Goals:

• Practice strategic questioning as a way to move from issues to possible solutions

• Understand the difference between "rock" questions and "water" questions

• Develop skills for asking questions that encourage deeper reflection

• Explore how thoughtful questioning can strengthen human connection

• Create a foundation for more effective dialogue across differences

Steps:

The first step is preparing workshop materials, including a slide deck or informational display about strategic questioning, strategic questioning handout (linked below) with the 11 question types, name tags, and evaluation survey (linked below). These materials form the foundation of the workshop experience.

Next, arrange a comfortable room setup that supports both full group discussion and small group activities. Ideally, the space should accommodate participants working in triads with enough distance between groups for private conversation.

Print a community agreements poster (linked below) that outlines ground rules such as active listening, using "I" statements, challenging ideas rather than people, and acknowledging assumptions. This establishes a brave space for practice.

Develop a facilitator script with timing for each segment of the 60-minute workshop: welcome (5 minutes), strategic questioning activity (50 minutes), and closing (5 minutes). Include key talking points and transition language.

Prepare reflection prompts and clear instructions for the practice sessions, where participants will work in triads to apply both first-level questions (focus, observation, analysis, feelings) and second-level questions (visioning, change, alternatives, etc.).

Test any digital materials. Have backup plans for technology failures to ensure smooth facilitation. This activity can be done without the use of any technology.

Take photos of the room setup and, with permission, of participant engagement to document the program and use in future promotion.

Promote the workshop as an opportunity to develop practical skills for more meaningful conversations, particularly with people who hold different perspectives. Emphasize the value of these skills in both personal and civic life. This workshop is a great sequel to the active skills listening workshop.

Create descriptive materials that explain strategic questioning in accessible language, highlighting its ability to move conversations from problems to possibilities. Avoid overly academic or technical terminology.

Target outreach to community groups interested in dialogue, conflict resolution, or civic engagement. These audiences may have immediate applications for the skills.

Encourage library staff to personally invite patrons who have expressed interest in community building, difficult conversations, or bridging divides.

Take photos during the workshop (with appropriate permissions) to use in future promotional materials and to document engagement.

The program requires attention to the following costs:

• Printing: $5-15 (handouts, name tags, evaluation forms)

• Markers and supplies: $5-10

• Refreshments (optional): $25-50

• Facilitator preparation time: 90 minutes

• Room setup and cleanup: 30 minutes each

Tips to cut costs:

• Consider digital handouts that participants can access on personal devices

• Skip refreshments or request donations

• Repurpose existing library supplies for activities

Arrive 30 minutes before the workshop to set up the room, arrange seating for small group discussions, and create a welcoming atmosphere. Consider playing soft background music as participants arrive.

Set up a name tag station with markers and prepare handouts at each seat or at a central distribution point. Display the community agreements poster prominently.

Test all technical equipment one final time.

Greet participants as they arrive, directing them to name tags and seating.

Take photos of the setup and, with permission, of the workshop in progress to document the program and use in future promotion.

Begin with a warm welcome and brief introductions (5 minutes). Facilitators should introduce themselves and ask participants to share their names and briefly what brought them to the session.

Review the session goals and ground rules (linked below), emphasizing that this is a practice space where participants can explore strategic questioning in a supportive environment.

Introduce the concept of strategic questioning using the handout (5 minutes). Explain the difference between "rock" questions (focused on hard truths) and "water" questions (which flow and find a way through differences). Review the 11 question types, from focus questions to personal action questions.

Guide participants through the reflective prompt (3 minutes): "Think of a recent challenging conversation. Write down what was said and your initial reaction."

Facilitate the strategic questioning practice (30 minutes) by having participants form triads. One person shares their challenge (2 minutes), others ask first-level questions (4 minutes), then second-level questions (4 minutes). Rotate roles and repeat for each participant.

Lead a debrief discussion (15 minutes) exploring how it felt to be both questioner and responder, what participants learned about their own thought processes, and how strategic questioning might support community dialogue.

Close the session with final reflections and next steps (5 minutes). Distribute and collect evaluation surveys and bookmarks to sign up for a One Small Step conversation (linked below), and invite participants to share one insight they're taking away from the workshop.

Document the session through photos (with permission) and collect evaluation forms to assess impact and refine future workshops.

Focus on practice over theory. While the conceptual framework is important, the real learning happens when participants actively engage in asking and answering strategic questions.

Create a brave space by acknowledging that this process can feel uncomfortable at first. Reassure participants that awkwardness is normal when trying new communication skills.

Emphasize that strategic questioning is not about manipulating conversations or leading someone to a predetermined conclusion. It's about genuine curiosity and openness to new understanding.

Be mindful of timing during the triad practice sessions. Provide clear time signals so all participants have equal opportunity to experience both asking and responding to questions.

Select facilitators who can model the questioning approach. Their ability to demonstrate strategic questioning in real time significantly enhances participant learning.

Consider the physical space carefully. Participants need enough privacy for honest conversation while still feeling part of the larger group experience.

Take photos throughout the workshop (with appropriate permissions) to document impact and create visual resources for future promotion.

Remind participants that these skills develop over time. Encourage participants to continue practicing strategic questioning in their daily conversations and consider offering follow-up sessions for deeper skill development.

Strategic questioning can be adapted as a self-guided station:

• Materials:

  • Strategic questioning handout with examples

  • Blank paper for reflection

  • Community Agreements handout (linked below)

  • Recorded introduction to the concepts

• Activity Flow:

  • Read introduction to strategic questioning concepts

  • Reflect on a recent challenging conversation

  • Practice formulating different levels of questions

  • Apply the questions in a future conversation

  • Return to journal to document outcomes

• Support:

  • Offer optional follow-up discussion

  • Include resources for further learning and bookmark to sign up for a One Small Step conversation (linked below)

• Connection:

  • Invite to future workshops

  • Suggest sharing insights with library staff

  • Take photos of self-guided materials to document usage (with appropriate permissions)