The 3-step blueprint to having deeper conversations and building lifelong friendships.

Struggling to turn acquaintances into close friends?

When I first started learning all these social skills I was meeting lots of people and befriending a few. But I couldn’t seem to form any deeper connections with anyone. I didn’t have anyone I felt I could go to my problem with or count on when I needed support.

I struggled to make a genuine connection.

To figure this out I did my research and went out to experiment. To my surprise, complete strangers we're willing to open up given the right push. Since starting I've had the most amazing conversations and formed the strongest friendships of my life.

I’ve put together this 3-step process to having deeper conversations and forming stronger bonds.

1. Strip Down Naked

*Metaphorically speaking.

You need to learn to become more vulnerable if you want anyone to be vulnerable with you.

The strongest bonds are between people who can share their vulnerabilities. Sharing a vulnerable moment builds a trust you can’t find anywhere else. Knowing someone still values you after seeing you emotionally naked forms a powerful bond.

But Introverts struggle to be vulnerable.

Tons of guys try to hide their flaws and mistakes because they think others won’t like them if they see them as they are. This was me most of my life. I did everything I could to appear perfect, even if it meant lying and covering up my mistakes.

Guys think having a flawlessly smooth exterior will finally make people like them.

But the opposite is true.

When you have a smooth exterior there is nothing for other people to stick to.

Robert Glover Exclaims in his book “No More Mr. Nice Guy” (My favorite book on men's mental health)

Bill Clinton understood this. 

5 months before the 1992 presidential elections Clinton's polling ratings were terrible. He was lagging behind George Bush and Ross Perot. Political commentators called him irrelevant. His campaign needed a change of strategy. 

Clinton took an unconventional approach.

Instead of building trust by highlighting his strengths, he built rapport through vulnerability. Clinton shared stories about his childhood and difficult family situations on talk shows. Despite the Bush team calling the tactic “wacky”, within just 1-month Clinton's approval ratings soared from 33-77%. 

Clinton won the 1992 election and the 1998 election.

Being vulnerable makes you relatable.

Your favorite movie character isn’t perfect, they have flaws and make mistakes. THAT’S WHAT MAKES YOU LIKE THEM! Opening up gives people a reason to trust you and open up themselves.

If you want to have a deep conversation and get the other person to open up, you need to start by opening up yourself. Often, sharing your mistakes, struggles, and opinions is enough to prompt others to share their own.

If you want to prompt them to share you can say this:

If you share a vulnerable experience ask: “Have you ever experienced something like that?”

If you share how you feel: “Have you ever felt that way?”

If you share an opinion: “What do you think about that?”

If they feel comfortable they will share. If not, keep building trust. Accept that some people will never open up to you because some people haven’t even opened up to themselves.

2. The Toddler Trick - Asking Why

Toddlers are notorious for asking “Why” over and over again. We don’t want to be annoying but they are onto something.

If you want to go deeper into the conversation, layer by layer, why questions are an amazing tool. They are the best follow-up questions.

Most conversations never get past the polite "How are you?" and "What do you do?"

Conversations Die on the surface. But you won’t form a real connection until you learn a person's motivations. Why questions are how you learn about a person's hopes, dreams, fears, and insecurities. 

Our motivations make us who we are.

Each why question digs away at the mask everyone shows the world. You start by learning why they chose this career path. Soon you’re talking about how they’ve been chasing their parent's approval their whole life.

I once worked on a freelance project with another photographer.

We worked together over several days and had great conversations. I made a point of asking why questions, going deeper as we got more comfortable. By the end of the project, this recent stranger told me all about their past struggle with cancer.

It was amazing how connected we became in such a short amount of time.

Of course, you don’t have to go that deep with everyone.

But most people are never asked why they do what they do, why they like what they like about it. By asking these questions you make them feel appreciated.

No one does this but people love it.

In casual conversation start by asking about their most basic motivations.

Example:

But sometimes asking “Why” can come off as judgmental.

It's a good idea to disguise the why questions as what questions to make it sound more approachable.

Why did you pursue nursing? → What got you into nursing?

Some other good disguised why questions include:

• 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?

Whenever someone tells you something about themselves some form of “WHY?” is a great way to make interesting conversation while building trust.

2. Make them feel Understood

Getting someone to share something vulnerable is good. 

But if you want to be a black belt at deep conversation you also want to make them feel understood. If the other person feels like you get them, they will feel a stronger connection with you. 

First echo what they tell you.

After someone shares something, show you listening by summarizing what they said.’

Example:

It doesn’t have to be a super smart summary, a short sentence to show you we’re listening is enough.

Next, If you feel like you understand them, label them with a feeling.

If someone tells you about a struggle they went through say:

“I Imagine that left you feeling pretty discouraged”

Or

"I Imagine that was difficult"

Maybe you can’t relate, say:

“I imagine it difficult to find people who understand”

Please. Don't try to solve their problem. People don't want to be lectured, they want to be understood. If you strive to understand others, they will stand with you.

P.S. I have something big in the works so be on the lookout 🤫