Facilitating Challenging Conversations

Since October 7, 2023, Israel educators have been organizing and making space for challenging conversations. This resource provides practical examples, tips, and processes for supporting educators as they prepare for and facilitate challenging conversations.

It offers a guiding framework that supports educators in creating processes and conversations that feel natural and are your own. It is not intended to be a step-by-step script. 

While this guide was created with Israel-related topics in mind, the processes, principles, and tips apply to any challenging or charged topic.

1. Begin by identifying questions relating to a specific topic with which you want your learners to engage. Include a mix of content-based questions and critical thinking questions.

2. Consider what background information is needed for learners to be able to engage meaningfully and knowledgeably in the conversation.

Formulate a list of context and background pieces; it may be most productive to compile such a list in terms of questions (to create an FAQ of sorts, for example an FAQ on the subject of hostages).

3. Brainstorm and plan how you envision the discussion progressing. We’ve assembled a series of guiding principles here, as well as practical tips here.

a. Begin with the audience

b. Ask questions

c. Encourage critical thinking in place of overused or inaccurately used phrases

d. Create space for authentic voices

e. This can be achieved by bringing guests who share their stories, as well as by reading, watching, or listening to resources that spotlight people with a range of perspectives. Be aware of the choices you make in selecting the voices you bring to your setting.

f. Elevate timely conversation with timeless thinking.

g. While challenging conversations may be rooted in current events or controversies, it’s important to help people understand the big picture and context that frames the issues.

h. Remind learners that their relationships with each other can enrich difficult conversations and make them more fulfilling

4. Begin formulating the main discussion prompt/s. Include a combination of multimedia resources (news articles, images, videos, podcasts, etc.) in order to engage learners and maintain their interest. Enrich multimedia resources with probing questions that encourage reflection.

The resources you curate should reinforce the value of making space for multiple perspectives. They should shed light on a variety of experiences and opinions, including those that may invite respectful disagreement. This may include opposing political opinions, different forms of cultural expression, and contrasting ideologies.

5. You may want to formulate the introductory and concluding questions/discussions after you’ve planned the body of the activity. These introductory and concluding questions typically flow from the other discussion prompts.

6. Once a full rough draft is completed, it may be helpful to circulate the activity among colleagues for feedback. Educators are also welcome to schedule a consultation with an iCenter educator.

Best practices for facilitating challenging conversations:

Set group norms

If people know each other, remind them of the shared values and relationships already built. Acknowledge how these existing ties can shape the conversation.

If people are meeting each other for the first time, take a few minutes to establish values that will enable the group to maintain respectful and thoughtful dialogue.

Structure time

Think about how to structure the group’s time. If time is limited or educators sense that it is important to provide space exclusively for conversation and processing, a group discussion alone may suffice. Otherwise, educators might incorporate content learning and research into the session. Examples include:

1. Watch a video or read an article and pose hard questions around it.

2. Divide the group into smaller groups and ask them to research a specific topic or perspective; then, return to the large group and share multiple perspectives.

Encourage more than a few people to share

Conversations can become stale, one-sided, or inflammatory if they are limited in perspectives and participation. Some examples to encourage wider participation and buy-in include:

1. Give a journaling prompt before opening the conversation

2. Put people into pairs for the first round of discussion and progress toward larger group sharing. Consider asking people to share something they heard from their partner, rather than sharing their own thoughts

a. Direct questions toward learners’ experiences with the materials

b. Use “raise a hand if…” prompts to make participation less daunting

c. Get comfortable with uncomfortable silence, allow 30 seconds to pass without anyone sharing

De-escalate or re-direct when a conversation deteriorates

Depending on why or how the conversation is deteriorating (becoming too emotional, going off topic, becoming an echo chamber), practices for de-escalation or re-direction include:

1. Taking a break

2. Asking learners to use “I” statements

3. Asking learners to relate to the sources and material discussed when commenting

4. Shifting the dynamic by introducing a new discussion prompt

5. Using learner’s comment as a means to transition the conversation to a new place

Decide when to wrap up a conversation

Once learners begin to say the same thing or repeat themselves, or the conversation stalls in another way, it’s time to wrap up and leave time for reflection. Allowing a conversation to run long can detract from its impact (sometimes, short and sweet is best).

Occasionally, an otherwise ordinary moment can become challenging when someone offers an unexpected question or comment. Educators can respond in multiple ways:

1. Make space for initial thoughts and sharing of experiences and emotions.

2. Acknowledge the importance of the question or conversation and promise to make space another time to address it more fully.

3. Encourage learners to spend a few minutes researching the topic, reflecting on it on their own, and then returning to the large group for a discussion.


Challenging conversations are not limited to any particular setting or time; educators should strive to prepare learners to engage in these dialogues as a normal part of life. The principles detailed here are intended to support educators in facilitating challenging conversations and exposing learners to meaningful ways to engage with uncomfortable or controversial topics.

View the Guiding Principles for Challenging Conversations Resource

This resource provides practical tools to help educators facilitate challenging conversations with learners.

View the Tips and Examples for Facilitating Challenging Conversations Resource

תחנות יסוד קשורות בתחום החינוך לישראל

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