A fellow coach recently asked me, “How do you make your one-on-one retreat sessions so effective?” It made me pause and reflect on the key element of a successful executive retreat. At its heart, it is not about flashy exercises or polished presentations. It’s about seeing you—seeing who this person really is. Can we quickly get beyond how our friends, clients, and colleagues initially present themselves to discover authentically who they are? I use six distinct strategies to get to know someone before we begin our work.
1. Map How They Are Perceived
Yes, I will provoke you to share how you perceive yourself. More revealing than that, however, is what those who know you best have to say about you. Typically, I interview 6-8 people who know you deeply from different angles: family, colleagues, mentors, friends, adversaries even. I probe how they perceive your unique gifts–what you are great at–and your challenges–what you find hard or people find hard around you. I also collect how they score you on 20 traits, and compare all those perceptions with your own self-assessment.
When I feed back my summary of all this research, some of the insights gleaned are more obvious, some surprising and revelatory. More potently, there is a transfer that takes place. Those who really care about you carry a kind, sacred knowledge, a felt sense of who you are that is ultimately inexplicable. With just a few calls, a skillful and open-hearted coach can access that sacred sense of your deepest self.
2. Artistic Expression
Next, I want to let your subconscious mind, your right brain, talk to me. I have a somewhat massive collection of evocative images for you to create a collage: your life as it currently is, how you want it to be, and what is in the way. Sometimes I may have you draw, maybe even with your non‑dominant hand.
The subconscious is so gorgeously poetic! The more I go on, the more I realize that people are creating their lives to be the way they are because of dynamics and beliefs that are largely transparent to them. The pictures, sounds, words, and metaphors people choose speak volumes. I encourage anyone interested in coaching to become a student of the many ways people unconsciously give themselves away. It is not complicated. Just listen and watch. Something will resonate as carrying a previously hidden meaning.
3. Catch the Story: Your Most Impactful Moments
Most people feel known by the people with whom they have shared their life story. That can be exhausting! The trick for me to listen to your story efficiently is to dive only into the moments that shaped you—personal triumphs, challenges, and turning points. I use a life walk so you can identify the most emotionally charged events. As you unfold your journey, I am listening for patterns that reveal your values, fears, resilience, and ambition.
4. Desire
The most important parts of you are not found in what has already manifested. We are interested in what will be. Or, more accurately, what is driving what will be. I want to explore what you really want. When someone expresses desire, you glimpse their hunger, passion, and motivation. I find it helps to offer a range of possible wants to stimulate you to clarify your unique desire. When you nail it, when you speak your deepest goals—whether they’re personal, professional, or somewhere in between—you are revealing who you are at the core.
5. Risk
How do you approach risk or uncertainty? What dangers or threats trigger your fear response? As much as anything, your life takes the shape it does because of what you are averse to, the ‘bad’ things you want to make sure don’t happen. Whether bold and intuitive, or cautious and strategic, I want to meet your internal “risk manager”—the part of you that assesses threats and makes decisions. While it is helpful to know the motivation that switches you on, it is even more interesting to learn the big risks that switch you off.
6. Seeing Your Future
Finally, I want to know your future self. Using a vision walk and creative imagination, I can engage with how you see what is ahead. Sometimes, when you show me who you are becoming, it clicks for me, and I see what you are ultimately all about.
The greatest gifts of my life have been the opportunity to get to know people deeply.
There is always more. You might want to think of someone you care about. Are there ways you access them more deeply through one or all of the angles outlined here?
I am convinced that to help you or anyone grow, I must first know you. Not just who you may think you are, but the essence behind your story, fears, and ambitions. When you feel seen and met, real transformation becomes possible. I trust what I have offered here empowers you to give that gift to the people close to you.
All the best,
David Lesser