10 QUESTIONS FOR EVERY FIRST MEETING
BEFORE YOU START
The goal of a first meeting is not to sell. It's to understand.
Every question below is designed to get the client talking—and to show them you're thinking, not just pitching.
1. What's driving this decision right now?
Gets to the real motivation. Listen for the emotion, not just the logic.
2. Have you looked at other options? What stood out—or didn't?
Tells you what they value and what's already failed them.
3. What would the ideal outcome look like—3 years from now?
Shifts the frame from a transaction to a life decision.
4. What's your main concern at this stage?
Most clients have one core fear. Find it early.
5. What's your timeline—and what's driving it?
Real urgency and stated urgency are often different.
6. Has anything changed recently that's made this more of a priority?
Often reveals the real trigger behind the meeting.
7. What does a bad decision look like to you?
More powerful than asking what they want. Tells you their risk profile.
8. Who else is involved in this decision?
Surfaces stakeholders you need to understand or include.
9. What would make you feel confident moving forward?
Tells you exactly what they need to move forward.
10. Is there anything I haven't asked that you think I should know?
The most important question. Ask it last. Always.
THE SILENCE STRATEGY
After every question, pause.
Count to three in your head before you speak.
It feels uncomfortable. It shouldn't.
That silence is where clients tell you the truth.
Most salespeople fill it with noise.
Don't.
