What is the hardest part of Leadership?

Someone recently asked me a very thoughtful and curious question. I surprised myself with how quickly an answer came out of my mouth with a bit of emotion behind it.

“What is the hardest part of leadership?”

When it comes to leading people and organizations, there are many difficult things, but the answer that shot out of my mouth was this: 

“Being misunderstood.”

How would you answer that question?

Truth is, leadership requires making crucial decisions whether you lead at work, at home, or in a volunteer setting. When making decisions, a good leader will look at all of the information they have, or the information they need to gather, and decide what’s best for the entire organization and the team in order to move forward. 

This is different than making a decision that most people will agree with. Sometimes what’s best for the organization is not always the most popular vote.

No matter where you’ve led up until now, odds are there was a tough decision to make at some point. Ninety-percent of leadership requires making hard decisions. Making those difficult decisions hasn’t always been the hardest part for me. Being misunderstood afterwards is what gets me. This has been true for me as a leader in the workplace, a friend and coach in the community, and as a parent.

I could give numerous examples of being misunderstood when needing to let people go, or having to make a short-term decision that might not make sense to some because they don’t know the future plans, or why I chose to play one kid over another in flag football, but one story comes to mind as a parent. 

Years ago when our boys were little they had a really great friend from school that invited them over for a sleepover. Because of my position at work, I knew some private details of this family which informed the decision to not let our boys go to a sleepover out of concern for their safety. Our boys were devastated by the decision and didn’t understand it. They really didn’t understand the why behind the decision, but it would not have been appropriate for me to share the details I knew with our sons at that time. I did empathize with the pain and frustration they were feeling. They were upset with me and the decision I made, but I needed to stay firm in the decision. Some times the decisions we make do not just alter evening plans, they change someone’s career path, cause your character to be judged, or significantly change a  relationship. 

Here’s what being misunderstood has taught me. . . and I’m sharing them here, hoping these learnings can be an encouragement to you: 

  • Your difficult decisions will impact others, sometimes significantly. Learn to accept that this is just part of the role.
  • You most likely will disappoint someone along the way. If you make a decision from a place of fear, not wanting to disappoint people, you might make the wrong decision.
  • Keep your head up knowing you made the best decision possible with all of the information you had. No one knows what it is like to be in your shoes. As a leader, you have a unique perspective to see things from a broad perspective, and you may not always be able to share those things with others. This may cause misunderstanding, pain, or confusion. But you can still walk with confidence in knowing you did the right thing. 
  • Catch and release. There is a fishing practice called “catch and release.” You catch the fish, you pull it in (maybe even take a picture) and then you let it back into the water. This helps the fish population and the entire ecosystem. For me, when listening to criticism or feeling misunderstood, it is helpful to catch and release. I listen to the feedback, process it, and hold on to what is true and lessons I need to learn from it, and then release it. 
  • Find your community. Leadership can feel very lonely, especially when making big, difficult decision. You might not be able to share the particulars of what all went into the decision-making process because it is not your story to tell, it is confidential, or the timing is not right. That’s why it’s important to have people in your life who you are able to bounce things off of both from a leadership advice perspective, but also to share how you are doing personally both before and after making hard decisions. 
  • Don’t forget to lead yourself too. Often being misunderstood means receiving negative messages from others. There are voices telling you who you are and who you are not. It is crucial that you know deeply who you are, what you are called to do, and how you want to show up in the world, otherwise it will be easy for the negative voices to be the wind in the sails. Leading myself has looked like prioritizing therapy, spiritual direction, exploring in nature and adventuring with my family.

What’s been the hardest part of leadership for you? 

And what practices help you stay grounded in those difficult moments?

One thought on “What is the hardest part of Leadership?

  1. One of my tendencies is over explaining a decision when it’s questioned. I’m seeking full agreement and support even in moments where I’m not going to get it.

    Great post Matt!

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