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Courage - How Companies Should Develop Leaders in Their 20s

Our role is to prepare the next generation of leaders to do better than we did.

“OK! Now go lead those people who used to be your peers!”

That is what happens in a majority of organizations. When someone is promoted to lead people who used to be their peers, most companies do nothing to prepare new leaders for those unique challenges. They are promoted because they were good individual contributors and someone sees their potential to lead. But nobody is preparing them.

Some new leaders, if they are lucky, might go through a basic supervisor course, but those courses often focus on the administrative tasks a new leader needs to complete. The real challenges come from leading people who, just last week, were their peers.

Year after year. Generation after generation. New leaders are put in this difficult position and we are not preparing them. So why aren’t we doing something to prepare them?

Leaders, whoever and wherever you are, your role is to prepare the next generation of leaders to do better than our generation did.

Think about the challenges of leading former peers:

  • Coaching someone who has been with the company longer than you.

  • Leading someone who is twice as old as you.

  • Controlling a conversation in a meeting with people with whom you used to joke around.

  • Correcting a former peer who walks into training late.

All of these challenges require them to exercise character and character requires Courage. These same challenges probably pushed us outside our comfort zones and they will push someone in their twenties outside of their comfort zones as well. How can we prepare them for these challenges?

A team with leaders at every level will always beat a team that only has leadership at the top. We have to help people think and act like Leaders of Character now if we expect them to think and act like Leaders of Character in the future.

Character begins with our thoughts. Our thoughts lead us to our words. Our words influence our actions. Our actions, over time, become our habits. And our habits form our character. Using this model, we can begin to develop people in their twenties now.

One method is to have regular discussions with our future leaders about different case studies where a leader needs to exercise Courage. Reading a case study and then leading a discussion among our younger team members will prepare them. We can’t just hope they will exercise moral Courage in the face of a character test. We must prepare them for it beforehand.

Ask them:

  • What choices did the person in this case study have?

  • What did they choose and what should they have chosen?

  • What makes those choices difficult?

  • How were these choices a test of their character?

  • What would have happened if they made a different choice?

  • How does this situation compare to situations we face in our work?

  • How will these decisions make or break you as a leader now or in the future?

We may not get to send someone in their twenties to formal leadership training, but we can prepare them throughout their rise to leadership roles before they get there. As the current generation of leaders, the leaders coming up behind us are our legacy. We can shape our legacy and leave a lasting impact on the twenty-somethings that will be leading once we are retired.


  • What tests of character require Courage from your younger employees?

  • How will those tests prepare them to do your job someday?

  • Who will you mentor this week, to help them be prepared?


“Would you follow you?” That is a critical question we all need to ask ourselves if we want to become Leaders of Character. Research has proven that people want to follow character. But where is your character today?

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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