How to Be a Good Conversationalist

Key takeaways

  • Being a good conversationalist isn’t as easy as you might think.
  • A really good conversation requires that those involved follow a few rules, and some are harder than others.
  • Things like being brief, being present, and using open-ended questions are among the easier to follow, but many people have a harder time remembering to admit when they don’t know something and listening to understand rather than to reply.
  • If you can include these things in your next conversation, you and your discussion partner will probably end up getting a lot more out of it than usual.

Remember The Late Show Top 10 List with David Letterman? Most of the time, those were pretty funny. He’d start with number 10 and then go all the way up to number one. Today I have a top 10 things list: how to be a good conversationalist. They actually came from a Ted Talk and, by the way, when I reviewed these, I realized that I consistently violate about seven of them. This made me wonder how bad some of my conversations really are. Hopefully, not too bad.

That said, here are the top 10 things you need to be a good conversationalist:

  1. Be present. You already know what that means. You have to listen. You must be there; not somewhere else.
  2. Don’t pontificate. I’ve been known for doing this. Take care to avoid this because it turns people off.
  3. Use open-ended questions. Open-ended questions, rather than questions that require a simple ‘yes’ or ‘no’ answer, keep the conversation rolling along.
  4. Go with the flow. This one’s sometimes difficult to do, but it’s important. If the conversation starts to change and goes in a different direction, just go with it. Let the person you’re talking to take things down this different trajectory. It usually leads to some cool places and unique topics.
  5. If you don’t know, say you don’t know. I know many people have a hard time with this. Think about it—there’s a lot you don’t know, so it’s okay (and beneficial) to say so.
  6. Don’t equate your experience to theirs. People go through all sorts of things in life that we, personally, simply can’t understand. Many times, trying to get them to believe you truly understand doesn’t go off very well; so, this is an important one to remember.
  7. Listen to understand, not to reply. This is another difficult one to consistently put into action. It’s especially challenging when you’re having a conversation involving one of the many difficult topics people bring up.
  8. Be brief. Make sure you don’t go on and on when you’re adding your two cents to the conversation.
  9. Stay out of the weeds. Many people, when initiating a conversation, just want to know the time, not how to build a watch. Explaining the intricacies of watchmaking, in these instances, makes you boring.
  10. Try not to repeat yourself. At times, you might think the other person isn’t really hearing you. This makes it difficult to stick with the rule of not repeating yourself, but avoid doing it anyway. Instead, say what you need to say only once and say it in the best way you can.

Try these out during your next conversation. I know when we’re meeting with new prospects for the first time, we really make an effort to follow these rules. We’ve found that this gives them the space to have a very satisfying conversation and we get a lot out of it at the same time. I really enjoyed this particular Ted Talk and I learned new things about being a good conversationalist and maybe it will help you as well. Until next time, enjoy.


Gary Klaben is in our Glenview, IL office and serves our clients who are now located all over the country.  He has over 30 years of experience and is the author of Changing the Conversation, Wealth of Everything and co-author of The Business BattlefieldWhether advising his clients, mentoring his team, or coaching entrepreneurs, he is always simplifying complexity and motivating others to take the next action that’s right for them.

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