Leadership Means Cultivating Wisdom

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Leadership is about finding insight into the deepest levels of humanity.

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The father of the modern study of leadership, Warren Bennis says: “Leadership is about becoming more of oneself. It is just that simple and just that difficult.” The journey of the leader is journeying into the center of their being, the place of depth, insight, and wisdom. Many great leaders throughout history were able to motivate, inspire and bring people together over a common cause. Some took it a step further were able to reflect in quiet moments quite deeply about the human condition and became known for their insight. These leaders became known not as merely high achievers who created a successful company or led a nation state, but were well rounded in their ability to understand life itself, and teach others the true nature of the human journey. The insight into the nature of life is wisdom.

One of these leaders was Marcus Aurelius, a Roman Emperor who was a stoic philosopher. His book Meditations was written in quiet moments, on the war front in Bohemia or amidst a complex decision of governance. He practiced daily reflection and journaling, asking himself piercing questions about the nature of life, humans and decisions. The quiet moments of leadership force a burden of truth on a leader, where they face the weight of making decisions for many people and their families inside of the business, and exponentially more outside as customers and the community at large.

John  F. Kennedy was another leader, who in quiet times reflected on the human condition and like Marcus Aurelius wrote stories of leadership in Profiles of Courage. He is less known for his reflective capability, but it underscored some of his more difficult moments such as the Cuban Missile Crisis and how he built his cabinet as an intersecting team of the best and the brightest.

The journey of the leader to wisdom usually requires initiatory forces that deconstruct their own ego and reveal the nature of leadership as service and stewardship. These leaders realize it is no longer about their own glory and through their own awakening, realize that wisdom is using insight in service of a greater good. This awakening can be painful as many leaders begin the journey from a place of their own achievement. This transformation is detailed in the Hero’s Journey and many leaders go through it as they begin to bear the burden of responsibility for others. True wisdom is growing beyond oneself.

Wisdom requires insight, experience but stands on the foundation of presence, as we now know through the emerging field of neuroleadership a highly reactive or regressive leader does not have access to their logical/sense making part of their brain. Queens and Kings archetypally are rarely rushed, and the embodiment of the wise sage is one of peace, groundedness and presence. We all know the sense of deep clarity that comes from times of peace and relaxation: the moment after a Yoga class ends, the morning pages of journaling or a quiet evening near the fire. Cultivating presence allows for spacious inquiry, for openness to new ideas and creative ways of looking at an issue. This comes from an embodied state. Practicing presence means actively practicing embodiment of our physical form, emotional intelligence work and centering practices. 

From this place of presence, the practice of reflection is critical to cultivate Wisdom. Awakening to the true nature of self and others allows for the emergence of deeper truths and complexity. Regular practices of journaling and reflection with a coach, therapist or mentor take the insight deeper as to truly understand others, a leader must understand themself. Sometimes this complexity is paradoxical and the decision requires many intersecting variables including highly subjective elements such as “felt sense”. We know that instinct operates out of the reservoir of the subconscious, like a super computer analyzing complex data at infinite capability. Instinct is usually right based on millennia of evolutionary biology, but only truly effective when balanced with rigorous logic and analysis.

Wisdom in leadership does not mean simply reflecting from the place of presence. Knowing must turn to doing. In taking action with integrity, trust is built and leadership moves from reflection to impact. All humans can cultivate wisdom through presence and reflection. Leaders bear the burden of using the previous two steps to create an impact. Understanding how to support action through others is another part of the discretion. Leaders that cultivate wisdom create action and impact through others. As they do this, they can transfer knowledge and create capacity in others. They coach others to action.

The process of discretion is leadership and the heart of discretion is wisdom. Wisdom is a blend of the head and the heart, including multiple variables and usually choosing “the highest good for the most people” in opaque situations. Wisdom is not guaranteed by age, in fact many grow more reactive, brittle and hard as the years pile up. Only through a life of inquiry and practice does the prize of years add up to support the emergence of wisdom. Wisdom is a state and a practice. Cultivating it is at the heart of leadership development and engaging in all three practices of presence, reflection and action allows for a lifelong journey towards authenticity, purpose and service. This is the road less traveled and one worth taking given the immense impact leaders have on peoples lives. Organizations led by wise leaders will contribute to the evolution of the planet and support the transformation of the world.

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The Spirit and the Soul of Business