A Leader’s Hard Conversations

I’ve lost count of the number of occasions where I had to confront a person who I was leading or mentoring. Although it’s a natural part of leading a family, team or organization, I would often try to talk myself out of doing it, thinking that if I just ignored the problem it would go away. That, of course, is rarely true. I have never regretted confronting a situation when I did it in a healthy way. In fact, I believe successful confrontation was the most important lesson I learned as young leader. The following list represents the steps I generally take when confronting a person. Keep in mind that confrontation (or clarification) is right only when the issue is clear (i.e., the person is damaging themselves or someone else or has failed to keep a commitment). When this is the case, I recommend this process:

1. WORK THROUGH YOUR ANGER. Don’t let emotion lead you. Wait until you’re objective, but try to deal with issues before they become big ones.

2. INITIATE THE CONTACT. Don’t wait for them to initiate. Mentors and leaders must be proactive to make things right whether you’re the offender or the offended.

3. BEGIN WITH AFFIRMATION. Speak words of belief and encouragement first. Then receive fresh permission to challenge them.

4. TELL THEM YOU HAVE A PROBLEM OR STRUGGLE. Don’t hint that it’s their problem, but yours; own the fact that you are wrestling with an issue.

5. BRING UP THE ISSUE, AND EXPLAIN YOU DON’T UNDERSTAND. Aim to clarify. Ask questions. Always give them the benefit of the doubt. Believe the best and allow them to explain themselves. When you speak, however, be clear and firm.

6. LISTEN AND ALLOW THEM TO RESPOND. At this point, it’s your turn to listen. Allow them to respond to the issue. Commit yourself to actively engage in listening.

7. ESTABLISH FORGIVENESS AND REPENTANCE. Connect the issue with them—at their best. Don’t conclude until forgiveness is extended and the issues are resolved.

8. COMPROMISE ON OPINIONS, NOT ON CONVICTIONS OR PRINCIPLES. Determine what you’ll die for. Be flexible with your opinions, but not with your values or principles. Be gracious when you can; be firm when you must.

9. COME UP WITH A PLAN. Together, attempt to work on action steps to remedy the issue. Be sure you both have “skin in the game.” Sacrifice to make things work.

10. AFFIRM YOUR PURPOSE AND YOUR LOVE AS YOU CONCLUDE. Always close these times on a positive note if possible. Give them hope with your words. Be sure they know you believe in them.


Socrates told us an unexamined life is not worth living. Part of your job as a leader, parent, coach, teacher, youth pastor or boss is to help young leaders do just that.

Speaking into Someone’s Life

“Speaking into the life” of your team, students, children or employees is a learned art. Speaking with authority is an earned right. Both what you learn and earn can increase your influence with them. This is about the role and the soul of a leader. 

I love the term “speaking into their life.” It implies that we’re speaking personally and intimately to them. It also implies that we are speaking words of direction or perspective that will impact them. It means speaking to a relevant need in their life and empowering them. It may mean speaking words of vision for their future.

We see early evidence of this practice among the Hebrews when patriarchs would bless their sons. Back then it was common for fathers to speak words of blessing (affirmation and direction) to their children as they grew into adulthood. It was a “rite of passage” for young men. It was as though these fathers knew the intrinsic need we all have for someone in authority to believe in us and tell us so. Years ago, authors Gary Smalley and John Trent have released a book called, The Blessing. In it they describe the five elements of this blessing.

The Blessing Consists Of…

1. Meaningful Touch

2. Spoken Words

3. The Expression of High Value

4. A Description of a Special Future (Word Pictures)

5. The Application of Genuine Commitment

We live in an age where people seem more wounded than ever. It is now common to come from a past involving divorce, abuse, dysfunction, incest, neglect, addictive behavior or co-dependent relationships. Needy people are everywhere. So, how does this affect our leadership and mentoring? Do we simply try to avoid these issues? Do we ignore them or pretend they aren’t there? Obviously, we can’t do this if we intend to lead well. Instead, we must recover this practice performed by leaders of old with their people and families. This practice came to be known as “giving the blessing” to others. Because most families don’t practice giving this “blessing” to each other, I believe leaders/mentors must pick up the slack and do it for their followers. It is up to us.

Who could you do this for today?


A Leader’s Hard Conversations