Gratitude Retreats

Gratitude Storytelling Prompt Sheet

30 structured prompts to help participants surface and tell meaningful gratitude stories. Ideal for retreats, closing ceremonies, and team gatherings.

How to Use This Sheet

Choose two or three prompts that resonate with your context. Give participants 5–8 minutes of quiet reflection before sharing. Encourage stories over statements — the goal is a narrative with context, not just a name and a thank-you.


Prompts: People Who Shaped Your Path

  1. Think of someone who believed in you before you believed in yourself. What did they do specifically that showed it?

  2. Recall a time when someone gave you feedback that stung at first but ultimately changed how you work or lead. Who was it, and what did they say?

  3. Who taught you something about your own strengths that you hadn’t seen clearly? What did they notice, and how did they name it?

  4. Think of a colleague who showed up for you during a genuinely hard period at work. What did they do that made a difference?

  5. Recall a mentor — formal or informal — whose influence you still carry. What specific lesson or moment do you return to?

  6. Who in your professional life modeled integrity in a way that raised your own standard? What did you witness?


Prompts: Moments of Unexpected Grace

  1. Describe a moment when a difficult conversation turned into something meaningful. What shifted, and who helped shift it?

  2. Think of a time when someone extended trust to you before you’d fully earned it. What did they do, and what did it open up?

  3. Recall a project that failed but produced something you’re still grateful for. What was it, and who was alongside you?

  4. Describe a meeting, workshop, or conversation that changed how you think about your work. Who facilitated it, and what happened?

  5. Think of a time someone advocated for you publicly — in a room where it counted. What did they say, and what did it mean?

  6. Recall a moment when a stranger or near-stranger showed unexpected generosity. What did they do?


Prompts: This Team, This Season

  1. What’s the most meaningful contribution a teammate made to our shared work this quarter or year? Be specific about what they did.

  2. Describe a moment when the team was under pressure and someone’s behavior raised the collective standard. What did they do?

  3. What’s a “small” thing a colleague does consistently that has a larger impact than they probably know?

  4. Think of a time someone on this team handled conflict or difficulty in a way you deeply respected. What did you observe?

  5. Who on this team brings something to the culture that would be hard to name but immediately missed? What is it?

  6. Describe a moment when this team’s values showed up in action — not just as words on a wall. What happened?


Prompts: The Work Itself

  1. What’s a project or initiative that you’re proud to have been part of? What made it worth doing?

  2. Think of a problem you struggled with for a long time. Who or what finally helped you see it differently?

  3. Recall a moment when creative work landed exactly right — when an idea became real and it worked. Who helped make that happen?

  4. What’s a risk you took that was supported by someone’s confidence or encouragement? Who encouraged it?

  5. Think of feedback from a client, customer, or stakeholder that genuinely moved you. What did they say?


Prompts: Deeper Reflection

  1. What experience in your professional life are you most grateful for, in retrospect — even if it didn’t feel that way at the time?

  2. If you could send a letter to your younger professional self, what would you want to thank your early colleagues for teaching you?

  3. What aspect of this organization — its culture, its values, its people — are you most grateful to have found?

  4. If this team disbanded tomorrow, what would you carry forward? Who gave that to you?

  5. What has doing this work taught you about yourself that you’re grateful to know?

  6. What’s something you almost left — a job, a relationship, a path — that you’re now grateful you stayed with? Who or what kept you?

  7. If you could publicly acknowledge one contribution that has never been properly named, what would it be?


Facilitation Tip: The Story Arc

Encourage participants to structure their stories using this arc:

  • Context: What was the situation? What was at stake or uncertain?
  • The contribution: What specifically did this person do or say?
  • The impact: What did it make possible? What changed?

Three sentences minimum. The details are what make gratitude land.

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