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From Interrogation to Insight: 3 Tips to Avoid Grilling Your Prospects


Group of businessmen talking around a table.


That moment when a prospective client says they don’t understand the point of your question. Or worse yet, they say they feel interrogated.


I’ve been in this situation, and I’ve literally lost sleep over it.


If you don’t know how to address this issue on the spot, the damage is done. The deal is most likely lost.


As sellers, we obviously don’t intend to interrogate. But we mistakenly do it when we’re so focused on the process that we forget to be human.


I remember a time when I was just learning the Gap Selling framework. I was in discovery with a prospective client in England. He didn’t know all the answers to my questions.


I should have shifted to a conversational tone. I should have explained why the information would be helpful. Instead, I picked a new lane and asked about something else.


“Wait a minute,” he finally said. “I’m feeling back on my heels here.” What he meant was: I’m feeling interrogated.


I apologized. I felt horrible for him. I felt awful about myself.


But there was a gift in that experience.


It’s how I became clear on how to avoid doing that again.


Three tips to avoid grilling your prospects


1. Provide context for your questions so your buyer understands the destination.


  • The mistake sellers typically make is taking a “left turn” (i.e. asking a question that is unrelated to their previous question).

  • What to do instead: connect the dots between your questions. For example, if the prospect says they’re frustrated with their current manual process, and you know this may cause a certain business problem, explain how that manual process might result in a certain business problem, and then ask if it’s happening in their world.

  • An example of what this sounds like: “Often we see that businesses who use a manual process like yours can’t respond to customers quick enough. Typically this causes them to lose customers over time. So may I ask, what is your customer retention rate currently?”

  • Providing context and connecting the dots is how you provide new insight to your buyer, and it’s how you establish credibility.


2. Let them in on what you’re thinking – including when you’re not sure yet about the best solution or even what the problem is.


  • This might sound like: “Hmmm, I’m still trying to understand what’s causing your problem with XYZ. Part of me wonders if it could be A, and part of me thinks it could be B. So I’m curious, can you tell me more about…” 

  • Basically, stop being a seller. Start being a human. Remember that discovery is a conversation.


3.        Lead with empathy on every discovery.


  • Before every call, set the intention to see the world through the prospect’s eyes.

  • This includes understanding the business problems they’re facing, and how they might feel throughout the discovery process with you.


Toward Insight


By taking these three approaches, you can prevent the feeling of interrogation and instead create a collaborative dialogue that builds trust and understanding. The key is to stay focused on your prospect's needs and concerns.


A thoughtful and empathetic approach not only strengthens your relationship with the prospect but also enhances your credibility and sets you apart as a true partner in their success. Let your conversations be guided by curiosity, empathy, and a genuine desire to help, and you'll pave the way for meaningful connections.




"From Interrogation to Insight: 3 Tips to Avoid Grilling Your Prospects"

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