Facilitating Transformative Conversations

Vital Leadership in Times of Crisis

This past Sunday I had the pleasure of leading a conversation on Surviving to Thriving with the Transformative Learning Community.

Based on last week’s events, I decided to throw out my original intent for the conversation and instead get connected to how the folks in the room were feeling, meeting and/or grappling with the complexity of current conditions.

It was a moving and authentic conversation with leaders in our community who dedicate their lives and work to supporting others through higher education, growth and transformation. Perhaps because of the timing, many of them had not yet had the place and space to deeply process their own experience of last week’s, last year’s or even the last four year’s events. This became for many of us a welcome respite of reflection along the path.

One of the emerging themes that came out of the conversation was the practice of creating more spaces to listen, engage and grapple with complexity.

There is something healing in and of itself about being seen, heard and accepted as you are in the process. To not have to have the answers. To appreciate the opportunities inherent in the act of grappling. And to be witnessed in the unfolding of the questions.

With all of the trauma, change, uncertainty and conflict that folks have been through over the last year, are organizations providing the brave spaces — as Mary Winters calls them — for these conversations to unfold? Or are we still telling ourselves that we can’t talk about these things at work?

Are your executives, managers and teams gathering to grapple, heal and grow in conversation with each other? That is, having conversations that allow folks to:

  • reclaim a sense of wholeness and belonging,
  • share, understand and integrate varied and often divergent perspectives and values, and
  • foster a sense of orientation and cohesion, even as the level of volatility, uncertainty, complexity and ambiguity we face is on the rise.

What we see playing out in the public forum is a crisis of leadership on so many levels, both in self-leadership and in leading others. Those who stay landlocked in their old ways of thinking and reacting, risk extinction. While they hold tight to their ideals they simultaneously run their careers, their companies or the social currency they cling to off the edge of the cliff.

Without brave conversational spaces, we risk a devastating and prolonged impact to our mental health and well-being, performance, decision-making, engagement, communications, creativity, relationships and culture. In fact, the quality and authenticity of our conversations in many ways reveals the quality of our relationships and culture.

As leaders, its vital that we do this work for ourselves and become proficient at leading others through complexity and the messy middle as Brene Brown calls it — that comes along with it. When we adapt and evolve, we gain the ability to understand and integrate solutions that are inaccessible from our current vantage point. The art of transformative conversations gives us tools to do just that.



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Elan Bailey

Elan Bailey


Founder of UpLevel Leadership Academy helping individuals and organizations develop the competency, capacity and community to adapt, grow and thrive.