Chapter 95.
Be a Ruthless Optimist

A leader is a dealer in hope.

—Napoleon Bonaparte

Pessimism is the most fundamental of all the mistakes we managers can make. It is a position, a pose, taken by the manager of not being optimistic about the future of the organization and, therefore, the future of the team.

It is a refusal to prepare for team meetings by learning the rationale behind the latest company decisions. It is a refusal to take a stand for the success of the enterprise. It is a refusal to be an advocate for the organization’s ongoing strategy.

It is also an exaggerated tendency to acknowledge and agree with every issue’s downside without standing up for the upside. Sometimes optimism is a lonely and courageous position to take, which is why most managers don’t do it. The sad thing is, it is what the team wants and needs the most from its leader.

While the unconscious manager doesn’t realize what he or she is doing by being so pessimistic all the time, a true leader knows exactly what optimism is and what it is for: Optimism is the practice of focusing on opportunities and possibilities rather than complaints and fears.

A true optimist is not a brainless Pollyanna, wearing rose-colored glasses. A true optimist is more realistic than that. A true optimist is unafraid of confronting and understanding the problems in the organization. But once a problem is fully identified and understood, the optimist returns the thinking to opportunity and possibility.

Optimistic leaders acknowledge the downside of every situation, then focus the majority of their thinking on the upside. They also focus the majority of their communication on the upside. They know that the downside is always well-known throughout the team. But the upside is never as well-known. Who wants to look like an idiotic optimist? It is far more popular and easy to be a clever and witty pessimist. But it is not leadership.

Optimism in the face of a grumbling and pessimistic team takes courage and energy. It is something most team members would never be willing to do. It is the heart and soul of leadership. And while you may be questioned about it now and then, in the end, the very end, when your work is almost through, it is what your team members will love you for the most.