Leadership author Jeff Wetzler on asking the right question at the right time
What makes partnerships truly transformational rather than merely transactional? According to Jeff Wetzler, the difference lies in curiosity, psychological safety, and the willingness to learn from one another. In this conversation, Wetzler explains how leaders can unlock hidden insights by inviting honest feedback and asking better questions. His “Ask Approach” provides a structured way to uncover what people are thinking but not saying. When leaders build environments where truth can be shared safely, partnerships move faster, decisions improve, and trust compounds over time.
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Learn more about Jeff’s work: askapproach.com | Transcend Education
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The need-to-know:
Most critical insights are hidden in people’s “left-hand column”: What colleagues think but do not say often contains the breakthrough ideas, risks, or warnings leaders most need to hear.
Curiosity is a decision, not a personality trait: Leaders who consciously choose curiosity open the door to deeper insight, stronger relationships, and faster trust formation.
Great partnerships begin with small proof, not big strategy: The strongest collaborations often start with a single successful project that builds trust before expanding into larger initiatives.
Let’s go a little further
Most partnerships fail for a simple reason: people are not saying what they are really thinking.
Leaders often assume that if something important needs to be said, someone will say it. In reality, the opposite is usually true. Teams routinely withhold ideas, concerns, and feedback because they fear the consequences of speaking openly.
Jeff Wetzler calls this the “left-hand column.”
It comes from a simple exercise. On the right side of a page, you write what people said in a difficult conversation. On the left side, you write what they were actually thinking but chose not to say.
When leaders examine these columns, the insight is striking. The left-hand column often contains the most valuable information in the room: risks that were ignored, ideas that could have changed the strategy, or concerns that could have prevented failure.
The problem is not a lack of intelligence. It is a lack of conditions where truth feels safe to share.
Why curiosity is a leadership choice
The first step in Wetzler’s Ask Approach is deceptively simple: choose curiosity.
Many leaders treat curiosity as a personality trait. Some people are curious. Others are not.
Wetzler rejects that framing. Curiosity is a decision.
It begins with a simple question:
What can I learn from this person?
That question changes the energy of a conversation. Instead of preparing a rebuttal, you begin exploring perspective. Instead of defending your position, you start discovering information you may have missed.
This shift is powerful because people can sense genuine curiosity. When leaders show authentic interest in learning, others become more willing to share.
Curiosity becomes the gateway to trust.
The hidden barrier: psychological safety
Even when leaders are curious, people may still hesitate to speak.
Why?
Because sharing the truth often carries risk.
Employees worry about damaging relationships. Partners fear looking uninformed. Colleagues hesitate to challenge authority. In many organizations, honesty feels dangerous.
This is why the second step of the Ask Approach is making it safe.
Leaders signal safety by inviting feedback, demonstrating resilience when challenged, and showing appreciation when others speak candidly.
One simple phrase can shift the tone of a conversation dramatically:
“Give me your most critical feedback.”
When leaders consistently respond constructively, they prove that truth will not be punished.
Over time, people start sharing what they would otherwise keep hidden.
Asking better questions changes everything
The third step of the Ask Approach focuses on a skill few leaders are ever taught: asking quality questions.
Not every question invites learning.
Some questions subtly pressure agreement. Others signal judgment. Many are simply attempts to confirm what the leader already believes.
A quality question does something different. It opens thinking.
For example, after presenting an idea, a leader might ask:
“What’s your reaction to that?”
Or:
“What might I be missing?”
These questions invite perspective rather than compliance. They create space for disagreement, improvement, and insight.
And that space is where partnerships deepen.
Listening for more than words
Even when people speak openly, leaders often miss the full message.
Most people listen for content. But Wetzler argues that true listening requires attention to three layers:
Content (what is said)
Emotion (how it is said)
Action (what people are doing)
When leaders listen across all three dimensions, conversations reveal far more than the surface message.
Subtle hesitation may signal concern. Energy may reveal commitment. Silence may signal uncertainty.
Learning lives in those signals.
Reflection turns conversations into insight
The final step of the Ask Approach is reflection.
After a meaningful conversation, leaders should sift out the most important insights and then “turn” them in three ways:
How does this change my story about the situation?
What actions should I take as a result?
What assumptions or biases might this reveal about me?
Reflection transforms conversation into learning.
But the process does not end there.
Wetzler encourages leaders to reconnect with the person who shared their insight. Thank them for their honesty. Explain what you learned. Show how it influenced your thinking.
That simple act reinforces trust.
It tells people their perspective mattered.
Partnerships grow when learning flows both ways
The strongest partnerships are not transactional. They are learning relationships.
When both sides feel safe to share their thinking, ideas improve. Decisions sharpen. Trust accelerates.
And the partnership becomes something more powerful than either organization could build alone.
In Wetzler’s words, partnership is power.
Not power over one another.
But the power that emerges when people combine the best of what they each bring to the table.
Question for you
When was the last time you asked the right question at the right time?
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