Continuing on from my previous blog on Feelings, in this series on the Thinking Environment, I share my thoughts and experiences on the component of Incisive Questions in this one.
Definition
Nancy Kline describes the purpose of an Incisive Question as:
“Freeing the human mind of untrue assumptions lived as true.”
At the core of high-quality independent thinking lies a hidden obstacle—untrue limiting assumptions that we accept as truth. These assumptions subtly shape our perceptions and decisions, often without our conscious awareness. The power of an Incisive Question lies in its precision: it exposes these assumptions, dismantles them, and replaces them with liberating truths.
What This Means to Me
When I first encountered this definition, I was struck by both its simplicity and its profound implications. I hadn’t fully grasped how pivotal incisive questions were in creating a true Thinking Environment. But now, having seen their impact time and again, I no longer need philosophical debates to convince me—the evidence is in the transformation I’ve witnessed.
The Power of an Incisive Question: Olga’s Story
One of the most striking examples of this unfolded during a thinking session with my colleague, Olga (name changed for confidentiality). She was transitioning into a new role, yet despite her excitement, she struggled to fully step into it. For nearly two months, she found herself unable to disengage from her previous role, leading to overwork and declining performance in her new responsibilities.
As we explored what was holding her back, she articulated this goal:
“I want to have a clear conversation with the Office Principal that I am moving into the new role 100%, without feeling the guilt of betrayal.”
Through our dialogue, she uncovered a series of assumptions, eventally hitting a her key limiting assumption:
“If anyone disapproves of me, I am not good enough.”
There was a moment of stillness as this realization settled in. I could see it in her expression—the weight of years of internalized belief. From there, she dismantled it, replacing it with a liberating assumption:
“My value and worth lie in my own humanness and values, not external approval.”
The change was immediate. She resolved to have the long-overdue conversation, recognizing she had already done her fair share in the transition. The very next day, she completed her handover and officially stepped into her new role with confidence. Weeks later, she shared that this assumption had shaped her adult life, but now she had the awareness and tools to challenge it whenever it resurfaced.
A Personal Experience: A Shift in Minutes
I also experienced the power of incisive questions myself. During a thinking session with my teacher Maryse, I chose to explore a deeply personal and long-standing personal issue—something I had been grappling with for over two years.
My desired outcome was:
“I want to support my extended family members in their difficulties, without compromising my dignity or health.”
As I uncovered my assumptions, I reached a pivotal one:
“Despite their illness, they are capable of honoring my needs and boundaries consistently.”
The moment I voiced it, I knew it wasn’t true. Though our session ended soon after, something had already shifted within me. A weight lifted, and in the days that followed, I noticed a remarkable change in my behavior. When faced with difficult situations, I found myself able to provide support while maintaining my boundaries with grace.
The speed and depth of this transformation left me stunned. After years of struggle, a single question helped me see the situation more clearly and freed me from a cycle of frustration.
This image uses the magic wand as a metaphor for the Incisive Question. It can
magically cut through a dark spell of stuckness within moments sometimes.
Incisive Questions in Team Conversations
Incisive questions aren’t just transformative in personal reflections—they can shift the dynamics of an entire team.
At Thoughtworks, the Learning & Development function underwent a major structural shift a while ago, moving from country-based autonomy to a global Center of Excellence (CoE). As we appointed Regional Heads, I sensed unspoken assumptions that could put our organization at risk. To address this, I facilitated a reflective dialogue, beginning with two simple questions:
1. What are you assuming will change from how things are now?
2. What are you assuming will remain the same despite this shift?
As the team voiced their assumptions, some were validated, while others were dismantled. This clarity allowed us to design a concrete Start/Stop/Continue plan. Within three meetings, our new leaders stepped into their roles with confidence, aligned on their responsibilities and priorities. What could have been a chaotic transition instead became a well-grounded shift—simply through the power of incisive questioning.
When an Incisive Question Is Missing
As I reflect on the role of incisive questions in transformation, I realize how much time and energy I could have saved if I had used one on myself earlier.
For weeks, I procrastinated writing this very piece, convinced that I needed the perfect environment—a quiet space, uninterrupted time—to produce meaningful work. Life, of course, refused to cooperate. Finally, I challenged this assumption and simply began writing.
What happened next was unexpected. The momentum built effortlessly, and I found “flow” in the process despite ongoing challenges in my life. I now wonder—what if someone had asked me an incisive question about my procrastination earlier? How much doubt and delay could I have avoided?
Final Thoughts
Philosophers and psychologists have long sought answers to the question: How do we help people change for the better? I believe the Thinking Environment, particularly through Incisive Questions, holds a crucial key.
Even deeply entrenched assumptions, lived as truth for decades, can be dismantled in minutes with the right question. The process is both elegant and respectful—never intrusive, always empowering.
I can’t help but wonder: Could more therapists and psychologists benefit from integrating Thinking Environment principles into their practice? Maybe some already do. In my opinion, it would be valuable for them to do so.
In the following blog, I will share my experiences with the component of Encouragement.
Credit: Illustration by Chitra