Ask Powerful Questions: Create Conversations That Matter
| Will Wise and Chad Littlefield, April 2017
What’s It All About?
In Ask Powerful Questions:Create Conversations That Matter, authors Will Wise and Chad Littlefield lay out a simple, practical framework for turning surface-level talk into real conversations that build trust. It’s not about asking more questions — it’s about asking better ones. Ones that create connection, not compliance.
Will and Chad introduce what they call the Asking Powerful Questions Pyramid™. It has five levels:
- Start with Intention
- Build Rapport
- Create Openness
- Practice real Listening
- Finish with Empathy
The whole idea really clicked for me. The point that landed most for me is how often we think we’re being curious, but we’re really leading people to the answer we want.
That’s not curiosity... that’s control.
This book challenges that. It helps you step back and create space for people to think for themselves. It’s the perfect read for anyone leading a team or trying to build real engagement in high-pressure environments.
Favorite Quotes
“Asking powerful questions creates a new possibility — not a forced outcome—that creates something new.
Biggest Takeaway
It’s easy to slip into manipulation without realizing it, such as asking a question just to steer someone where we want them to go. This book reinforces the importance of intention. Are we asking to understand?
Or are we asking to push? When our intention is clean, we create space for people to discover their own thoughts — and that’s where real change happens. The power isn’t in having the cleverest response. It’s in being present enough to ask the question that gets someone thinking differently. Even if you get it wrong, the act of asking moves the conversation forward.
Bonus Information
This book had me thinking about real situations, like coaching moments with plant managers. I was reminded how often judgment gets in the way of curiosity. Another line stuck with me: they are the expert in their world. When we forget that, we’re not leading — we’re controlling.
It also challenged how I ask questions. Instead of “How did that make you feel?” what if I asked, “what was that like to experience?” One gets you a reaction. The other gets you reflection. That’s a big difference when you’re trying to build trust and drive behavior change.
Learn More on Mindfulness Manufacturing
I’m excited to have Chad Littlefield as an upcoming guest on the Mindfulness Manufacturing podcast. His episode is coming in August, so stay tuned to hear more great lessons on asking powerful questions.