Have you ever felt the terror of arriving at a party, a new job, or a social event and wondering if you will know what to say and who to talk to first?

You aren’t alone! But it doesn’t have to day that way.

Learning to have great conversations, like any other skill, can be developed.

Consider the following list of 10 ideas you can use and develop to strengthen your conversational abilities.  Whether you are terrified of conversations, or pretty good already, this list will contain something you can implement today to become just a little bit better.

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Ideas for Cultivating Great Conversations:

  1. Have a Plan – Write out 2-3 questions prior to an important conversation. This will ensure the conversation is productive.
  2. Have Coffee – For some reason, holding a coffee makes every conversation better.  Even if you don’t like coffee, it will set everyone at ease.
  3. Make the Ask – Great conversations require someone interesting to talk to.  Be constantly looking for people to talk with.  The next great conversation may be  sitting next to you on a bus, a plane, or coffee shop.  If you meet an interesting person… ask them out for coffee.
  4. Look to Learn – The point of a conversation is not to tell your perspective.  That is called a lecture. Great conversation are about learning as much as you can.
  5. Great Questions – Author Gordon MacDonald once shared that he loves to start conversations with strangers with the question, “Can you tell me your life story in 4 minutes, and don’t leave anything important out?”I have used this question countless times… it always leads to great conversations.
  6. Deepen Your Arsenal – Some conversations lag because we can’t think of good questions.  Deepen your question arsenal. Here are list of questions I love:
    • What is your life story in 4 minutes or less? (see above)
    • What is one word that would summarize each decade of your life so far?
    • What do you do with your free time?
    • What dreams do you have for your life?
    • What is fascinating about your family?
    • What have you learned lately?
    • Which 5 books that have had the greatest impact on your life?
    • If you could give advice to yourself 10 years ago, what would you tell yourself?
    • Check out this link for more – 350 Good Questions to Ask
  7. Listen Long – The longer a person listen before interrupting to contribute to the conversation, the better the conversation will be. We all love to jump in and tell our story.  The best conversationalists listen long and extract the other persons story.
  8. Ask the 2nd Question – Most conversations seem to resemble a form of verbal pingpong, with each person contributing their personal thoughts and perspectives in reciprocating turns.  Disrupt this pattern, by asking follow up questions like:
    • What did you mean when you said…?
    • Can you elaborate on that?
    • How did that make you feel?
    • Why do you feel that way?
  9. Look for Connections – The best conversations are built on common ground. Continually look for similarities.  As soon as these connections are made, look for what you can learn from the other persons experiences and perspectives.
  10. Take Notes – Taking notes on an app on your phone, in a journal or on a napkin will help you remember crucial details.  If you don’t feel comfortable doing that during the conversation, write a few things down immediately after the conversation to help you recall what you discussed later.  Your next conversation will be far richer if you can refresh your memory before you chat next.

Bonus: Schedule a Follow Up –  Single conversations seldom have enduring impact.  Quality conversations build over time.  When you run out of time, schedule your next coffee conversation before moving on.  Don’t leave conversations to chance.

Great conversations are like exercising.  They are handwork and can be painful at times, but if we stick with it, we will be much stronger in the long run.  The most influential people I have ever met are great conversationalists. They are continually growing and learning through their interactions with other great people.

How will your next conversation go?



Note: The quality of our conversations is the second of three factors that determine how influential we become (Click here to read the an overview of this framework). 


2 thoughts on “10 Ideas for Cultivating Great Conversations 

  1. I love this!!!!!

    Great material to teach at a leader lab too!!!!

    (I have a great image to share on ask the 2nd question)

    You are so gifted!


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