In discovery meetings, not every question moves the conversation forward. In our analysis of over 100 recorded discovery meetings, we found that more than 90% of the questions asked were closed-ended.
Prompts like, “Do you have a will?” or “Are you happy with your current advisor?” may check a box for the advisor, but they rarely open a door. These kinds of questions gather data, not depth. For the prospect, it can feel less like a conversation and more like a checklist.
The best advisors take a different approach. They ask questions that slow things down and invite reflection. Instead of seeking a quick answer, they open space for the prospect to share the story behind the fact.
Questions like, “Tell me about how you decided to create your will,” or “What’s important to you in an advisory relationship?” signal that this is about understanding, not assessment.
These moments can’t be rushed. They require presence, patience, and the willingness to sit with whatever comes up. That’s where trust starts to build. Not in the facts alone, but in the feeling that someone is truly listening.
Asking questions that make prospects think
Not all questions are created equal, and not all conversations invite change. The kinds of questions you ask shape not only what you learn, but what the prospect learns about themselves. Closed-ended prompts tend to trigger quick replies: polished scripts, surface details, minimal reflection.
But open-ended questions interrupt that rhythm. A prompt like “Tell me about…” invites a story. “What led you to…?” opens the door to memory, emotion, and deeper motivation.
When a prospect pauses before answering, that silence isn’t resistance. It’s a signal. They’re thinking, maybe in a new way. And that’s where real discovery begins.
Skilled advisors make space for that pause. They follow threads gently, layering questions like “What else?” or “How did you come to feel that way?,” often surfacing insights the prospect hadn’t yet put into words. Framing matters, too. A question like “Are you worried about running out of money?” narrows the mind. “What would financial peace of mind look like for you?” opens it.
Neuroscience backs this up. Responding to open-ended questions activates broader and more complex brain networks than closed-ended ones. The prefrontal cortex, the brain’s hub for decision-making, memory, and reasoning, lights up as prospects generate original thoughts. They’re doing more than answering. They’re making sense of things as they go.
This effort creates cognitive engagement, which often feels like emotional engagement. What may look like a pause is actually mental scaffolding being built in real time.
By contrast, closed-ended questions trigger recognition and recall, faster, easier, and far less revealing. Advisors who get this do more than ask smart questions. They shape spaces where better thinking can happen.
Why thinking matters in discovery
Thinking is where change begins. When a prospect is asked a question they haven’t rehearsed, they share more than information. They begin to engage with their own thinking in a deeper way. They start connecting financial facts to personal values, past decisions to future possibilities. “I have a trust” becomes “I wanted my kids to have what I didn’t.”
Many advisors stack questions, firing off two or three in a row without waiting for a response. That overloads the prospect and short-circuits real reflection.
These responses often go beyond surface-level answers. They mark a shift, moments where understanding deepens and something meaningful starts to take shape. When prospects reflect aloud, trust builds. They don’t feel examined or judged. Reflection creates emotional safety, and emotional safety makes honesty possible.
And the more they think, the more it becomes theirs. Decisions anchored in personal insight tend to stick, because they’re self-generated, not advisor imposed. Prospects leave with answers, and a sense of conviction. That’s the shift discovery is designed to create.
The risk, and power, of ‘why’
“Why” can be illuminating, but it can also be provocative.
A question like “Why haven’t you saved more?” makes a prospect brace. It sounds like judgment, even if it isn’t.
The alternative is curiosity over critique. Asking “What has shaped your approach to saving over the years?” or “What led you to that decision?” lands as an invitation, not an interrogation.
Used thoughtfully, “why” uncovers motivation. Used carelessly, it creates resistance. The difference is tone, timing, and trust.
Reaching the why beneath the what
Moving from surface concerns to deeper meaning often depends on more than a single question. It takes a thoughtful sequence that builds trust and invites reflection. Some advisors use a simple tool we call the Insight Ladder, a conversational rhythm that gently guides prospects from facts to values.
It starts with an open-ended question, something straightforward like, “What’s your biggest concern about retirement?” That’s the first rung, naming the worry.
But the power comes in the follow-up. Asking, “Why is that important to you?” or “What makes that a top priority?” invites the prospect to connect the concern to something deeper. The follow-up question creates space for the prospect to reflect, often uncovering motivations that aren’t immediately visible. Facts start to take shape as values. Worries become windows into what really matters.
Sometimes that second question opens everything. Other times, a softer approach works better: “Tell me more about what’s behind that,” or “What’s driving that for you?” The wording can shift, but the goal is the same, creating space for reflection and revealing the motivations that guide financial choices.
‘How can I help you?’
One common opening question advisors like to ask is, “How can I help you?” On the surface, it sounds warm and empathetic, even generous. But this question is more flawed than it appears.
First, it centers the advisor rather than the client. By leading with I, the question subtly reorients the conversation around the advisor’s role, availability, and usefulness. The prospect is asked to engage with you before they’ve even clarified what they are thinking, wanting, or concerned about.
Instead of opening space for the prospect’s reality, it puts them in the position of needing to articulate how you fit into their picture, when, more often than not, they’re still trying to form that picture themselves.
Second, this question assumes a level of clarity that many prospects don’t yet have. It presumes they understand both the nature of their concern and the breadth of ways an experienced advisor might help.
But that’s rarely the case. Most prospects arrive with a mix of vague unease, partial questions, and tentative priorities. They may not yet have the language, or the confidence, to name what’s most important.
So while “How can I help you?” sounds helpful, it often falls flat in practice. It invites a canned answer or forces the prospect into a premature role: that of a client who already knows what they want and how to ask for it.
A more skillful question begins where the prospect actually is. What are they noticing about their financial concerns or aspirations…right now? What have they been thinking about lately? What’s prompted them to have this conversation today?
These types of questions locate the prospect in their own experience, and from there, the conversation can build.
Phrasing difficult questions with care
Even a powerful question can fall flat if phrased poorly. Tone matters. Timing matters. Word choice matters. Instead of “Why did you do that?,” try “What led you to that decision?” Instead of “You should consider...” try “I’ve seen others find success with...”
Reframe challenges as invitations: “Are you sure that’s the right plan?” becomes “Would you be open to exploring a few other options?”
And when emotions run high, shift the timeline. “What mistakes have you made?” becomes “If you could go back 10 years, what would you do differently?” Good questions feel safe. Great ones bring agency to the prospect.
Bringing it into the room
You don’t need to change your entire approach to improve discovery. Start by asking better questions.
Before your next meeting, review a recorded conversation. How many of your questions invited real reflection rather than simply collecting facts? Then, prepare three open-ended questions in advance. When you ask, give the question space. Pause for a full three seconds. Let the prospect think.
It’s easy to unintentionally rush this moment. Many advisors stack questions, firing off two or three in a row without waiting for a response. It might sound like, “What’s most important to you about retirement? Is it freedom? Time with family?” That overloads the prospect and short-circuits real reflection.
Ask one question. Then stop. Let silence carry some of the weight.
One final challenge: Change one question in your next meeting. Replace a fact-finding prompt with one that invites reflection. Then watch what happens. That moment when the prospect stops reacting and starts thinking is where real discovery begins.
Thoughts to carry forward
- Closed-ended questions trigger reflex and shut down engagement, while open-ended questions invite reflection, emotional honesty, and deeper insight.
- When prospects pause to think, they move from rehearsed answers to personal truth, and that’s where real trust and transformation begin.
- Techniques like asking follow-up questions, careful phrasing, and reflective silence help advisors surface values and turn conversations into moments of meaningful discovery.