Unlocking the Power of Thoughtful Leadership
How a Single Question Can Bring Out Your Team’s Best Thinking
Have you ever watched a team open up with one thoughtful question? Or noticed how the same conversation can lead to new insights or annoyance depending on how a question is phrased?
I recently experienced this firsthand while working with Pipeline Entrepreneurs, a program for high-growth entrepreneurs. As I applied my coaching skills, I framed questions to get below the surface. Lightbulbs. Faces lit up, founders made unexpected comparisons, and new opportunities for revenue emerged.
That's the magic of being thoughtful. It's about creating conditions for shared learning and natural connections.
Why does this matter now? Because while AI is busy handling the predictable, our very human superpowers (e.g. empathy, intuition, the courage to sit in awkward silence) are skyrocketing in market value.
In today's newsletter, we'll explore why thoughtfulness is an undervalued leadership strength, especially in the wild world of AI and human collaboration.
AI Revolution: Unleashing Our Human Superpowers
We're witnessing a fundamental shift in leadership. As AI handles more routine tasks, our human capabilities like empathy, intuition, and thoughtful connection are becoming our most valuable assets.
Here's a real-world example: A friend fed their schedule to ChatGPT and received a week with fewer meetings, more gym time, and something called “lunch”. The result? Less context switching, more meeting delegation, and open spots for life.
This isn't about AI making us obsolete. It's about AI allowing us to be more human. When machines handle the predictable, we can focus on what matters.
The shift is happening everywhere:
At the Dallas-Fort Worth Airport, AI empowers customer service agents to solve problems without waiting for a team lead - like why gate C17 always feels five degrees colder than the Arctic.
In product development, tools like ChatPRD and platforms like Lovable, Bolt, and Bubble spit out prototypes before your coffee cools. If you still measure progress in tedious product briefs, I have a fax machine to sell you.
The leaders who will thrive in this new world won't demand "do it my way." Instead, they'll champion their team by being thoughtful and deeply human.
Science Behind Thoughtful Connection
So what does a thoughtful leader actually do? They reflect and provide time for their team do the same.
Dr. Nancy Kline's research on the "Thinking Environment" reveals a powerful truth: the quality of everything we do depends on the quality of our thinking. She asks: "What does it take for people to help each other think well for themselves?"
“To be interrupted is not good. To get lucky and not be interrupted is better. But to know you will not be interrupted allows you truly to think for yourself.” - Nancy Kline
The first step to create a Thinking Environment is to pay attention. Dr. Kline notes that when we feel truly heard, our brains access different neural pathways, leading to more creative and insightful thinking.
Want to try this out? In your next team meeting, use this prompt to evoke a Thinking Environment: “What would you like to think about and what are your thoughts?” Then count to ten. Resist the urge to break the silence. You’ll feel like a mime at first. It passes.
This question reinforces the importance of direct conversations and can lead to new product capabilities. The thoughtfulness creates space for insights that may not emerge in traditional metrics-focused meetings.
Mastering Intentional Listening
Traditional leaders try to be on top of everything, which leads them to miss what matters. Thoughtful ones practice "intentional listening." They listen for the unsaid.
Consider the difference between these responses to a team member saying, "We tried that approach before and it didn't work":
Command-and-control response: "We need to try something different. What other options do we have?"
Thoughtful response: "What insights did we learn from that experience that could influence our approach?"
The first shuts down exploration. The second opens possibilities. Same situation, different outcomes.
In your next meeting, consider how you’re listening:
If you're listening to learn —> you pay attention to new concepts and connections.
If you're listening to validate —> you’ll find it and miss everything interesting.
If you're listening for problems —> you’ll drown in them.
I recommend listening for what’s missing, not just what’s said or what you hope to hear.
Power of Micro Questions
I keep returning to one key insight as I reread the paragraphs above: the most powerful questions are often the smallest ones. These "micro questions" create space for thinking without being overwhelming. It's a technique master coaches use. One well-placed question can change a conversation.
The question can be as simple as: "And then?" "What else?" "Say more?"
I applied this technique while onboarding new team members for a fractional project. at Pearson and SimplePractice. The new hires who made the most connections asked variations of these simple questions.
For example, one engineer paused after a new PM asked "What else?" following an explanation of a technical constraint. Then he said, "There's something I’ve been wanting to try." That insight became the foundation for a new mobile direction.
The power isn't in the questions. It's in the patience to let insights emerge naturally rather than rushing to solutions. This is crucial in our AI-accelerated world where the temptation to jump to answers is stronger than ever.
Designing Conversations for Collective Intelligence
Thoughtful leaders spend time designing conversations as much as planning strategies. They understand collective intelligence unlocks new ideas.
I work with Chris Shipley, an author, thinker, and producer (including the DEMO conference). When she leads events or facilitates team calls, I'm impressed by her thoughtful approach.
She considers questions such as:
What type of thinking do we need right now: creative, analytical, or blue sky?
Who brings perspectives we haven't considered?
What would help challenge our assumptions?
This approach requires humility, admitting that surfacing the most important insights requires a brief pause. I’m learning not to rush to the punchline by observing Chris. For example, when roadmapping, I’m taking people through the journey, allowing them to challenge me and their viewpoints, instead of jumping to the end.
This thoughtful approach makes people less likely to dismiss ideas that don't immediately make sense. Because I'm genuinely curious about how people reach their conclusions, I can ask better questions.
Key Takeaways and Next Steps: A Four Day Plan
Thoughtful leadership isn't just about today. It's about building your team's capacity to navigate an uncertain future. Let’s summarize the key insights and next steps:
Day One: Start Small, Think Big
Ask one teammate, “What’s your thinking on this?” And, truly listen.
In your next conversation, use micro-questions like "And?" or "Tell me more" to uncover hidden ideas.
Day Two: Create Space for Thinking:
Identify time for team members to explore challenges together to encourage collective problem-solving and innovation.
Day Three: Practice Pre-mortems:
Identify your next major milestone.
Plan for 15 minutes listing potential issues and 15 minutes brainstorming preventive measures.
Day Four: Keep Building a Thoughtful Culture:
Identify the meeting where insight goes to nap and wake it up with a thoughtful prompt.
After the meeting, note observations on the immediate impact.
Keep iterating based on the learning and consider the changes.
The question isn't whether you have time to be thoughtful. It's whether you can afford not to be. In our rapidly changing world, leaders who bring out the best thinking in others will shape what's possible, not settle for what is.
What’s one question you’ll use to elevate your team’s thinking this week? I'd love to hear about your experiences and results. Let's continue this leadership journey! And, as Lancaster says, the nose knows.
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Reach out over LinkedIn: Diana Stepner
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