Essential Follow-Up Questions for Client Interviews

Stop Asking Clients What They Have  Start Asking Them What They Want Why Financial Advisors Need to Master High-Impact Discovery Questions “The quality of your questions determines the quality of your relationships.” Most advisors are great at fact-finding. Assets. Income. Retirement goals. That’s important—but it’s not enough. Here’s the part we don’t talk about enough: The quality of your questions determines the quality of your relationships. Want better referrals? Want higher client retention? Want to uncover held-away assets? Then ask better questions. High-impact discovery questions go beyond numbers. They uncover emotion, motivation, fear, legacy, identity. Try these: “What do you want your money to do for you?” “What’s a financial decision you regret—and why?” “When you think about your family 10 years from now, what do you hope is different?” “What keeps you up at night that most people wouldn’t guess?” They’re business-building questions. They lead to deeper trust—and trust leads to action. 💡 Aha moment: Most advisors are trying to give better answers. The best advisors are learning to ask better questions. Stop filling out a form. Start opening a conversation. Because the best discovery questions don’t just collect data. They create insight. And insight is what makes you unforgettable. Actions You Can Use Tomorrow: ✅ Replace data-first questions with meaning-first questions Instead of asking: “How much do you have in retirement accounts?” Start with: “What does retirement look like for you?” (Follow-up: “Why is that vision important to you?”) ✅ Start every discovery meeting with one deep-opening question “What would make this relationship feel incredibly valuable to you—beyond just investment returns?” (This instantly uncovers expectations, values, and service opportunities.) ✅ Use the “Before and After” Frame “Before we dive into numbers, can I ask—what would a great outcome from our work together look like for you a year from now?” (This sets a future-focused, client-centered tone.) ✅ Introduce emotion into financial priorities “When you think about money, what emotion shows up most often—stress, excitement, confidence?” (Then ask: “Why do you think that is?”) ✅ Turn hesitation into a trust opportunity When a client seems unsure or vague: “That pause tells me something—can we explore that a little?” (This validates their hesitation and invites honesty.) ✅ Add this question to every client review “Has anything changed in your life that I should know about—even if it doesn’t feel financial yet?” (Captures early-stage changes before they become major events.) 🔁 Practice This as a Habit (Bonus Tip) Tomorrow morning, write down 3 high-impact questions on a sticky note and bring it to every client meeting. Pick one to lead with—before talking numbers. Even if nothing else changes, this one habit can dramatically deepen your client engagement. 👉 How will you use this guide to develop your client relationships?

Ever ask your customers to grade your work? 🔠 "Would you give us a grade A-F on how we are doing?" Their first answer is interesting. The follow-on discussion is where the gold is. Assuming the world isn't on fire, customers will usually give you somewhere between a B- and a B+. If you get anything below a B-, there is work to be done. Anything over an A- and you've got a potential advocate who you should be activating. Be careful to use the correct pronouns; you are asking them to grade the company ("we") not your personal performance ("I"). After they give you their grade, dig in: ➡ "What is the main reason you gave us that grade?" ➡ "What would it take to for us to move up 1/3 of grade?" ➡ "What grade do you wish you could give to us?" ➡ "What's one thing we could do to improve?" ➡ "How do you typically grade your vendors?" ➡ "Which vendor consistently rates an 'A' for you? What do they do that makes them stand out?" ➡ "Have we consistently been at that grade since you started working with us? Are we trending up or down?" ➡ "Let's pretend you are renewing tomorrow. Does the grade you gave us warrant your renewal?" First-level discovery questions are important. Second and third-level questions is essential. Oh, and for my international friends where letter grading may vary by region, feel free to substitute a score of 1-10. Works essentially the same. #customersuccess

Never wait until a "renewal call" to ask a customer to extend or renew their contract. By then it's too late. Instead, have a "step-back" convo 4 - 6 months into the relationship to uncover hidden risks and insights to ensure the renewal and inoculate against surprise churn. What is a step-back convo? 👉 Uses truth-sparking questions about THEM to drive engagement and trust, and uncover actionable insights. 👉 Occurs sometime during the first half of the relationship (like 4 - 6 months into a one-year contract). 👉 Either a standalone meeting or a 10-minute agenda item during a regularly scheduled meeting. Here's your mini-playbook for step-back convos: ❓ "We'd love to take a step back and get your perspective on a few topics above the day-to-day. I'm wondering, what's the biggest thing that surprised you since you started working with us?" In my experience, about half the time it's a positive surprise. This is great because you can pursue why it was so positive and how working with your company has led to their desired business outcomes. This info comes in handy when you do ask them to renew their contract. And of course a negative surprise means you should dig in to understand how it is impacting their world and offer potential solutions. Here's the second question to ask during the step-back convo: ❓ "If you got an outreach from our competitor tomorrow, how would you react on a scale of 1 - 5 where 1 = ignore and 5 = you'd pretty quickly get back to them to learn more?" No matter what number they give, instead of assuming what they mean by it, ask this follow-up question: ❓ "Is there something a competitor might mention that would definitely get your attention and cause you to get back to them?" Their response will help you identify gaps in your product or service that may be important to their decision. Once again, this keeps you ahead of the game because you can address their perceptions and concerns either on the spot or in subsequent meetings in advance of the renewal conversation. Lastly, make sure to say this: "Thanks for being so candid. That's exactly the type of info we are looking for." This rewards the behaviors you want from them - transparency, candor, and authenticity. -------- Having a step-back convo gives: 👉 The customer a chance to open up in a non-sales context where they tend to be more relaxed and transparent. 👉 You an opportunity to course correct if their perceptions are not where they should be. 👉 You the insight into the benefits they're getting from your solution, so you can double down on those leading up to the contract renewal date. --------- Hey #customersuccess and #accountmanagement professionals: Want ALL 25 questions, tips and techniques for having more strategic and revealing step-back convos? Take my Radically Authentic Discovery Online Course. Just visit my profile and click the “upskill” link.