How To Lead The 5 Most Difficult People

As a church leader, I’m confident you love and care about people, but If you have been leading for more than one week, you have encountered a difficult person or two.

Recently a wonderful volunteer on the hospitality team told me that someone just left because of the coffee. The unhappy attendee said, “This coffee tastes like dirt.” He said it was weak and insisted that we do something about it. It didn’t matter that it was free. (Free is not an excuse for lousy coffee, but thousands of people seem to like it.) The volunteer offered the Starbucks brand, but the attendee was upset that it wasn’t free.

We all can be difficult or have a bad day, but there are chronic personalities that require intentional effort, maturity, and specific skill to lead.

As leaders we are called to love everyone, Jesus made that clear in John 13:34-35, but that does not mean we are to consistently tolerate behavior that harms the people and mission of the church.

Our coffee story is not a big deal, but it illustrates the picture in a simple and quick way. Difficult is difficult.

In the context of this article, the tension in leadership is how to love and extend grace to people who are difficult and lead them in a way that serves them well, and advances the mission of the church.

I wrote another article on this topic, that takes a more general approach. It’s great complementary content to this post. You can read it here.

The 5 most difficult people to lead:

This does not assume adversarial relationships, but acknowledges the reality of leading difficult people.

This is not a comprehensive treatment of the subject. It is not my intent to place anyone in a box, lower the responsibility of a leader, or reduce the transforming ability of Christ, but only to provide a few helpful insights so leaders can love and lead better.

1) The Discontent Person

The discontent personality always wants something more than what is. Whatever it may be, from a certain ministry to a training program, or from the amount of bible content in a sermon to time with a pastor, it’s just never enough.

An ungrateful or critical spirit typically characterizes the discontent person.

Lead by helping the person to consider and adopt a different perspective. Start by asking them what they are content with (in context with the specific issue) and insist that they articulate precisely what they want.

Lead without promising you or anyone, can or will deliver all they want. You can’t. But the place to begin is establishing realistic expectations and a more grateful disposition.

2) The Negative Person

The negative personality appears to be unhappy by choice and is often the wet blanket to any group gathering or meeting. It’s not just the difference between a glass half empty or a glass half full, but this person seems to have poured out half of a full glass on purpose.

The negative person is typically characterized as one who sees only problems and not solutions.

Lead by acknowledging the problem but focus on the positive and insist on moving toward solutions.

3) The Argumentative Person

The argumentative personality needs to win. It often doesn’t matter what the topic is, and with this person, you usually feel more like you are in a courtroom debate rather than a conversation. The need to be right and win is greater than the goals of the ministry.

The argumentative person is usually a strong personality and articulate, characterized by a very aggressive approach and must win at all cost.

Lead by establishing boundaries for a healthy and productive conversation. Continually keep the big picture in the forefront and agree on the end goal before starting the conversation.

4) The Duplicitous Person

The duplicitous person has a political bent and can be two-faced. They are not loyal to relationships and maybe passive-aggressive. That is kind one moment and turn on you the next.

Thankfully, this personality is the rarest of the five, but can also do the most damage.

The duplicitous person is known for gossip, changing opinions, and rarely taking a stand that does not benefit them personally.

Don’t lead by fear or from a distance, but straight on with bold confidence and direct language. Don’t put them in charge of anything until you see change.

5) The Apathetic Person

Always love this person, as with all five personalities, but don’t invest too much time. Lead by letting them know you would love to see them grow and be part of something great, but they have to show some initiative.

Essentially, this personality just doesn’t care. They don’t necessarily hurt anything, but neither do they help anything. This person isn’t as aggressive as the first four personalities but can be just as difficult because they are simply unmotivated.

The apathetic person is characterized as pleasant but unhelpful, without an opinion, and lacking passion.

Always love this person, as with all five personalities, but don’t invest too much time. Lead by letting them know you would love to see them grow and be part of something great, but they have to show some initiative.

5 practical steps to lead difficult people:

1) Assess what’s going on under the surface.

Very few people want to be difficult. Some don’t know they are perceived that way. Take a little time to dig deeper than the issue at hand to see if you can discover what might be troubling them at a heart level.

2) Establish a reasonable and honest conversation.

Any reasonable conversation includes two people who are willing to listen, understand both sides, and move toward the greater good. This always requires personal authenticity and full honesty.

3) Discover what they really want.

Expectations are often at the core of someone who appears to be difficult or is genuinely a difficult person. Ask this direct question, “What do you want?” It is a liberating question because there is freedom in the answer.

You may discover they don’t know what they want. That is not only a problematic person but a dangerous one. Proceed with caution until they can verbalize what they want.

4) Set limits and boundaries.

The person can disagree with you, but it must be done with respect. Their tone and demeanor matter.

Agreement on the overall mission over anyone’s personal agenda must be agreed upon.

Progress is essential. You may get stuck for a brief time, but moving forward both relationally and according to the purpose of the ministry is mandatory.

5) Lead them to adapt a different perspective.

The purpose here is not to make someone think like you do, but to help them become a healthy and happy part of the body of Christ. We never want to see someone leave the church, but sometimes that’s OK.

I trust that this brief article is helpful and that the Holy Spirit brought it to you at just the right time either for you or someone on your team.

Increasing your ability to lead a difficult person, not only allows you to appreciate them in a more meaningful way but helps the greater mission move forward.

2 thoughts on “How To Lead The 5 Most Difficult People”

  1. Hi, Dan.
    Excellent post. I have another question for you, I´ve learned how to deal with difficult people, but how to deal with difficult LEADERS? Those who don´t think the way you do, those who love drama about everything and those whose pride is bit evident.

  2. That can be complicated Marco.

    I recommend John Maxwell’s book, Be A People Person. The focus isn’t necessarily on difficult leaders, but the principles will be of great help to you.

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