How to Have Better Conversations With Successful People

Have you ever sat down with someone who has an impressive title and immediately felt the conversation pulled toward their work?
Perhaps they're a CEO.
Maybe a successful author.
Maybe an award-winning chef.
Or they’ve accomplished something that naturally makes people curious.
Those accomplishments may matter in many, maybe most rooms.

And sometimes the person sitting across from us wants a very different experience. 
They want to talk about scuba diving.
Maybe they want to talk about pumpkin carving.
Or even share frozen pizza and wine with friends.
These aren’t random examples.

I've noticed that friends with prestigious roles often want conversations where the projections that come with their titles don't take over the experience.

One of my favorite examples happened at my wedding.
A very famous author joined our wedding.
Most people didn't know what he looks like, although they know his name.
When I introduced him, I deliberately mention his books or use his last name so he could remain anonymous.
I used his first name and mentioned that he'd written stories featured in The New Yorker so others didn’t think he was hiding his professional life.

Then something wonderful happened.
My friend Scott sat down with this author friend on the beach.
They talked for well over an hour about scuba diving.
At the end of the wedding week, Scott came to me and said, "Oh my goodness, I didn't realize it was that author."
He regretted not knowing.
He said that if he'd known, he would have asked about the books, writing, and all the stories behind them.
I understood why he felt that way.
There was a reason he didn't know.
This author probably gets very few opportunities to sit down with someone for an hour and a half and simply talk about scuba diving.
That conversation gave him something special.
It gave him a chance to be a person rather than a projection. 

Our Titles Can Enter the Room Before We Do

When someone has a prestigious role, their title often enters the conversation before they do.
We see the title and start filling in the blanks.
We imagine what they want to discuss, what they know, and what might interest them.
Soon, their accomplishments can start to feel like the most interesting thing about them.
And without ever planning it, we steer the conversation toward the persona instead of the person.
The same thing can happen with an award-winning chef.
My chef friend doesn't want every dinner with friends to turn into a conversation about restaurants, food, awards, or her career.
I heard from one award winning chef friend that sometimes she wants to share frozen pizza and wine with people she cares about.
She never gets to do that. 
She wants no culinary performance required and no expectation to teach anyone anything.
She just wants unpretentious time in friendship.

Let People Step Outside Their Professional Role

Zvi Band shared another example that captures this perfectly.
He once had dinner with a friend who happened to be an executive at a very well-known consumer electronics company.
We may expect a conversation like that to drift toward technology, business, leadership, or the industry.
Instead, they talked about pumpkin carving.
His friend was an amazing pumpkin carver.
That life detail never comes up in a business podcast.
Because Zvi gave room to talk about it, they had a rich and deep conversation about things they’re passionate about.

When we only see people through their professional identities, we can miss so much of who they want to share about themselves.
A person can run a company and carve extraordinary pumpkins as an artist.
Someone can write bestselling books and love scuba diving.
An award-winning chef can still want to sit around with friends, sharing frozen pizza and wine.
A title tells us what someone does.
It doesn't tell us everything that makes them who they are in other areas of their lives.

Sometimes the Most Meaningful Conversation Happens 

After the Achievement

There is another moment when this matters deeply.
Consider someone who just sold their company.

As Zvi described it, selling a company can bring emotional exhaustion, fear, loneliness, and a loss of identity.
Someone who spent years building a company suddenly has to figure out what comes next.
This can feel painful and lonely.
The outside world may see a milestone.
The person living through it may experience a profound transition that doesn’t feel proud-filled.
That means a simple question can sometimes matter more than another congratulations.
"So, what are you doing now?"
The answer might be surprisingly honest.
"Honestly, I just need to stare at a blank wall."
Or:
"I'd love to grab coffee because I have no idea what to do next with my life."
Those aren't answers from someone looking for another business conversation.
They're answers from a person navigating a major life transition.

We Go Through More Transitions Than We Realize

This perspective extends far beyond executives, authors, and chefs.
We all move through major transitions.
Student to professional.
Single to married.
No children to parenthood.
Each transition needs learning new skills.
During these periods, people are often helped by others around them who can recognize, support and witness what they're experiencing.
Someone can deserve congratulations and still long for companionship.
A major milestone can bring uncertainty about what comes next.
Even extraordinary achievements can leave someone wondering where to go next.
Recognizing both sides of a transition gives us a richer way to care for people.

How to Have Conversations That Let People Be People

Ask About Something Outside Their Role

The next time you meet someone with an impressive title, resist the urge to steer the conversation straight toward their work.
Instead, ask what they enjoy.
You could ask what fills their time or what they look forward to when they aren't working.
Those questions may uncover a passion you never expected.
The person may light up when they talk about something that has nothing to do with their professional identity.

Notice What Gives Them Energy

Pay attention to the subjects that change someone's expression.
When they mention their garden, their whole face might light up.
A favorite hobby might bring a new energy to their voice.
Perhaps they have an unusual skill that never appears on their professional biography.
Those details can open the door to a more personal conversation.

Give People Permission to Leave the Script

Sometimes we enter a conversation with an invisible script.
We expect the famous author to talk about books.
The chef gets questions about food.
People ask the executive about business.

When someone sells a company, we naturally want to hear about the deal.
You don't have to follow that script.
Instead, ask about scuba diving when it comes up.
Follow the pumpkin carving thread.
Talk about whatever helps the person enjoy and open up, and enjoy the conversation yourself.

Pay Attention During Life Transitions

Milestones can hide difficult transitions.
When someone gets married, has a child, sells a company, changes careers, or reaches another major milestone, congratulations are appropriate.
And a second question may matter just as much.
"How are you doing with all of this?"
That question creates room for an honest answer.
It tells someone that you care about the experience, not simply the milestone.

What Would You Talk About If You Didn't Know Their Title?

We can stop treating people's titles as instructions for conversation.
We can start looking for the identities behind the titles.
The famous author at my wedding had an hour and a half on the beach talking about scuba diving.
My friend didn't know he was famous.
And perhaps that was exactly what made the conversation so valuable.
For once, the author didn't have to be an author.
He could simply be a person talking with another person.
That's something I want more of in my own relationships.
I want to know what people care about when nobody is asking them to perform their role.
I pay attention to the passions that don't fit neatly into a biography.
A major achievement can bring joy and uncertainty at the same time.
Most of all, I hope to give people room to step outside the identity everyone else has assigned to them.
Who in your life is carrying a title that may be hiding part of who they are?
What could you ask them if you didn't know their job?
And what might you learn if you simply gave them room to talk about something else?


Get free resources on building the community you long for at www.charlesvogl.com

Order the 2nd Edition with 25% new content