About the Course

Navigating Difficult Conversations Masterclass is an asynchronous learning experience, adapting our Facilitating Difficult Conversations workshop series into a flexible online format. This course is created to support you as a rabbi or Jewish spiritual leader navigating conflict and complexity in your community. You’ll engage a series of concise video teachings led by experienced mediator and facilitator Cara Raich, offering practical frameworks, language, and tools for approaching hard conversations with greater confidence, clarity, and care.  At the end of the course, you’re invited to continue the learning by signing up for a live skills session with Cara and exploring the take-home resources, including a PDF of key strategies from the course and text sheets for Torah study.

Comprehensive Video Lessons

Learn the skills needed to navigate difficult conversations with care.

Interactive Learning Materials

Access slides and worksheets for in-depth understanding and practical application.

Engagement and Collaboration

Participate in a live session after the course to ask questions and practice the skills in real time.

Meet Your Instructor

Cara Raich is a New York–based conflict consultant and former attorney who helps leaders and communities navigate tough conversations with clarity and care. She has guided institutions, organizations, and families through conflict, crisis, and change—bringing order to chaos and clarity to confusion. A “how” expert, Cara specializes in mediation, facilitation, and conflict resolution, equipping others to move through tension toward productive action.

Cost

Thanks to the generous support of the Hayom Fund, participation in this initiative is free of charge. If you have professional development funds available and would like to support the ongoing production and offering of this experience, we warmly invite you to contribute in an amount that feels right to you (up to $18) using the link included in your registration email. Your contribution helps us continue creating meaningful opportunities for everyone.

Course Curriculum

7 Chapters · 18 Lessons

  1. 1

    Welcome to the series

    1. (Included in full purchase)

      Course Overview

    2. (Included in full purchase)

      An Introduction from Cara Raich

  2. 2

    Introduction to Difficult Conversations

    1. (Included in full purchase)

      Building the Container for Difficult Conversations

    2. (Included in full purchase)

      Cara's Favorite Shared Agreements

  3. 3

    Transforming Conflict

    1. (Included in full purchase)

      Redefining Conflict in Community Work

    2. (Included in full purchase)

      The Recipe for Transformative Dialogue

  4. 4

    Stabilizing Moves that Leaders Can Make

    1. (Included in full purchase)

      Your Role as Rabbi in Difficult Conversations

    2. (Included in full purchase)

      Mediation and Mediator Definition

  5. 5

    Why We Get Stuck

    1. (Included in full purchase)

      Conflict Traps

    2. (Included in full purchase)

      Slides: Conflict Traps

  6. 6

    Getting Ourselves Unstuck

    1. (Included in full purchase)

      Conflict Remedies

    2. (Included in full purchase)

      Slides: Conflict Remedies

    3. (Included in full purchase)

      Listening Through Looping

  7. 7

    Conclusion

    1. (Included in full purchase)

      Staying in Community When We Disagree about Things That Matter

    2. (Included in full purchase)

      Take-Home Resources

    3. (Included in full purchase)

      Sign Up for Live Sessions

    4. (Included in full purchase)

      Thank You!

    5. (Included in full purchase)

      Share your Feedback

Ready to Master Difficult Conversations?

Sign up now to gain valuable skills for navigating tough conversations with confidence. Help your community stay connected across difference!

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