🔑 discovery = pipeline

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How to structure discovery calls that land

Chris Orlob turned a cold, painful discovery call into one of his best by using structure, empathy, and a compelling problem narrative:

Warm up a cold buyer without pushing

The call started rough. The VP was closed off, giving short answers and showing no interest.

Chris didn’t jump straight into questions.

Instead, he acknowledged her likely expectations:

➤ She didn’t want to be interrogated.
➤ She’d probably prefer hearing context first.

So he set a light agenda:

→ First, a few slides on the problems they solve
→ Then, turn the conversation to her world

She agreed. That reset the tone of the call.

Lead with insight, not a pitch

The deck had nothing about products.

It focused on:

✔ Market trends in revenue orgs
✔ Common struggles sales leaders are facing
✔ Skills most teams are missing today

He paused often to ask questions and stop screen sharing, making it a conversation - not a monologue.

Once context was set, he turned it over:

→ “Enough about what we solve. Help me understand your unique challenges.”

The VP opened up.

The rest of the call became a rich back-and-forth - no more pulling teeth.

What worked (and why most reps miss it)

✔ You have to earn the right to ask questions

If you go outbound and open with discovery questions, it feels like an ambush. Cold buyers won’t engage unless they trust you first.

✔ Set expectations before diving in

Orlob named the dynamic: she likely didn’t want to be grilled. By saying, “Let me give you context first,” he flipped the power dynamic.

✔ Use a strong “pain narrative” instead of a demo

Walking through industry problems helped her feel understood. She saw her story in his deck. That built trust.

When your problem framing resonates more than their own self-diagnosis, they’ll start to lean in.

Kick off discovery with confidence

Matt Macnamara discusses how to lead the first minutes of a discovery call so you always stay in control and build client’s trust fast:

The "Buy the book" Script

Matt's go-to agenda script includes four critical parts:

✔ Check for time constraints

→ “I have this down for 60 minutes…any hard stops we should be aware of?”

This prevents rushed endings or missed next steps.

✔ State the primary end goal

→ “I want to learn how you're managing your [process today], and if it makes sense, walk through how we might help.”

Clear goals help avoid wandering conversations.

✔ Lay out the main agenda

→ What you’ll cover, and in what order.

Tailor the demo based on their specific context.

✔ Set up a mutual decision

→ “By the end, I’d love for us to either agree on a good next step - or not. Totally fine either way. Sound fair?”

This removes pressure and makes closing natural.

The “To-the-point” script

A more casual version with the same structure:

➤ Confirm time availability of both parties.

➤ Walk through what you want to cover.

➤ Offer to customize based on their needs.

➤ End with: “What’s one thing you want to accomplish today?”

Great for reps who want something lean but still structured.

The “Honest AF” script

This one’s bold - and not for everyone. But it works:

➤ Ask for their primary expectations first.

➤ Then say: “Let me share all the reasons folks like you don’t buy from us, so you get the bad news up front. If it’s not a fit, we both save time.”

This diffuses tension and creates space for a real conversation.

Key discovery lessons:

✔ Webcam on always

→ Closed deals use video 41% more than lost ones.

✔ Don’t skip the agenda

→ It’s the guide roadmap for a productive call.

✔ Set the outcome early

→ That way, the closing outcome isn’t a surprise.

Just a taste of what Premium gets you

Move from symptoms to real problems

Richard Smith explains why outbound discovery often fails and gives five questions that uncover real pain from cold prospects.

Why outbound discovery breaks

Inbound prospects know their problem.

They’re already looking.

They’re ready to talk.

Outbound prospects don’t know you.

They aren’t sure they have a problem.

They don’t feel urgency.

Most reps ask too early, too fast.

That leads to vague answers and flat calls.

These five questions change that.

Five questions that work

1. “What motivated you to carve out time for this today?”

⇢ Start with their reason. Let them lead.

2. “You mentioned interest in coaching… what triggered that feeling?”

⇢ Go past the click. Find the moment that sparked action.

3. “When you say discovery is a gap, can you tell me more about that?”

⇢ Most problems shared first are not the real ones.

4. “I don’t want to assume it’s a big issue - but usually when I hear ‘weak discovery’, it means lost deals that should’ve been won. Is that what’s happening here, or something else?”

⇢ Show them you’ve seen the pattern. Make it easy to agree or correct.

5. “Just so we know if this is worth solving… how’s this affecting quota attainment right now?”

⇢ No numbers means no urgency. Connect pain to impact.

These questions open cold prospects.

They don’t assume. They guide.

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