The following post comes from David Lee, founder of HumanNature@Work. David presented “Courageous Conversations at Work” at the Maine HR Convention in 2018.


Is Your Organization Paying the Price of Conversational Cowardice?

Jacob (not his real name) was considered to be the most mission critical and hard to replace member of the executive team by the CEO, because he possessed institutional knowledge and acumen that no one else in the organization had.

His employer was actively working with him to create a viable succession plan if something were to happen to him.

Jacob worked long hours, was passionate about his work, and was devoted to the organization he worked for. It was not unusual for him to work weekends rather than rest and recuperate.

His goal was to someday head up the organization.

That is, until he decided to leave.

Why he left can be a useful teachable moment for any employer, leader, or manager who recognizes the importance of keeping A-List Talent and being an employer that attracts more A-List Talent.

In Here’s Why Your Employees Are Just Not That Into You, I outlined seven factors that contribute to employee disengagement, despite the billions of dollars thrown at this problem. These under-recognized errors of omission and commission lead to apathy and indifference. One of the factors identified was this one:

“Bad Behavior and Poor Performance Go Unchallenged”

In Jacob’s situation, his supervisor was unwilling to confront two of Jacob’s colleagues who were—to put it bluntly—rather lazy and not particularly competent.

Because they weren’t doing their jobs well, and in some circumstances, not doing their jobs, it fell on Jacob’s shoulders to take up the slack or fix their errors. This added to Jacob’s already crushing work load which was burning him out.

It also prevented him from doing some of the more strategic, high-value projects only he could do, projects that would make significant contributions to his employer.

Jacob would bring up this issue to his boss, who we will call Celeste, when he was required to fix errors either colleague made or do a task they should do, in order to meet a deadline.

Celeste would either wave aside Jacob’s complaints by saying “Hey…you wanted this position…this is part of the deal” or, in moments of greater honesty, admit: “I’m not going through the process of hiring another executive again.”

The process of finding and hiring one of the underperforming executives had arduous and time-consuming. Celeste, who was coasting towards retirement, didn’t want to put herself through that amount of difficulty again. Her goal was to cause herself the least amount of stress and strain during this final chapter of her career.

“Because I’m not willing to face my discomfort of having the hard conversations—you have to do your job, and…some of theirs.”

In essence, what Celeste was telling Jacob was “I’m willing to subject you to unfair workloads and compromise the organization’s functioning because I’m unwilling to address the poor performance of your peers. I’m willing to do that because it’s easier for me to do that than to have difficult conversations with your colleagues.”

When Jacob would try to engage Celeste in a conversation about his impossibly long To Do List—in part because of his underperforming colleagues—he was repeatedly told “I know you can do it. You always do.”

Jacob found this double standard infuriating.

Celeste gladly required him to be accountable (for his work and his peer’s) but refused to hold them accountable. She was unwilling to face her anxiety about confrontation—something she readily admitted.

Instead, she took the path of least resistance: requiring the high performer to pick up the slack.

“OK…if you’re not willing to do your job and have the conversation, I’m leaving”

When Jacob told me in our coaching session that he was leaving the organization, I was stunned.

He had expressed numerous times his desire to finish out his career with this company and his vision of eventually becoming the CEO. His decision, while a surprise, was not rash. He had tried numerous times to engage Celeste in constructive conversations about this issue and had been repeatedly brushed off.

He finally had had enough.

He had reached the tipping point.

Celeste was also stunned when Jacob told her he was leaving. She had no idea her unwillingness to do her job and have the important conversations would eventually come with a very steep price tag.

Now, the organization—and Celeste—has to deal with the very issue they had dreaded: Jacob’s departure, along with his vast institutional knowledge and expertise.

What Conversations Are Being Avoided In Your Organization and What Are The Costs and Potential Risks?

How can you take this story and make it a useful cautionary tale?

Share it with your managers and leaders and use it to catalyze a discussion around this critical issue.

Here are some questions to get you started:

  1. What problems do we face as an organization, and for each problem, what conversations are we NOT having that are contributing to these problems?
  2. What fears do we have that keep us from engaging in these conversations? (For each fear: How realistic is this? If it is, how can we mitigate the risk?)
  3. What other conversations do we know we need to have—as an organization and as individuals—that, if they went well, could make a major difference in the results we produce?
  4. Are we willing to develop our courageous conversation skill-set so we are more willing and able to have these conversations?
  5. What’s our next step?

You can also use this story to catalyze coaching conversations. Whether you are supervising a supervisor, manager, or individual contributor, you can adapt the above questions and then coach the person through how to have the conversation.

A Final Thought to Ponder

From years of working with managers at all levels of organizations and interviewing employees who are both highly engaged and very disengaged, I’ve come to this conclusion:

“Every better business result you desire requires having a better conversation”


An earlier version of this article was previously published at

Related Articles:

Can We Talk for a Change?

How to Stop Groundhog Day Conversations

Is Relationship Friction Causing Operational Friction in Your Organization?

What’s the One Conversation You’ve Been Avoiding?