There’s a leadership trap I see so often that I’ve given it a name:
The How Hole.
It usually happens about five minutes after I’ve finished guiding a CEO to craft a compelling vision for the future.
The CEO sits back, looks at the vision, and says:
“This is exactly where we need to go, but… how are we ever going to get there?”
That’s when I know they’ve fallen into The How Hole.
Here are five principles I use to help them climb back out:
1️⃣ Stay anchored in the WHAT.
Don’t let today’s uncertainty weaken tomorrow’s vision.
2️⃣ Don’t confuse uncertainty with impossibility.
Not knowing the path doesn’t mean the destination is out of reach.
3️⃣ Trust your team to find the HOW.
Your job is to inspire the future – not invent every step.
4️⃣ Shift from doubt to possibility.
Ask, “What would have to be true for this vision to become reality?”
5️⃣ Lead with conviction, not certainty.
The best leaders don’t wait until they know the path before they commit to the destination.
The biggest breakthroughs I’ve seen in organizations didn’t happen because the CEO knew exactly how to get there.
They happened because the CEO never let go of the WHAT while the team discovered the HOW.
❓How do YOU keep yourself from falling into The How Hole?
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