xSellerate Blog | Sales, Lead Generation & Business Growth Tips

The Questions Top-Performing Salespeople Ask That Others Don’t

Written by Sean Piggott | Jun 20, 2025 2:00:00 PM

Top-performing salespeople don’t just talk more. They ask better.

Because better questions = better deals.

If your team is stuck in pitch mode, here’s the shift: Train them to ask questions that uncover truth, urgency, and budget.

Here’s a breakdown of what elite reps ask — and why it works.

1. "Why now?"

Most reps ask: “When are you looking to make a decision?”

Top reps ask:

“What’s changed that made you start looking into this now?”

Why it works:

  • Uncovers urgency
  • Surfaces pain
  • Builds emotional connection

2. "What happens if nothing changes?"

This question forces the prospect to picture the cost of inaction.

It drives:

  • Emotional clarity
  • Realisation of stakes
  • Momentum toward a solution

3. "How have you tried to solve this before?"

Why it’s powerful:

  • Reveals buying history
  • Exposes dissatisfaction with past solutions
  • Helps position your offer as different

4. "Who else cares about fixing this?"

Not just about the decision-maker — about the influencers.

Top reps map the full decision landscape. This tells you:

  • Who’s in the loop
  • Who might block the deal
  • Who to align with

5. "What would a home run look like 90 days from now?"

This isn’t about features. It’s about outcomes.

Elite reps help the buyer imagine success.

That creates:

  • Stronger vision
  • Better framing of value
  • More reason to act

Coaching Tip:

Train your team to ask these early in the process — not just at close.

And coach them to listen. Most insights aren’t in the first answer — they’re in the follow-up:

“Tell me more about that.” “Why is that important to you?”

Want to Uplevel the Way Your Team Sells?

Our sales coaching includes:

  • Call reviews
  • Objection handling
  • Advanced question training

We don’t just help you close more — we help you close better.

Book your Free Sales Audit today >>