Monday Kickstarter October 12, 2020

Oct 12, 2020
Turn stressful interactions and challenges into conversations worth having in our free Monday Kickstarter events.

Monday Kickstarters is a working session designed for everyone on the call to figure out how to have conversations worth having when faced with a tough situation or problem. The process is based upon the book, Conversations Worth Having. The way it works:

  1. Anyone with an issue, challenge, or negative situation types it in the chat box.
  2. We choose one issue at a time; the person who posted the issue is in the “driver’s seat.”
  3. Everyone on the call offers the flip: the positive opposite of the issue.  The “driver” chooses the flip that most reflects what they see as the positive opposite.
  4. Everyone on the call then offers a suggestion for a positive frame: the desired outcome if the flip were true. The “driver” chooses the frame that best fits their desired outcome.
  5. Then everyone offers generative questions, posting them to a whiteboard. These are questions to engage stakeholders in a conversation that will move them towards the desired outcome.

You can listen live on the Conversations Worth Having YouTube Channel.

Here are the topics brought forward by our guests, the positive frame (desired outcome) for the conversation, and generative questions that were developed during Monday Kickstarter!


The challenge: The staff is feeling high level of fear and anxiety about returning to face-to-face full classrooms in November.

The flip: The staff feels safe and confident to return to school.

The frame:

  • Staff are open-minded to return to school.
  • Teachers and students are healthy and thriving when we return to school.
  • There are new approaches to stay safe and confident.
  • We have implemented everything we need to feel safe and confident.
  • Staff collaborate on the best ways to return for safe and healthy work/teaching environment (and are supportive).
  • The school is taking all necessary measures to keep staff and students safe.
  • Choice: Teachers and students are living in a healthy and thriving environment for learning.


The challenge: The supervisor is uncomfortable with the direction of library renovation plans.

Flip it: The supervisor is comfortable with the direction of library renovation plans.

Frame it:

  • Project completion on time.
  • The supervisor is comfortable and inspires other staff in embracing the renovation.
  • The new layout of library will meet the multi-faceted needs of all departments.
  • Our renovation boosts our morale and helps us thrive.
  • Supervisor and department are open to change and new ways to do work through renovation process.
  • Renovation provides an opportunity for departments to refocus and enhance their work.
  • Choice: The updated library will better serve the greater community (students/faculty/others).


The challenge: Administrators are unwilling to address racism and bias in our school.

Flip it: Administrators are will to address racism and bias in our school.

Frame it: Addressing racism and bias makes the whole school better.

Insight:  With more time to reflect on this, asking a few generative questions might help to make the frame for the conversation better.  For example, What are some of the key goals (or responsibilities) your administrator must meet? The answer might suggest that achieving one or more of them might be supported by addressing racism and bias. Then the frame for the conversation would be in the context of what the administration is already trying to do.  For example, if student success is a goal, a frame might be: Raising overall student success by addressing racism and bias.  If adjusting curricula for today’s social and economic climate is a goal, a frame might be: Addressing racism and bias to support relevant curricula changes. Each of these would inspire different kinds of generative questions.


To view past Monday Kickstarter sessions, please visit our  Conversations Worth Having YouTube Channel.

To learn more about fostering conversations worth having, visit the website and download your conversation toolkit, read or listen to Conversations Worth Having: Using Appreciative Inquiry to Fuel Productive and Meaningful Engagement, and sign up for a Conversation Bootcamp.


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