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The 13 Toughest Challenges of Leadership

Indifference is easy, but empty.

Compassion requires more courage, resolve, and wisdom than standing aloof.

Every tough challenge of leadership is made better with compassion.

The 13 toughest challenges of leadership:

  1. Confronting.
  2. Correcting.
  3. Expecting results.
  4. Rejecting excuses.
  5. Expecting people to do things they haven’t done before.
  6. Holding people accountable to their talent and aspirations.
  7. Helping others to become greater than yourself.
  8. Addressing topics others would like to sweep under the carpet.
  9. Building trust when you feel others should extend it because of your position.
  10. Addressing conflict and solving problems.
  11. Delegating authority while maintaining responsibility.
  12. Deciding to intervene or letting things play out.
  13. Spending personal leadership collateral on people who don’t get it.

The challenges you face are no excuse to close your heart.

Bob Sutton writes in, The No Asshole Rule, that the average worker has about a 50% chance of working for an asshole boss.

Compassion solves issues caused by assholery.

The first secret of compassion:

Compassion requires boundaries.

An inability to set boundaries encourages indifference. I’ve withheld compassion because I felt I couldn’t fully meet a need. Additionally, I’ve been concerned that I might enable incompetence in others.

You can’t do everything, but you can do something. Compassion is part of the answer, if it isn’t the whole.

Compassionate leaders explain what they can’t or won’t do with an eye focused on what they can.

  1. Give second chances and maintain high standards. “The best single question for testing an organization’s character is: What happens when people make mistakes?” Bob Sutton
  2. Allow people to face and solve the consequences of their mistakes. Be helpful without enabling incompetence.
  3. Affirm the good while dealing with the bad.
  4. Bring up tough issues optimistically.

What prevents leaders from showing compassion?

How might leaders navigate the challenges and opportunities of showing compassion?

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