The Art of Conversation: A Salesperson’s Guide To Conducting Conversation


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Mark Twain once said, “Let us make a special effort to stop communicating with each other, so we can have some conversation.”

The Art of Conversation: A Salesperson's Guide to Conducting Conversations

It’s a bit snarky and that’s why we like it. Because, if we’re honest with ourselves, we spend a lot of time communicating with others but little time in a conversation that actually means something. This is dangerous territory for salespeople and entrepreneurs alike. We have no time to waste. Each minute you spend “communicating”, you lose one minute to spend in a meaningful conversation with a valuable prospect.

What is the “art of conversation”?

To set up our own conversation about the “art of conversation”, take a short peek at this video:

(If you’re more of an internal thinker, consider reading this post: What If We Were Taught How to Have a Conversation?)

The art of conversation is difficult to define, but you know when you’re in a good conversation. Each party is aligned and you seem to be progressing toward a solution that works for both parties. You can’t do this by simply “communicating”. You have to create impact.

How can I, as a salesperson, spend more time in meaningful conversations?

Think about the last 10 conversations you engaged in. Become your own critic or find a mentor that will provide feedback.

Identify successful conversations.

Ok, now. Forget about those.

Now, identify conversations that didn’t go as you had hoped when you walked into the meeting or when your prospect answered your phone call.

What part of the conversation was weak? Be honest with yourself and think about just one area that you can improve. Here are some examples:

  • Did you create alignment in the first few moments of the conversation? If not, use the Purpose Benefit Check.
  • Did you ask questions that made the person stop and think before responding? If not, ask more impact questions.
  • Did you walk away with an understanding of when this prospect may be ready to buy, if at all? If not, ask qualifying questions.

These are the three most essential tools to communicating with influence. (And influence lives within meaningful conversations.)

Want to take it to the next level?

You’re in luck. We have created a short eBook for salespeople and entrepreneurs that want to learn how to communicate with greater influence.

We think it’s a great resource to get you started.

How to Communicate with Influence: For Sales Pros and Leaders (click to download!)

Do you think conversation is an art form? How do you know when you’re in an meaningful conversation?

What tips and strategies would you give a rookie salesperson when it comes to conversations with prospects?

Let us know by leaving a comment below or sending us a Tweet! (@SalesEngine)

Republished with author's permission from original post.

Jenny Poore
Jenny is the Director of Sales and Marketing for Sales Engine, a sales consulting firm based in Chicago that helps companies build and tune their sales engine. Feel free to connect on Twitter: @salesengine and @salesengineJP.


  1. Jenny: I admire that you took on this topic – it’s not an easy one to tackle. I think conversational abilities are vanishing as more of our social and business communications become asynchronous (text, email, blog, blog comments etc.). Some people I work with these days are fine when crafting an email, but can get really flummoxed when they are face-to-face.

    As one who has written quite a bit (some might say too much) about question-asking in sales calls, I have come to the understanding that most approach this challenge from the wrong angle: they describe types of questions people should concentrate on asking, rather than emphasizing what’s fundamentally needed for successful discovery: 1) empathy, 2) a sincere curiosity, and 3) a sense for what information needs to be uncovered.

    In the workshops that I’ve conducted, I find that people feel more natural thinking about what they really want to know, and a little nervous when it comes to whether they should ask “open-ended,” “closed-ended,” or some other type of question. What I have found is that if you know what you’re after to begin with, the questions will take care of themselves.


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