Did you ever wonder what causes transactional agents to lose a prospect faster than almost anything else?
Assumptions.
- They assume the prospect is happy with their current agent.
- They assume the prospect wants quotes.
- They assume the prospect will switch if the price is right.
Unfortunately, many prospects don’t even know what they want!
They need a risk advisor who asks the right questions instead of a transactional agent who makes assumptions.
So, if you’re ready to be the advisor they choose—not the one they shop—then stop pitching, ask more questions, and start listening to the answers.
1. “What made you agree to meet with me today?”
Start at the root. People don’t give you time unless something's nagging them about the incumbent. Maybe it’s curiosity. Maybe it’s dissatisfaction. Figure out their motivation for meeting with you.
2. “How long have you been with your current agent?”
You're not digging for dirt—you’re reading the room. Is this a 20-year relationship or a transactional one? Context is everything.
3. “On a referability index (0 meaning low and 10 being high), where would you rate your current agent?”
Numbers cut through noise. This gives you a clean, uninflated data point—how loyal are they, really? A “7” or less opens the door to ask, “What would make them a 10?”
4. “Would you put your current agent at the same level as your CPA or attorney?”
Are they seen as a strategic partner, or just another vendor? Advisors get seats at the big table. Transactional agents get bids.
5. “Would you feel comfortable calling your current agent at 2:00 in the morning if your company had a disaster?”
Trust isn’t built during the good times—it’s built in the crisis. This is a gut-check question. If they say no, that “relationship” might be built on sand.
6. “What do you like about your current broker?”
You’re not the hero yet. First, acknowledge what’s working. Respect earns trust. Trust earns openness.
7. “What would you change about that relationship if you could?”
Now you’re unlocking the door. The cracks. The missed calls. The annual renewal scramble. This is where the real conversation starts.
8. “How do you decide which agent gets your business?”
Don’t ask at first how many agents are quoting. Ask how they choose. That’s where their values live.
9. “Do you believe it helps you to have multiple agents involved—or does it create confusion?”
This question shakes things up. Be bold. Most prospects have never thought about how inefficient quoting can be. You’re here to give them clarity.
10. “What one or two risk issues keep you awake at night? Is your current agent working to resolve them?”
Listen very carefully to this response. Because if they say “cyber,” or “fleet accidents,” or “employee lawsuits,” and their agent isn’t even talking about them, you’ve just drawn the line between reaction and proactive strategy.
11. “Besides the quote, what do you really want from your insurance risk advisor?”
Now you're not a salesperson. You’re an advisor in the making. Their answer tells you everything you need to win.
12. “How often does your current broker bring you proactive strategies—not just coverage?”
If they hesitate, you’ve just created space for a new conversation. One only a true risk advisor can fill.
13. “What does success look like for your insurance program this year?”
They’ll talk about stability. Cost control. Time savings. Less stress. This is your blueprint. Take notes.
14. “If I could bring you a smarter strategy, would you consider working with me?”
You’re not begging. You’re asking for permission. And people respect someone who shows them another way and asks to earn the seat.
15. “What would you need to see to feel confident making that change?”
This isn’t the close—it’s the clarity. You're not guessing. You’re building the bridge to exactly what they need.
So, stop pitching. Start probing. Start listening. Because the right question, asked with real curiosity, can do more than any quote ever could.