Most discovery calls die in the first five minutes - not because buyers lie, but because reps don’t dig. They hear “we need a better AI strategy” and move on, missing the gold buried underneath. The best reps don’t chase random pain points; they use smart, layered questions that peel back motivation, reveal executive-level problems, and set up demos that actually convert.

Today’s playbook breaks down six “dangerous” discovery questions that turn surface-level chatter into six-figure deals.

SALES

Most reps ask a discovery question like “What are your biggest challenges?”

They get a surface-level answer like “we need a better AI strategy.”

And then… they move on.

But a great rep turns a surface level problem into a 6-figure problem with deeper questions.

Thing is that’s easier said than done. We’ve interviewed the best sales reps out there and there is an art to drawing out pain through discovery questions.

So today, we’re breaking down 6 dangerous discovery questions you can use to uncover massive business problems in your next deal:

Let’s get into it.

The first five minutes of any discovery call is your opportunity to understand your buyer’s motivation and steer the direction for the rest of the call.

Here’re a few of my favorites I’ve heard over the years to ask off the bat:

This question is intentionally broad and gives you a ton of information right out the gate.

If for example they say they’re looking for a partner to help build their tech strategy - then you just found exactly where to start your discovery process (instead of fishing for every random problem you could solve).

A lot of people think you can’t ask this for outbound calls. But the reality is you can and should because they took the call for some reason:

"I know I emailed you last week, I’d think you don’t take meetings with everyone that emails you, what prompted you to take this one?”

A customer will often come with something they want to do. But that’s not a problem.

Uncover the motivation behind the need with this question:

“Okay, you’re looking for a partner to help you build a technology strategy. What’s motivating you to look in the first place?”

They’ll either admit there’s a business problem behind their evaluation or that they’re just window shopping… which tells you if their need is even worth chasing.

Once you’ve uncovered their initial problem and why they care, you uncover specific challenges and business impact with these questions:

After you’ve uncovered the main problem, you can suggest 3 bigger executive problems:

“Most CIOs I talk to run into three challenges when building a tech strategy — making data usable, keeping things secure, and budgeting to support the vision. Which one’s toughest for you right now?”

This explains why the problem is even worth solving.

Now you know specifically what they’re challenged with and what to dig deeper on.

Everyone says stories sell. That’s because stories often involve emotional pain.

The easiest way to get a story is to ask this question the moment your prospect admits a problem:

“I can't imagine that you woke up earlier this week and you were like, we've got to fix this insurer billing issue. When was the moment that you realized this thing was something you had to fix.”

They’re likely to reveal a story with visceral, detailed pain — like a $200K insurance bill that never got paid. That’s exactly the kind of problem that warrants a six-figure solution.

Now that you’ve uncovered a specific, executive-level problem, it’s time to ask two final questions that set you up for success in the demo:

This question tells you whether the executive-level problem you uncovered is impacting anyone beyond the person you’re speaking with.

That way you know exactly who needs to be in the demo, here’s exactly how to ask it:

“Who else is getting driven crazy by this? Do you feel like Mark on the security team is feeling it too?”

When you name-drop someone, they don’t have to mentally scan the org chart — they just confirm, “Yeah, Mark’s dealing with it too,” and you’ve got another stakeholder to include in your future demo.

Before you demo, figure out exactly what they need to see:

"I have to imagine you’ve given some thought to how you want your new technology strategy to look.

Honestly, there’s a ton I could show you in the demo — but as you think about your wish list, are there specific things you’re really hoping to see or do? I want to make sure we hit those.”

Now you know what to prioritize in the demo — what to show, what to skip, and what’s going to actually move the deal forward.

And that’s a wrap folks!

HEADLINES

→ Automated sales follow-ups: How to close more deals with less effort

SOFTWARE

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That’s all for today.

Until next time,
Team B2B Whales

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