If you think you're boring read this:

In 1874 Benjamin Disraeli and his rival William Gladstone ran for British prime minister.

Weeks before the election, both men dinned with the same woman — Winston Churchill's mother.

Her Insights predicted the winner and taught us how to be the most interesting person in the room.

The two men were very different

Gladstone was serious and well-spoken. Disraeli was much more vibrant, witty, and prone to flattery. But both were well-educated. 

No one knew who'd win the election.

As part of their campaign, both men mingled with high society looking for support.

On separate evenings, the rivals dinned with Jennie Jerome — Winston Churchill's mother.

When a journalist asked what her impression of the two men was, she said:

"When I left the dining room after sitting next to Gladstone, I thought he was the cleverest man in England. But when I sat next to Disraeli, I left feeling that I was the cleverest woman."

A week later, Disraeli won the election.

What separated the two?

Gladstone spoke at length about his accomplishments to make himself look important. Disraeli focused instead on others. He gave Jennie Jerome his full attention, asked her questions, and made her feel important. 

People were impressed by Gladstone but they liked Disraeli.

We tend to think: "I'm boring, if I had cool stuff to talk about then people would be more interested in me."

But talking about all the cool stuff you did often makes people less interested in you.

One of the most interesting people I know is also one of the most boring.

They've been all over the world, met famous people, and seen the most incredible things. But all they ever talk about are the things they’ve done. Without asking, you’d be stuck listening to a drawn-out story about them.

Eventually, People started to avoid talking to them.

Having cool stories doesn't make people more interested in you.

Coming home from my Europe trip I thought everyone would want to hear about my crazy adventures. Do you know what happened? When I brought up my trip most people said "Oh cool" before moving on.

People aren't half as interested in others as they are in themselves.

Everyone’s favorite subject is themselves.

By staying interested in others you let them do most of the talking. If you let them, they'll go on forever. You don’t need to worry about what to say if you let them do most of the talking.

All you need to do is chime in with the occasional question.

People will forget what you tell them.

But they will always remember how you made them feel. You make people feel bored If all you talk about is yourself. Instead, make them feel important by asking questions, listening, and being curious.

Make people feel important and they’ll remember you forever.

The best part?

By being interested in other people, they become interested in you.

To be interesting you need to be interested.

How?

3 Steps to becoming more interesting by being more interested.

1. Foster curiosity.

People are fascinating, you’re just blind to it

Everyone you meet, everyone you walk past, everyone you see... is as complicated and messed up as you are. They all have their own fears and anxieties, interests and hobbies, complicated pasts and hopes for the future. 

Everyone you meet is the most interesting person in the world.

I’ve found it helpful to go into interactions thinking:

“This person knows something I don’t, something that could make my life better”

Then I make it my mission to find out what that thing is. 

2. Avoid Yes and No questions

Once you’re in the conversation avoid yes or no questions like:

• Did you have a good weekend?

• Did you like the event?

These boring questions don’t lead anywhere.

Instead, ask open-ended questions to foster conversations.

• What do you do for fun?

• What are your plans for the summer?

• What did you think about the event?

These questions get longer answers. With longer answers, it’s easier to foster conversation with follow-up questions.

3. Go Deeper

When you learn something about someone, instead of moving on to the next thing, go deeper.

Ask them WHY questions (sometimes disguised as what questions):

• Why did you decide to become a mechanic?

• Why do you like fishing so much?

• What do you like so much about soccer?

• What made you choose to become an engineer?

These questions reveal a person's motivations, values, and dreams.

These are your silver bullet. 

Nobody asks questions like this. But people love answering them. It makes them feel important to have someone interested in them.

The more interesting you make others feel the more they become interested in you.

P.S. You might feel weird going into deeper conversations with people you just met. It’s only because you’ve never done it before. Don’t worry, I’ve asked strangers about their battle with cancer, they don’t think you’re a creep, they appreciate it.