The Two Most Important Questions in Discovery

Editor’s note: Join Chris Holman for his two-day Discovery Meeting Workshop, being offered September 8–9. Learn more and register here.

When most advisors prepare for a discovery meeting, they focus on building a list of questions to ask the prospect. That’s reasonable. After all, good discovery requires listening, probing, and surfacing what’s not immediately obvious.

But the most important questions in a discovery meeting aren’t directed outward. They’re the questions the advisor asks themselves.

These fall into two categories: self-checks to guide your posture, and core questions to keep you on track during the conversation.

Why? Because no matter how well you script your external questions, the real leverage lies in how you show up to the conversation. Your presence, your posture, your ability to create safety and elicit truth, and your skill in guiding toward clarity without rushing to diagnosis.

In other words, your internal orientation determines the depth and impact of the external exchange.

Trust and clarity: The real work of discovery

At its core, a discovery meeting has two essential aims:

1. To build trust
2. To establish shared clarity

Trust opens the door. Without it, prospects withhold, perform, or comply without commitment. Clarity walks you through the door, making it possible to see the real landscape, name the real constraints, and agree on what needs to change.

If you don’t reach mutual clarity, even the warmest conversation won’t move anything forward.

These aren’t passive outcomes. They have to be earned through the advisor’s choices: how they listen, what they notice, when they press, and where they pause.

So how does an advisor know they’re on track?

By returning to these two sets of questions. Not once, but throughout the conversation.

Internal question 1: Am I earning the right to this conversation?

Trust isn’t just about rapport. It’s about safety, respect, and the felt sense that the advisor is here to help the prospect, not judge, pitch, or impress.

Use these questions to check your own posture:

• Do they feel heard, not just listened to?

  Are you reflecting back what they’ve said in their own terms, or subtly reshaping it to fit your framing?

• Have I reflected their language without distorting meaning?

  Mirror their vocabulary and emphasis. It shows you’re paying close attention.

• Have I acknowledged their context before offering perspective?

  Don’t rush to “solve” before you’ve fully seen the terrain.

• Have I made it safe for them to be honest, even about things that are messy or uncertain?

  People don’t open up unless they trust they won’t be judged for what they say.

• Am I speaking with them, not at them?

  Avoid the trap of sounding like a pitch deck with a pulse.

• Have I signaled respect for their intelligence, experience, and role?

  Treat them as a peer in the process, not a subject to be fixed.

• Do they seem more open at the end of this conversation than at the start?

  That’s the real sign of earned trust: increased openness, not just agreement.

Internal question 2: Are we seeing the real picture together?

Clarity isn’t just data. It’s mutual understanding of what matters most, what’s not working, and what might be possible.

These questions help gauge whether you’re getting there:

• Have I asked questions that go beneath the surface?

  It’s easy to stay on the level of symptoms. Clarity lives at the level of causes.

• Am I clear on what problem they’re actually trying to solve, and are they?

  Misdiagnosis happens most often when clarity is one-sided.

• Have I surfaced any tensions, contradictions, or gaps without rushing to resolve them?

  Let discomfort breathe. That’s often where the truth is hiding.

• Have I avoided premature framing or diagnosis?

  Resist the urge to label too quickly. Discovery isn’t a race to the proposal.

• Did I get to the “why now” behind this conversation?

  There’s always a reason this meeting is happening today, and not six months ago. Find it.

• Have I challenged assumptions constructively?

  Clarifying questions are often more powerful than definitive answers.

• Can we both clearly articulate the stakes of doing nothing?

  Until that’s clear, urgency will remain manufactured, not felt.

Two core questions to stay oriented in discovery

If you remember nothing else, let these two questions be your constant touchpoints throughout the meeting:

1. Am I deepening trust, or just collecting information?
2. Are we uncovering clarity, or just circling what’s comfortable?

When you feel the conversation drifting, re-center on these. They’ll pull you back toward the real work of discovery.

A different kind of preparation

Instead of preparing just a list of questions to ask the prospect, prepare yourself. Walk into the room with these self-checks top of mind. Print them. Carry them in your notebook. Review them in your car or on your walk beforehand.

They’ll do more than guide your behavior. They’ll shape your presence of mind. And it’s your presence of mind, not a sales spiel, that earns the right to lead the next conversation.