Wealth and Relationships: You Can’t Ask Your Clients the Hard Questions Until You’ve Asked Yourself
By: Amy Castoro, B.Sc., M.A. | President & CEO, The Williams Group
One family member was preparing to sue.
A family office head had called us, concerned. The next generation had stopped showing up. They were skipping meetings, slow to respond, and vocal in conflict with themselves and the office. One of them now believed the office wasn’t administering the trust as his parents had intended, and was consulting lawyers. On paper, the office had done everything right: strong governance, skilled leadership, returns to match. The risk to retaining the client wasn’t financial. It was the conversations no one was having.
Our twenty-year study of 2,500 ultra-high-net-worth families found that trust and communication, not governance, not tax strategies, not portfolio performance sits at the center of why relationships fail. The Williams Group has worked with these families for sixty years; I’ve led it for the last nine, and we trained advisors directly through our Institute for Preparing Heirs. The same pattern emerges everywhere.
Most clients can afford the best advisors and structures in the world. The biggest opportunity for advisors is often their biggest blind spot: building real relationships with their clients requires a skill set the industry has not taught them.
The inner work is yours, not your clients’. Four questions to ask yourself:
What matters to me about the impact of wealth on the families I serve? Clients feel your answer, whether you’ve articulated it or not. An advisor who treats wealth as a problem to optimize runs different meetings than one who sees it as something that can deepen or distort family harmony. Rather than mirroring your client’s goals such as portfolio performance, ask deeper ones: How do you and your spouse work through conflict? Which of your children is most likely to be negatively impacted by the wealth? What do you do now to help them stay connected after you are gone?
If you were the client, what questions would you wish I would ask? Not the estate planning version. You’d want someone to ask what you saw in your grandson’s face at Thanksgiving when he realized his family was different. Questions like: What’s uncomfortable for you about being wealthy? What conversations are you having with your children about how it is for them to be wealthy?
What will it take for me to ask questions I don’t have the answer to? Advisors are trained to be the person with the answer. But the biggest breakdown we find in families is people who don’t feel heard — usually spouses and the next generation. Ask the spouse: What matters most to you about the impact of this wealth on the family? Ask the next generation: What’s your biggest fear of being in a wealthy family? Resist filling the silence with a framework. Clients trust us more when they know they’re being listened to, not sold to.
How can you take your listening to the next level? Most of us are average listeners with good manners. Three practices help: pause three seconds before responding; ask the question underneath the one that first comes to mind; and “what else?” which surfaces what they actually wanted to say. One advisor told me she asked, “What else?” three times in a row with a long-time client. On the third round, the client said something she’d never told anyone. It changed everything between them.
That family office? They didn’t lose the client. They started asking different questions.