How to Foster Open Dialogue About Client Pain

I’ve developed a repeatable framework that consistently gets prospects to open up about pain points and acknowledge the impact. 1. “Menu of Pain” Questions: Instead of asking generic things like “What keeps you up at night?”, I list the three most common problems I solve and let the prospect choose. I’ll say: “Typically, when I speak with others in your role, they’re facing challenges like A, B, or C. Which one is most relevant for you?” By giving them a menu, I keep the conversation focused, demonstrate expertise, and make it easier for them to open up. 2. The “Magic Moment” Question: Once a problem surfaces, I’ll ask: “When was the moment you realized that was a problem?” That question always gets a story. And stories give me context, emotion, and insight into what actually triggered the pain. It’s one of the best ways I’ve found to connect tactical issues to their larger business implications. 3. Humbling Disclaimers: I’m not afraid of bold questions, but I always preface them with humility. I might say: “I know this may be a direct question, but would it be ridiculous to assume this issue needs to be fixed to hit your goals this quarter?” That disclaimer softens the delivery, makes the question palatable, and gets me honest, candid answers. I’ve found that you don’t need 20 impact questions - one or two, framed the right way, can uncover massive problems that drive urgency. 4. Transparency on Next Steps: At the end of discovery, I want transparency, not ambiguity. I’ll often say: “People usually take these calls for one of a few reasons - just researching, needing to solve something immediately, or somewhere in between. Which bucket are you in?” That way, I either secure real next steps with someone serious or I gracefully qualify out. For me, it’s better to know the truth than chase a deal that isn’t real. Stay curious.

On #WorkingWithClients | I employ something called a 3 to 1 ratio when working with clients. When a client asks me a question, I have to ask three clarifying questions before I give one response. This does three things: 1.) It slows my processor down. My initial inclination is to solve the client's problem. And boy, does my mind race with all types of plausible solutions. Utilizing the 3 to 1 method helps me self-regulate my excited emotional state while not triggering that of the clients. 2.) Over the years, I've learned that hearing the client and listening to the client are separate activities. When I hear my clients, my biases and interpretations of what they say usually get in the way of my judgment. When I listen to the client, I navigate an empathetic process to deliver a compassionate solution. 3.) Lastly, compassion can only happen when I genuinely understand and feel the spirit of my client's needs. I can only do this effectively by asking follow-up questions that allow us to get closer to the truth about my client's situation. Remember, story truth and factual truth can be the same to the client because they are speaking to the emotion of their experience. I aim to work from story truth to factual truth and back to story truth again. Where does this come from? When I worked at LaGrange College (circa 2008/2009), our college President, Dan McAlexander, gave a presentation on engaging dissonance. He used the metaphor of peeling the onion to identify friction points in the workplace—we could only understand and solve a problem by understanding it two to three levels beneath the surface. Given my role working with families and students, it made sense to treat them in the same manner. I haven't looked back since and have encouraged thousands of young financial professionals to do the same. Cheers! Dr. Thomas

Looking to break in or stay in medical sales? Repeat after me: Seek first to understand. Then be understood. Think less pitching. More asking. Until you understand your customer- their workflow, their pain points, their preferences, their motivations- you’re just guessing. And guesses don’t close business. Insight does. Insight comes through thoughtful, well-timed, open-ended questions. And the discipline to actually listen to the answers. This isn't passive listening. Don’t just wait for them to stop so you can respond. This is active, locked-in listening. The kind where you're not just nodding, you’re learning. Where you pause, reflect back, and clarify. “What I’m hearing you say is your team prefers X because Y, is that right?” That alone can build trust. Be the one who actually hears them. Here’s 10 simple but powerful questions to open things up: 1. Can you walk me through how you currently handle [X]? 2. What’s working well for you right now and what’s not? 3. What does success look like for your team? 4. What’s something you wish was easier in your day-to-day? 5. How do you evaluate new products or technologies? 6. What’s most important to you in a partner or vendor relationship? 7. Where do you see things heading in your practice over the next 6–12 months? 8. What’s been your experience with [competing product]? 9. If you could wave a magic wand and fix one thing in your current process, what would it be? 10. Can I ask a follow-up question about that? Notice- none of these are pushy. They’re not designed to trap or corner. They’re designed to understand. And once you understand you can respond, position, educate, and ultimately serve. Because in this job, when you ask better questions, you gain the intel to make better decisions. Get after it and lmk what you’d add! 👊

Had an interesting conversation last week with a founder who was ready to walk away from a client a few months ago. The issue? A massive misunderstanding on project scope that spiraled into a heated argument. Instead of calling it quits, he did something simple but worked- He called the client and started with, “I think we’re misaligned. Help me understand where things went off track.” No defensiveness. No excuses. Just a question. It defused the tension immediately. They laid out all the frustrations, and he just listened. Next question - “What does success look like from here?” That one shifted the conversation from blame to solution. They ended up not only saving the relationship but also closing a bigger deal with them the following month. It made me realize this: Most client conflicts aren’t about the actual problem. They’re about feeling unheard and misunderstood.. Similar to personal relationships outside of work. I’ve seen this happen and workout by doing the following- Acknowledge the frustration. Even if you disagree. Ask what success looks like. It shifts the focus from the past to the future. Make a commitment—and follow through. Even if it’s just a small step, action rebuilds trust. Conflicts are going to happen. But if you lean into them with curiosity instead of combativeness, you’ll not only solve the issue but also strengthen the relationship. What do you do when you're lost in the woods ? Start with one step.