01 June 2025
The secret to better prospecting: Ask smarter questions
Good questions can open doors, build trust, and move the conversation forward.
Why questions matter
Questions show prospects that we care about their needs and opinions. The right ones spark curiosity and uncover what matters most to them.
Three power questions for instant rapport
- “What’s your biggest challenge right now?” – Shows empathy and uncovers pain points.
- “What would you change about your current situation?” – Helps them identify areas they’re unhappy with.
- “What does success look like to you?” – Opens the door to positive and aspirational conversations.
Story: The one question that changed everything
A prospect once told me they were “just browsing” and not interested. Instead of pushing, I asked, “What would you change if you could?” That simple question turned into a 20-minute conversation and a signed agreement the following week.
Humour
I asked a prospect, “What’s your biggest challenge?” They said, “Answering all these questions!”
Why do salespeople love questions? Because answers are where the gold is.
My favourite question to prospects: “What do you think of my humour?” (No one answers that one.)
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