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Centering Courageous Conversations


The Necessary “Messy Middle” for Creating Leaderful Organizations &

Movements for Social Change


“I have had to learn that my voice has value. And if I don't use it, what's the point of being in the room?” -Michelle Obama


There I was sitting in space after space with leaders and organizations grappling with ways to intentionally address complex social change. Was it through civic engagement focused on leaders from across sectors, communities, and regions; or town hall meetings that ushered in waves of community groups, concerned citizens, and stakeholders; or convening diverse grassroots leaders, institutions, or political stakeholders working in concert with one another through coalitions, movements, or broader networks. Given this new awareness, I stepped back, reflected, and processed or as Gary Hubbell would say, “ gave it time to breath.” I couldn’t help but to drop down into a space of appreciating the artful and beautiful weaving of these experiences as not just activity, but as the beginning of a set of orchestrated courageous conversations that would intentionally activate and cultivate critical thought leadership who could address social issues in diverse spaces. Prompting a set of curious “What if” questions in response to this awareness:


What if we shifted courageous conversations from the fringes of our work to the center to build leaderful organizations and movements to solve complex issues and social change?

What if we viewed these conversations as a non-negotiable in our work to facilitate “foundational change processes “that allow for innovation, centering of people and communities, and sharing and building of power?


What if these questions provide permission to pause and think deeply about the right puzzle pieces that are necessary to cultivate thought leaders as futurist, advocates, rainmakers, and change agents working vertically, horizontally, and foundationally throughout institutions and communities, with a shared belief that transformational change work requires individual, community, and institutional transformation?


Courageous Conversations represent the “messy middle” of our collective work. It illuminates the invisible, dark and tender spots, while challenging us all to resist complicity, embrace discomfort, and address harm and trauma. They represent the “ wide spaces” between us and a clear line of sight that must be filled with carefully crafted dialogues, that serve as important primers and catalyst, that are working to shift mental models-deeply-held beliefs, biases, and shared thinking- towards creating leaderful movements to facilitate change.


Courageous Conversations are grounded in a fundamental expectation that we will start where people and institutions are and expect them to move. This expectation creates a clear line of sight towards shared understanding and consensus that this transformational process will naturally move along two parallel tracks that unapologetically views this work as both an explicit outcome and as an incremental process and strategy. By embracing this intentional process, we are able to move others along a continuum of innovation, systemic change, and design thinking to create a new vision for tomorrow. A tomorrow that is grounded in explicit values of equity, collective solutions, centering of people and community, and sharing and building of power to address complex social issues and build the capacity of leaders across social change movements.


Consequently, in this journey, there are five iterative steps to navigate in order to activate impactful thought-leadership in the courageous conversations’ space. I affectionately refer to this process as SAY IT.


  • S =Setting Intentions

  • A= Activation

  • Y= Your Individual Work

  • I= Invite Inquiry

  • T= Transformation


SAY IT is a set of principles that are designed to move individuals, communities, and institutions through a transformational process that accelerates leadership and conversations to enable the courageous positioning of ideas, voices, and spaces in new ways. These principles have the ability to amplify, interrupt, and innovatethoughts, practices, behaviors and systems to address complex change. While providing space for “messy thinking” and permission for deep reflection and emergent processes to test, do, learn, and adjust or pivot.


“Being brave is not about being unafraid but feeling the fear and doing it anyway…when you feel fear, try using it as a signal that something really important is about to happen”-Gloria Steinem


S: Setting Intentions

Setting intentions is the foundational component for your entire process. It safeguards your commitments to the process, the naming of uncomfortable or tender spots that may emerge along the way and serves as an accountability tool as you move deeper into your individual and organizational work.


Your intentions should include creating a practice of being present, learning, and permission to make course corrections as needed. It should include a listing of all of your promises to yourself and others in this process, desires and wishes as it pertains to the outcomes, and most importantly create intentional space for this work. Arguably, setting intentions and creating intentional space go hand in hand. One without the other does not allow for the heavy lift that is necessary to build intentional practices in your work that are sustainable and impactful. Creating intentional space to integrate new thinking and practices into your journey will allow you to shift your thinking, schedule, and seamless practice to create multiple entry points, structure, and clear communication that can extend beyond current relationships and boundaries.


