Working with Friends is Hard

Several years ago, I was helping a leader through some strategic decisions. His organization had stopped growing, and it was beginning to lose good staff members. He was trying to figure out what needed to change to reverse the trend.

He was telling me stories that illustrated the problem and said some of the staff members who left felt he was distant and unavailable. He said to me in frustration, “I don’t want to be their friend. I just want them to do their damn job!”

This is a guy who had been burned by working with friends. And if you’ve been in leadership for very long, you’ve also been burned.

About ten years ago, I was beginning a tough conversation with a friend who had worked with me for a long time. He had been an amazing leader, helping grow one of our departments to a significant level. But the pace of growth and change was beginning to stretch his capacity, and I felt there might need to be a new leader in place. I had not made it far in the conversation when he blurted out, “You are going to fire me, aren’t you?” Once that was in his mind, there was no convincing him otherwise. He angrily left my office that day, and I haven’t seen him since. I didn’t just lose an employee; I lost a friend. I had an especially tight connection with his entire family, and I lost them all as friends that day.

Another time I had to let a close friend go for financial reasons. We could no longer afford to keep her on staff. I had become sort of a father figure to her, and it was incredibly painful to see her go. I had hoped my family could keep up the friendship, and I could continue to help her grow and succeed. But I soon realized she no longer wanted us in her life.

Those types of experiences are what cause people to say, “Never again. I will never hire another friend, and I will keep a distance so I don’t get too close to the people I work with.” We think, It’s just not worth the pain.

I get that. I don’t like pain. I don’t like losing friends. Just as a little kid who gets burned by touching the stove stays away from it, I want to get as far away as possible from it. Why even go in the kitchen again? If I don’t go in the kitchen, the stove can’t burn me.

And yet I’ve learned over the years that the benefits of working with friends far outweigh the potential pain. Being able to do ministry with people I love being around is a rare joy that few people get to experience. Going to work with people I like, and who like me, and who are fun to hang with—I wouldn’t trade those benefits.

Even amid the painful stories, I have had far more long-lasting friendships with people who, although we no longer work together, continue to be close friends to this day. When you are working with friends, it takes a much higher commitment to communication. Sometimes you have to say out loud, “Right now I’m wearing my leader hat. In a few minutes I’ll put my friend hat back on.” Sometimes I’ve said, “As your friend I would advise you in one way, but as your employer I would counsel you differently.”

Recently I said to a friend (who also worked for me), “Someone repeated something you said about my leadership last week, and it’s been eating at me. It really hurt, but I realized it was unfair to assume they were representing you accurately. Can we talk about it?”

Without that level of commitment to honesty, stuff builds up and friendships erode. Working in a place where friendships once existed but are now tense is worse than starting at a place where everyone is just an associate.

I know it’s messy when you choose to work with your friends. In the church, I don’t know how we model true disciple-making communities without doing so at the staff level. And for Christian leaders in the business world, you have the opportunity to show others how followers of Jesus love through work relationships—caring for one another and pushing through the conflict that occasionally arises.

Yeah, it’s messy. But as for me, I choose the mess.

Read more in Fairness is Overrated: And 51 Other Leadership Principles to Revolutionize Your Workplace