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Every New Leader Faces this Courage Test

The first time I faced this test, I failed miserably.

How do you lead people who used to be your peers? New leaders in large corporations, family owned businesses, non-profit organizations, law enforcement agencies, and the fire service organizations face the same test. I faced it when I was a new sales leader, and I failed miserably. What amazes me now is how prevalent the test is, and how unprepared most leaders are when they face that test!

Leading in this situation tests your moral Courage. My moral Courage failed me even when I saw some warning signs about a former peer. But I chose to look past them. I chose to believe he was doing what he was supposed to do, even though there were red flags. In the midst of the situation, I swept those issues under the rug.

After he left the team, I found out that those little red flags were just the tip of the iceberg. I lacked the moral Courage, at the moment of testing, to ask simple questions and maintain my standards for someone I was called to lead. As a result, the team saw a leader who claimed to have standards, but really only maintained those standards when he felt comfortable doing it.

Now some people may not face this test because they change jobs before that can happen. But if you stay in a job long enough to earn a promotion within that same organization, you will have to face this test. The challenges of leading former peers include:

  • They know what you used to say and do.

  • They think they deserved the promotion.

  • You still have a personal relationship with them outside of work.

Here are some suggestions on how to exercise Courage when you face these challenges.

They Know What You Used to Say and Do

When you were an individual on a team, you probably cut some corners or criticized the decisions of some of your leaders. The people you are now leading watched you and heard you.

It takes Courage to face this challenge head on. Try saying:

“You’re right. I did cut that corner (or complained about that decision). I was wrong then, and I’d be wrong now to continue to let it happen on our team. My goal is to get better and our goal as a team is to always get better. That is what I commit to doing and that is what we need everyone on the team to commit to doing as well.”

They Think They Deserved The Promotion

It is likely that whenever you take over a team, there will be someone there who also wanted that job. They may have even interviewed for that position. They have some choices in how they react. But you have some choices too. Do you face this challenge head on? Or do you hope it goes away?

Again, it takes Courage to proactively have a conversation that starts with:

  • Acknowledging their disappointment.

  • Asking them to be the leader the team needs now even though they didn’t get the title.

  • Promise to do your best to help them prepare for the next opportunity.

You Still Have a Relationship with them Outside of Work

This is a very tough situation. Nobody wants to lose a relationship. But the truth is, those relationships need to change. A new line needs to be drawn. The buddy to boss dynamic does not just impact the two of you. Everyone on the team is impacted as well. So even if you are navigating the new dynamic well, the perception of others could damage your ability to lead the rest of the team.

It takes Courage to step away from the old relationship for the good of the team. In my 30 plus years of leadership experience, I have rarely seen a leader be successful in this situation without changing the nature of the old relationship.

New leaders are going to be tested when they are called to lead a former peer - I guarantee that! If you are that new leader, how will you prepare yourself? If you are promoting someone to a new position, how will you prepare them?

It’s your time to take action and do the things that make you uncomfortable. Navigating these relationships as you move into your new role will test your Courage. Learn from my mistakes and get ready. The test is coming!

Dig Deep Questions:

  • When have you faced this challenge in your past?

  • When have you seen a buddy to boss relationship damage a team?

  • Why do so many leaders fail this test?


Here is a quick assessment that will take you 5 minutes to figure it out. Nobody will ever see your results but you.

Warning: If you are not going to be honest with yourself this is a worthless assessment.

To take the assessment use the QR code above or go to

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