Working with Difficult People

Whether in your professional, church or personal lives we've all come across difficult people. The disorganized, the arrogant, the critical, the bully, the mess maker, the slacker. These people slow us down, frustrate our teams and ultimately cause damage to the morale of every one around them. How do you effectively work with difficult people?

Disorganized Dora

Typically Disorganized Dora is the Sanguine or people type. She is the life of the party and loves connecting with people.  It's her greatest strength, and she focuses on people not tasks. Because of this, her life is a time-management nightmare. She considers to-do lists a chore and is often accused of being unfocused.

When dealing with someone who greatest struggle is time management it's important to realize that organization is a skill that can be taught.  Show them how being organized will actually allow them to better connect with more people. You want them to focus on their strengths, so celebrate them, while at the same time work with them by teaching them simple, repeatable, organization skills. And if you can, try to partner them with another staff member who is remarkably organized to help them stay on track.

Critical Charlie

He is the planner and can be one of the most valuable leaders to have on your team. But without the necessary skills to enhance his natural abilities, he can become so detail focused that he becomes fixated on the negative aspect of anything and everything.When their well thought out plan finds resistance or reveals a flaw they become the proverbial bull in a china shop, without a filter to guide their thoughts and more importantly what they say and to whom. 

Sadly, most insecure leaders chase Critical Charlie away because they feed their own insecurities. But critical people have a critiquing gift that just needs to be coached. Teach him the art of challenging the process without challenging the authority of the leader. (See How to Challenge the Process on    

We need to understand that there is a big difference between being critical and critiquing. It is a fine line. Teach your critics the difference between a problem and a symptom. Most people don’t solve problems, they solve symptoms. For example, when you have a headache, you take Tylenol. That’s solving a symptom, but not the problem. A headache could be caused by a number of different things, some of them dangerous, so solving just the symptom is not always enough. In an organization, this is especially true. Teach all of your people to try to categorize every problem as a symptom. This will help you dig deeper to solve the real problem. For example, someone might say, “we have a problem, our church is not growing anymore.” Help them see this as a symptom, not a problem. Treating it as a symptom causes you to dig deeper to ask, “Why is our church not growing as quickly any more?” Keep asking that question and you will eventually get to the real problem - and then teach them how to solve it.

Now you have created an invaluable leader in your organization.

Hyper Harry

Hyper Harry is enthusiastic about everything!  He leads the charge, rallying others to the cause as they stampede down the path of a new project until Hyper Harry is distracted by a new and shiny brilliant idea that has captured his attention. So while he is the guy who passionately starts projects... he usually can't be counted on to finish them, leaving others to come along being him to clean up half completed, discarded projects. 

I love working with idea people because who doesn’t love new ideas? But, not every idea is a great idea and learning how to distinguish the good from the great is a skill that can be trained — sometimes simply through experience.

So don't be quick to give the Hyper Harry’s in your team a leadership position initially. Partner them with a seasoned leader whom they respect, who will take their ideas and filter the good ones from the bad, the doable ones from the fantasies, and then walk them through the process and stages of growth:

  1. You watch — I do

  2. You help me do

  3. You do — I help

  4. You do — I watch

  5. You do

When utilized properly on a team and trained in the skill of follow through, Hyper Harry will never be short of ideas that will push your team to new levels.

In-a-Slump Suzy

Suzy was once making things happen. She had a great deal of momentum going for her but one day she seemed to lose it and her momentum just seemed to drain away. She used to produce results at every turn, but lately all she’s producing are excuses.  Suzy loves to reminisce about the good old days and her attitude is often depressed. Ultimately, she’s lost her confidence.

We've all been there, and as a leader, when you see someone in a slump there are a few things you can do to help them regain their confidence and momentum.

  1. Set them up for a small win - this helps them get their confidence back.

  2. Change their position and give them a new challenge - sometimes a change is exactly what they need to break out of a rut.

  3. Resource them - With books, podcasts, take them along to a conference.

  4. Give them a break - Teach them the difference between rest and recreation and how to do both.

The key here, is to understand people development and sensitively dig into their world. Learn which of the four they need most for the season they are in. They are in a rut for a reason (that’s the symptom), but what is the problem? Why are they in a rut?

Fearful Franky

He lives under the influence of his fears, petrified of the unknown.He avoids anything different from where he’s always been or what he’s always done. Without constant encouragement, insecurity soon takes over and he freezes. 

It is important to realize that it is not necessary to erase his fears in order for him to get things done. Courage is not the absence of fear, it is the ability to move ahead despite the fear. One of the best motivators of the courage is to help them focus on the “why”. When your “why” is stronger than your fear, you will discover courage. For instance despite being terrified of snakes, you would quickly overcome that fear to protect your child should you walk into your baby's bedroom and discover a snake beneath the crib. Your why becomes stronger than your fear.

As a leader, realize anyone who is paralyzed with fear and refuses to take risks simply needs help in discovering a why that is stronger than their fear to act.

Stevie Sniper

Confrontational, pushy and aggressive, Stevie Sniper lives to make leaders look foolish. He's the man with the hidden agenda. Smooth talking and praising you one moment, backstabbing you the next.

Of all the difficult people we have discussed thus far, this personality is the most toxic to you and to those around him. Ask yourself “is he affecting anyone else in my organization? And is he having a negative impact on our culture?” He needs to be confronted about his behaviour, one on one but ultimately, he many have to go. 

Talk with him about his behaviour, the effect on the team and the damage he is causing. If he refuses to listen and still doesn't adjust his attitude, he needs to be confronted again. This time with an ultimatum, “if this behaviour does not change, I am going to have to ask your to leave the team.”  If there is still no change, then the third meeting is simply a meeting to dismiss him from the team.

DO NOT give him another position or be timid in dealing with him, because above all else you need to protect your culture and the good people on your team. 

Maybe Mabel

The queen of indecision, she can stop momentum on a dime. She won't give you a solid answer and often those 'maybes' responses drain the energy out of a room and your team.

The best way to deal with a someone who is indecisive is to force a decision by asking for a commitment on the task at hand and assigning a deadline. Then, hold her accountable for the result. If she follows through, celebrate her! What gets celebrated, gets repeated.

If she fails to follow through though, there must be a consequence for her actions. Accountability is an important part of the process, because what you tolerate becomes your standard. Having someone that’s indecisive on your team is frustrating to everyone around her, so it is imperative for the morale of the whole and the culture of the organization that they see that that behaviour is dealt with.

We've all met a Disorganized Dora, Critical Charlie, Hyper Harry, In-a-Slump Suzy, or Fearful Franky. And somewhere along the way we've probably locked horns with Stevie Sniper and groaned in frustration at the Maybe Mabel's. But realize, while it's easy to recognize the types in someone else... you are probably someone else's difficult person. Sometimes you appear difficult to another person because of a disagreement or a personality conflict. And, sometimes it comes with being a person in leadership. Everyone deals with difficult people, from the the grocery clerk to the church member. What makes you a leader, is how you respond.

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