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Leadership and Painful Decisions

One of the most frequent misunderstandings people have is that painful decisions and difficult decisions are one and the same. They are not. Leaders have many painful decisions. But most of the painful decisions are not difficult. For instance, if you have to remove a long-time employee because of moral integrity failure. Is it painful? Yes. Is it difficult? No. It’s the wise thing, in the fact the only thing to do. If you have been a leader for any length of time at all, you know that avoiding conversations that must be had and decisions that must be made is a recipe for multiplying problems.

If you equate “painful” and “difficult” when making decisions as a leader, you may delay a decision because you hate discomfort. You will talk yourself into delaying the decision because you believe the decision is difficult, but it’s only painful. You will over-think the simple and obvious. You will spend a lot of emotional energy on something not worth it and not have time and energy for the truly great challenges. If you confuse painful with difficult, you will lose credibility as a leader. When everyone else can see the obvious solution and you fail to see it because it is painful, your followers won’t see you in the same way.

Leadership is not simple or fun, but that doesn’t automatically mean that painful and difficult are one and the same. Leaders know that pain is temporary, but decisions create the future and last. Leaders are willing to make the painful decisions when they are the right decisions. Something good will always come out of a good decision even if it’s a hard one.

Great leaders don’t take too long to make a decision they know is right but difficult. Few of us are great at it to start, but we grow as we keep working at it. An area that has always been most painful for me has been letting employees go. My first one was actually a friend I valued deeply, but all we did to remedy the situation and get him to be a fit for the job we had available just didn’t work. It was very painful, but the decision was clear. It wasn’t difficult, just painful. I could have made it easier had I moved with more persuasion and quickly. It was painful, no doubt—for all of us. But the years have proven for him and for us that it was the right decision.

Change is part of leadership. There can be no progress without it. Change is both difficult and painful. The conversations that must happen can be very painful and hurt deeply. But difficult decisions must be made. They grow and strengthen you and eventually good comes for everyone when wisdom is allowed to reign.

You have made painful and difficult decisions in your past. Some of these are still painful because of the regrets you have over the manner in which you made those decisions. Some of those decisions are ones that make you proud, and the pain was worth it. All of those experiences have brought you to where you are. You will get better and better as you work to make the wise decision even when it’s painful.

Here are a few things that help me in these times when change is necessary, and the painful conversations and difficult decisions surface. Maybe they will help you remain strong as well.

Schedule time with people who support you. They don’t have to agree with your decision, but you need to spend time with people who support you and your decision-making. Sharing your pain and grief and even your deliberation with them can really help. Knowing we are not alone helps us make better decisions for better reasons.


Give yourself permission to cry. Crying is not a female thing. It’s a human thing. Trying to swallow down tears is stressful, and it distorts our view of the world and the people involved. It helps us believe things that aren’t even true. Tears can actually cleanse our minds and souls to think more clearly and helpfully. Crying can move us through the process of change and lessen the pain we experience overall. Tears can actually help us see more clearly and experience helpful intimacy with others.

Find time to pray and meditate. Prayer and meditation cause us to slow down and not act rashly. As we share our pain, confusion, and grief with God, we get clarity, understanding, and direction. We are able to feel more confident with our decision. We gain peace.

When you have done all you can do to think clearly and wisely, trust your decision. No one knows the life you need to lead better than you. No one knows all the ingredients that need to go into the decision better than you do. Friends, other leaders, family—they all can have input and opinions, but when the buck stops with you, you need to trust yourself and the decision you made. Don’t overthink.

As time goes on, you will become more and more equipped and confident of doing the next wise thing, even when it hurts.

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