How to Understand What Really Matters to Your Clients

Listening Can Be Challenging

With all this said, this week’s column is dedicated to improving two of the most critical skills: asking strong open-ended questions and listening in an active and reflective way.

Let’s start with the harder part — listening. Most advisors have great questions they have developed over the years, but listening with empathy — truly and deeply listening — is a practiced art. Most of the time, when someone is speaking to us, we are stuck in our heads. We are thinking about what we want to say next, or why that person is saying what they are. We might be distracted or even disinterested.

It gets even harder when the person speaking is a prospect or client. An advisor listens for the problem to solve and then often just jumps in to solve it. The advisor might not want to forget a comment or response, so they may be focused on what they want to say next to address it.

This removes the opportunity to deepen the connection and really engage. Circling back to my trip, an advisor might focus just on the cost to get three of us to Portugal and Spain and help me allocate the necessary funds to pay for the trip. While this would be helpful, it isn’t the whole story. I’d want to be asked about where else I’d like to go and how much, over time, these trips would cost. I’d like my advisor to care about my relationship with my best friend from second grade who lost her husband a few years ago and might need financial counseling herself to make sure she is still okay.

I’d like my advisor to listen while I talk about the stress of being away at the busiest time of the year for my work, my business travel, and the grad classes I teach. I’d like my advisor to help me determine whether I need to budget for additional support in managing things while I am away in the future. While the topics themselves are important, the financial allocations and support needed also align to every decision that gets made.

Ultimately, the trip and its cost isn’t my whole story. Anything we do in life isn’t just one surface discussion; there are layers. Learn to listen to the layers.

Practice reflective listening too. This sounds easy — just feed back to the person what you’ve heard. It’s much harder than it sounds though. You have to really listen, connect the dots and create a story that you can repeat back to someone from what they have just said. This shows active listening and it also helps forge a connection with what you’ve heard to ensure you understand.

Asking Effective Questions

When it comes to helping your prospect or client open up, be sure you are asking good open-ended (not leading) questions. Remain open and patient while someone responds. Try incorporating a few different ones. But please do not ask the question I have heard over 10,000 times in my career: “What keeps you up at night?” Yes, understanding the answer is important. But you can stand out by finding a different way to ask this.

Questions with numbers are good, because it forces the brain to think differently in order to understand. Questions that are too broad can be difficult for someone if they haven’t thought about the topic in advance.

Here are some suggestions to try incorporating into your repertoire:

1. What are the top three things that concern you most about your goals and plans right now?
2. What obstacles will you face in meeting your financial goals?
3. When you envision a future with no limits, what two things are most important for you to achieve?
4. Who matters most in your life and why? What would you want to do to support this person or these individuals?
5. What scares you when you think about your future?
6. What excites you when you think about your future?
7. What is the number one thing would you change regarding past financial decisions you have made?

These questions are very provocative, and you would likely not ask all of them because the answers you receive will lead you to ask additional clarifying questions. Be careful not to take an answer at face value and start to solve without going deeper. Just like my travel story, there are often layers under layers you can uncover if you ask the right follow-up questions.

Strengthening Ties With Clients

Advisors know the more they understand about their clients, the easier it is to deepen the connection. There is a difference, however, between having knowledge about your client (“she is going to a wedding in Barcelona”) and understanding what matters to your client about the knowledge you have.

For your next meetings, force yourself to step out of your comfort zone a bit. Review your standard list of questions to see if you can incorporate something new. Practice listening at a deeper level, and get really good at reflective listening. Doing these things will make you a better advisor, and as a bonus, they will make you a better spouse, partner, parent and friend as well!

Beverly Flaxington co-founded The Collaborative, a consulting firm devoted to business building for the financial services industry, in 1995. The firm also founded and manages the Advisors Sales Academy. The firm has won the Wealthbriefing WealthTech award for Best Training Solution for 2022, 2023, 2024, 2025 and 2026. Beverly is currently an adjunct professor at Suffolk University teaching Executive MBA students Leadership and Managing Teams. She is a Certified Professional Behavioral Analyst (CPBA) and Certified Professional Values Analyst (CPVA).

She has spent over 25 years in the investment industry and has been featured in Selling Power Magazine and quoted in hundreds of media outlets, including The Wall Street Journal, MSNBC.com, Investment News and Solutions Magazine for the FPA. She speaks frequently at investment industry conferences and is a speaker for the CFA Institute.

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