Facing the Challenge of Challenging Others


Challenge people! Fully prepared is boring.


Who is ready for opportunities?” is the wrong question. Ready is overrated.

You weren’t ready. Remember how you didn’t know? You see your skills but forget where they came from. Experience taught you.

Are you ready for the challenges you’re currently facing? I hope not.

It’s foolish and wasteful to expect others to develop skills apart from experience. It’s too late if they’re ready.


Courage trumps skill because skill without courage is wasted.   “Have they stepped up in the past?” is the right question. Who they are comes before what they do.

Courage enables learning during the journey. Education provides foundations. Experience activates education.


Challenge those who:

  1. Learn from failure. Those who can’t fail, can’t grow.
  2. Fall and get up.
  3. Complain. Complaining may be frustrated desire. Challenge complainers to take responsibility.
  4. Feel apprehensive. They say, “I’d like to but …” Ask, “Would you really like to?”
  5. Display character qualities like curiosity, compassion, and transparency.
  6. Faced their fears in the past and pushed through.
  7. Desire opportunities. Desire trumps talent.
  8. Currently contribute.


After new challenges are accepted:

  1. Listen to their concerns. Don’t minimize.
  2. Clarify expectations.
  3. Create structures where feedback is expected, frequent, and welcomed.
  4. Provide support. Mentor, coach, encourage, and educate.
  5. Ask, “What are you learning about yourself?” Exclusive focus on tasks, while neglecting the person, discourages.
  6. Don’t step in quickly, as long as there’s progress.

Five bonus questions:

During follow-up sessions, after new challenges are accepted, ask:

  1. How are you becoming who you want to be?
  2. What makes you proud of who you are becoming?
  3. What fears or apprehensions are you facing?
  4. How does your behavior express who you are?
  5. What’s next for you?

Help people say, “I never thought I’d do what I did?”

How can leaders challenge the “right” people to do more than they thought they could do?