The 7 Hardest People to Lead

Someone once asked me, “Who has been the most difficult person you’ve had to lead?” It’s a great reflection question. You learn a lot about yourself answering it. As a leader for over 35 years, I’ve experienced just about everything you can imagine in leading people. And there are certain people who are the hardest to lead. 

I once had an employee call in sick for several days because her snake was peeling. Apparently, the snake got depressed when he shed. She needed to be home to comfort the snake.

That was a new one – and a story for another time – but she proved to be difficult to lead and reminded me not to be surprised at what people may say or do.

I thought about that question through the years and made a list. These are from my perspective.

7 of the hardest people to lead:

The know it all

It’s difficult to lead someone who won’t listen, because they don’t think they have a need for what you have to say. They think they know more than you and everyone else. In reality that may or may not be true, but it makes them very hard to lead.

I have found at times I have to challenge these people if I’m going to be able to lead them. Sometimes it works. At times it simply doesn’t. 

A gifted leader

Don’t misunderstand this one. I don’t mean they try to be difficult. Someone with lots of prior leadership experience just bring higher expectations for those who try to lead them.

I have had some very successful retired pastors in my churches and on our staff. I love that I’ve served with seasoned people with more experience in ministry than me. But they keep me on my toes! (And this is a good thing.)

Hyper-critical people

When someone is always negative it becomes difficult to lead them. They can zap the motivation from the team. They never have anything positive to add to the team, the glass is always half-empty or the sky is always about to fall. It can be draining.

Again, these are people I will eventually challenge – and hopefully encourage. If this type person is channeled correctly they can actually be valuable on a team. They see holes others don’t see. But they must be willing to be team players when things move forward even against their objections, concerns or fears. 

Wounded people

Wounded people are more resistant to being led well until they heal. They may struggle with trust issues, be reserved with their input or injure others with their words and actions. Hurt people hurt people. 

We have added a number of staff members to our church knowing already they were injured. I actually love this as a Kingdom ministry to give them a place to heal. But knowing where they are currently is key to effectively leading them to a healthier future. I have offered them counseling, giving them clear boundaries (which they often need) and simply say things to them such as, “The sooner you learn to trust again the sooner you can be at your best.”

Insecure people

Those who lack self-confidence are harder to lead. They are hesitant to take a risk. The best leadership involves delegation to people who will assume responsibility for a task. That makes it hard when people have no confidence in their abilities. 

I have learned insecure people will move when they are given specific tasks to complete. They need consistent feedback and assurance, which can be exceptionally time demanding for leaders. But over time it helps them gain confidence to not only follow but lead. 

Overly change-resistant people

Leadership always involve change. Without change there is no need for leadership. So, those who cling so tightly to the past are harder to lead to something new.

There is nothing wrong with tradition or with enjoying the memories of the past. But when someone’s love of their history prevents them from embracing their future it becomes difficult leading them.

I like to try and bring them along by allowing them to celebrate the past. At times, we can rediscover rather than reinvent by building upon the success of the past, rather than simply ignoring it. 

Myself

Without any doubt the hardest person for me to lead has always been me. Truth is I can be guilty of holding others to unrealistic expectations I can’t live up to either.

One way I battle this is to ask myself questions such as, “If I were that person, with their skills and interests, would I feel this is a reasonable expectation?” 

Everyone can be difficult to lead at times and during some seasons. It is what makes leadership fun, right?

To be clear, my goal is not immediately to remove these people from a team. Actually, I think the role of leadership is to learn how to better lead them. The reality is that all of these scenarios and types of people can serve a role. Whether or not they prove to be a good fit for a team might still be a question, but often if handled wisely they can sharpen our skills of leadership and add value to the team. 

On every team I have led I have had a few people that proved to be more difficult to lead. If I can figure out what style of leadership they need and how I can tap into the best of them they have almost always proven to be a good fit in time. If not, I want to make that decision sooner rather than later. 

What type person have you found hardest for you to lead?

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