A: Activation

Nothing happens without you activating or moving it. This single act is about creating the necessary momentum and synergy that has the power to motivate whole groups, organizations and institutions, while extending an invitation into an intentional collaborative relationship for “cothinkking” as a means to explore the what, why, how and when.


Activation creates the necessary movement to assess and align appropriate levers to achieve a vision and shared line of sight for the future. In this inflection point, there is an opportunity to be explicit about equity, discomfort, and reflection as core competencies to voice what you are fighting for, your superpowers, values, and non-negotiables.


Activation usually happens as a result of a signal or indicator that something “must change.” The Coach Diversity Team “describes this process as signaling and the first step or an inflection point that is the primer for moving leaders and institutions to a visioning process that has the potential to create a new story for the future. This can take a variety of forms- from an impactful community event that has had either devastating consequences or positive ripples within the community, from data gleaned from quantitative and qualitative sources, and leadership changes to deployment of capital (financial, relational, social, human, infrastructure, political, and cultural capital) or broader world or field issues that everyone is beginning to think about and desire to act on.


“There are some elegant solutions that are not harmful,”- Rudy


Y: Your Individual Work.

Addressing complex social change is hard and requires us all to model a new way of moving, building relationships, embracing discomfort, centering people, sharing and building power. Consequently, the effort to show up as our best selves and maintain the integrity of this work is constant and necessitates individual self-reflection, learning, and on-going growth. It requires us all to go deeper into ourselves by constantly grappling with a set of guiding principles grounded in building healthy, equitable and positive relationships. See my article called “The Year of The Stretch” to view a listing of principles and practices that are critical to moving you from stretching to being a game changer.


I: Invite Inquiry

Inquiry is the process of intentionally challenging yourself and others to uncover deeply held biases, assumptions, and personal filters that color our collective experiences.


Inquiry is the consistent work of checking in with yourself and others. Inquiry embraces curiosity and creates the right conditions to remove limits, resist waiting for permission, and allow each of us to move into an emergent posture of test, do, and learn in order to think bigger, dream wider, and serve as activators and leaders in our communities. Finally, inquiry allows for the necessary space to examine the pre-conditions to consistency create authentic solidarity with each other and communities that are most impacted, and build robust networks working in an intersectional manner across diverse movements.


“I am deliberate and afraid of nothing.”-Audre Lorde


T: Transformation:

The process of creating a leaderful movement requires transformational processes that are incremental and long-term. It requires shifts that are reflected individually to structurally through exploring the “The I,” The We,” Our Work”, and “Our Walk.”

Transformation requires incremental processes that include transforming and shifting organizational/institutional culture to ground efforts in equity, authentic relationships, and trust to shift structures, policies, and practices.


Transformation requires understanding that addressing complex social change is a team sport that requires everyone. It extends invitations beyond our individual comfort zones to build authentic relationships, promote curiosity, and to heal damaged or broken relationships.

Transformation requires the shifting of physical spaces that create intentional invitations that are explicit about sharing and building power towards a collective strategy for change. How can we be explicit about the role, impact, and expectations of these spaces... what it is and what it isn’t?


Transformation requires activating voice and positioning teams to create narratives that are innovative and future focused to address complex situations. This can only take place after deeply exploring the why and rationale for moving to action. The development of shared language and frameworks allow for strategic implementation and strategy decision points along multiple levels for change.


See my article called Transformation Trauma, as a guide to support transformation without being paralyzed.


“Be Brave Enough to Start A Conversation That Matters”

We look forward to serving as a thought partner to help you accelerate and innovate complex social change with the organization you lead? Visit our website to learn more about Indigo Innovation Group and join our mailing list and/or set up a consultation.

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