The Prison of Certainty

Chris Thyberg  

Executive Coach at The Serving Way | when you need an outfitter / guide to cross your growing edge

 

How Your Need to "Know" Is Keeping You Locked Up (And the Key to Your Liberation)

Let's be brutally honest: your addiction to certainty is probably the most expensive habit you've never addressed. We worship at the altar of the confident leader—the one with all the answers, the five-year plan, the unwavering vision.

What a dangerous myth!

Here's what I've discovered after 30+ years leading at senior levels and a decade coaching executives: The most powerful leaders aren't clutching their certainty like a security blanket. They're the ones who've learned to dance with doubt, to stand in the question, to whisper those three liberating words: "I don't know."

And in that space of not knowing? That's where magic happens. That's where you transform from someone who has all the answers into someone who creates conditions for extraordinary thinking to emerge.

Boxed In By "Knowing"

The leaders I meet are often trapped in a high-security enclosure of their own making. The walls? Built over time with "I know" statements. The source? Fear of looking foolish.

They stride into conversations radiating certainty, pre-packaged with their diagnosis:

"My team lacks the right skills."

"The board is too conservative."

"The market isn't ready for our solution."

Let's call this what it is: intellectual addiction. The high of being right is more potent than any substance—and every bit as dangerous because it offers simplifications in a complex, chaotic world.

Your certainty isn't wisdom. It's often just a comfortable prison you've decorated to feel like home. And worse? It's turned you into what Nancy Kline calls the Expert Teller role* —always dispensing answers, never creating space for discovery.

Instead of feeding this addiction, I invite leaders to ask themselves questions that crack the foundation of certainty:

"What if the opposite of my current belief is true?"

"For my current belief to be true, what else has to be true ... and is it?"

"What scares me about being wrong here?”

"Penalty Box" John Dykstra - used with permission

The Great Escape: Sofia's Liberation Story

Let me tell you about Sofia*, a tech CEO who discovered what's possible when you trade the prison of certainty for the freedom of collaborative discovery.

Sofia came to me convinced her innovation pipeline had stalled because her team lacked technical expertise. She wanted to fire half her leadership team and recruit "real talent."

Sofia had perfected the Expert Teller role—she diagnosed problems, prescribed solutions, and expected execution. But her team had stopped bringing her their wildest ideas because they knew she'd immediately sort them into "viable" or "waste of time."

When I asked what she was afraid might happen if she considered her own role in the innovation drought, she went silent for a full minute. Then came the breakthrough:

"I'm terrified we'll discover I'm the bottleneck. That I've been shutting down ideas because they don't fit my vision."

This moment of naked vulnerability—this willingness to shatter her own certainty—unlocked everything. Sofia transformed from Expert Teller to Thinking Partner. Instead of having all the answers, she started asking better questions:

"What if we tried this differently?"

"What aren't we seeing?"

"What could we do if we knew it's safe to fail-smart and learn-fast?"

The liberation was extraordinary. Her team began bringing ideas she'd never imagined. Energy returned to their innovation sessions. People started building on each other's thinking instead of competing for her approval.

Six months later, that same "won't innovate" team launched two breakthrough product lines using talent that was there all along.

Thinking Partner At Work (iStock)

Your Leadership Liberation: The Transformation That Changes Everything

Here's the leadership revelation most "experts" won't tell you: Your greatest strength emerges precisely when you stop being the Expert Teller and become a Thinking Partner.

The Expert Teller believes their job is to have answers. The result? Dependency, bottlenecks, and a team that stops thinking for themselves.

The Thinking Partner knows their job is to ask better questions. The result? Collective brilliance, breakthrough thinking, and a team that can't wait to bring you their best ideas.

• The Expert Teller hoards knowledge. The Thinking Partner generates wisdom.
• The Expert Teller creates dependency. The Thinking Partner develops capability.
• The Expert Teller exhausts themselves being the smartest person in the room. The Thinking Partner energizes themselves by making everyone else smarter.

Think of certainty as a closed fist—you can hold tightly to what you know, but you can't receive anything new. The Thinking Partner approach is an open palm, ready to release and receive, to give and take, to touch and be touched by new possibility.

When you make this shift, you transform from the bottleneck in your organization's hourglass to the wide-open space where ideas can collide and combine. You become the catalyst rather than the cap.

Your Freedom Trek: 3-2-1

>>> Three Questions to Break the Chains

What's the most expensive belief you're holding, the one that's costing your organization the most in terms of lost opportunity?

If you had to argue passionately against your current strategy, what would be your three strongest points?

What truth are you avoiding that everyone else can see?

>> Two Pivots When You're Trapped in "Knowing"

Get Curious, Open, and Nonjudgmental: Stop dispensing answers and start generating questions. Instead of "Here's what you need to do," try "What possibilities are we not seeing?"

From Interrogation to Investigation: Instead of defending your position, interrogate your assumptions like they're uncooperative witnesses. What evidence actually exists? What contrary data are you conveniently ignoring?

> One Ongoing Practice: The Not-Knowing Appointment

Schedule regular 15-minute "dates with uncertainty." Sit in silence with nothing but a blank page and this question: "What do I now sense as I accept that I may not know?"

These questions will make you squirm—that's how you know they're working. Good News! The answer that makes you most uncomfortable is likely the one you need most.

The Revolution Starts within You

The typical leadership development industry wants to sell you certainty—frameworks, matrices, and five-step processes that promise control in a world of chaos.

I'm offering something harder but way more valuable: the courage to hold your knowledge like water in cupped hands—present but not grasped, useful but not controlling.

This is what I call "leading yourself well"—the internal revolution that changes how everyone around you shows up. When you stop playing the exhausting game of Expert Teller and embrace being a Thinking Partner, you create space for everyone to contribute their best thinking.

Where is your growing edge calling you to leave the cell of being right for the collaborative territory of shared discovery?

If you're ready to trade the false comfort of certainty for the exhilarating potential of breakthrough, let's connect via LinkedIn. No sales pitch, no ten-step program—just a conversation about where you are and where your next liberation might be hiding.

Water Hands (visual explorer)

* Hat-tip to Nancy Kline for the distinction between Expert Teller and Thinking Partner. Check out her classic, Time to Think: Listening to Ignite the Human Mind

* Sofia is a composite of many senior leaders I've worked with as their thinking partner.

#LeadYourselfWell #BeyondCertainty #TheServingWay #EmbraceTheVoid #LeadershipTransformation