Often, leaders need to choose between being comfortable and being leaders. During times of organizational transformation, this is especially true.

One of the hardest jobs of a leader is to push people out of their comfort zones in order to set an organization on a new course. It requires communicating the new direction with passion and conviction and coaching your people to do their work in new ways. To do this, leaders must risk making people unhappy or angry, which for most human beings is hard enough.

But, that’s not the hardest part. Advocating for a new course means running the risk of being accused of being naïve, or selfish, or out of touch. Or perhaps most terrifying for many leaders, it involves the risk being wrong.

Most leaders hate to be wrong. Being wrong is embarrassing and potentially costly. But leading organizational change is an entrepreneurial act. Being an entrepreneur requires living with the constant threat of failure…of being wrong.

Living with the threat of failure requires two seemingly opposing qualities of leaders: Passionate conviction and humility. When you are setting a new direction, you can’t communicate any uncertainty to your stakeholders. Your communication must radiate optimism and confidence, i.e. never in doubt.

Yet, you must also never stop listening. This is the humility part. Because, it is also inevitable that you will get it wrong sometimes. Each of us is only given the gift of seeing a part of reality. We need to allow others to fill in our blind spots and be willing to course correct when necessary. This requires listening for the wisdom that sometimes resides in what seems like endless resistance from followers.

So, when leading change, remember, “Sometimes wrong, but never in doubt” and push forward, in spite of your fear.

Need help finding your inner entrepreneur? Call The Bailey Group and talk with one of our experienced executive coaches. We can help you find the right balance between conviction and humility for your situation.

Minneapolis | CEO Advisory