The List -vs- The Experience:

Coaching’s great detour and the one question that can avoid it.

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Rene Magritte, “High Society”

Over the years I’ve had the privilege and joy of coaching entrepreneurs, executives, artists, and colleagues in my own firms. During that time, I’ve also been asking them about their overall coaching experiences for my own growth and learning as a person and a coach. Through that, I’ve become aware of a consistent event that could be holding both coaches and their clients back from the kind of transformational experiences that had motivated them into coaching to begin with.

At the onset of the coaching experience, through the omission of one simple question, the coach and client can send themselves on a many month detour that may, or sadly may not, ever get them to their promised land.

This is how the detour happens:

The coach asks, “What does success look like for you?”

The client may then express a list of goals, achievements, and personal betterments.

The coach may then reply: “Great. Let’s develop a way forward for you to hit your goals.”

With that, the detour begins.

This is how the detour can be avoided and a more direct route to success taken:

The coach asks, “What does success look like for you?”

The client may then express a list of goals, achievements, and what they perceive as personal betterments.

The coach may then reply: “Great. I really hear you on those being valuable goals for you. But I wonder how certain it is that these will mean true success for you. I have one more question that might help us know that for sure: What is the kind of daily experience you would like to be having as a result of attaining those goals?”

What happens in the direct route, as opposed to the detour, is a diligent focus on the “Why” behind the client’s stated goals even if the client isn’t fully aware of it as their “Why” in that moment. It is quite natural for a client, when faced with the “What does success look like?” question, to habitually respond with a quantitative list of achievements, as opposed to a qualitative description of the daily experience they are ideally having as result of having attained those achievements. This habitual response is based on their mind’s cultural conditioning, and perhaps life’s most giant and insidious assumption, that the quantitative list of goals and achievements is synonymous with the qualitative experience of happiness, fulfillment, connectedness and joy. That through the achievement of that certain title, that certain salary, that certain start-up, that certain funding round, and that certain relationship, the experience of happiness and fulfillment will reflexively occur.

The truth is, it may or may not.

The truth is, the mind is a relative outsider in terms of knowing what makes us happy, and so it resorts to cultural conditioning, guessing, and lists to make us feel more comfortable that it actually may have a clue.

In fact, it happens more than not, that we arrive at the achievement of the list only to discover we are not having the experience we hoped for at all. And so, if the purpose of being here on the planet is to have as beautiful, happy, fulfilled, and transformational an experience as possible, why not go right for that as opposed what may be a long meandering detour, or worse yet, a dead end?

The role of coaching, if anything, is to be in service to the client by helping them first become aware of the distinction between the List and the Experience. And then help them create a newly evolved process that will truly serve the “Why” behind their list — the actual experience they wish to be having.

Recently I’ve been working with a prolific and quite conscious entrepreneur who is in the process of bringing a new social impact business into the world. During one meeting she told me she was about to embark on a round of series A funding and was looking on how to maximize her success on her tour. She shared her number goals with me. I prized her ambition on those and then asked her a question she hadn’t yet considered: “What’s the experience you want be having during this? When you are actually sitting down across the table from a potential investor, what are the ideal qualities of your experience in that moment?” She paused at that, but then slowly smiled as she began to enthusiastically recount a qualitative experience of relaxedness, mutual respect, shared purpose, and connection. But then her smile turned into a wince. I asked her about that. She then, with powerful vulnerability, began to describe things she recognized as getting in the way of her having that experience — things like her limiting beliefs about herself, her business plan, and even some judgments about the people she’d be sitting across the table from. This enabled us to do the real work we were there for— first help her become aware of the experience she wants to have, then uncover the barriers she’d placed between her and that experience, and then one-by-one resolve and release those barriers. She proceeded to have a funding round that went beyond her expectations, and not coincidentally, she had an invigorating, cathartic, and even joyful experience in the process. The important thing here to recognize: the focus on the experience prior to the list of goals is not at the expense or neglect of real-world goals, but frequently enables one to go exponentially beyond them, because in letting go of the limiting beliefs inside, we frequently see there is so much more available to us on the outside.

Similarly, I’ve been working with a creative technologist in a global firm that builds digital platforms for large blue-chip brands. During a session, he began to describe to me the list of items he saw as important for him to get to the next level of his organization. As he relayed the list, I noticed a certain deflation in his energy. This was very different for him. This is a person who can erupt in boisterous enthusiasm even when observing something that to mere mortals might be seen as mundane. It’s why I love spending time with him — each moment is a lesson for me in being able to see the miraculous in absolutely everything. And so I asked him about my perception of his energy deflating. He confessed that what he was describing didn’t feel that joyful to him. I asked him when he felt that kind of joy as connected to his work. He described his beginnings as an artist and how he grew into technology in order to serve his art — to bring it to life in fresh new multidimensional ways. He became so good at the technology part that it created its own forward vein into a powerful career, and in the process, his life as a creative technologist had become more “technologist” and less “creative”. In seeing this insight, he architected a new northstar vision for the experience he wanted to be having, found an alignment that would create wins for both him and his organization, and is now having a prolific and joyful experience making his way toward that.

As a last example, I’ve been working with an artist who while having achieved enormous things in his career, was still looking for a life-partner to share it all with. I asked him what that looked like. He proceeded to list a set of attributes, qualities, and achievements this person would have — things like physical appearance, common interests, career status, etc. I then asked him to qualitatively describe a day in partnership with this person — what is he feeling, what is he experiencing, what is lighting him up inside? He joyfully shared that. I then asked him what the real causal correlation was between the qualitative experience he just described and his previous list of mandates and attributes. He quickly realized that there actually wasn’t a strong causal correlation between those things at all, and that he had unconsciously created a very, very tiny box for the universe to work in. He recognized that a relationship beyond his dreams could be just out beyond the artificial mandates his conditioned mind had concocted. Soon after, I received an almost giddy voicemail from him about how, since he let go of his tiny box, multiple people outside of his mandate list had emerged in his experience that were “lighting him up”.

What is really happening when we move from the List to the Experience?

What is happening is the movement from the finiteness of the mind to the vast openness and infinite possibilities of a deeper and exponentially more powerful part of us. It’s a movement from the thinker to the creator. The thinker is guided by conditioning. The creator is guided by its own authentic nature to manifest the experience we are having moment to moment. Which is, ultimately, as compared to a list, the only thing that is real, and therefore the only thing that can make us happy, fulfilled, connected, and joyful.

When coaching helps us flip around our worldly conditioning, making the Experience the master, and the List the servant, this in turn makes the Creator the master and the Thinker the servant.

With that hierarchy in place, things beyond what we can think of begin to happen.

And then we know we’re no longer on the detour.

We know we’ve arrived.


“What you can plan is too small for you to live.

What you can live wholeheartedly will make plans enough for the vitality hidden in your sleep.”

— David Whyte, from “What to Remember When Waking”

Written by

enso / leadership coach. Helping the transformation of leaders that they might transform their worlds. https://www.enso.co/leadershipforimpact

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