The Leadership Question That Saved a 100-Day Plan From Quiet Failure

It didn’t come from a strategy deck. It came from a moment of silence.

She had just landed the biggest role of her career.

New CXO. Big title. Bigger expectations. We were two weeks into our coaching engagement when she walked me through her 100-day plan. It was neatly structured, aligned with board priorities, and full of energy. On paper, it looked flawless. But she didn’t look… settled.

I’ve learned to trust that look. So I asked a simple question: “If this plan failed, what would have caused it?”

She laughed. Then paused. Then said quietly, “If I spend the next 100 days trying to prove I belong in the room… instead of listening to what the room really needs.”

That moment? That was her crossing the threshold.

Up until that point, she was still playing defense. Subtly guarding her promotion, trying to outwork her doubts, masking it all with bullet points and confidence. But in that one moment of inversion, flipping the question from “How can I succeed?” to “What will make me fail?”,  the armour cracked.

That’s when her real leadership arc began.

She slowed down. Started making space in meetings instead of filling them. Asked questions she already knew the answers to because she realised others needed to be heard. She stopped trying to “own” every outcome. And started enabling outcomes through others.

Her plan didn’t change. But her posture did. And that made all the difference.

This is the quiet power of inversion, the mental model that most leaders skip. We’re taught to think forward: add value, build plans, drive outcomes. But in senior roles, progress often comes from subtraction and not addition. It’s not about having more answers. It’s about eliminating avoidable errors. Silent traps. Subconscious patterns.

And inversion helps you see them before they cost you.

If you're leading something high-stakes right now. A new team, a turnaround, a transition, pause and ask:

• What fear is subtly running in the background?
• What am I trying too hard to prove?
• If this fails… what will have quietly caused it?

That one question might just save your plan. Or even more importantly  reveal the leader you're becoming.

 If this post helped you, give it a small like so it reaches the one leader who needs it this week.

If someone in your circle is starting a 100-day sprint, pass this along and save them an avoidable mistake.

And if you want a discreet sparring partner for your next 100 days, send me a note. I’m happy to listen first, then help you decide what to subtract.