12/30/2014 10:51 pm ET Updated Mar 01, 2015

Wonderful Leadership: Seeking a Contemplative Approach to Guiding Others (and Ourselves)

I had a boss once who I really liked. He and I had a friendly relationship, he provided insightful guidance whenever I ran into a problem with my work, and he encouraged me both in formal and informal ways. I'm almost tempted to say he was the best manager I ever worked for, but there was one towering problem.

The man wasn't a very good listener. He was very bright, and typically would cut me off before I could finish detailing a problem, often with helpful feedback, but sometimes way off the mark. When he was off-base, I would patiently try to keep explaining what was going on, and eventually he would grasp the issue and all of his skills would go on display. But it took 10 minutes to work through a three minute problem, all because he wouldn't hear me out the first time.

If I found an effective manager troubling because he was a poor listener, I can only imagine the frustration so many people feel when they work for a mediocre or poor leader who also can't listen. Listening, it seems, is a natural part of effective leadership -- but perhaps it points to an entire style of leadership that often gets overlooked in our world, whether we're talking about business, civic, nonprofit, or religious settings.

What does it mean to lead well? How can we lead others (and ourselves) most effectively? What can we do to improve our leadership skills? How can leaders best be equipped to make a difference in our time of rapid cultural change?

I'm posing these questions as a Christian writer and speaker, so naturally I'm looking at leadership through the lens of faith. But hopefully my thoughts will have a broader application than the confines of the church institution.

There are various types of leadership models: authoritarian, directive, collaborative, participatory, empowering, and so forth. Each model may be appropriate in a given circumstance: in the midst of war, leadership by consensus probably won't work, whereas a clear, hierarchical chain of command is more likely to get the job done. And so it goes.

But one category that I don't often see in charts that detail leadership styles: contemplative leadership, which I like of think of as wonderful leadership. It's not a specific model or category that you can contrast with all the other types of leaders; rather, it is an approach or underlying stance that can inform (and transform) any form of leadership, in any type organization or network -- from the most centralized to the most consensual.

I call this contemplative model "wonderful leadership" because the heart of this approach is wonder. I'm using the word contemplative not in the narrow sense of a kind of meditative practice, but in the broadest possible sense: of a way of being, or relating, that is characterized by non-attachment, ability to wait, emphasis on watching and listening, comfort with ambiguity, paradox and mystery, and trust in the process.

"It is not certain that everything is uncertain," mused Pascal, but I suspect that for many leaders, the opposite seems true: uncertainty is perhaps the only thing we can be certain of. So the question becomes, how do I lead in and through uncertainty? Can I accept it? Can I be okay with it? Can I convey that acceptance and confidence to my team, thereby empowering them to reach their fullest potential in a world where all bets are off?

Contemplative leadership means embracing, rather than fighting, the uncertainty, the mystery, even the anxiety. We do this by consciously choosing to live in wonder.

Perhaps one way to choose this way of leading is to allow it to shape the very words we use when we communicate with others. I wonder what it would be like to lead, if leaders made it a priority to live in wonder? If leaders asked plenty of questions (questions that begin with "I wonder")? I wonder how our approach to leadership might undergo a radical transformation if we made qualities like allowing, recognizing, compassion, investigation, and creativity more essential to our understanding of good and effective leadership?

I think these qualities can be applied to almost any non-emergency setting. A business that fosters a culture of creativity and open-ended investigation may be in a much stronger position to deal with emergent market conditions, just as a flexible tree is more likely to survive gale-force winds. A religious organization that empowers its membership through recognition and allowing initiative can more fully embody such non-hierarchical values as "the priesthood of all believers."

Even in the flattest organizations, leaders set the tone. A leader with enough faith and trust to foster a sense of wonder in the organization will create an exciting culture where anything is possible. "I wonder what will happen if..." becomes almost a mission statement.

"If you want to build a ship, don't drum up people to collect wood and don't assign them tasks and work," said Antoine de Saint-Exupéry, "but rather teach them to long for the endless immensity of the sea." That's contemplative leadership. I wonder what would happen in our churches (let alone our businesses and government) if more leaders took the time to listen to the longings in their own hearts, and allowed those mysterious whispers to guide their own path?