A great story at the wrong time is a terrible story. If you don't believe me,  try telling a funny story in the middle of a funeral.

How do you know that it's the right time to tell the story? There's no perfect rule (it's more of an art than a science) but here are a few things to look for:

  • Don't interrupt another person's story.

People will often introduce their stories with a short statement to get your interest. You are supposed to ask a question in response to this opening statement to launch their story. You are not supposed to tell a story of your own.

For instance, if your friend says “So the other day I went to the movie theater” he probably wants you to ask him about his trip to the movie theater. He does not want you to jump in and say “Oh yeah, I was just there last week! I saw the coolest movie, let me tell you all about it...

  • Avoid interrupting their story before it reaches the “punchline.”

If it doesn't seem like the story is finished, wait before you jump in with a story of your own. Instead, ask questions to show interest in the other person's story.

  • Make sure your story fits the mood of the conversation.

If people are sharing light, funny stories and you share a chilling ghost story, you'll bring down the mood. Conversely, if people are somberly discussing a recent tragedy, it's not the time to tell the story of your zany Uncle Bob.

  • Try to make your story relate to something in the conversation.

If everyone is telling travel stories, tell a travel story. If everyone is telling funny stories, share something humorous. The connection doesn't need to be very strong, but other people should be able to tell how your story is connected to the previous conversation.

  • Make sure your audience has the necessary context to understand the story.

If I tell a story about my friend Greg to an audience that knows Greg, they will probably appreciate the story. But if the audience has never heard of Greg, then I might want to choose another story to tell (or at least, make sure I begin the story by giving a little background on Greg.)

  • Observe the rest of the group to see when others share stories.

Observing others is a great option, especially if you feel very uncomfortable about sharing. If you spend a little time noticing when other share stories, you will develop an intutition for when it's appropriate to share your own story. Don't stay on the sidelines forever, but it's okay to wait and observe sometimes if needed.

Next: Show, Don't Tell