Mark Chamberlain is a wealth management principal who has spent decades sitting across from people at their most financially anxious. He has learned something that applies far beyond finance: the reason someone gives for needing help is almost never the real reason.
“Somebody does not make an appointment to see me for the first time unless there’s pain,” Chamberlain says. “If they just come in and tell me their returns are not good enough, that’s not the real pain.” So, he keeps asking. He stays curious. Eventually, he reaches emotion. If he can help the client access the deeper feelings behind the motivation, he can solve the problem. If they stay on the surface, the real issues have not been addressed.
Chamberlain told me the story of a client named Bob, a successful businessman and third-generation car dealer, finally ready to exit the company. Chamberlain started not with numbers but with a question: “What’s your first memory of money?”
What came back was a story from when Bob was seven years old. He and his older brother were grocery shopping with their mother, who was carefully tracking every item on a small tabulator, a pre-calculator budgeting device, to stay within the family’s means. Before they reached the checkout, his brother slipped an eight-track tape into the cart without their mother seeing it.
When the cashier read out the total and their mother realized she was over budget, she began to cry. It was the only time in his life Bob had ever seen his mother cry. She stood in the checkout line, embarrassed, unable to buy what her family needed. Bob never forgot that moment.
Beneath all the successful years, the business, the financial comfort, Bob’s greatest fear was that there would not be enough for his family. By being curious and patient, by asking one question and letting the answer lead to the next, Chamberlain created the conditions for Bob to be vulnerable about something he had probably never shared with anyone.
As a Courage Keeper, Chamberlain knows that his own vulnerability is part of the tool. “To get someone else vulnerable enough to be curious,” he says, “you have to be willing to be vulnerable yourself.” He will open a conversation with a CEO by asking: “What’s the dumbest thing you’ve ever done as a leader?” That usually gets them to ask him the same question.
What Chamberlain does with Bob, and what Courage Keepers do with Seekers, is not a technique so much as a discipline: keep asking. Let each answer open the next question, going deeper into cause or broader in perspective. Each response is an invitation.
Asking more questions is important, but Chamberlain has learned that it is even more important to ask better ones. Digging deeper is part of it, but it is important to put in the effort to learn how to ask better questions.
Sometimes the next question drills down. “Why does that matter to you?” Sometimes it opens things wider. “What else might be going on here?” The Keeper knows which direction to go and then has the patience to stay in the conversation long enough to find out.
This is an excerpt from John’s book Courage Keepers – A Guide to Brave Leadership and Inspiring Bold Action in Others coming out in September 2026!