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How “contemplative leadership” can help us face uncertainty with confidence

A contemplative approach to leading others can help us accept the tension of not always knowing how things will play out.
The image shows the book cover for "The Contemplative Leader" by Patrick Boland, with his name prominently displayed next to the text “an excerpt from” on a split pale blue and beige background.
Matt Holt Books / Big Think
Key Takeaways
  • Reframing the concept of leadership as our “ability to influence others” is a helpful first step in taking responsibility for what we do and how we do it.
  • Contemplation helps us look out on the world with a humble attitude of accepting that we are not fully in control.
  • Contemplative leaders notice the difference between doing something just to feel good about themselves and acting from a place of inner conviction.
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Excerpted from The Contemplative Leader, copyright © 2024 by Patrick Boland. Reprinted with permission from Matt Holt Books, an imprint of BenBella Books, Inc. All rights reserved.

When I was sixteen, I asked my parents for a copy of Niccolò Machiavelli’s classic Renaissance-era book The Prince as my Christmas present. It might seem strange, but I’d just read an excerpt in history class, and it had sounded like perfect reading for any young person looking to make their way in the world. There’s a lot of pragmatic wisdom in The Prince, all focused on achieving significant leadership goals. However, as the critics of its time so succinctly put it, one key message of the book is that, when it comes to leadership, “the ends justify the means.” Although it is now often regarded as an outdated manual for acquiring and maintaining power, some of the utilitarian conclusions that Machiavelli draws are very similar to how outcome-oriented leaders rationalize their achievements today. 

We can easily forget that the way we participate in everything we do communicates the kind of leader we are. This greatly impacts the way we show up in every interaction, impacting the quality of our presence in each meeting and our ability to authentically connect with, and influence, the wider organizational context. When our focus is on achieving big results, we can become too task-focused to consider the means we are using to get things done. We need to find ways to focus on both the means and the ends. This is where a contemplative approach to leadership is most valuable. 

Book cover of "The Contemplative Leader" by Patrick Boland, featuring a textured blue and white abstract design and subtitle: "Uncover the Power of Presence and Connection.

Reframing the concept of leadership as our ability to influence others is a helpful first step in actively taking responsibility for what we do and how we do it. When our external world is ever-changing, we need to go inside to our internal world and connect with what is most valuable, meaningful, and true of ourselves. It’s only as we do this that we build a solid foundation on which to base the why and the how of our leadership. 

We can only lead others as far as we have first gone ourselves. 

From my experience coaching leaders in a variety of global organizations, as well as my work as a psychotherapist, it’s clear to me that we can only meaningfully engage with others to the extent that we have already engaged with ourselves. Our capacity to lead others is based on the overflow of our own sense of presence and inner connection.

No matter how much we know about our organization, our people, and our own capabilities and leadership, the uncertainties of tomorrow and the complexities of our contexts and relationships today all invite us beyond a tips-and-techniques approach to leading. We need to practice holding the tension between influencing from a place of authenticity and accepting that we cannot fully control any situation or outcome. Contemplation helps us look out on the world with a humble attitude of accepting that we are not fully in control; that we will never have all the relevant data to make a decision or know exactly what to do in every situation; that there will always be more to see, to learn, and to experience in our lived moments of leadership. But instead of growing despondent at this awareness, we can instead use contemplation to help us focus our attention on our lived experiences in this moment. 

Leading in a contemplative way is both process oriented and outcome oriented. It endows us with a humble confidence that awakens and opens us to experiencing what is happening rather than simply projecting our own version of reality into every situation we face. We can listen to others because we have first listened to ourselves. Sitting with the challenges that have shaped us, far from something negative, teaches us to notice when we are spurred to act out of scarcity and fear. This helps us become aware of our deeper motivations for building, overcoming, and achieving “great goals.” Contemplative leaders notice the energetic difference between doing something just to feel good about themselves and acting from a place of inner conviction. They don’t need to lead anything. Power, position, and proving oneself are not that important to them. What is most important is how they bring their energies into the causes that compel them to lead. 

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No matter how much we long for it to be the case, most real-world leadership challenges don’t have simple solutions. They require a nuanced kind of processing on our part. And this is where non-dualistic ways of thinking and seeing come in:

  • I can be friendly with my colleagues and have clear boundaries with them around work. 
  • I can stand behind my actions and know that the board members may not be happy with the decisions I have made. 
  • I can recommend that we proceed with this merger and accept that I cannot totally control how things will pan out in five years’ time.

As we learn and practice non-dualistic thinking, we become less attached to controlling outcomes to go exactly our way. This “letting go” frees us to experience the kind of change and evolution that is fundamental to all organisms and systems. When we let go of some of our assumptions about leadership, we allow ourselves to experience the situations we face without a list of preconceived ideas of “how things should be.” The goal of dualistic thinking is to feel in control, but the goal of non-dualistic, nonattached thinking is to be open to what unfolds as a result of our participation and best efforts, which, paradoxically, creates the conditions for even greater things to happen than what we could have planned. The paradoxical theory of change tells us that it is only when we stop trying to control how and when change takes place that we allow the conditions for change to occur. 

Contemplative leadership trusts that great outcomes follow great processes, so once an overarching strategy is in place, it then turns its attention to focusing on the process. It is this “both/and” way of thinking about things that makes contemplative leadership different. It focuses on, for example:

  • Both the financials and the people 
  • Both the results and the road that gets us there 
  • Both the personal benefits to me and the impact on the wider organization and community 

When we lead from this contemplative standpoint of nonattachment, we become comfortable embracing paradox, sitting with the tension of not always knowing how things will play out. Tempting as it is to seek more and more control in the face of uncertainty, contemplative leaders instead focus on being present to themselves, listening to others, and connecting with their environment.

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