Written by Tricia Conyers, June 2022
Traditional leadership is losing popularity. Historically those who rose to the top exemplified traditional skills like crafting inspiring visions, being powerful influencers, witty communicators, or rallying others to the verge of action. More recently there seems to be a calling for a new wave of leadership, with leaders being recognized for their heart, passion, kindness, authenticity, and vulnerability. Courageous leadership or what researcher Brene Brown calls Daring Leadership is on the rise.
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Yet at the heart of great leadership lies something wicked.
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I recently sat in a workshop with facilitator colleague Jeremy Akers, entitled the Think Slow Dojo, a Never Been Done Before community session (an amazing community created and hosted by Myriam Hadnes). In this session, Jeremy encouraged attendees to slow down their thinking in order to think better, think deeper, and think differently.
To do this we agreed to intentionally seek questions over answers, observations over evaluations, changing perspectives over points of view, and self-reflection over criticism.
We set out to explore what makes powerful questions and ultimately to surface some provocative and deeply thoughtful questions of our own. We were looking for questions that surface complexities and possibilities. Questions that are paradoxical and complementary. Questions that illuminate polarities, dualities, tensions, juxtapositions, and layers of complex forces. Questions that reveal behaviors and beliefs.
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What questions surfaced? Here are a few.
How is it that we can be satisfied and grateful in life while also being ambitious and greedy for a better future?
How is it that we might be attentive and generous listeners and advocates for others while also being in service of our own beliefs, values, and experiences?
How is it that we might embrace and encourage curiosity while also being certain and confident?
How is it that we can build organizations that can respond to crises while simultaneously creating and role modeling peace and ease?
How is it that we can encourage and promote self-centered self-care while also being in generous support and service of others?
How might we be well versed and experienced while also being present in and embracing the unknown?
How is it that we might build a culture that encourages loyalty to organizations while also supporting the independent desires and potential of our people?
How might we create organizations that move fast and drive action while simultaneously taking pause to learn and reflect?
How might we build organizations that are good and that do good?
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The yin and yang of these questions highlight the messiness of life, of living, and of learning.
And of leading.
The paradoxical reality of these types of questions is known to us, facilitators, as Wicked Questions and it is this wickedness that is at the heart of leadership. Great leaders sit with and embrace wicked questions every day. Wicked questions accompany leaders like a shadow, lingering closely and needing inspiration and imagination.
Articulating and surfacing wicked questions is needed in today’s leadership. Similarly, the ability to continuously seek inspiration in service of these questions with no easy or obvious answer or solution is another skill.
How do you begin to solve wicked questions?
Wicked questions require wisdom, experience, and imagination to be shared in service of them, a recent practice that the team at Inflection Consulting has been leading with our Leadership Circles. Ignoring wicked questions can result in conflict, confusion, and disillusion.
Wicked questions require us to embrace the seemingly paradoxical states that exist, as both elements represent a desired and undeniable reality. They are not an either-or state but rather a both-and-state where ideas and inspirations need to be able to service both. By accepting both realities we can unearth deeper strategic and adaptive thinking and ignite new possibilities.
The challenge of great leadership is living and leading through the ambiguity and tensions of the many wicked questions that arise each day. And this takes leaders who are willing to show heart, be human and give hope.
Island Inspirations Leadership Model
To learn more about Wicked Question, check out the Liberating Structure by Henri Lipmanowicz and Keith McCandless
Interested to learn more, download our Leadership Aspirations worksheet and sign up for our monthly inspiration newsletter
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Written by Tricia Conyers, Founder Island Inspirations Ltd., INIFAC Certified Master Facilitator, and Certified Virtual Facilitator
