5 Steps to Becoming a Bosshole

You’re a bosshole if the bar is high and you kick people when they fall short.

High expectation apart from kindness is cruel.

Bossholes kick people when they’re down.

5 steps to becoming a bosshole:

  1. Belief. You believe in someone’s potential. When you commit to developing people, you see things in them that they don’t see in themselves.
  2. Excellence. You work with someone in the pursuit of excellence. They’re motivated. They make progress.
  3. Skills. They acquire new skills and begin to deliver great results.
  4. Enthusiasm. Everyone’s excited about progress and potential.
  5. Disappointment.
    • Performance drops. The person you believed in runs aground.
    • “Your” high-potential does well and quits after all you’ve done for them.

Disappointment is a tipping point between kindness and bossholery.

You either push through disappointment and become kind or you pull back and become a bosshole.

Untended disappointment kicks kindness to the curb.


Kindness requires grit. Bossholery feeds on disappointment.

It’s easy to pull back when disappointment hits. You assume a self-protective posture and think, “It’s not worth it.”

A closed heart never builds the team you aspire to create.


#1. Kindness is acting with the best interest of others while serving the best interest of your organization.

If you have to fire someone, do it in such a way that they will thank you in a year.

#2. Kindness is aligning personal aspirations with organizational interests.

#3. Kindness is bringing up difficult issues before they escalate to a crisis.

It’s unkind to tolerate patterns of poor performance. Kindness intervenes. Patterns of failure call for active intervention that serve the best interest of individuals and teams.


Disappointment chokes kindness but long-term success with people requires kindness.

Kindness is the flip side of high expectations.

If you can get there being a bosshole, you need a new destination.

What turns good leaders into bossholes?

What is the cure for bossholery?