How to Face Tough Conversations

It’s natural to avoid a tough moment, an awkward conversation or difficult decision.

Nobody likes the stress, pain and pressure of courageous leadership—in the moment.

However, most of us can recount times where we fretted for dozens of hours or weeks or even months of stress, attempting to delay or avoid taking responsibility for a leadership conversation that must occur.

It may have been that moment you had to let someone go. Or you were walking into a tension filled meeting. Perhaps you had to tell someone they would not receive the funding they wanted or the promotion they desired. Maybe it was time to declare the new vision you had in your heart. We all know those moments.

When a leader refuses to take responsibility in a tough moment, he or she loses leadership. If you do that often enough, over time, you will no longer be the leader. The person who will step up becomes the leader.

Sleepless nights can be replaced with one tough conversation. It’s not easy, but it needs to happen.

We avoid tough conversations for natural and normal reasons. Fears and insecurities are in the mix. We love people. We don’t want to hurt or disappoint anyone. But in the big picture far more harm is done by not rising to the leadership need of the moment.

Most churches are one tough call away from a breakthrough. That always involves at least one difficult moment.

It’s also true that making that tough call and having a tough conversation can be the door for a personal breakthrough for the leader.


1. Learn the power of one sentence.

When we’re anxious about delivering a difficult decision or having a confrontational conversation we tend to over-talk. We talk all around the core of the topic. We end up not being direct enough to accomplish the desired results.

In the vast majority of those tough moments, the heart of the entire situation is delivered in one sentence.

You may need a long conversation to process that sentence, but it’s delivered in those few but powerful words. When you have the conversation in reverse—meaning talk for a long time and maybe get to the bottom line at the end—or miss the point altogether, the moment and desired result is lost.

Know exactly what your one sentence is. Write it down. Practice saying it if you need to. Don’t beat around the bush, flower it up or try to dodge the bullet. Clarity is essential. Just say it.

Never deliver the message fueled by emotion. Preparation, not emotion, is what will give you courage and success.

2. Understand the secret behind the moment.

It’s not really a secret, but we don’t talk about this very often. When you try to power up and power through tough moments on your own, you overdo it and mess it up.

The “secret” is in the preparation, and involves how you engage God.

When you invite God into your process of preparation, you gain a quiet confidence that translates to spiritual strength.

Stillness before God. If you’re like me, you’re on the go. You have little time and so you process fast. I’ve learned that if I’m not still before God long enough to gain his mind and heart on the issue at hand, it’s not going to go well.

Taking that invaluable time to be quiet before God and seeking his voice is essential to this process.

Sometimes I’ll just sit in my prayer room with a cup of tea, quiet before God. I have 3×5 cards that I write notes on as I pray. It’s not like an audible voice, but the stillness before God results in peace and confidence that is core to preparation.

Conviction is the non-negotiable foundation. Stillness before God is required to gain the conviction that you are doing the right thing. Wise counsel from trusted insiders is always helpful, but if you are the leader and you are delivering the message, you need personal conviction.

This doesn’t guarantee you’ll never make a mistake; great leaders still make mistakes. Perfect outcomes are not part of the equation in any of these moments.

The intent is to know you are doing the right thing according to what you believe God is saying to you.

When you have conviction you are ready. When you possess resolve in your heart and mind, you are ready. Now you can deliver the sentence and have the conversation without angst.

3. Measure your outcome by inner peace, not outer perfection.

As I mentioned, outcomes are never guaranteed. The other person or group, etc. can choose their response. But when you enter into a tough conversation with inner peace the potential for great results increases exponentially.

When you are clear and at peace with before God, you have done your best and need to leave the outcome to him.

When you enter in unsure, you will not likely gain the results you want. When you enter a tough conversation with an inner peace, the potential for a great result increases exponentially.

The longer I lead, the more I understand that the core of leadership is in these conversations. These are the defining moments that shape the trajectory of your leadership and the ministry of your church.

Dan Reiland is the executive pastor at 12Stone Church in Lawrenceville, Georgia. This article was originally published on Reiland’s blog, Developing Church Leaders.

Dan Reiland
Dan Reiland

Dan Reiland is the executive pastor at 12Stone Church in Lawrenceville, Georgia, and the author of several books including Confident Leader! Become One, Stay One (Thomas Nelson).