Discovery Meeting Agenda: Structure For Establishing Trust

A well-executed discovery meeting agenda, in some cases, can feel like a planned interrogation.

You may feel like you’re asking question after question after question—and you are.

Of course, you’ll want to pause, share relevant examples, and talk about your product or service when appropriate. But at its core, a strong discovery meeting agenda is built around asking great questions.

Why a Question-Driven Discovery Meeting Agenda Works

If you ever think, “Jeepers, I’m asking a lot of questions, I’m interrogating this prospect,” that’s okay! When you sense that, take a breath.

You can even say to your prospect:

“I know there are a lot of questions here, but I’m just really interested in your unique situation.”

From there, continue with your questions—because the best way to learn about your prospect is to listen. And believe it or not, by asking deep, thoughtful questions, you’ll build trust and position yourself as the right solution to their challenges.

Many sales professionals make the mistake of jumping straight into a pitch, but the most effective way to engage a prospect is by asking deep, thoughtful questions. Here’s why this approach is so powerful:

• It builds trust. People trust those who take the time to understand them. Asking the right questions shows you care about their unique situation.
• It uncovers real pain points. Prospects often don’t fully articulate their challenges upfront. Digging deeper helps reveal their core concerns.
• It keeps the focus on them. The more your prospect talks about their needs, the more invested they become in the conversation—and in finding a solution.

Key Elements of a Strong Discovery Meeting Agenda

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To make sure your discovery meetings are both effective and engaging, follow this structured agenda:

1. Set the Stage (3-5 Minutes)

Begin by creating a comfortable atmosphere:

• Thank them for their time
• Outline the purpose of the meeting
• Let them know you’ll be asking a lot of questions to better understand their needs
• Get their buy-in: “Does that sound good to you?” This prepares them for the conversation and reduces any discomfort from the number of questions you’ll be asking.

2. Ask Thoughtful, Open-Ended Questions (15-20 Minutes)

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Questions are the heart of the discovery process. Focus on:

• Their current situation – “What’s working well for you right now?”
• Challenges & frustrations – “What’s your biggest obstacle when it comes to [problem]?”
• Goals & priorities – “If we were to fast-forward six months, what would success look like for you?”
• Don’t be afraid of the interrogation feeling—this is where real insights happen. If you sense hesitation, simply say:
  “I know I’m asking a lot of questions, but I’m genuinely interested in your unique situation.”

3. Share Relevant Stories (5-10 Minutes)

Once you’ve gathered enough information, connect their challenges to real-world examples:

• Case studies
• Testimonials
• Success stories from similar clients – This reassures them that you’ve helped others in their situation before.

4. Discuss Next Steps (5 Minutes)

Wrap up by:

• Summarizing key insights from the discussion
• Outlining potential solutions (without diving into a hard sell)
• Setting clear next steps

Try This: Apply the 80/20 Rule

A great discovery meeting follows the 80/20 rule—your prospect should be talking 80% of the time, and you should be speaking only 20%.

👉 Challenge yourself: In your next meeting, focus on asking one more question before offering your insights. You might be surprised by what you uncover.

Dive Deeper Into Discovery Meetings

© Shawn Casemore 2025. All Rights Reserved.