Ship It Conversations: Running Retros as Tabletop RPGs, With Jinger Meilani of Mountain on Chapters and Characters, Technical Archetypes, Reading the Room, Following Through, and Why Silliness Gets You Honest Answers
This is a guest conversation episode of Ship It Weekly, separate from the weekly news recaps. In this Ship It Conversations episode, I talk with Jinger Meilani about Tabletop Retro, her way of turning an engineering retrospective into a tabletop role-playing game, and why a little silliness gets teams to give honest answers. Jinger is a Senior Software Engineer in DevOps at Mountain. She says Tabletop Retro brings together three things she loves: world building, psychological safety on teams, and engineering enablement. We start with why she reinvented the retro at all. She was bored of them, and even the themed ones got rote. At a previous company, the team rotated who ran the retro, and her turn landed around Halloween, so she built a story around the team. She calls the result retro plus plus plus. The usual formats and outcomes are all still there, inside a story. A lot of it comes down to silliness. Jinger compares it to hiding vegetables in a fruit smoothie: it disarms people, and she gets honest answers, sometimes while everyone thinks they're talking about something else. That's also why she won't run one during a fire. People have to feel comfortable before they'll speak their truth, so the flame-breathing dragon can wait. Then we get into how one is built. A Tabletop Retro is a series of chapters, and each chapter holds part of the story and at least one activity. Players fill out character sheets, and each in-game race maps to a technical archetype, like a Goliath for a high-level systems thinker or a gnome for a tinkering automation engineer. Afterward the team talks through what those picks say about their strengths and weaknesses. She presents it like a storybook, in Lucidchart or Canva over Zoom. Characters cut both ways. For some people, an orc is permission to say what they'd never put on a retro board, because it's not really how they feel. They're just an orc. Others find role-play intimidating, so she reads the room: improv for an outgoing teammate, a line on screen for someone else, or no speaking part at all. If you want to try one, start with the questions, not the world. Where is the team unaligned? When does communication break down? Then keep the setting small. Kids trick-or-treating is plenty. The big takeaway: a Tabletop Retro is still a retro, and Jinger holds it to a higher bar. If everyone has fun and tells you something honest, and then nothing changes, it failed. Someone still has to do the work. Highlights • Why she calls it retro plus plus plus • Hiding vegetables in a fruit smoothie • Why you don't run one during a fire • Chapters, character sheets and technical archetypes • "I'm just an orc," and why role-play makes some people nervous • Reading the room: improv, on-screen lines, or no lines at all • Start with the questions, then keep the world small • Fun with no follow-through is a failed retro Links Tabletop Retro, Jinger's framework: https://tsn.io/wXdtL Jinger Meilani on LinkedIn: https://tsn.io/xn8Jr Jinger's IaCConf talk, Designing IaC Interfaces That Work for Humans, AI Agents, and Whatever Comes Next: https://tsn.io/5b4DM More episodes and show notes: https://tsn.io/NqkdP On Call Brief: https://tsn.io/Gpz2d LMGT Awards: https://tsn.io/lAERA
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