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5 Keys to Leading Difficult People (Without Losing Your Mind)

  • Name
    Dan Reiland
If you’ve been leading for longer than a week or two, you know what it means to interact with difficult people. A friend of mine called last week to ask advice about how to better lead one of his board members for a small nonprofit. My friend, let’s call him Jeremy, is the director (and founder) of the nonprofit. In the middle of one of the meetings, the board member started a non-agenda discussion regarding his belief that the board members should have more decision-making authority in the day-to-day operations of the nonprofit’s endeavors. This was obviously a big surprise and felt like an ambush. Jeremy asked if there was a specific agenda or issue that the board member wanted to talk about, and the response was no, we just need more authority in general. Jeremy asked if he was unhappy with the ministry or his performance. The same response was given: “Everything is fine, we just need to have more say in how things are done.” This went on for over an hour getting nowhere. Finally, Jeremy asked: “What would you change if you had more authority?” The response was, “Well, we can talk about that later. But let’s figure out the authority thing first.” OK, that is a difficult situation with a difficult person leading the charge. The outcome is still undetermined! Difficult people are difficult, and nothing can move forward for the nonprofit ministry until this is resolved. Before we tackle the practical ideas, I want to suggest that it’s important to determine the difference between a difficult person and an unreasonable person. One of the baristas in our café at 12Stone® Church told me about a person who brought in their coffee cup from a local coffee franchise and asked for a free refill at 12Stone. The barista graciously explained that we don’t do free refills and the person became extremely upset, raised their voice saying: “Well you are a church, it should be free!” Our barista calmly told them that we do have free coffee stations conveniently located in four areas of the church for anyone who does not wish to purchase coffee in the café. The person then exclaimed, “I don’t want free coffee, I want a refill, no charge!” This person was simply unreasonable. You can’t help an unreasonable person. Not in the moment anyway. It’s best to say, “I’m sorry, I can’t help you,” and move on. In the moment, that is the most loving thing to do. Leading difficult people begins with loving them. It’s not always easy, but with that in mind, let’s take a look at some principles and practices.

1) Difficult isn’t a disease.

It is natural to recoil from difficult people, but it isn’t beneficial. While it may be counterintuitive to move toward difficult people, we know that’s part of the responsibility of a good leader. It’s easy to love our friends and followers, but the real test of our leadership is how we influence those who test us. Your friends and followers may tell you what you want to hear, and they can make life too comfortable. Being stretched by a “difficult” person is a healthy part of a leader’s life.

2) Difficult may be a helpful voice in disguise.

It takes time to learn this, but it’s often the “different (difficult) voice” that brings new ideas. What seems difficult and challenging is often a gift in disguise. I love having tough conversations with staff and volunteer leaders who disagree with me. When I was younger I would quickly try to win them to my way of thinking. I charged forward for the “win” without listening like I should have. And in doing that, any new perspective is lost. It’s often true that what appears to be a difficult person is someone who isn’t so difficult at all. They just see things a little differently, and that is often very helpful to see and understand.

3) Find out what is underneath.

If “difficult” seems to persist and it becomes apparent it’s more than a new and challenging idea, try setting the actual topic aside and take the conversation to a more personal level. Ask if you are doing something that is bothering them. Ask if there is something difficult in their personal life. It’s not uncommon that there is financial pressure, or something with their kids, or perhaps their marriage. When you connect with the real issue, it’s much easier to love and care for someone. And when they know you care, it’s much easier to deal with the original issue. Do whatever you can to add value to his/her life!

4) Look for the hidden gold.

The conflict may be an issue of chemistry. Part of what makes human beings so delightful can also drive us crazy. We are all different, not everyone gets along naturally. Chemistry can’t be forced, but as leaders we can rise to maturity and find the best of what otherwise would be a connection between two people that feels like sandpaper. One of the best ways to do this is to look for the best in the other person. If I focus on what makes them difficult, nothing improves. And I must remember, they most likely find something difficult about me! When I find the hidden gold, their talents and gifts, I begin to appreciate them. When I appreciate something about them, even though they may not have changed, I have changed in how I see them and that improves the interaction.

5) Set boundaries and focus on common ground.

So far, I’ve been writing with a bias toward you and changing your perspective about “difficult.” But I must admit that some people, not many, but some, are just plain difficult nearly all the time. Jesus still calls us to love them! That doesn’t mean, however, that we should place them in leadership or give them significant amounts of our time. Boundaries are healthy and necessary. My first boundary is to make sure we are headed in the same direction. It’s OK to disagree with me, or express dissatisfaction with my leadership, or try to convince me to do something in a different way. But if the person has an agenda that essentially opposes the mission of the church then a boundary must be set in place. Essentially this boundary means that the “conflict” must cease until we establish common ground that we can stand on together. From there we can make productive progress.