How To Entertain Groups of People

Entertaining a group is like public speaking without the preparation time.

Entertaining groups of people is the most difficult, but most rewarding of all social skills.

đź‘Š The Punch List:

  • 75% of people fear public speaking more than anything else.

  • Entertaining a group is like public speaking without the preparation time.

  • Nearly all leadership roles require speaking and entertaining groups.

  • People that lead group conversations are seen as more influential and attractive.

3 Methods to Entertain Groups of People

Be A Storyteller

This works because all humans are hardwired to enjoy and engage with good stories. Stories transport people to a time and place to “re-experience” something. Well told stories can entertain any amount of people, because each person envisions it in their own entertaining way.

In the real world you should always have a go to story that you like to share with people. Whenever you’re in a group ask if someone wants to hear a crazy story, and many will say yes. You can also reshare or rephrase other interesting stories as long as they seem relevant to the group.

Examples of being a storyteller is telling your spouse’s family or coworkers the story of how the two of you met.

Be A Comedian

This works because the best way to entertain groups of people is to get them to feel some kind of emotion. The core psychology of boredom is really just feeling no emotions. The emotion everyone enjoys no matter their situation, is humor. So if you can make a group laugh, they will look to you for more positive emotions.

In the real world you should be writing down any and every joke that makes you laugh. And I mean really keel over in a belly laugh. It’s hard to be funny to others. But most people feed off others emotions. When you laugh hard at your own jokes, others will laugh from pure contagion.

Examples of being a comedian are making light of how late you or someone was to an event, or sending funny memes in the company group chat.

Be A Debater

This works because most conversations have zero stakes and people aren’t interested in engaging. When you bring up a hot topic, most people will feel compelled to join the conversation. The more opinionated the topics, the more likely it will entertain the group. But you have to keep control, and stifle any animosity

In the real world you should watch the news often so that you’re aware of the current event or topics that people are talking about. Rather than sharing your personal opinion, you can play moderator or devil’s advocate to the popular opinion. And always try to keep things light-hearted.

Examples of being a debater is at lunch asking your friends whether flats or drums are better for chicken wings, or just asking coworkers thoughts on any debate trending on Twitter.

Overall the skill of people will always be hard to get good at. But it only gets exponentially harder when it comes to groups of people. The bright side is that because we’re all humans, you know how other humans act. Whatever entertains you, is what will entertain groups of you.

With these tactics, you can go and be the life of any party when they need it the most.

And for WIPs, your progress will eventually bring you down the path of leadership. And as we become leaders and teachers of groups, we can use these skills to entertain those groups as well.

So anytime you’re in an awkward group situation, don’t be afraid to be a storyteller, be a comedian, or be a debater.

The group will thank you for it…

In progress,


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