Last week, I received a call from a salesperson. He was frustrated with some recent customer conversations and wanted my advice.

This salesperson, “Joe,” interacts with his customers mostly through telephone and email, and has been able to build good relationships with many customers he has never met in person. Occasionally, a customer will come to the company’s warehouse to pick up an order, and Joe will have a chance to meet the customer face to face.

“These meetings often don’t go very well,” Joe told me. “The customers don’t seem that excited by our conversation, and they seem to get impatient with me. This never happens when we’re on the phone.”

Joe is very personable. In case you are wondering, he is a “normal” looking person, so his appearance is certainly not the reason he’s having problems with in-person meetings.

“Tell me about these meetings,” I say to Joe.

“I try to ask my customers questions, to show I’m interested in them.” Joe paused.  “Maybe I’m asking too many questions, but I thought it was good to ask your customers questions.”

“Ah,” I thought. “Joe just self-diagnosed his problem.”

How to Ask Questions in a Customer Conversation

Questions are effective, but they are most effective in the context of a conversation. To Joe’s customers, these questions didn’t feel like a conversation. They felt like an interrogation.

Conversation is a key element of any relationship-building customer interaction. Customers will feel more comfortable if the questions you ask are integrated into a back-and-forth dialogue than if they come rapid-fire, one after another.

Here are some tips for ensuring that your questions engage, instead of overwhelm, your customer:

  • Think granularly — The best dialogue includes much back and forth, with each person speaking for only a short period of time before returning the focus to the other person.
  • Use questions to generate dialogue, not just answers — Avoid moving through a list of questions. Ensure that any follow-up question directly flows from your customer’s answer to a previous questions.
  • Explore and heighten — find out what your customer cares about, and then discuss what your customer cares about.
  • Focus the conversation on the customer — Keep the subject of the dialogue focused 95% on the customer. This way, you will show care for the customer’s issues, as you would do with questions, but you will do it in a way that will feel more engaging and interesting to the customer.

A series of questions is not a sales pitch, but it can feel like pitching if it isn’t engaging, two-way and conversational.  When you are with a customer, think less about the questions you want to ask and more about the conversation you want to have.


  • Dan Caramanico
    May 21, 2014 - 17:50 pm

    Really great points. I would like to add that the development of a relationship that ‘Joe” is seeking will go through three phases: Interaction (this is where Joe got stuck) then on to involvement (this is what you describe so eloquently) then on to connection (which is where the bond is created).

    you will know it’s a relationship if they get what you are about and you get that they “get it” and the other way around

  • Steve Yastrow
    May 21, 2014 - 18:15 pm

    Thanks Joe!

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