“A person’s success in life can usually be measured by the number of uncomfortable conversations he or she is willing to have.” -Timothy Ferris


When you die, how many people do you think will come to your funeral?

Will the service be full of people whose lives you’ve touched? Will it be a small but dedicated group of friends and family? Or a handful of connections you’ve nurtured?

Close your eyes and tune in. Are you comfortable with that image? Is that the positive legacy you want to leave?


One of the most powerful ways to set the vision for your life is to define the positive legacy you want to leave behind. 


Of course, your legacy encompasses the work you did and the things you built. But most of all it’s about the people you impacted. 

As Maya Angelou famously said, “I’ve learned that people will forget what you said, people will forget what you did, but people will never forget how you made them feel.”

I used to be terrified of deep conversations—afraid they would bring up some pain that I wouldn’t be able to handle. Afraid of being uncomfortable and feeling awkward. Afraid of saying the wrong thing. Most of all, terrified that the other person would find out something about me that they wouldn’t like. 

Though scary, these kinds of conversations are the ones that make us feel alive, fully human, connected to each other. As we expose ourselves, we open ourselves up to freedom and transformation. As we’re there to help others open up, they become more alive themselves. 

Over the past years as a coach, I’ve fallen in love with the feeling of slowly pushing deeper into meaningful conversations. Sure, I enjoy talking about the weather just as much as the next person, but what I truly love is to hear someone’s truth. I want to know what they really care about, what’s on their mind, what’s bothering them, what’s exciting them. 

I’ve found that being willing to go to uncomfortable places in conversations, to say what I really think, to expose myself and be open to another’s vulnerability, has given me more meaningful friendships and helped me deepen my relationships with the people I love. 


In a working world where people are afraid of their feelings and everyone is busy around the clock, how can we create more space for these conversations that make us shimmer alive and connect deeply? 


First, you might reflect on what holds you back from having deep, meaningful conversations?

Is it that you don’t make the time?

Do you not know what questions to ask?

Are you afraid, as I was, of exposing yourself and being rejected?

Get clear on what has held you back in the past, so you can make new choices in the future. 


Exploring this topic from the perspective of my role as a coach and mastermind facilitator, here are a few tips for you to go deeper in conversation, connect more meaningfully with others, and leave a positive legacy. 


1. Make a point to look people in the eye


I’m sure you do this already, so this might seem like an easy one. I’m going to challenge you to go deeper.

Look people in the eye as they’re talking with the intention of seeing the being inside of them.

If you’ve ever practiced eye-gazing, you know that it can be an intensely transformative experience. First, your mind goes crazy and you’re squirming, laughing, so uncomfortable and wanting it to be over. Then you become calm, present, connected. Then you’re overcome with a sense of love for this person—perhaps someone you don’t know or have never talked to. 

There’s something really beautiful about connecting beyond external appearance, beyond words, to the level of life force, which is the same life force animating you. When you’re connected to that energy, and looking into their eyes with the intention of seeing it, the level of connection and conversation will change.

Don’t worry, you don’t have to be creepy about it and stare at them. Just naturally look at them as they’re speaking with the intention of seeing the being inside.

You can also practice this with yourself in the mirror. It’s actually an awesome self-love practice! Listen to this Podcast episode where Jesse Elder explains how to connect with your own being inside: Owning Your Ultimate Energy. 

Yes, you can practice eye-gazing on video calls as well as in person. Try this exercise with Tim Ferris to see for yourself!


2. Ask people about their values


I attended an event recently where we shared our values and what each value meant to us. I was amazed at how quickly I connected with the people I was talking to. 

The exercise was simple. First we reflected on our top 5 values. Once we had our list, we partnered up and told each other what each value meant to us and why each one was important to us. 

The fascinating thing about the experience was that we might share the same value, like “freedom,” or “love,” but we each had a different way of describing it, and a different reason for choosing it. Conversely, even if we had different labels for our values we could be completely aligned on our ultimate desire for the way we wanted to live our lives and serve others.

As a group we learned so much about each other from the conversation, and I’m still in contact with those people, though our time together was short. 

To have the values conversation yourself, you might start with someone you trust, and build your confidence to talk about it with others. 

