Most sellers unknowingly ask cringey, leading sales questions that make prospects internally groan—like:

👉 “What would you do with all that time back in your calendar?”

Yikes. Let's do better.

Instead of pushing prospects into a corner, great sellers guide them through the 4 levels of problems in discovery:

1. Situation – How they literally do the thing
2. Operational Problem – Something painful in their workflow
3. Executive Problem – Bad news a VP has to explain to the CEO
4. Business Impact – A C-Level metric, risk, or initiative

Now, the real magic: asking the right questions to uncover six or seven-figure problems without sounding like a salesperson.

Here’s how:

1.  Ask why they took the call (twice!)
   "You probably don’t take every call that comes your way. What made you take this one?"

• If they mention a lead source → Ask why again
• If they describe a situation → Offer multiple-choice options
• If they state what they want → Invert the feature-benefit

2. Use ‘Magic Moment’ questions to move from operational pain to executive problems
   "…you probably didn’t wake up in a cold sweat thinking about renewal tracking. When did you realize this was a problem? Did you renew software you didn’t need, overbuy licenses, or was it just a gut feeling?"
3. Use push-pull questions to turn executive problems into business impact
   "You mentioned reducing software spend from $1.5M to $1M was a key priority. Would sorting renewals put a real dent in that, or is there a bigger play you’re planning?"
4. (Implied multiple-choice question to pinpoint the real issue)

“Typically, when someone's worried about tracking vendors on spreadsheets, it's because they’re struggling to track existing renewals or control new spend. Which is it for you?”

No pressure. No salesy vibes. Just real business conversations.

Oh, and I actually had 7 killer discovery questions but had to trim it down to 4 for this post. Want the rest?

Drop a “Discovery” in the comments, and I’ll send you my 7 Discovery Questions That Don’t Feel Like Sales Questions Toolkit.