From Surface to Substance: Mastering Second and Third-Level Questions in Sales

Wayne Johnson
Jun 2
2 min read

We’ve all been there — a discovery call that starts strong but flatlines after a few basic questions. You ask, “What’s your biggest challenge right now?” and they reply, “We’re trying to streamline operations.” You nod. Maybe even sympathize. And then? Crickets.

The difference between mediocre and masterful discovery often comes down to your ability to ask second- and third-level questions — the kind that peel back the layers and reveal the real motivations, pain, and urgency behind the deal.

Why It Matters

In the world of MEDDIC, the quality of your discovery determines the quality of your deal. Metrics, Economic Buyer, Decision Criteria — these don't fall in your lap. You uncover them by digging, probing, and going beyond the surface.

Second- and third-level questions are your shovel.

First-Level vs. Second & Third-Level

First-Level Question: “What CRM are you using now?”
Second-Level Question: “What do you like or dislike about that CRM?”
Third-Level Question: “How do those limitations affect your ability to hit revenue targets or forecast accurately?”

See the difference? First-level gets information. Second- and third-level uncover impact.

Use This Framework: Peel the Onion

Every answer should lead to a follow-up. Try this progression:

Observation → Exploration: “You said operations are a challenge. What’s causing the bottlenecks?”
Impact → Urgency: “How is that impacting your team’s productivity or customer satisfaction?”
Personalization → Consequence: “How does that affect you personally? Are you on the hook for those metrics?”

Quick Cheat Sheet: Elevate Your Questions

Instead of...	Ask...
“What’s the problem?”	“What happens if this doesn’t get solved?”
“Who’s involved?”	“Who feels the pain the most when this breaks?”
“What’s your timeline?”	“What’s driving that timeline?”
“What’s your budget?”	“How was budget handled for similar projects?”

Pro Tip: Embrace the Silence

The pause after a great second- or third-level question? That’s gold. Resist the urge to fill it. Let your buyer think. Let them go deeper.

You’ll be amazed at what comes out.

Your MEDDIC Homework:

This week, challenge yourself on every call to:

Ask at least two follow-up questions after every key response.
Track which questions helped you uncover Metrics, Pain, or the Decision Process.
Reflect: Did I learn something that a competitor likely missed?