How to Have a Difficult Conversation

If you’ve been in any kind of leadership long you know how important it is to have difficult conversations. Depending on your personality, either because you had them and realized how important they were after or maybe you didn’t and regretted the actions you had to take later.

The truth is an honest, open, and many times difficult conversation can keep an unfortunate outcome from happening. In church world that means, a family leaving the church, a volunteer stepping down, or even having to let a staff member go.

After having a difficult conversation a few weekends ago, I thought it’d be great to write down some things I learned from it.

1. Understand most problems are misunderstandings

It’s important to not see the other side as the enemy. Most likely there’s been a misunderstanding. Keep in mind misunderstandings usually begin when an expectation didn’t match the execution. It’s usually a good idea to go back and ask what they expected and make sure that you adequately communicated your expectations.

2. Have a plan and rehearse

I would never recommend having a difficult conversation without having a little time to think about it. The very nature of difficult conversations means sometimes you don’t have much time at all. But that doesn’t mean you have to go in off the cuff. Run it by someone you trust to check your emotion and motives and do a mental check-list of what the most important thing you are trying to communicate is.

3. Listen, adapt, speak, shut-up, listen.

Technically that’s 5 things, but stay with me. The order above is pretty important. In this most recent conversation I had, I started by just asking for more information on where the disagreement had begun. After listening to the person I realized, some of my instincts were right and some were wrong. I adapted, gave my opinion, and then stopped talking. Sometimes I’ll ramble or get off topic. Say what needs to be said then stop talking, and get back to listening.

4. Push for honesty, clarity, and directness.

After the conversation seems to have naturally run it’s course, it’s usually a good idea to push on the other person and make sure they have been honest and as direct as possible. The problem is sometimes after a difficult conversation, especially when you are having to come from a position of authority, people will shut down without being direct. I’ve made the mistake before of leaving, thinking everything was resolved. Later I found out they weren’t and because I hadn’t pushed for directness and even been vulnerable enough to ask for feedback, that person was disgruntled and fed that attitude down rather than up.

5. Aim for a resolution.

I touched on this a little bit on the last one. The point here is that if it’s not resolved it can lead to more problems and more difficult conversations or actions later on. In the instance I named above, the problem that I didn’t resolve led to that volunteer having to move positions. They couldn’t make it work. Resolution doesn’t mean you leave agreeing, though. It means you leave, both sides feel heard, and the next steps have been communicated.

6. If you part- part friends.

Sometimes after a difficult conversation you’ll realize that the volunteer is quitting, the family is leaving the church, or the staff member is going to resign. Whatever that looks like in your context remember that a difficult conversation is just that. One conversation. It shouldn’t define the whole relationship nor should it define either person’s entire reputation. Understanding that on both sides and making sure that it’s communicated well, shows maturity. You may have to part, but part friends.

7. Let it Go

The last tip I have is more for my own sanity. After a difficult conversation if you feel that you kept your cool and said what needed to be said, but in a respectful way, let it go. Obviously there may be a circumstance where you have to go back and revisit or clarify. At the heart of this though is learning to accept this role in leadership. For some reason in church world and in ministry you can tend to beat yourself up or question yourself after the fact. You run through the scenario over and over and wish you’d said or done something differently. Especially if it didn’t go the way you hoped. It’s important to realize though, that most of the time this is unhealthy guilt. Let it go and move on.

Photo by: Joshua Ness on Unsplash

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