🎯 ask better questions

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Discovery questions that dig deeper

Brian LaManna provides actionable discovery call strategies to help salespeople maximize learning and guide conversations effectively.

Start with these 3 discovery questions

⇢ How did you determine ___ was #1?
⇢ How is ____ showing up in the business today?
⇢ Where is that today and where are you hoping to get it to?

These questions uncover the prospect’s current state and ideal future state, setting a solid foundation for your conversation.

Follow up with these questions

⇢ Have you done the math on what that would be worth if you got ___?
⇢ What have you tried so far to solve that?

These questions help to quantify the potential value and understand previous attempts to solve the problem.

Tier 2 questions to deepen the conversation

⇢ What are the biggest challenges you’d regret not solving in the next ___ days?
⇢ How long has ____ been happening?
⇢ When you think about this year, what are we driving towards?
⇢ If we were able to help solve that, why would that be important?
⇢ How would not achieving ____ derail where we are headed?

These questions drive urgency and a sense of missed opportunity, making the conversation more impactful.

Maximize learning, minimize talking

The prospect should be speaking 60-70% of the time. Focus on asking the right questions and letting the prospect share their thoughts and challenges.

Avoid discussing your product early in the conversation.

Questions to ask during the discovery process

Jeremy Miner breaks down exactly what to ask in discovery to get prospects to open up, reveal real problems, and build urgency.

Repeat emotional words

When a prospect says they’re “frustrated,” “annoyed,” or “stressed”:

✔ Just repeat the word: “Frustrated?” or “How do you mean by stressed?”
✔ This triggers them to explain in more detail
✔ It surfaces emotion and opens them up

Don’t overthink it—mirror the word, then pause.

Clarify timelines and impact

Use these to dig into the pain:

✔ “How long has that been going on?”
⇢ Makes them relive how long the issue has lasted
✔ “Has that had an impact on you?”
⇢ Pause after “impact”—this makes them think deeper
✔ “In what way?”
⇢ Forces them to go specific

This helps them feel the cost of inaction.

Pull out urgency and motivation

Ask questions that connect the issue to timing and personal stakes:

✔ “What’s causing this to happen?”
✔ “What’s prompting you to look into this now?”
✔ “Why is this so important to you now though?”
✔ “What would it mean to solve this?”
✔ “What’s in it for you to implement this at your company?”

These make it emotional, not just logical.

Uncover blockers and failed past attempts

Look for signs they’ve struggled before:

Prospect: “We’ve been trying to get this project going for months.”
You: “Trying? What hasn’t worked for you so far?”

⇢ That word “trying” signals frustration—dig in
⇢ This opens space for them to vent and builds your credibility to help

You’re not prying—you’re helping them verbalize what’s not working.

Lead discovery calls with insightful questions

Chris Orlob offers insights on how to ask better questions when engaging C-suite executives, based on his experience closing large deals.

Ask different questions for C-suite

Avoid asking the same questions to C-suite executives as you would to mid-level buyers.
C-suite executives need questions that make them think, not just answer.

Lead with insight

Instead of asking generic questions, lead with an observation based on research.

For example: “I see you’ve been in the COO role for three months, focusing on consolidating your sales team. How are you preparing your team for the shift?”

✔ This approach commands attention and starts the conversation with a relevant, specific insight.

Be perceptive and thoughtful

Ask questions that show you understand their challenges and anticipate problems.

For example: “How are you planning for sellers to adjust to new roles with more complex discovery?”

✔ This shows you’re thinking beyond the surface and addressing their unique situation.

Focus on problems, not products

Ask questions that highlight the issues they face, not how your product can help.

For example: “What’s the biggest challenge in integrating a unified sales team?”

This keeps the conversation about their needs, not your solution.

Make them think or feel

Good questions spark a reaction—either make them think or trigger an emotional response.

You want the prospect to lean in and feel like you understand their struggles.

✔ Their voice should change, or they should respond with enthusiasm.

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