Billie Holiday's Unexpected Lessons on Leadership

Billie Holiday (Wikimedia Commons/Public Domain)

I am haunted by the smoky notes of the late Billie Holiday. Hardly any voice in the jazz world reaches me as hers does. Of all her songs, perhaps my favorite is "All of Me." Other artists have covered the tune, including such disparate singers as Willie Nelson, Paul McCartney and even The Muppets, but no one can touch Billie Holiday. Here are a few lines of this famous jazz classic.

All of me./Why not take all of me?

Can't you see/I'm no good without you?

You took the part that once was my heart,/So why not take all of me?

Paraphrasing only a bit, those simple lyrics ask one of the crucial questions of leadership: Why not all of you?

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Someone asked me why Christians in general and pastors in particular tend to make some weak-headed business decisions. First of all, I'm not 100 percent sure Christians and pastors do actually make more poor decisions than pagans do. Second, when bad decisions do get made by Christian leaders, it is most often because they make "heart" decisions. Relying on feelings, hunches, emotions, empathy and sympathy, they may tend to be too slow to confront, too vague in discipline and not strong enough with employees that need it. Likewise, the emotional leaders may tend to fly off the handle. Soft-hearted leaders can also be hot-headed.

Even worse, bad economic decisions often get made by leaders too slow to cut their losses and too emotionally involved in the project. Soft-hearted can also turn into soft-headed. It gets even worse when "spiritual" language starts getting tossed around the board room. Faith is not denial. One man told me proudly that his pastor was "all heart." I thought, oh my, what a tragedy. Leaders who are all heart may be unwilling to look at—say, nagging little things such as budget, revenue, P and L and real attendance numbers.

On the other hand, this is hardly a rationale for becoming Ebenezer Scrooge. One needn't be a cold-hearted misanthrope to become a serious-minded leader who can ask all the tough questions, and more importantly by far, hear all the tough answers. Reality and generosity are hardly mutually exclusive. Grace and grit are not opposites. Leadership is not well done by partial people.

I was once berated by a board member for giving an errant employee a quiet and discrete exit. He said, "You are not harsh enough." He evidently saw harsh as synonymous with firm. At another place of leadership, as a new president, I quickly closed a day care center that had lost money every quarter of its existence. The college was in serious financial trouble when I arrived. Tough decisions had to be made, and they had to be made rapidly. One board member at that school said, "That wasn't right. That was just too cold for a Christian school."

We are not cardboard cutouts, flat and one-dimensional. We do have emotions. We can also think.

In fact, harsh is not the same thing as firm. Generosity is not the opposite of good business. Caring, servant leadership is not the opposite of strength in authority. All of us. That's the answer. All of us engaged all the time, all at the same time. That's real, wholistic leadership, and it is no easy task. No leader wants his employees or customers or constituents asking, "Who took the part that once was your heart?" Or sideline kibitzers yelling, "Get your head in the game."

Great leaders know they are heart, head and spirit, and they strive to be engaged as complete persons. It is possible to think, feel and pray your way into the strenuous task of leadership.

Dr. Mark Rutland is president of both Global Servants ( and the National Institute of Christian Leadership ( A renowned communicator and New York Times best-selling author, he has more than 30 years of experience in organizational leadership, having served as a senior pastor and a university president.

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