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“Tough” Conversations Aren’t Always Tough

As a leader, our job isn’t to do what makes us comfortable.

Just like New Year’s Eve is rarely as fun as advertised, tough conversations are rarely as bad as advertised. I found this to be true during a time in which I had to inform a West Point classmate I would not be offering him a promotion onto my team.

He had the skills for the promotion. He was—and is—a man of character who would have been a solid addition to the team. Plus, I knew him personally! But, I chose someone else for the promotion. To top it off, this was a person I just met. Yet, when it came down to it—the new guy was someone who was the obvious best choice for the position on this team.

The idea of calling my classmate to share my decision ate at me. I tossed and turned the whole night before making the phone call. I kept thinking, “Maybe I should give it to the guy with whom I have history. A guy who is obviously good, but maybe just not the best for this team at this time.” But I couldn’t convince myself.

I had just been promoted into my first corporate leadership job the week before. I was already faced with one of the toughest conversations in my career. There was no way to avoid it. I decided I needed to rip the Band-Aid off and make the call.

To my surprise, the call went great! My classmate was gracious and understood my reasoning. He demonstrated the class and character I knew he possessed. When I hung up, I muttered out loud, “Wow! That wasn’t as bad as I thought it would be.”

The person I hired turned out to be a rock star. He rose in the ranks of our company even beyond me. My classmate - he did a great job too! He got promoted into a different role in a location which suited his family better. He was hugely successful in his position as well.

This early lesson in my corporate career taught me about the damage the voices in your head can do if we listen to them. Those voices could have convinced me to make the easier decision so I would avoid a tough conversation. Fortunately, I made a different choice and did what was best for my team instead of what made me comfortable. When I faced my fears and made a tough phone call, it prepared me for hard conversations to come.

Everyone faces hard decisions and hard conversations. Sometimes we build these conversations up to the point in our minds in which we give in to our internal fears and do what will make us comfortable. But, as a leader, our job is not to do what makes us comfortable. It is to do the right thing for the individuals and the team we lead.

Exercising Courage to engage in difficult conversations is a test of our character. Each time we pass that test and exercise Courage, it makes it easier to make that choice again in the future. With each choice we make, we are getting closer and closer to building a habit.

Sometimes tough conversations end up being just that—tough conversations. Sometimes those conversations end up going better than advertised. But in both cases, a Leader of Character is needed. Having the Courage to proactively address a tough issue makes us prepared for bigger issues in the future.

Dig Deep Questions:

  • Have you had to face a “tough” conversation which went easier than you imagined? If so, what made it easier?

  • What one conversation have you been putting off which may not be as difficult as imagined? Why would it be worth it to have the conversation no matter the outcome?


It is important to us for you to have an opportunity to exercise Courage, not only individually, but together as a team. This is why we have created practice cards with scenarios.

We invite you to discuss as a team what it means to exercise Courage via our

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