Stranger Things: The Upside Down Retrospective

Name the hidden problems and risks lurking in your sprint

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The Real World

What went well and kept us grounded this sprint?

Our daily standups were quick and focused, and we always knew where everyone stood.
The new deployment pipeline saved us hours and felt rock solid.
Great collaboration between design and dev meant no surprises at handoff.
The Upside Down

What problems dragged us down or felt darker than expected?

Unclear requirements left us guessing and reworking the same screens.
Flaky tests kept failing and ate up our debugging time.
Too many context switches made it hard to get into deep work.
The Demogorgons

What monsters, risks or threats are lurking ahead?

The upcoming dependency upgrade could break large parts of the app.
Key knowledge sits with only one person, a single point of failure.
Scope creep is starting to threaten our release deadline.
The Party's Arsenal

What tools, allies or actions will help us fight back?

Let's create a runbook so knowledge isn't trapped with one person.
We should add automated monitoring and alerts to the new service.
Bring the client into a mid-sprint sync to keep expectations aligned.

What is the Stranger Things: The Upside Down Retrospective

The Upside Down Retrospective borrows the two-world setup of the Netflix series Stranger Things. Your team looks at the sprint from both sides: the normal world where things worked, and the Upside Down, where problems quietly dragged everyone down. The board has four columns. The Real World is for wins and processes that ran smoothly. The Upside Down holds the blockers and frustrations that drained energy. The Demogorgons are the risks ahead, like a single point of failure or a release date under threat from scope creep. The Party's Arsenal is where you gather the tools, allies and actions to fight back, and it becomes your action list. Calling a risk a monster makes it easier to raise in front of the team, and the Demogorgons column means you talk about what could go wrong next, not only what already did. Run it around Halloween, after a chaotic sprint, or when the usual format has gone flat. In TeamRetro you can run it live or asynchronously, group similar ideas and vote on which monsters to tackle first.

Stranger Things: The Upside Down retrospective format

The Real World

What went well and kept us grounded this sprint?

This is Hawkins on a normal day: the things that worked as they should. Ask for wins, smooth processes and moments of success. Starting here puts people at ease before you head into the Upside Down.

The Upside Down

What problems dragged us down or felt darker than expected?

The Upside Down is where things went wrong. Ask for the blockers and frustrations that quietly drained energy. The theme makes it easier to name a problem without blaming anyone, so treat each one as something to understand and beat.

The Demogorgons

What monsters, risks or threats are lurking ahead?

Demogorgons are the dangers that could strike if nobody deals with them. Ask the team for emerging risks and warning signs. Naming them now gives you time to prepare.

The Party's Arsenal

What tools, allies or actions will help us fight back?

Like the kids pulling together weapons, friends and a plan, this column is about fixes and support. Ask for actions, resources and people who can help with the problems and risks above, then give each action an owner.

When to use this retrospective

  • Around Halloween, or whenever you want a themed change from your regular sprint retrospective.
  • After a tough or chaotic sprint, when problems feel hard to raise. The playful frame lowers the stakes.
  • When energy is low and you want a format that gets more people adding notes.
  • With newer or quieter team members, who may find it easier to raise risks and blockers as monsters.

Suggested icebreaker questions

  • If you could have one Stranger Things character on your team this sprint, who would it be and why?
  • What's one 'monster' (work or otherwise) you defeated recently that you're proud of?

Want a warm-up your team plays, not just answers out loud? Browse free icebreakers →

Ideas and tips for your retrospective meeting

  • Open with a quick intro to the four areas (the Real World, the Upside Down, the Demogorgons and the Party's Arsenal) so everyone knows where each note goes.
  • Keep the theme light but take every concern seriously. A monster label shouldn't make a real risk sound trivial.
  • Vote on which Demogorgons and Upside Down problems to tackle first.
  • Close by turning the Party's Arsenal ideas into actions, each with an owner and a due date.
  • Timebox brainstorming and invite quieter members to share their monsters and wins.
  • Use a themed video background or some synth music as people arrive to set the mood.

Frequently asked questions

What is the Stranger Things: The Upside Down Retrospective?
It's a themed retrospective based on the Netflix series. Your team celebrates wins (The Real World), surfaces problems (The Upside Down), names risks ahead (The Demogorgons) and plans fixes (The Party's Arsenal).
When should I use this themed retrospective?
Use it around Halloween, after a difficult sprint, or any time your team needs a change from its usual format.
How long does it take to run?
Plan for 45 to 60 minutes, depending on team size. That covers brainstorming in each column, grouping and voting, and agreeing on actions.
Does the theme make it harder to address serious issues?
Usually the opposite. Calling a problem a monster lowers the stakes, so people raise risks they might otherwise keep to themselves. Keep the discussion itself serious.
How is it different from a standard sprint retrospective?
It covers the same ground as Start Stop Continue or What Went Well, and adds a column for risks ahead (The Demogorgons). Most standard formats only look back.
Can I run this retrospective remotely in TeamRetro?
Yes. Run it live or asynchronously: team members add ideas to each column, then you group, vote and turn the top items into tracked actions.

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