Successfully Navigating Hard Conversations

Leadership / Leadership //

Let’s face it, tough conversations suck. And, to be honest, I also suck at leading them. I’ve been guilty of avoiding, blowing through them, and putting them off. Even when I finally get around to having them, I often feel like I come across as muddled.

However, after four years in leadership, it’s clear that there’s no way to avoid them and succeed. Every decent leader needs to be able to have them, and know how to lead them well. In the last couple of weeks I’ve had to initiate several different conversations that I didn’t look forward to. I’d say that my skills at leading difficult conversations still need to grow quite a bit, but by this point I’ve also picked up some important knowledge about them. Here are some things I’ve learned (mostly the hard way).

  • Plan it out. Something I used to do is dread the conversation and choose not to think about it, which meant that when I finally sat down with somebody or made a phone call, my thoughts came out jumbled. Sometimes this made the conversations more awkward than they needed to be, other times this left me open to waffling on my decisions. That’s why I now rehearse the conversation carefully beforehand. Specifically, I remind myself what my reasons are for having the discussion, I plan out how I’ll start the conversation, and I’ll decide on what I’ll be asking from the other party. I’ll also spend time practicing explaining my “why”. That way I’m confident in why this conversation is necessary, and why I’m taking the actions I’m taking. Planning these talks is stressful, and it’s tempting to simply dive in and try to get it over with. I’ve learned, however, that planning out my part of the conversation always results in a clearer conclusion.
  • Do it when you know you need to. The temptation that we all face is to ignore a problem, hoping that (a) it will go away on its own or (b) something will come up that will make the conversation easier. Unfortunately, 95% of the time you find yourself having to deal with a larger issue much later than you needed to. Simply put, the best time to have a hard conversation is as soon as you know there’s an issue worth addressing. Sure it’s tempting to hope it works itself out, but you’ll probably only end up with a larger mess to clean. Nip things in the bud, and everyone ends up happier.
  • Know the end. This is so important. Most people will try to negotiate when someone in authority comes to correct them. This may mean something as little as trying to save a ministry program or something as big as negotiating to save their job. That’s why, as a leader, you need to have a range of acceptable conclusions decided upon before the conversation starts. This may mean a set of parameters you honestly believe are tenable (“No, we can’t pull off this program, but you can tweak another one to reach a new demographic”), or it may mean being resolute in a decision you’ve already made (“I’m sorry, but we will have to let you go”). Whatever it is, make sure you know before the conversation even starts, so you don’t find yourself regretting a compromise later.
  • Do what it takes to prepare yourself/calm down. Hard conversations are taxing. Know yourself enough to know what you need to do to manage your emotions before, during, and after the talk. Even more important, remind yourself why this conversation is necessary. Even if you made mistakes that led up to it, remember to remind yourself why going through an emotional encounter is wise in the long run. Make sure you’re mentally in the best place to navigate a tricky experience.

I can’t tell you how much I wish that none of us were forced to go into these difficult conversations. (especially me!) However, honoring God with our calling means guarding our ministries well. I’m praying that all of us will have the courage to take on the full cost of leadership, and do whatever it takes to create great ministries – even when the road is difficult.

What about you? How do you navigate difficult conversations?





About the Author

Collie Coburn is the pastor of children's ministries at First Christian Church in Santa Maria, CA. He loves doing, strategizing, and writing about children's ministry. He loves spending time with his wife and son even more. Collie blogs at, and is also on twitter.