The Dark Side of Leadership

It has been said, “Be careful what you wish for, you just might get it.” That can definitely be true in a leadership position. Many people aspire to be leaders. Leader of the pack. Top of the mountain. While that is certainly an admirable goal, no one ever wants to talk about the tough choices leaders are tasked with making. It’s a nice place to be when things are good. It can be the worst place to be when things don’t go as planned. Coincidentally, the tough times are where true leadership is tested and great leaders are forged.

I feel that in general I deliver on one of my key goals and values of making my team members feel valued. I have the ability to coach them and encourage them to push themselves and to overall achieve more than they would on their own. I enjoy sowing into others and sharing the wisdom I’ve gained through bad decisions and difficult circumstances. I relish watching someone thrive from a foundation of support and guidance that I’ve provided. There really is nothing better than leading a team that achieves its goals.

There is, however, a dark side behind all the tales of success and accomplishment. The dark side of success is failure. Nothing hurts worse or carries a heavier burden than failure. Worse than failing yourself is failing others. In these times of defeat I make it a rule to always self-evaluate in order to make sure that any responsibility I failed in or opportunity I missed that would have prevented this particular outcome, doesn’t happen again.

In the case of employment termination or reprimand, I’ll wonder what else I could have done. I’ll wonder what it feels like to be in the home or heart of that person. I’ll wonder if it will cause them financial hardship. I’ll hope they don’t think it’s personal and that I’m just some jerk who doesn’t like them. I’ll pray about it before and I’ll continue to pray about it and for that person, after. I’ll hope that after the time we’ve gotten to know each other they’ll take something positive away. I’ll hope they do some reflecting and self-evaluation. I know I will. Then, I’ll move on and they will too.

Even when it was the right choice, the best choice and even if it was the only choice. This is part of the burden of the leader.  

The best leaders don’t spend time beating their chest for all the victories. The big deals they’ve closed. The lives they’ve saved. The homeruns they’ve hit. They spend their time wondering how to avoid the lost deal, the lost life, the soured employee, the strikeout. How to be better. Chasing perfection. Constant improvement.

Next.