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Free Resource: 37 Discovery Questions

Discovery winning prospects respect and deals

Mor Assouline breaks down why “perfect” discovery often leads to ghosting—and how to fix it by creating insight that gets the prospect thinking differently:

Start with insight, not interrogation

⇒ Average: “What’s your biggest challenge with your current solution?”

✓ Better: “I was just talking to another CEO in your space. They told me their biggest frustration was X. Is that something you’re seeing too?”

→ Use insight when starting the conversation, especially with outbound.

Dig itowards impact, not just pain

⇒ Average: “What problems are you having?”

✓ Better: “How do you know that this is an issue?”

→ Move beyond surface pain—uncover the consequences of doing nothing.

Focus on vision, not just current state

⇒ Average: “How are you handling this today?”

✓ Better: “If this problem was gone, what would success look like for you and your team?”

→ Help them visualize outcomes, not just frustrations.

Disqualify instead of overqualifying

⇒ Average: “Do you have a budget for this?”

✓ Better: “What would have to be true for this to not be worth investing in?”

→ When you’re willing to walk away, you build more trust and get to the truth faster.

When prospects say, “I never thought about it that way,” that’s how you know your discovery is working.

The goal isn’t extracting client’s information.

It’s to build clarity and understanding together.

Open using this proven discovery call framework

Chris Bussing discusses a simple framework to nail your first 90 seconds of every B2B discovery call — setting the perfect atmosphere for a high-converting conversation:

Start with a personal touch

➤ Mention something personal you found in your prep

Example:

“I noticed you’re a Bears fan and I’m a Packers fan — is that going to be a deal breaker?”

↳ Lightens the mood instantly

↳ Shows you did your homework

Confirm time commitments

➤ Confirm if the scheduled time remains viable. Add:

“I’ll manage the time and check in at the 5-minute mark to see where we’re at — hopefully, I can get you a few minutes back.”

❖ Builds trust with your prospects instantly

❖ Shows you respect client’s personal time

Set clear, professional agenda

➤ Run through this structure:

1. Quick introductions on both your sides

2. Understand what matters most to them:

   “We did some research, but want to hear what’s important to you.”

3. Provide several ideas on how we might be able to help

4. Have an open discussion with challenges and priorities

5. Decide together whether next steps make sense — and if not, that’s totally fine

» Makes the discovery feel collaborative, not forceful and pushy

» Reduce sales pressure by assurance if there’s no immediate fit

Why this actually works

✔ Checking time availability shows professionalism and respect

✔ A clear agenda demonstrates you’re prepared and focused

✔ Mentioning options to not move forward diffuses sales resistance

✔ Offering to give time back earns credibility with busy sales leaders

This intro sets the tone for a productive call built on respect, curiosity, and transparency.

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Real discovery makes you uncomfortable

Charles Muhlbauer explains that getting better at discovery isn’t about memorizing good questions — it’s about getting comfortable in being uncomfortable:

Discovery is a tough journey

Most reps believe the path looks like:

❖ Knowledge → Comfort → Practice → Progress

But the real journey is messier:

✓ Knowledge → Discomfort → Practice → More discomfort → Slight progress → More practice → Eventually, comfort → Back to discomfort

Great discovery doesn’t come from knowing what to say.

It comes from saying it even when you’re unsure how the prospect will respond.

Disarm the evasive prospect

“I might be off here, but I get the sense this is something you’ve been tasked to explore, rather than something you’re pushing for personally. Is that fair?”

• Forces prospects in revealing their hidden intentions

• Exhibits whether they’re serious or just window-shopping

• Uncomfortable at first, but getting clarity is worth it

Testing costs for real urgency

“Let’s say we fast-forward three months and nothing’s changed — same tools, same process. Is there a cost to that or does it really not make a difference?”

➤ Makes them confront whether status quo is acceptable

➤ If there’s no significant cost, you can qualify them out

➤ If there is, your primary objective getting their urgency

Smooth deals are bad signals

✔ If your discovery calls feel easy, you’re not actually learning

✔ If your questions are comfortable, you’re not deep enough

✔ If every talk lands perfectly, you’re not diving to pontetial risks

The fastest way to improve discovery?

Lean into the discomfort as something normal.

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