything, is holding them back from doing their ideal activity more frequently.

This open-ended question allows clients to express the most-pressing financial issue on their minds during our session. This makes the session about them and their current concerns. The key is to let the client lead the session so that it’s beneficial to them.

I ask this open-ended question at the beginning of a relationship. The response highlights the client’s goals and provides a powerful glimpse at their values. There is so much psychology that goes into good financial planning. The answer to this question helps me understand what’s important to a client with respect to career, family, wealth. Future conversations about financial goals and strategies are much stronger once I understand a client’s values.

Most often, I get a joking response about work or kids’ grades. But occasionally, I see clients get vulnerable and express concerns they haven’t admitted before. It could be the fear of having to care for a loved one, worry over a volatile economic environment or searching for permission to make a large purchase. If, on the other hand, they sleep soundly, then I know I am doing my job.

I found the ‘paint me a picture ...’ approach is a revealing way to elicit important information. It gives the client permission to really think about it and elaborate on the response. The wording surfaces important information about what a successful relationship can look like. And do you know the best part? It is not actually a question at all. It’s an invitation. I’ve never had a single prospect push back on the invitation. Instead they tell me about their hopes and dreams.

When it comes to discussions about money, many clients model the ostrich. They put their head in the sand to avoid the topic. When we onboard clients, we want to get to the juice. This question and follow-ups help all parties understand what is important and then translate those values into plans, accounts and strategies. Money is a tool. If handled with care and attention, clients will have a better chance of getting what they want.

This is a showstopper of a question. The most common client response is that they want their loved ones to be happy, supported and live productive lives. What they would find awful is if their close-knit families splintered apart. Yet while clients believe they have put a thoughtful plan in place, execution is likely to be anything but smooth and collegial. This question offers an opportunity for an advisor to engage the entire family in a plan that is likely to avoid the client’s fears. Sometimes the question enables the advisor to get to know the next generation and ultimately become a more trusted advisor.

I recently put this question to a couple. Their individual responses revealed that savings was not a priority for the husband. At the same time, the wife was concerned that their savings were too low. In the ensuing conversation, the wife revealed that, growing up poor, she was forced to wear a hand-me-down dress to her high school prom. It was a humiliating memory, and she vowed that she never wanted to experience anything like that again. Hence her desire to have more in savings. This was the first time the husband had ever heard that story. The couple ended up becoming clients.