7 of the 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 30 years (wow, sounds old), I’ve experienced just about everything you can imagine in leading people.

I once had an employee call in sick because her snake was peeling. And 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 I’ve learned not to be surprised at what people you are trying to lead may say or do.

I’ve also learned some people are easier to lead than others. Often personalities, experiences and preferences negatively impact a person’s ability to be led effectively.

But, I thought through the years and made a list.

Here are 7 of the hardest people to lead:

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. They may or may not, but it makes them very hard to lead.

Gifted leader

Don’t misunderstand this one. I don’t mean they try to be difficult. They 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. Our staff is full of seasoned ministers with more experience in ministry than me. I love having them, but they keep me on my toes! (And, this is a good thing.)


When someone is always negative it becomes difficult to lead them, mostly because they zap the motivation from you to do so. They never have anything positive to add to the team, the glass is always have empty, and the sky is always about to fall. Draining.


Wounded people are more resistant to being led to something new until they heal. I’ve had a number staff members who came to our church injured. I actually love this as a Kingdom ministry. I knew before I could effectively lead them I had to help them heal from their past.


Those who lack self-confidence are harder to lead, because they are hesitant to take a risk. The best leadership involves delegation. It’s people who assume responsibility for a task. Insecure people will usually only move when they are given specific tasks to complete. And, while good leaders encourage followers, insecure people need constant feedback and assurance, which can be exceptionally time demanding for leaders.

Change Resistant

Leadership always involve change. Always. 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. It’s when someone’s love of our history prevents them from embracing their future it becomes difficult leading them.


The hardest person to lead is almost always the leaders. If leaders could always perform as we’d have others perform, we’d be better leaders. In fact, most of us would be excellent leaders.

I’m sure I missed some. The fact is everyone can be difficult to lead at times and during seasons. It’s what makes leadership fun, right? Seriously, all of these scenarios and types of people serve a role. Whether or not they prove to be a good fit for your team, they sharpen our skills of leadership.

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

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19 thoughts on “7 of the Hardest People to Lead

  1. The saboteur – one who appears on board during planning sessions and stages, who makes every effort to appear supportive of a program or focus (sometimes overly so), to only do what they want once the rubber hits the road. These people rely on the tenants of grace and forgiveness to continue in their actions, especially in the presence of a leader who works to avoid confrontation.

  2. To me the hardest person is the lazy person. Hands down. A close second is leading staff you inherited who grew up in the church. Almost impossible. When a person has both qualities….well, that's called "my church."

  3. Add "The Perfectionist" to the list. That person that has to have everything just so and doesn't give grace for the weaknesses of others. Or the one who has to have everything perfectly planned before agreeing to anything.

  4. How about the one convinced they are more gifted as a leader than they have reason to be?
    They're a blast!
    Twitter: bryankr

  5. For my own benefit, I would like to see a list of "7 things that weaken leadership". I have seen/been leaders with good ideas, plans, and people; but our own style, past history, personality, etc. have made leading/following difficult. Unless we have good mentors/partners around us, we often tend to be blind and blame the potential followers.

  6. Great list! I would add "outsiders." When someone comes from a different background and doesn't yet fully understand our unique culture and vision, I have to work harder to lead them. It can take time to recognize when we have different assumed values or unspoken philosophies, so I have to communicate clearly when leading people who are new to our environment.