True transformation in leadership begins with the courage to ask—and sit with—the hard questions.
When Dave Reynolds and I sat down for a recent conversation, we didn’t start with metrics or goals. We started with *potential*. Not as a theory—but as a practice. Dave shared how the word “potential” has guided his leadership journey and informed his book, Radical Growth. And it set the tone for everything we unpacked: the limits of change, the power of transformation, and the courage it takes to lead through questions instead of commands.
We agreed—radical growth doesn’t come from external pressure. It emerges when a leader creates the right environment for what’s already inside a person to rise. In that way, leadership isn’t about controlling the outcome. It’s about cultivating the process.
This is where transformation begins: when a leader has the courage to ask meaningful questions *and* sit with the discomfort of honest answers.
I couldn’t help but smile when he said it, because hanging on the wall in my office—where the word I chose for the year, “Transform,” sits next to a framed photo of a butterfly. It’s a daily reminder that real growth doesn’t begin with motion. It begins with metamorphosis.
And transformation is rarely convenient. It happens in the soil of discomfort. The space between clarity and courage.
From Directives to Dialogue: Why Leadership Courage to Ask Hard Questions Matters
We’ve all worked in organizations that thrive on clarity and control. But as Dave said, ‘You can manage change from the top down. But transformation only happens from the inside out.’
This reminded me of a Harvard Business Review article I read recently on the power of asking better questions—how the right questions shape culture more than rigid answers ever could.
Transformation requires a different leadership posture—one that replaces answers with questions, and pressure with presence. Leaders who truly unlock potential don’t demand change. They invite it. They ask:
– What do you want to become—not just what do you want to do?
– What belief are you carrying that’s holding you back?
– What are we pretending not to know?
These aren’t just coaching prompts. These are cultural levers. They pull people into ownership, reflection, and deeper alignment.
Coaching as Leadership, and Leadership as Coaching
Dave’s Socratic-based coaching model focuses on unlocking internal insight. As he put it, ‘There’s so much buried wisdom in people that never gets accessed because no one’s asking the questions that would unlock it.’
That’s what great leaders do. They stop performing for their teams and start listening to them. They turn feedback into a mirror—not a weapon. And they stop pushing people to change and start pulling potential forward through clarity, compassion, and curiosity.
Difficult Conversations and Leadership Courage to Ask Hard Questions
Toward the end of our conversation, Dave and I went deep on a topic most leaders avoid: difficult conversations. Dave said something that truly reframed it for me:
“If you care, but you’re not candid, you create distance. If you’re candid, but you don’t care, you create dysfunction. But if you care and you’re candid, you can create transformation.”
That’s the leadership challenge—balancing both. Care without candor becomes passivity. Candor without care becomes cruelty. But when the two are in harmony? That’s when people feel safe *and* stretched.
We agreed: difficult conversations aren’t about confrontation. They’re about *calling people up*. They signal that we value someone enough to be honest with them—even when it’s uncomfortable. And when handled well, those conversations become the very place transformation starts to take root.
I often say, “Feedback is love in action,” which I also unpacked in False Stories, Real Consequences—a post about how leadership missteps and silence can quietly erode trust.
Radical Growth Starts with Leadership Courage to Ask Hard Questions
Radical growth isn’t just a leadership strategy. It’s a mindset. A calling. A way of showing up that says, “I believe there’s more inside you—and I’m willing to go there with you.”
It starts when we stop managing behavior and start developing belief. When we lean into the conversations that matter most, and stop fearing the questions we haven’t answered yet.
Radical growth starts with leadership courage to ask hard questions—every single day.
