Stop Asking Surface-Level Questions: How to Win More Discovery Calls

I’ve done countless discovery call coaching over the years

Here’s the #1 thing people get wrong in discovery

Not getting specific enough.

Discovery isn’t just about understanding the pain point and scoping a project. It’s about making sure the prospect understands and internalizes the pain point(s) you address.

Here’s a real-life example I’ve seen many times:

🔹 Me: What’s the problem?🔹 Rep: They don’t have a formal system.🔹 Me: Okay… but does anyone care? If so, who cares? How big of a deal is this? Are there any real consequences?

"No formal system" isn’t a problem—it’s just a description of their reality. You’re job in discovery is to analyze this high level description and digger deeper.

Now, here’s the same conversation with the specificity:

🔹 Me: What’s the problem?🔹 Rep: They lost a couple of clients and aren’t closing leads to replace them like they expected to. They don’t know how to reverse the slump, and if they don’t, they’ll be in a tough financial spot in six months.🔹 Me: We can help with that.

See the difference? In the second version, we:  ✅ Understand exactly what’s happening in their business. ✅ Confirm they recognize the pain, and consequences. ✅ Identified urgency to take action.

Small Axe Ideal Client Highlight:

So, your business is growing, but your exhausted by recreating the wheel every time you need to sell? An effective, repeatable system will help.

We should talk 

Book time here

If you stop at surface-level answers in discovery, you’re leaving too much to chance. You might close the deal—but only if the prospect already understands their problem well enough to act. And trust me, that happens far less often than you’d think.

So, on your next discovery call, don’t settle. Push deeper. Get specific. Your pipeline (and your prospects) will thank you.