What’s the best way to get into an engaging conversation with inspiring, remarkable and extraordinary people?

That’s a question I have been asking for many years because it’s a major part of the work I do with my clients.

What if every conversation you had with an influential person would start from a place of mutual passion, energy and excitement? How much easier would it be to connect with them if you could talk about something that is most important to both of you?

In this article, I share some of the most powerful questions you can ask people to connect with them in the most authentic and engaging way.


1. What Inspired You to Start This Business?

That question directly goes to the heart. Instead of talking about what people do, you get to talk about why they do what they do.

In a world full of stuff and meaningless conversations, this question lets people share their drive for what they do and talk about their story.

Think about the people who inspire you. Why do they inspire you? Is it just because they are extremely successful? I doubt it.

It’s usually their story, it’s the challenges they were able to overcome and it’s the reason why they do what they do.

Give yourself the permission to be curious and let people tell you their stories. Be amazed at the inspiration that comes from this conversation and the deep connectedness that emerges.


2. Tell Me More About Your Passion

What is usually one of the first questions that people ask at an event or whenever they meet somebody new?

“What do you do?”

The issue with this question is that it puts people into a box.

“I’m an entrepreneur”, “I’m a wealth management consultant”, “I’m a banker”, “I’m a kindergarten teacher”, “I work at a non-profit foundation”.

To which one of these statements are you more drawn to? Is there a certain variety that you would more likely respond to with “Interesting, tell me more!” and others where you would say “Mhm, interesting” and then drift off in your mind or look for somebody else to talk to?

As hard as it is for me to admit but that’s what I do sometimes. I have stories in my head and based on those stories I judge people differently based on what they say they do.

That’s why I force myself to start conversations in a different way. “Tell me more about your passion” is one way for me to start a conversation based on what I’m really curious about to hear compared to what I think I should be asking.


3. What Do You Love Most About Your Work?

Instead of talking about what people do, why not talk about what they love most about their work?

It makes such a difference in terms of people’s energy.

This morning, I had a meeting with somebody I got introduced to. He does wealth management consulting and has a huge passion for sports.

Initially, he told me all about his work in wealth management consulting and it was just another conversation. At some point, I asked him what he loves most about his work with football clubs. That’s when the energy of the conversation completely shifted.

He said “It’s making a difference”. I asked him what that means and he told me that when football clubs can grow their revenue and create new sources of revenue, they can give back more to the community. They can get more involved with local schools, charities and help the entire local community.

Now that was an energetic conversation!

Asking about the love behind somebody’s work can shift a conversation from average to inspiring, energetic and engaging.


4. What’s Your Vision for What You Want to Create Through Your Work?

Another powerful question to get to heart of the matter. Talking about vision, purpose and Why usually goes to what’s most important to somebody.

It can even be incredibly beneficial to the person who is asked that question. Even the most driven leaders and entrepreneurs can sometimes let their vision be buried in day to day business.

Asking this question reminds people of why they do what they do, and we all need that from time to time.


5. How Do You Deal With Failure?

Every successful leader and entrepreneur has failed at least once. Most probably, they have failed more times than they succeeded.

One of the major reasons why they are successful is that they deal with failure differently that most people.

Every person has a unique way of dealing with failure.

This question engages people to share some more vulnerable parts of themselves which in turn creates a highly authentic and truthful conversation.

When people share how they deal with failure, they talk parts about who they are at their core. They talk about mindset, their behavior and thinking patterns.

I recently had a conversation with a very wealthy entrepreneur in Zurich. He has been building businesses since more than 15 years, some succeeded and others failed.

When I asked him how he deals with failure, the conversation shifted from what he had achieved to why entrepreneurship is something noble and having the right mindset.


6. If You Would Loose Everything Today, What Would You Do Tomorrow?

Somebody recently told me she asked that question to a wealthy business women and her answer was “I would go for dinner at the most expensive restaurant in Zurich, order a salad and just sit there and listen what people talk about.”

I love that question.

This women obviously knows about Jim Rohn’s quote “You are the average of the five people you spend the most time with” because she would surround herself with wealthy people immediately again.

It’s these unconventional questions that cut through the clutter of everyday stuff.


7. Who Inspires You?

I heard JB Glossinger talk about an interview he did when I spent two days with him at Awaken My Life in Fort Lauderdale this month.

When the interviewer asked him “Who inspire you?” He said “Oh that’s easy. It’s the nurse who deeply cares about her work and patients. It’s the artist who follows her dream while taking care of her three children.”

Stunned, the interviewer looked at him and said “Nobody ever said something like that.”

That’s why I love these questions. You never know how people respond.

If people are honest and true to themselves, the answers are always inspiring and deeply connect.


Having Powerful Conversations – Every Time

Now it’s on you to use these questions in every conversation you have.

Initially, it may feel uncomfortable. However, you will see huge benefits immediately if you can get over that feeling of discomfort.

Your conversations will flow much smoother. They will be more inspiring, engaging, energetic and you will quickly see who you truly resonate with and who you don’t.

There is no easier way to connect with inspiring, remarkable and extraordinary people than by having meaningful and powerful conversations that get to the heart of people.


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