In Necessary Endings, Dr. Henry Cloud describes the idea of a season and how the metaphor applies to activities, organizations, and especially relationships. Knowing when things have to end is a huge challenge for leaders. Having to stop something is never a fun conversation, but the cost of continuing a futile cause exceeds the benefit of ending it. One of the most helpful distinctions Dr. Cloud makes in his book is three types of people you will encounter when leading:

Wise people - those who not only receive your feedback kindly because they know your goal is to help them, but who also demonstrate change resulting from your input. Your aim, then, is to maintain a strong level of communication.

Foolish people - those who have good intentions to follow through when you coach them, but struggle with consistency. Your approach should be to keep expectations as clear as possible, designing a supportive and direct path for them. This way, they will be confident in meeting your standards.

Evil people - people who deliberately cause problems and make life difficult for others. You need to set boundaries. Don't expect evil people to take them seriously unless you enforce accountability and consequences. If you get to a point where firing them is inevitable, you have to see dismissing them as necessary and loving. The burden on your team and organization is too great to get caught up in emotional attachment. Hoping they'll come around is neither prudent nor realistic.

Takeaways:
1. Be certain of when to let go. I happened to serve as director of a church class in its twilight, a status no one seemed to acknowledge until reversing course was no longer possible. People weren't embracing leadership roles, nor were they building relationships with newcomers. While broadcasting any pessimism would not help, I wish I had more specific criteria and courage to pull the plug before things completely derailed. Having tripwires in place (as mentioned in Chip and Dan Heath's Decisive) would have given the decision process more clarity on how and when to act.

2. Don't just know when to let go; you still have to actually do it. I once hired an employee who turned out to be a terrible contributor. We gave her every benefit of the doubt in hopes that she would turn things around, only to see her revert to the destructive habits we confronted her about to begin with. If you find yourself struggling to pull the trigger, ask for help. You don't have to be the hero. Just get the job done.

3. Be kind to yourself. Too often, I associated quitting with the shame of perceived failure. Having read Built to Last by Jim Collins, I felt that an enduring legacy was the hallmark of success. Revisiting the church class example, I thought I drafted a vision compelling enough for anyone to support. I hoped for a community where everyone knew his role in maintaining class integrity, even if he didn't hold an official title. Seeing that dream crumble gave me humility, as I had to admit my limits. I also learned to focus on the lessons, not the loss. Finally, the end of the class refined my belief in God, trusting His love was bigger than my failures as director to keep the class going.

Necessary Endings helped me appreciate the blessing closure provides. Whether dealing with a difficult friendship, an unsatisfactory job, or an activity that has lost its fun, I hope we all strive to enjoy the relief we'll get when we find courage to follow through with letting go.