When a client makes a surface statement, dig deeper to peel 3 layers:

1. The first layer: What do they say?
   • Functional Layer – The immediate issue
   • e.g., pricing, process, timing complexity, friction
2. The second layer: What might they be protecting or avoiding?
   • Emotional Layer – Their feeling or real pain?
   • e.g., fear, pressure, doubt, ego, embarrassment, frustration
3. The third layer: What’s the long-term consequence?
   • Strategic Layer – The bigger risk or stake they’re managing.
   • e.g., Credibility, KPIs, career risk, missed opportunities, delayed goals.

Examples & Strategic Follow-Up Questions

• When a prospect says, “We’re just exploring options.”

1. 1. What’s going on: They’re hesitant or afraid to commit. They’re gathering information to protect themselves from making the wrong move.
   2. Strategic Questions to Ask:
      • What prompted you to explore right now?
      • What are the most important criteria you’re using to evaluate options right now?
      • If you don’t move forward with anything, what happens?

• When a prospect says, “We’re happy with our current provider.”

1. 1. What’s going on: They’re not ready to change unless they see a risk or opportunity their current provider misses.
   2. Strategic Questions to Ask:
      • What do you value most about them?
      • Is there anything you wish they did better or differently?
      • If things changed internally, what would make you consider an alternative?

• When a prospect says, “Can you just send over a deck and pricing?”

1. 1. What’s going on: They’re trying to stay in control and avoid a sales pitch — or pass info to a decision-maker.
   2. Strategic Questions to Ask:
      • Absolutely — before I do that, can I ask what outcomes matter most so I can tailor it?
      • Who else will be reviewing it? Anything they care about that I should highlight?
      • Have you seen something that caught your interest—or a concern I should clarify?

• When a prospect says, “We’ve had bad experiences with similar vendors.”

1. 1. What’s going on: They’re risk-averse. One wrong step could cost them personally or politically.
   2. Strategic Questions to Ask:
      • What made the (past) experience difficult?
      • What would make this feel safer or different for you?
      • If this were to go well, what would need to be true for your team to feel confident?

Part 2: Strategic Questions for Existing Clients

Your current clients won’t always voice dissatisfaction — but they still have pain. Approach them with these 5 Questions:

• “What’s changed in your world since we last spoke?”
• “What are you currently tolerating that you wish worked better?”
• “If we could solve one thing faster or more completely — what would it be?”
• “Where do you feel your team isn’t getting full value from us?”
• “What does success look like over the next 6 months, and how can we align better?”