“The life of the spirit, by integrating us in the real order established by God, puts us in the fullest possible contact with reality—not as we imagine it, but as it really is. It does so by making us aware of our own real selves, and placing them in the presence of God.” – Thomas Merton

The first and most important practice of the contemplative leader is learning to cultivate the ability to ask the right questions. Unfortunately, many of us never learn to ask the right questions. Leadership involves agency among real people in real situations in real time. An effective leader must be able to discern all the moving parts and all the connected relationships as things unfold. The ability to ask the right questions is crucial.

I believe the right questions must shine light on the obstacles in front of us, even if those obstacles are rooted in our own learning disabilities. Whether we use Edgar Schein’s “naming the anxiety’s that lead to change”, Peter Senge’s “ruthlessly, compassionate truthtelling”, Ronald Heifetz’s “naming the elephants in the room”, or the Apostle Paul’s, “speak the truth in love”, we must be willing to name the things that keep us from learning, growing, and changing. If we refuse to do the hard work of naming the truth in love we risk a variety of problems, the biggest of which is short-sighted leadership.

So, what questions do we ask? At the beginning, I would answer this question with another question. What question we afraid to ask? Usually this is not a question regarding how to lead our organization, it is usually a question that has something to do with our understanding of self, or lack thereof. Why are we afraid to ask the question? Are we afraid of the fallout? Are we afraid it will point back to our own inadequacy? Or, are we afraid there will be no answer to the question?

In trying to find the right questions to ask, leaders must be honest. Christian leaders must be honest in love.