How to Face Big Challenges and Successfully Climb Steep Hills

The Little Blue Engine begins,

The little blue engine looked up at the hill.
His light was weak, his whistle was shrill.
He was tired and small, and the hill was tall,
And his face blushed red as he softly said,
“I think I can, I think I can, I think I can.”

The Little Blue Engine ends,

He was almost there, when — CRASH! SMASH! BASH!
He slid down and mashed into engine hash
On the rocks below… which goes to show
If the track is tough and the hill is rough,
THINKING you can just ain’t enough!

Read all four verses of Shel Silverstein’s poem.


Difficulty and disruption teach you that self-sufficiency is a dangerous myth.

Don’t climb steep hills by yourself.

A with:

Three questions for steep hills:

  1. How might your team feel you pulling WITH them?
  2. How might you let others pull WITH you?
  3. How might you create environments where people pull WITH each other?

If you feel alone when climbing big hills:

  1. Assess your perception. Perhaps people are helping, and you don’t notice.
  2. Confess the truth to yourself. You’ve chosen to climb on your own because you lack humility.
  3. Don’t be a whiner. Don’t complain that people aren’t helping. “Woe is me” is a plea for validation and sympathy.

Practices for climbing big hills:

  1. Use “we.” Ask, “How can WE get this done?”
  2. Invite suggestions. “What do you think?”
  3. Assign tasks based on strengths and passions.
  4. Find a friend that affirms AND challenges. Affirmation is only half the formula for success. The other half is a swift kick in the pants.

The answer to steep hills isn’t thinking you can’t.

The answer to climbing steep hills is knowing you need others.

The skill of climbing steep hills is teaching others how to help others.

How might leaders build organizations with a “how can I help” approach to steep hills?

Bonus material:

Where Grit Really Comes From (Leadership Freak)