If you want to lead well for a long time—and be respected by those you lead—you must figure out how to handle difficult conversations. If you don’t . . . you put a cap on your how many people God can trust you to lead well.

During the month of October, we honor pastors and show appreciation for them. The team here at Converge Coaching admires and respects what pastors do to live out their calling. And so, we are writing a series of posts this month on how we as leaders can grow and become more deserving of honor and appreciation (in a healthy, non-people-pleasing-centric way).

Pastoral ministry requires pastors to occasionally make tough people-decisions, and from time-to-time handle difficult conversations. Dealing with dividers, boundary-crashers, triangulators (fancy term for gossipers), square pegs in round holes, and under-performing staff members creates stress for any leader. Even more so when the leader feels unequipped for the task of having an honest conversation about these items.

Today’s post focuses on six practical ideas around how to execute these tough conversations. It won’t be an exhaustive treatment on the subject . . . more like a starter-kit.

When it comes to tough conversations, some leaders tend to bully, while others tend to be a doormat. Health lies somewhere between the two. If you get your jollies dealing with these difficult scenarios, you may have bully tendencies. If you delay, avoid, obsess, and pray for Jesus to come back before you have a tough conversation, you may have doormat tendencies.

How do we find the sweet spot between these two extremes? Here are six practical steps I think might help:

Step 1: Be curious

When it’s time for a difficult talk with a teammate or a church attender, understand you probably don’t have all the facts. So, here’s an idea to get the conversation started: “Joe, here’s the issue as I see it. Explain at a high level how you see it. Help me understand it from your perspective.”

Trying to understand their perspective doesn’t necessarily mean you’ll end up agreeing with it. But as Douglas Stone writes: “People almost never change without first feeling understood.” So, start with humility and curiosity. Stephen Covey says it this way: “Seek first to understand, then to be understood.”

Step 2: Assume the best

Assuming the best about the person on the other end of a difficult conversation isn’t easy. Try asking yourself before the conversation starts: “Is it possible I’m not accurately interpreting what they said/did? Is there a chance what they said/did was unintentional? Is their behavior symptomatic of something deeper?”

If you’re dealing with a performance issue, before entering the conversation with guns blazing, ask yourself: “Was I crystal clear about my expectations of this team member? Are those expectations in writing and do they have a copy? Did I explain the expectations more than once?” It’s possible the person isn’t performing well because they’re unclear about what success looks like. Coach yourself up with these questions prior to the conversation.

Step 3: Own your part

What, if anything, have you as leader done or failed to do that may have contributed to the problem?

In most (not all) relational conflicts, the parties involved each contributed in some way. Some more than others perhaps, but most of the time both parties have a share in the problem.

For example, if I’m a pastor who’s refused to have hard conversations for weeks/months/years—then I’ve contributed to the problem. If I’ve triangulated—meaning I’ve talked to someone else about the issue as a means of avoidance instead of talking directly with the person causing the issue—then I’ve contributed to the problem. If people fear coming to me as a leader with the issues they’re facing because I’m unapproachable—I’ve contributed to the problem. Own and admit your part of the issue.

Step 4: Listen . . . for real

Listening to the other party helps you learn. It communicates care. And it helps them listen better to you. Acknowledge the other person’s point of view and the emotions they’ve attached to it. Again, this doesn’t mean you agree with their point of view or emotions. It means their point of view/emotions matter to you.

Step 5: Share your perspective clearly

Express your feelings/perspective about the situation(s). You deserve to be heard too. This helps the other party understand you. Let the other person know what’s important to you, why getting this situation resolved matters, and what the stakes are if it doesn’t get resolved. Calmly state how their behavior is negatively impacting you. “When you say/do X, I feel Y.”

Step 6: Articulate a way forward

Based on the Bible, what is the proper behavior(s) in this instance? Explore the available options, commit to change on your part where appropriate, and ask them to commit to change as well.

Now the ball is in their court. Will they stay and work through the problem . . . or not? Is the disagreement so deep it would be better for all parties to agree to disagree and move on? Remember, the apostle Paul had such a sharp disagreement with his brother in Christ, Barnabas, they parted company.

I doubt we’ll ever get to a place where we feel totally comfortable when it’s time for a difficult conversation. The goal is to get comfortable being uncomfortable.

Pastor you can—and you must—learn how to make tough calls. To have honest, loving, conversations with difficult people. These conversations are growth opportunities for you and your people. You limit your leadership potential when you refuse to speak the truth wrapped in huge amounts of love.

Your church’s health, your health, and the difficult person’s health hang in the balance.

Cheering for you,

John