How To Face Tough Conversations

It’s natural to avoid a tough moment, an awkward conversation or a difficult decision – but without them your leadership becomes ineffective.

Nobody likes the stress, pain, and pressure of courageous leadership – at that moment, but it’s in those moments that your leadership is defined and refined.

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 moment of leadership that must be done.

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 or you had to close down a ministry that wasn’t working. Maybe it was time to declare the new vision you had in your heart,  but you knew not everyone would be for it. We all know those moments.

When a leader refuses to take responsibility for the difficult conversations, 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.

Those sleepless nights can be replaced with one tough moment. It’s not easy, but it needs to be done.

We avoid the tough moment 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 conversation and decision.

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 him or herself.

3 guidelines to help you prepare for the tough conversation:

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 real issue, and 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 best 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 it altogether, the moment and desired result is lost.

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

Never deliver the message fueled by emotion. Preparation, not emotion, is what will strengthen your courage help you realize positive and productive results.

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 the 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 the process, you gain quiet confidence that translates to spiritual strength in the moment.

A) Stillness before God.
As leaders, we’re on the go. We often have little time, and so we process fast. I’ve If we are 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 great 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.

B) 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, the outcomes are never guaranteed. The other person or group can choose their response. But when you enter into the tough moment with inner peace, the potential for great results increases exponentially.

When you enter in unsure, you will not likely gain the results you want.

When you are clear, and at peace with God, you have done your best and need to leave the outcomes to Him.

Experience may be gained slowly because you don’t practice this on a daily basis. But the companion to tough conversations are honest conversations, and they can happen often and will help you become better at the tough ones.


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

9 thoughts on “How To Face Tough Conversations”

  1. Just had a hard conversation yesterday, and as good as it went, it’s so helpful to visit a resource like this afterwards for reassurance! I especially appreciated this portion “Know exactly what you want to say in one sentence. Write it down. Practice saying it if you need to. Don’t beat around the bush, flower it up and unintentionally dodge the bullet. Clarity is essential. Just say it.”

    I noticed the fellow brother in this meeting did a great job of this and helped the 3rd brother we were confronting understand and own his fault immediately without confusion.

    Going to save this article in the HARD CONVERSATIONS file to revisit before the next one, thank you Dan!

    1. Excellent post, Dan. Wish I had had your insights before the tough conservations I have had in 63 years of ministry. So enjoyed our interview. May God’s devine favor continue to rest on you.

      1. Hi Jim!
        Good to hear from you and, hey, even after 63 years of ministry, you aren’t done yet! Maybe it will still come in handy! Yes, I enjoyed the interview as well!!

  2. Frankie Capparelli

    This is so good and will add to my arsenal of communication! A constant reminder “ When a leader refuses to take responsibility for the difficult conversations, 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.” Seen this so many times.

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