Better Than Pick-up Lines: Starting Client Conversations the Right Way

Starting the conversationPicture this: You’re in a large room surrounded by dozens of potential new clients. You’re mixing and mingling with people you’d love to do business with. You know you need to seize the opportunity and strike up conversations. You approach a VP from a firm that’s on your dream-client list, and ask him what’s going on in his business that you might be able to help with …

And the conversation turns over like an old truck. Struggling, slow, and promising to die at any moment.
This scenario probably isn’t that hard to imagine. It’s playing out in every business event in every city across the world — and you’ve probably gone through it a dozen times just this year.

At events like this, you want to appropriately and intelligently engage these prospective clients in a business discussion — but your go-to questions just don’t get you very far. You exchange cards and move on to the next conversation, knowing you’ve likely diminished your chances of getting that account.

You leave feeling defeated.

We’re going to put a stop to that right here, right now.

In this article, we’re going to tell you the five questions you can use to start a conversation with any prospective business opportunity.


First: What NOT to Ask

We’re all pretty aware of general no-no questions. We don’t ask somebody how much money they make. We don’t ask someone their age. And we don’t ask if their hair is real.

The questions you’ve likely been using to start conversations are what I call “innocent but meaningless” questions. While these questions seem harmless enough, they actually lead to wandering discussions that don’t get you where you want to go — and leave little if any impression on the prospective client.

Here are some common examples:

  • Where are you from?
  • Tell me about your family.
  • Where do your kids go to school?
  • Do you have any work coming up?
  • Tell me something that’s difficult in your business that I can help you with.

First, these questions drive no meaningful conversation. Second, they put your prospect in the “about to be sold” mindset. (Remember how you felt when you were last shopping for a car, and a car salesman approached you and asked you how he could help you. That knot in the pit of your stomach, knowing that a hard sell was coming — the one that made you immediately feel guarded and defensive — that’s the “about to be sold” mindset.)
These questions aren’t wrong — but there are better questions to ask. Ones that drive meaningful conversation and put you in the power seat to follow up with the prospect later.

5 Questions for Safeguarding Meaningful Conversation

No matter what industry that prospect is in, or what level they’re at in the business, these 5 key questions will start the conversation you want to have:

  1.  What is going on with your customers?
  2.  What is going on with your stakeholders?
  3.  What is going on with your staff?
  4.  What is going on with your operating model?
  5.  What is going on with your competition?

These questions are more likely to get you the kind of response that gives you real insight into what’s really happening with that client. This insight then enables you to approach them later with a solution or an idea.
Remember, one of the rules of connecting with smart clients is always start the conversation the right way. This will put you in the power seat with the people you really want to talk to.

The Bottom Line

No matter what the environment is, and no matter who it is you want to talk to, asking questions about the five fundamental elements of the client’s business and political issues is a surefire way to start off on the right foot. You’ll position yourself as a leader, open the conversation with meaningful topics, and create the opportunity for an easy follow up later on.


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