By The Intrepid in Tutelary — 22 Apr 2025

How to Turn Your Retro into a TTRPG One-Shot

Where the d20 meets the Kanban board.

How to Turn Your Retro into a TTRPG One-Shot

Okay, you’re sold on the idea—or at least curious enough to try it. But how do you go from sticky notes to slaying the Bugbear of the Broken Build? It’s simpler than you think, and you don’t need to be a Dungeon Master or a Jira wizard to make it work. Here’s what it takes to transform your next retrospective into a 45-minute quest that’s equal parts reflection, laughter, and team glue.

What You’ll Need

A Lightweight Ruleset: Grab a one-page TTRPG system like Lasers & Feelings or Honey Heist (free online, just search “one-page RPG”). These are built for quick, narrative fun—no 400-page manuals here. Think simple: roll a die, succeed or fail, tell a story.
Character Prompts: Write 4-8 archetypes based on your team. The Code Conjurer (Dev), The Backlog Bard (PM), The Bugbane Seer (QA), The Stakeholder Specter (Client). Bonus points: let players pick someone else’s role to spark empathy.
Your Sprint’s Story: Skim your Jira tickets, Slack threads, or incident logs. That 5XX outage? It’s now The Great Server Wraith. Late scope change? The Oracle’s Trickery. Pick 2-3 moments to weave in.
A Facilitator: One person to narrate, nudge, and keep things moving. No experience needed—just a knack for improv and a willingness to say, “Roll for debugging!”
Dice (or Not): Got d6s? Great. No dice? Use a random number app (free on any phone).
Courage to Be Weird: Your team needs to lean into the silliness for an hour. Pitch it as a low-stakes experiment: “Let’s try something nuts.”

How It Plays Out

Setup (5-10 Minutes)
The facilitator sets the scene: “You’re in the CI/CD Citadel, hunting the fabled Production Relic. The pipelines hum, but danger lurks…” Hand out character sheets (just a name, a strength, a flaw). Players pick roles—ideally not their own. Example: Your grumpy SRE plays The Ticket Trickster (Designer), while the PM becomes The Merge Marauder (Dev).
Pro tip: Keep it snappy. No one needs a backstory longer than “I hate flaky tests.”
The Quest (25-30 Minutes)
Run 2-3 “encounters” tied to your sprint. Each is a mini-story:
- Encounter 1: The Bug Beast (e.g., a test failure). The team rolls to slay it. Success? They gain Code Confidence. Fail? They’re Stressed (-1 to focus).
- Encounter 2: The Shifting Scope (e.g., a late requirement). The Backlog Bard tries to charm the Client Wraith, but the dice betray them. Now everyone’s navigating Feature Fog.
- Encounter 3: The Final Push (e.g., the deploy). Everyone rolls together to seal the Production Relic. Win or lose, it’s a shared tale.
  The facilitator weaves in your sprint’s specifics: a Slack outage becomes The Great Silence, a clutch fix is The Hero’s Patch. Encourage theatrics—let the QA Oracle gloat when they spot a hidden trap.
Debrief (5-10 Minutes)
End with a “loot” phase. Each player names one thing their character learned or gained: The Amulet of Early PRs, The Scroll of Clearer Specs. Then, drop the roleplay for a quick chat:
- What did playing another role show you?
- What sprint moment felt truer in the story?
- What “artifact” are we bringing to the next sprint?
  This is where the magic happens—when someone says, “I didn’t get how much that bug stressed you out.”

Tips to Avoid a TPK (Total Party Kerfuffle)

Skeptics on Board: Got an eye-roller? Start small—one encounter, 20 minutes. Frame it as a “quick test” to win them over.
Keep It Light: Satire’s great, but don’t roast anyone. Punch up at the process (The Curse of Unscoped Tickets), not people.
Stay on Track: Cap it at 45 minutes. If the Bugbear fight drags, skip to the deploy.
Make It Yours: Sprinkle team memes or tools. A Kubernetes crash? It’s The Pod Plague. A Slack thread gone wild? The Channel Chimera.

Why It’s Worth the Roll

This isn’t just a game—it’s a mirror. When your quiet designer plays the PM and groans at a scope pivot, they get it. When the team laughs about The Night of the Null Pointer, that outage stings less. And when you turn a sprint’s chaos into a story—with dice, drama, and a dash of courage—you’re not just reviewing. You’re building lore.

That flaky pipeline isn’t just a ticket anymore—it’s The Hydra of Unmocked APIs. That crunch-time win? The Dawn of the Merged PR. Your team walks away with more than action items. They carry a shared myth—one that teaches, connects, and maybe even heals.

Your First Quest

Try it. Next retro, pitch a 30-minute “Sprint Saga.” Pick one moment—like a gnarly bug or a heroic deploy—and turn it into a scene: “You face the Gremlin of the 404 Void!” Hand out roles, roll some dice, and let the story unfold. Worst case? You giggle and move on. Best case? Your team’s next sprint starts with a legend—and a little more heart.

What’s one sprint story you’d slay in your retro? Roll for initiative, and let’s make it epic.

Afterword: Enlisting the LLM Owlbear

Lurking in the corner of this quest is a mythic ally: the large language model. Picture an Owlbear of Infinite Tales—claws sharp with code, feathers woven from data. Feed it your one-page ruleset and a CSV of your sprint’s stories (Jira tickets, incident logs, that frantic Slack thread), and it can spin a bespoke scenario faster than you can say “critical failure.”

Try this: Hand it a Lasers & Feelings SRD and your sprint’s chaos—say, a botched OAuth bug and a last-minute feature pivot. Ask it to craft a one-shot with cyberpunk flair, four team archetypes, and three encounters tied to real pain points. You might get The Neon Grid Gauntlet, where the Glitchbane Coder battles the Token Wraith and the Vision Weaver wrestles a Scope Hydra. It’s a head start, turning dry data into narrative gold.

Here's an example prompt:

Using the [SRD name] ruleset (attached) and the sprint stories (attached CSV/JSON), generate a 45-minute TTRPG one-shot scenario for a team retrospective.
- Create 4-6 character archetypes based on team roles (e.g., Dev, PM, QA).
- Turn sprint events into narrative beats (e.g., a bug becomes a “Chaos Gremlin”).
- Include 2-3 encounters tied to real incidents, with stakes (e.g., “Save the deploy”).
- Keep it collaborative, lighthearted, and empathy-focused.
- Output: A scenario with a setting, characters, encounters, and resolution prompts.

But beware—this Owlbear’s powerful, not perfect. It might churn out generic dragons if your prompt’s too vague, or miss the sarcasm your team thrives on. Tell it your vibe: “We’re snarky DevOps folks who meme about Kubernetes.” Review its output, too—tweak that Bug Beast to mention your flaky CI pipeline, or soften a jab at the PM’s late specs. The LLM builds the map; you sprinkle the soul.

With this ally, your retro becomes less prep, more play. Yet the real magic stays human: the laughter, the “oh, that’s how you felt,” the myth you forge together. So, summon the Owlbear if you dare—but wield its tales with care, and never let it outshine the team rolling the dice.