You might find that with some people, such as your colleagues, it’s uncomfortable to ask about their personal values. Another way to approach the conversation in that case is to ask about how they relate to the values of your company. Do they resonate? Do the align with their personal values? 

If they’re an entrepreneur you can ask how they came up with their company values, and why each one is important to them.

The key to go beyond the word itself (i.e. “freedom”) is to ask people, “why is that value important for you?” or “what does that value mean for you?”

You’ll find yourself surprisingly fulfilled by this quality of conversation. 


3. Be a detective to understand peoples’ motivations


In April, Spirit Drivers Mastermind studied the DISC and Values Assessment with Leah M. Ward of Authentically Connected Coaching. The values part of the assessment reveals what motivates, inspires, and drives us. There are seven key values, according to the DISC philosophy.

One of the most amazing exercises we did as a group was to practice asking each other questions that reveal the others’ values. Questions like: 

How do you enjoy spending your time?

Would you prefer to sell your art or passion project, or just create it?

How do you like to spend your money?

If you had your own TV show, what would it be about?

If you had an extra hour every day, what would you like to do?

What words would you pass onto your childhood self?

What stands between you and happiness?

What is your idea of practical results?

How comfortable are you in leadership roles?


These questions helped us to discover what was important to the other person, what motivates them. We each came out of the exercise with a better understanding of both ourselves and the other members. A truly meaningful experience that strengthened our bond. 


4. Use the 36 Questions to Fall in Love


You may have heard about these 36 questions that go progressively deeper to accelerate intimacy between strangers. Here’s the NY Times article that explains the study.

I’ve done this set of questions with a friend of mine and she has become one of my best friends in Zurich!

Obviously, you don’t have to ask these 36 questions with every person you meet! Instead you might choose one question that you like to weave it into conversation. However, I’d highly recommend the full exercise with anyone with whom you’d like to create a deeper connection. 


5. Ask about vision


People so often focus on their challenges, obligations, and problems. In fact, according to a National Science Foundation study, 80% of an average person’s thoughts are negative, and 95% are repetitive. 

When you ask someone about their vision, about what they truly want for their life, you give them a chance to focus on possibilities that excite them. 

I’ve found that asking people, “what’s your vision for your life?” is too broad and catches people off guard (unless I’ve already established connection with that person).

However, you could ask it in the context of something you’re already talking about, or about something they’re interested in.

For example, “what’s your vision for the next 5 years of your career?” “what’s your vision for your relationship with your dad?”

Another way to phrase it is to ask, “what do you want to create?” or “what’s your goal for…” As in, “what do you want to create with your new woodworking hobby?” or “what’s your goal for your fitness routine?”

When someone shares their vision with you, celebrate it with them, and cheer them on. You’ll leave them feeling hopeful, and perhaps more motivated than they were before. 


6. Stay curious, and listen to understand 


Have you noticed a theme among these tips for building deeper relationships? (Hint: ASK A LOT OF QUESTIONS). 

What follows a great question is receiving the person’s answer, in all its glory, with your two big, open ears. Listen without crafting your response in your head while they’re talking. Listen for the emotions behind the words. Listen for what connects you to them. 

Then, challenge yourself to dig deeper. Ask another question. Ask them, “anything else?”

One of my favorite parts of Stephen Covey’s 7 Habits of Highly Effective People is in Habit 5: Seek First To Understand, Then To Be Understood. Covey writes, “Next to physical survival, the greatest need of a human being is psychological survival—to be understood, to be affirmed, to be validated, to be appreciated. When you listen with empathy to another person, you give that person psychological air. After that vital need is met, you can then focus on influencing or problem solving.” 

Simply listening to another person is an enormous gift you can give them. 

Even if you never ask any of the kinds of questions I suggested above, and you only focus on listening to understand, you will deepen your relationships and leave a lasting, positive impact on people. Because they will feel heard, seen, and validated by you. 


If you’ve made it this far, I want to thank you. Thank you for caring enough about your relationships to want to deepen them. Thank you for wanting to leave a positive legacy. I hope that as you integrate a few of these suggestions into your life, it brings you fulfilment from knowing you’re doing good in the world.