Tips for Facilitating Challenging Conversations

This resource provides practical tools to help educators facilitate challenging conversations with learners. These tips can support the implementation of the principles outlined here.

The ability to engage in challenging conversations has universal utility, but the same conversation looks different depending on its context (time, space, and audience). Consider the particulars of your setting and which practices will be most effective.



Start and end discussions with questions like “What does X mean to you?”;  “What is your experience with X?”; “How do you now understand X?; and “What new questions about X have emerged for you?”

Use these questions to present relevant, foundational terms and ideas (i.e. war, democracy, freedom, etc.) and see how learners relate to and understand them. At the beginning of a conversation, this can help educators understand “where the learners are at” and tailor what follows to feel accessible and natural. Ideally, this can empower learners to summarize their takeaways and continue to raise questions beyond the formal setting of the conversation.

(from Words Matter: Ceasefire resource)

Rather than diving directly into the current debate over a ceasefire in the Israel-Hamas war or the legalistic and common-use meanings of the term ceasefire, try to begin the discussion by opening space for learners to unpack their understandings of and experiences with the essential terms. Consider questions such as:

– When you hear the word “ceasefire,” what comes to mind?

– What are the goals of a ceasefire? What are the reasons a group might agree to, or oppose, a ceasefire?

– In what ways have you heard the word “ceasefire” used in regards to the Israel-Hamas war?

By posing these introductory questions, educators can gain insights about what interests the learners, what may be emotionally difficult for them, what they have heard or been told, and what they already know. This information can help shape the conversation that follows.


– Encourage learners to define and critically analyze commonly used words. Guide them to assess legal, historical, political, and common-use meanings of these words; help people explore what different individuals mean when they use the same word.

– Strive to maintain space for legitimate criticism. Even as you facilitate explorations of how certain words are overused and/or inaccurately used, make clear that critical thinking and thoughtful criticism of specific policies, actions, or ideas are welcome. Educators might ask learners to restate an argument that they believe misuses a word or phrase.


After engaging with an article, video, or image, ask learners to consider what the subject is explicitly or implicitly asking or what question they are responding to (rather than what they are saying).

(from Words Matter: Ceasefire resource)

Depending on the forum and speaker, calls for a ceasefire take on very different connotations. The discussion prompts below will guide learners in exploring how the context of calls for ceasefire—their who, when, where, and how—shapes their connotations and how these calls are received.

Present learners with the following statements:

– “Ceasefire now! From the River to the Sea, Palestine will be free. Israel must stop the genocide in Gaza.”

– “Ceasefire now! Bring the hostages home now. We can’t wait any longer.”

Questions to consider:

– What does each statement emphasize?

– What is “missing” from each statement?

– Are both statements calling for the same thing?

Next, show learners these video clips. Feel free to use other videos that feel more timely or appropriate for your setting.

Pro-Palestine Ceasefire March in Washington

Pope Francis (0:00-1:40)

Tel Aviv Rally (0:00-1:23)

After each clip, ask learners:

– Who is calling for a ceasefire?

– Where are they calling for a ceasefire?

– How are they calling for a ceasefire?

– Why are they calling for a ceasefire?

– What do you understand each to mean when they call for a ceasefire?


– Make room for processing, either through pre-planned “open forums” to discuss thoughts, feelings, experiences, and reflections or through questions before, during, and after conversations that allow learners to express their reactions, emotions, and concerns.

– Introduce learners to Israelis—either through in-person and virtual interactions or through multimedia sources—so they can hear and engage with authentic Israeli voices and experiences. What other kinds of voices might enhance the conversation? Palestinians? Arabs from around the Mideast? Americans?

Note for educator: Be aware of the choices you make in selecting the voices you bring to your setting.

– Especially in highly sensitive and emotional moments, making space for learners to process and unpack what they are feeling, thinking, hearing, and confused about is important. Hindering authentic expression can impede healthy and productive education.


– Explore with learners how people prioritize their values differently (even if they share similar or identical values). For an example activity, see: Values in Tension.

– Empower learners to ask and respond to questions that feel relevant. Encourage them to elevate their thinking by considering the larger implications, meanings, or questions underlying any timely discussion.

(from Social Media in This Moment resource)

– In processing learners’ experiences with social media since October 7, educators might pair the following timely and timeless questions:

– How have you used social media since October 7? Does your usage now differ from before October 7?

– When are other times that your usage of social media has changed? Is there a pattern connecting these moments?

– Can you recall a post that was frustrating? Why was it frustrating? Can you recall a post that was uplifting? Why was it uplifting?

– Why do you think social media elicits such strong emotional responses?

– Has social media made your life easier or harder since October 7?

– Can you think of ways that social media can be dangerous? Can you think of ways that it might be important?

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