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Journey Strategic Wealth

How To Connect Deeply in Conversations

Active listening is a powerful tool advisors can use to gain insight into how to communicate with clients and effectively coach them toward intentional action.


Did you know that you could create a referable experience for your clients simply by listening to them?

It’s been proven that active listening causes “feel good” chemicals to be produced in the brain. In other words, simply by showing someone you’re present in conversation—making eye contact, acknowledging what the other person is saying, mirroring body language—you can make them feel happy, ultimately creating a positive and validating experience for them.

Active listening is more than just a mood-boosting skill, however. It’s a powerful tool that advisors can use to gain insight into how to communicate with clients and effectively coach them toward intentional action.

In this blog I’ll provide three ways in which you can immediately take your active listening skills to the next level, resulting in deeper bonds with clients and positive planning outcomes for them and their families.

Know What You Are Listening For

We all have belief systems and structures that shape the way in which we think and act. Being able to identify a clients’ long-held belief systems can provide you with insight around how to frame your questions and comments to better resonate with them.

Sometimes, a client’s belief systems will reveal themselves early on during discovery. Take the following example: you have a client who owns a construction company. He has three sons who work with him in the business. When talking about the business, he makes statements like, “I’ll be here forever. There is no such thing as retirement when you work in a family business” or “My sons will take over eventually. We don’t have any of that formally written down, but we don’t need to! We’re family. We’ll always do what’s right.” 

Clearly the client has strong beliefs about 1) what retirement means to him, 2) about what “family” represents, and 3) about what is “wrong” and “right” in terms of business planning. Over the course of your relationship with the client, you’ll want to dig deeper into the following:

  • What is it about the formality of an “agreement” that makes the client uncomfortable?
  • What have you learned about the clients’ communication style that could provide insight into how to best articulate your message to them? 
  • How does the client view his role in his business and/or family evolving over time? 

There may be other times when you’ll have to listen deeper for a client’s belief systems. For example, let’s say a client always jokes about how much money their non-working spouse spends. A number of things may be underlying their jokes and comments: fear about not being able to provide or “keep up” (or conversely, pride in being able to provide a certain lifestyle), resentment, frustration, or even a subconscious need for validation.

Consider asking yourself the following after each meeting:

  • What am I noticing about the dynamic between the two spouses? How might that disrupt this process? How might it help?
  • How should I structure our meeting agenda so that I can elevate both voices equally?

Establish a “Powerful Role” in the Conversation

Once you’ve built enough trust and rapport with a client, you might consider using what you are hearing and observing to gently help them explore negative mindsets, beliefs, or communication patterns. Helping clients break free of hindrances can be incredibly powerful for them and can reinforce your role as their trusted partner. 

You’ll want to make sure that you only share your observations after enough trust has been established and after the client has granted you permission to share feedback, by answering affirmatively to a question like, “May I share an observation I am having?” Or “Might it be helpful for me to provide feedback on what I am hearing and seeing?”

Here are a couple of examples on how to do this effectively:

  • You are meeting with a couple where one client talks over the other client or disregards their comments. You could address either client or both.

“Your body language is telling me that you feel really “shut down” right now. What is on your mind right now?”   

“As an observer, it seems you are not hearing what your spouse is saying regarding this topic. Is there a way I can be helpful in getting the two of you to discuss this further.”

  • You are meeting with a couple who seem to be avoiding confrontation or a necessary discussion.

“May I share an observation with you. I am hearing two totally different opinions and approaches. And it seems there is something underlying this discussion. May I repeat back to you what I think I’ve heard, and then ask some questions to help you address this at a deeper level?  

  • You are meeting with a couple where one spouse is naturally more dominant, and you get the sense that the other spouse may have a different thought or opinion.

“It’s really important that I hear your thoughts on this. I get the sense that you’ll have some good insight on this topic. Would it be okay to explore that with just you right now?”

“It’s really important for me to give equal space to both parties in a discussion like this. I’m going to ask you to listen to your spouse speak for 5 minutes without interruption, and then I’d love to get your take on what you heard.”  

  • You notice that a client’s body language or emotional state has completely changed.

“I want to pause for a second. I can see a lot of emotion on your face right now.  Tell me what’s happening. Are you comfortable sharing what’s triggered you?”

  • You work with a client who is overly critical of themselves.

“I notice how hard you are on yourself. I want to take a moment to just recognize how much you have accomplished and how far you have come. What is one thing you personally feel really proud of right now?”

Helping clients confront their own challenges and communicate openly can be a very powerful exercise for them; it can also establish you as their most trusted confidante and resource.

Always Be Curious

Curiosity—without bias or preconceived judgement—is a skill that should be leveraged daily and used in conjunction with your active listening.

Being curious can help you formulate questions when you feel “stuck” in a conversation. It can also help produce more “feel good chemicals” for the person talking, as the more curious you are, the more evidence the speaker has that you are interested in what they are saying. It could also provide you with a way to reign yourself back into a conversation when you feel yourself wandering or tuning out.

Lean into curiosity by focusing on details and asking questions pertaining to those details so that you can stay present and deeply engaged.

  • If a client is sharing something personal with you, and is excitedly sharing details, use your curiosity to get the client to talk more, rather than moving on to the next subject (or meeting agenda!)
  • “How was the food? Was there a favorite dish of the trip?
  • “I’m so happy you were able to spend time with them. When is the next time you’ll get to see them?”
  • “Are these the same neighbors you were mentioning to me last time? How are they doing?”
  • If a client is sharing something upsetting or sad with you, rather than express your sympathy and move on, be gently curious about what the client is feeling and how they are coping.
  • “I can’t even imagine how you’re feeling. How are you coping right now?”
  • “Wow.  What are you feeling most right now?”
  • “I want you to know we’re here for you.  How can we be helpful as you navigate through this?”

On a final note, you can also use your curiosity to create unique and engaging agendas for future meeting with clients you have been working with for a while. A simple statement and question like, “We’ve been working together for some time, and I would love to pause and get your reflections on our work together. How would each of you describe the role you both play within the financial planning process?” can spark an important discussion between two partners that can be powerfully facilitated by you.

Penny Phillips is the co-founder and president of Journey Strategic Wealth. 

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