Leadership Mostly Sucks

I try to tell this to young, aspirational leaders all the time.

I really believe the weight of leadership being heavy is critical to an authentic leader.

Transactional leaders inconvenience others. Transformational leaders shoulder as much of the inconvenience as they can.

I think a leader who is self involved leaves his work there. I don’t think you can lead multiple people, have to make decisions that are hard sometimes, and claim to be an effective leader if you don’t carry an empathy for the people you have to leave behind.

During my 10 year collegiate head coaching career, I can think of 2 specific players who had to go. They were anchors on our program, and we did everything we could to get them to the standard, and we probably gave them a few to many opportunities. 

I haven’t coached either other of them in over years. And I still carry the guilt in my gut of what cost we inflicted on their lives. Our team benefited - without a doubt. And also, when I informed one he wasn’t going to be in our program any longer, I immediately went home, curled up in a ball, and wept. It was around 3 pm - I didn’t get out of that bed until the next morning. 

I often tell leaders that the best internal measurement of how well they are leading is two questions:

1. How much are my personal interests inconvenienced

2. How much do my decisions that impact others weight on me

Transcendent leaders must embrace that burden. To fail to do so is to transactionalize your teammates, to reject their humanity.

Failure of deep, gut wrenching empathy IS failure of leadership. 

You can’t lead effectively if you aren’t inconvenienced. 

The relationship between inconvenience and effectiveness may not be absolute, but odds are the worst leaders you’ve worked with rarely inconvenienced themselves.

I remember in 2010 I was stuck on the idea and cruelty of coaches who posted rosters for cut lists instead of dignifying every single young person who tried out with a conversation. When I left coaching in 2026, I still know college coaches who posted travel lists and starting lineups without every uttering a word to an athlete who just had his or her whole world wrecked. I worked for multiple administrators who made little to no effort to ever connect with their employees, then would send letters of reprimand via email.

One is easy for the leader. One requires a hard conversation and the leader to own it.

Embrace the suck. Be willing to shoulder the burden.

The belonging you create will outweigh any personal cost.

Transformational Leadership is mostly inconvenient.