How To Be in the Top 10 of All Conversationalists



“You can discover more about a person in an hour of play than in a year of conversation.” — Plato

What if you’re shy, unfunny, or just plain not much of a talker?

You can join the ranks of the top 10 conversationalists by learning a few tricks of the trade.

Being a great conversationalist is a learnable skill.

Whether you want to go from bad to good, or good to great, it helps to know the fundamentals that help you take your conversational abilities to the next level.

In the book, How to Fail at Almost Everything and Still Win Big: Kind of the Story of My Life, Scott Adams shares what he’s learned about how to be a great conversationalist.

Join the Top 10 Percent of All Conversationalists

You, too, can join the ranks.

It helps to know that Adams was a shy guy and that he was clueless the first half of his life about conversation skills.  He thought conversations were a waste of time and something to be avoided.  He then learned some skills and changed his game.

Via How to Fail at Almost Everything and Still Win Big: Kind of the Story of My Life:

“Smile, ask questions, avoid complaining and sad topics, and have some entertaining stories ready to go.  It’s all you need to be in the top 10 percent of all conversationalists.”

A Summary of Good Conversation Technique

To be a great conversationalist, or at least a better one, there are a few rules of the road.

Via How to Fail at Almost Everything and Still Win Big: Kind of the Story of My Life:

  1. Ask questions.
  2. Don’t complain (much).
  3. Don’t talk about boring experiences (TV show, meal, dream, etc.)
  4. Don’t dominate the conversation.  Let others talk.
  5. Don’t get stuck on a topic. Keep moving.
  6. Planning is useful but it isn’t conversation.
  7. Keep the sad stories short, especially medical stories.

Why You Might Start a Conversation

It helps to know the various reasons why you might start a conversation.

Via How to Fail at Almost Everything and Still Win Big: Kind of the Story of My Life:

Exchange information
Feel connected
Be polite
Avoid awkward silence

According to Adams, people that are bad conversationalists focus on bragging, complaining, and exchanging information.

The Dale Carnegie Question Stack

According to Adams, the technique is laughably simple, but 100% effective.  Here are the questions as best as Adam’s remembers them:

  1. What’s your name?
  2. Where do you live?
  3. Do you have a family?
  4. What do you do for a living?
  5. Do you have any hobbies / sports?
  6. Do you have any travel plans?

If asking personal questions feels awkward, remember that strangers usually feel awkward, too.  Personal questions break the ice, and give the other person a chance to talk about something they know.

Faking Social Confidence Leads to the Real Thing Over Time

If you step out of your comfort zone often enough, you’ll learn to be comfortable living outside of your comfort zone.

Via How to Fail at Almost Everything and Still Win Big: Kind of the Story of My Life:

“When you ask a stranger a personal question, you make that person happy.  Your question relieves the stress of awkward silence and gets the conversation moving.  Best of all, it signals that you have interest in the stranger, which most people interpret as friendliness and social confidence, even if you’re faking it  And faking social confidence leads to the real thing over time.”

Joking Mode Has a Low Success Rate

We all like a good laugh.  But with strangers, not as much.  You might find people laugh at you, or near you, but what you really want is for them to laugh with you. And that comes with time.

Via How to Fail at Almost Everything and Still Win Big: Kind of the Story of My Life:

“I discovered that perhaps only 5 percent of the general population wants to get into joking mode with a stranger.  And of that 5 percent, maybe only half of them will appreciate whatever you think is funny.  Everyone else will want you to go away.  While most people enjoy humor, the typical person doesn’t go directly there before getting to know someone.”

Find Something Interesting

Your job as a conversationalist is to find something interesting.

Via How to Fail at Almost Everything and Still Win Big: Kind of the Story of My Life:

“Your job as a conversationalist is to keep asking questions and keep looking for something you have in common with the stranger, or something that interests you enough to wade into the topic.  In my entire life I have never met a stranger who didn’t have some fascinating life experience that spilled out if I asked the right questions.   Everyone is interesting if you make the situation feel safe.”

Make the Other Person Feel Good

If people feel good when they are round you, they’ll want to be around you more.

Via How to Fail at Almost Everything and Still Win Big: Kind of the Story of My Life:

“The point of conversation is to make the other person feel good.  If you do that one simple thing correctly, the other benefits come along with the deal.  For example, a person who likes you is more likely to be persuaded to recommend you for good opportunities, to share information, and to want a relationship with you.  And if you must complain, because it’s just too hard to keep it in, you’re better off complaining to someone who already likes you; that way you’ll get the empathy you want.”

Learn How to Tell a Funny Story

According to Adams, storytelling is a learnable skill, and you can learn how to tell better stories through preparation.  Look for them, practice them, collect them.

Here are the parts of a good story, according to Adams:

  • SetupKeep it brief.  And I mean really brief, as in ‘So, I took my car in for a brake job …’
  • PatternEstablish a pattern that your story will violate.  For example, you could say, ‘Whenever I take my car for any kind of service, I’m always amazed how expensive it is.’
  • ForeshadowingForeshadowing means you leave some clues about where the story is going.  The foreshadowing can happen as early as the setup, as in ‘My in-laws in Arkansas have something they call the ‘fraidy hole’ that everyone climbs into in case of tornadoes.  It’s meant to hold no more than four people.’
  • The CharactersFill in the story with some characters traits that will be relevant. For example, ‘Our friend Bob has been borrowing our power tools for years because he’s too cheap to buy his own.’
  • RelatabilityPick story topics that your listeners will relate to.
  • The TwistYour story isn’t a story unless something unexpected or unusual happens. … If you don’t have a twist, it’s not a story.  It’s just a regurgitation of your day.

One way to think about all this is to be brief, be bright, be gone, or wander you way into an interesting topic, and wade around for more.

In any event, if it’s all about you, you’re doing it wrong.

Share the air, and let people know, you really care.

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Image by Kris Hoet.