The Penalty Box: Plight of a Good Leader


Believe it or not, leaders are human too. They make mistakes. And they suffer the consequences like the rest of us.

These mistakes can result from many reasons:

  • Not having all the right information before a decision is made
  • Not understanding the impact to all levels of the organization
  • Underestimating underlying relationships between stakeholdersmanagerscustomers, or peers
  • Not comprehending where alliances reside within the organization and among the upper ranks

Mistakes can also happen when a split-second-decision or choice ends up being the wrong one sending waves of repercussion.

On Mistakes and The Penalty Box

I recently reconnected with a dear friend of mine who I deeply respect as a manager and a leader. She shared with me her story of the Penalty Box. With her permission, here is Janet’s story.

Things are going good…

Janet had the pleasure of being promoted to manage a phenomenal team. The organization felt the stars had aligned and the teams were finally under the right umbrella.

Things turned bad…

But unfortunately paradise was short-lived. The leader of the larger organization (who we will call Bob) continually made bad choices that seemed to come straight from “Five Leadership Mistakes of the Galactic Empire.” Janet had made several attempts to escalate the issue to his managers. But this backfired on her. And unfortunately, this was a big mistake.

Her efforts backfired on her because she failed to comprehend the alignment of “The Good Ole Boys Club.”  

But things got better…

But over time, fate finally prevailed and the leader’s bad deeds caught up with Bob through an anonymous tip to the Ethics Committee. When the investigation hit, all of the documentation of issues she had provided to senior leaders were disclosed.

  • Hands were slapped for years of inaction.
  • The time between the escalation of the issue and the termination of Bob was quick.
  • Janet felt for once that “the system worked.

But things got worse…

What Janet did not comprehend was the aftermath it would have on her as a leader. The victory of a bad apple finally ousted became overshadowed by hurt egos from the VPs who had allowed a poor leader to wreak havoc for years.

Vengeance was swift, too:

  • Janet’s team was yanked and dispersed to the winds
  • She was moved to an individual contributor role; career death to any manager
  • She was told by Human Resources they couldn’t talk to her about it
  • And oddly, HR couldn’t explain her high manager feedback scores

The process finally became crystal clear:  “protect the manager and the company at all cost.

And they got even worse…

The additional consequence was her team believed she too must have done something wrong.

She was wrongly convicted:  Guilt by association.

Because everything had to be kept confidential, suspicion turned to distrust.

As the saying goes… No good deed goes unpunished.

On Misery and Its Company

What amazed me even more than the plight was what Janet told me next. She started to have conversations with other leaders and managers she trusted to get some advice on what to do.

Story after story emerged that was very similar to her own plight. She discovered that with high-stress, individuals take one of two actions:  Fight or Flight.

  • Many of the trusted colleagues fled
  • They left the company
  • Took a leave of absent
  • Accepted a demotion
  • Or moved to a different department

My friend had tried to move to another internal position, but was blocked from jobs she was more than qualified for.

This was when she decided to FIGHT!

Bringing It

Janet took the initiative to encouraged her manager to take on a critical transformation program. Within 18 weeks, she delivered a program that had not yet successfully been delivered before. Within 13 months the team developed a fully comprehensive world-class employee development system.

What a fight indeed!

Unhappy Endings

Unfortunately this isn’t a fairy tale with a happy ending. My friend is still in the Penalty Box because the VPs of the past still lead the organization.

Despite her accomplishments, she has not regained much needed trust to make her career there a success. Unfortunately for her, her company, and her career, her next step will probably be to leave the company.

She will take with her some valuable leadership lessons:

  •  Always understand underlying relationships within an organization, past, present and future
  • Comprehend where alliances reside amongst the leadership ranks

True Leadership

True leaders fight for their teams and their companies first and foremost. Unfortunately, many individuals today who hold leadership positions have regressed to “Survival of the Fittest.” As companies continue to get more and more top-heavy, the battle will continue to get uglier. The need for true leaders is more important than ever.

My final question to her was, where do you go from here? She told me her new golden rules: Even when others don’t believe in you, believe in yourself. Trust your gut, and those few trusted advisors.

Hopefully for this true leader, fate will prevail to release her from the Penalty Box landing her in the best job of her life.


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Cheryl Dilley 
is a Program Director at Intel Corporation
She is a transformation leader, coach, and program strategist
Email | LinkedIn WebFacebook

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6 responses to “The Penalty Box: Plight of a Good Leader

  1. Pingback: Leadership Thought #300 – Never Get To the Point Where You Think You Know It All « Ed Robinson's Blog·

  2. Good story with some good lessons! The fighting back and believing in oneself are certainly valid strategies- ones that we admire. Yet as this gutsy story points out, there’s a larger context and group dynamics at play as well, and individual heroics often don’t have the outcome we want. Years ago, I became very interested in the unconscious psychology of “group-as-a-whole,” how individuals end up “holding” certain roles in a group – whether they want those roles or not. (Think of your elementary school classroom. There was always the teacher’s pet, class clown, problem kid, etc.) “Whistle blower” ends up holding a certain role in an organization that transcends the individual because it’s held (unconsciously) by the group. And the group will (mostly unconsciously) protect itself. There are ways to deal with this, but pretending it isn’t so or railing against it is a recipe for burnout.


  3. Reading your friend’s story made me think of my wife. She did much the same as Janet in letting issues be known. For years she was ignored because it was a “Good old boys” club. Once she left, things started rolling.

    Others followed her lead and left, bosses were fired, and changes were made.

    If only these things could happen without a major push.


  4. It never fails to amaze me how common Janet’s story is. Very unfortunate and such a loss and waste for any working environment.

    My best wishes to her and I hope that as a result of all that Janet has been through that she does end up in the perfect role very soon.

    Thank you for posting this.


  5. Pingback: Never Get To the Point Where You Think You Know It All·

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