Bridge divides with courage and compassion.
In a time of rapid change and social reckoning, Courageous Conversations offers a framework for extending across lines of difference, building trust, and leaning into the tension of honest disagreement. Rather than beginning with issues, opinions, facts, or figures, this tool starts with learning — about ourselves and our conversation partners. Participants reflect on the values that motivate them, the lived experiences that shape their views, and the “shoulders upon which they stand.” From this foundation, dialogue can unfold with courage and compassion, moving us toward shared understanding and a more just world.

What’s included

• Deck of image cards for reflection and discussion.
• “How It Works”, “Take Action” and “The Invitation” instructions included to guide individuals or groups in using the tool effectively.
• Cards can be selected and sorted to identify the legacy that resonates most.
• High-quality, recycled materials, printed in the U.S.
• Facilitates individual reflection, small group exercises, or large group discussions.
  
  

How it works

• Structured exercises guide participants to clarify their values and share personal experiences.
• Encourages a deeper understanding of one another before approaching difficult topics.
• Builds the skills needed to listen actively, hold tension, and find common ground.

Who it’s for
Leaders, facilitators, advisors, and groups seeking ways to:

• Navigate disagreement constructively.
• Strengthen leadership capacity for inclusion and dialogue.
• Engage families, teams, or communities in meaningful conversations about difference.

Use it in practice

• Ideal for one-on-one sessions, family conversations, organizational retreats, or community forums.
• Complements leadership development, DEI initiatives, and philanthropic advising.
• Featured in the Courageous Conversations in Leadership Training, co-led by 21/64 with Simon Greer and Tina Grace, bringing decades of experience in social justice, convening, and lived experience to the program.

Pairs well with

• Motivational Values
• Generational Styles
• Money Messages

See it in action
Experience this tool firsthand in Courageous Conversations in Leadership, a training co-led by Simon Greer and Tina Grace in collaboration with 21/64. Together we create safe space, build active listening skills, and catalyze courageous dialogue across difference.

About the Collaborator
Simon Greer has been a social change entrepreneur for more than 25 years. His Courageous Conversations project in partnership with The Nantucket Project and collaborations on American Neighbor (2020), For The Common Good (2019), and Opening of the American Mind (2022) helped inspire this toolkit. Simon is the founder of Cambridge Heath Ventures, Bridging the Gap, Face to Face, and Courageous Conversations.

Click here to download the Courageous Conversations Booklet (booklet included with the tool).