From Certainty to Curiosity
A Leadership Paradigm Shift
“I want to be known for my conviction. When I die, I want people to remember me as someone who never wavered from my beliefs.”
I said these words to a friend as we sat in my truck one night in our early twenties. Both of us were wide-eyed idealists, certain we were destined to change the world.
What I couldn’t have known at the time was that my beliefs—about myself, others, and the world—were about to be profoundly disrupted. Shortly after that conversation, I entered a three-year period a wise mentor later referred to as a “wilderness season.”
It was a time of disillusionment, suffering, and deconstruction. A slow unraveling of certainty. And while I wouldn’t wish the wilderness on anyone, I wouldn’t trade it for anything.
Nearly 15 years later, I’m still learning lessons from that season.
The wilderness taught me many things, but one of the most profound paradigm shifts was this:
I moved from being someone who valued conviction as a core attribute—often untested, sometimes rigid— to someone who values curiosity.
Early in our careers and leadership journeys, we often cling to certainty. We believe that if we can just find certainty then we will feel safe, secure, and at peace.
But certainty, by and large, only exists in the minds of the young—or the unchallenged.
As our dreams and ideals come into contact with the real world we're faced with a choice:
Do we double down on our need for certainty?
Or do we embrace uncertainty and see what it has to offer?
Choosing certainty may feel safe in the short term. But in the long run, it leads to frustration, misalignment, and missed opportunities.
You’ll be disappointed when people don’t behave the way you expected.
You’ll resist feedback that challenges your beliefs and assumptions.
You’ll become fixed in a fluid world.
In executive coaching, clients will often bring situations they’re faced with that feel overwhelming to them based on the ambiguity and complexity of the situation.
Often, they expect that through coaching they will arrive at a solution that eliminates the ambiguity and complexity.
And sometimes they’ll believe they’ve done just that, taking the action they designed in coaching and applying it to the situation. Occasionally, in the short term, they are met with relief.
Problem solved. Ambiguity removed. Complexity eradicated.
But complexity and ambiguity are like dust - after wiping down the shelf it appears to be gone, only to begin accumulating again just moments after you’ve dusted.
Inevitably, at the following session, the situation they felt they had resolved has returned, or a new situation has taken its place that feels equally overwhelming.
This may feel bleak, but it’s not!
Disillusionment has a negative connotation, but it’s a remarkably positive state. It means, simply, to remove illusion.
And, when you realize that what you were holding onto before is nothing more than a mirage, it frees you to seek the truth.
What does this mean for leaders?
It means that rather than clinging to the need for certainty - through the elimination of ambiguity and complexity - leaders must rather learn to embrace these states and leverage them to their benefit and advantage. Specifically, by choosing curiosity.
When this shift happens, it frees the leader from expectations that those they lead will behave in expected ways or that situations will conform to their plans, no matter how well thought out and constructed those plans are.
Therefore, when things go awry, rather than responding with outrage, frustration, overwhelm, and a need to control, you can be responsive, adaptable, compassionate, and flexible.
Paradoxically, when we release our grip on certainty, we begin to experience the very things we were chasing: safety, security, and peacefulness.
Not because we or the world are static, but because we’ve normalized disruption and change.
So, how do leaders make the shift from certainty to curiosity?
Cultivating curiosity may feel like a passive process, it’s anything but passive. To be a curious leader is to be an explorer, not a settler.
In practice, it looks like:
Asking more questions and offering fewer answers.
Listening more and speaking less.
Make plans, but hold to them loosely. As Dwight Eisenhower said, “Plans are useless, but planning is indispensable.”
Changing your beliefs when new evidence presents itself.
Staying open to new ideas, perspectives, and people.
Seeking alternative evidence by asking yourself questions like “If my assumptions and beliefs are wrong, what would be the most likely reasons?”
Framing ideas as “hypotheses to be tested” rather than “conclusions to be defended”.
Looking for inspiration from unlikely people and places.
Being more interested in others than you are in yourself.
Instilling processes to assess progress against expectations and creating permission to iterate as feedback is provided.
As the pace of the world continues to increase, business continues to globalize, and social media threatens to create division, curiosity becomes not just a “nice to have” attribute for leaders, but a non-negotiable.
15 years and what feels like several lifetimes later, I still want to be a person of conviction. But, rather than be a person who feels conviction for what I believe and know, I want to be a person who feels conviction in my curiosity, openness, and compassion for self and others.
