The Real Challenge Isn’t Leading—It’s Questioning
Leadership isn’t about having all the answers. It’s about asking the right questions.
Most leaders get this—at least conceptually. We’re trained to ask the big strategic questions of our teams: Where are we going? How do we win? What’s standing in our way? But there’s one question—the hardest question—that often goes unasked.
And it’s not directed at our teams. It’s directed at ourselves.
That question is this:
What am I pretending not to know?
Why This Question Changes Everything
That’s an uncomfortable question. It cuts through the noise and exposes the blind spots we conveniently ignore. The tough reality is that as leaders, we’re often the bottleneck. The stories we tell ourselves—the narratives we cling to—are the very things holding our teams and organizations back.
You might be thinking, I don’t pretend. I face reality head-on. But let’s be real. Every leader has areas they resist looking at too closely. It might be an underperforming executive you’ve been avoiding a tough conversation with. A strategy that’s not working but is too deeply ingrained in the culture to kill. A personal leadership habit that’s limiting your effectiveness.
Leaders don’t just struggle with execution—they struggle with self-awareness. And the best ones interrogate their own thinking ruthlessly.
Breaking Through Your Own Blind Spots
In my work coaching Fortune 500 executives, I see this pattern over and over. The biggest breakthroughs don’t come from new strategies or better processes. They come when leaders finally confront what they’ve been avoiding.
So how do you use this question effectively? Here’s a simple framework to integrate it into your leadership rhythm.
1. Make It a Habit
Reflection isn’t a luxury—it’s a discipline. Build a cadence into your leadership routine where you sit with this question. Whether it’s weekly journaling, a debrief after major decisions, or a check-in with your executive team, carve out space to ask:
“What am I pretending not to know?”
2. Get Outside Perspectives
You can’t see the whole chessboard when you’re playing the game. Surround yourself with people who challenge you—trusted advisors, executive peers, or an objective coach. Give them permission to point out what you might be missing.
Most importantly, listen. Without defensiveness. Without justifying. Just absorb the insight.
3. Turn Awareness into Action
Self-awareness without action is just intellectual entertainment. Once you recognize a blind spot, do something about it. Make the tough call. Have the conversation. Change the system.
Because here’s the thing—your team already sees what you’ve been avoiding. They just don’t know if you have the courage to address it.
The Leadership Edge: Daily Alignment
This is exactly why leadership development isn’t a one-time event—it’s a daily practice. It’s why platforms like Cloverleaf and frameworks like the TEAMS Methodology exist: to create the ongoing nudges and strategic alignment that keep leaders on top of their game.
When you and your team operate with clarity, simplicity, and systems-driven thinking, leadership becomes easier. Not effortless—but easier. The right questions surface. The right conversations happen. And the right decisions follow.
What You Need to Do Next
So here’s my challenge to you:
Block out 10 minutes today. No distractions. No meetings. Just you and this question:
“What am I pretending not to know?”
Then, do something with the answer.
That’s the work of real leadership. And that’s what separates the best from the rest.
Now, your turn—what’s the one leadership challenge you know you need to face? Let’s talk. Drop a comment or share your thoughts.Let’s raise the bar on execution. It’s the job.
About Michael King
I’m Michael King, an executive coach dedicated to helping leaders like you craft clear, focused strategies that drive results. With years of experience guiding high-level executives through the challenges of leadership, team engagement, and effective communication, I’ve seen firsthand what works—and what doesn’t. My approach is straightforward, no-nonsense, and always aimed at creating systems that lead to sustained success. If you’re ready to take your leadership and your team’s performance to the next level, let’s schedule a time to chat. Together, we can develop a tailored strategy that aligns your team, amplifies your marketing efforts, and propels your business forward. Click below to book a call with me today!
