Stranger Things: The Upside Down Retrospective

A fun, themed retro to surface hidden issues and wins

Use this template in TeamRetro

The Real World

What went well and kept us grounded this sprint?

Our daily standups were quick and focused — 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

Step into the parallel world of your sprint with the Stranger Things: The Upside Down Retrospective — a playfully themed format inspired by the hit Netflix series. Just as the residents of Hawkins navigate between the everyday world and the eerie Upside Down, your team will explore both the bright, successful side of your work ("The Real World") and the lurking dangers, blockers, and hidden problems that pull you down ("The Upside Down"). This themed approach lowers the emotional barrier to discussing difficult topics, making it easier for teams to name the "Demogorgons" — the threats and risks they might otherwise avoid raising. The retrospective works by guiding your team through four themed quadrants: celebrating what went well, confronting the problems dragging you down, identifying the monsters and risks on the horizon, and arming yourselves with the tools and allies needed to fight back. Each topic invites honest reflection wrapped in a familiar, engaging narrative that keeps energy high and participation strong. By framing challenges as monsters to defeat rather than failures to dwell on, teams build psychological safety and a shared sense of mission. Perfect for teams looking to break the routine of standard sprint retrospectives, this pop-culture format is especially effective around Halloween, after a tough sprint, or whenever you want to inject some fun while still driving meaningful improvement. In TeamRetro, you can run it asynchronously or live, group similar ideas, vote on the biggest monsters to tackle, and turn insights into actionable next steps — all while having a great time exploring the Upside Down together.

Stranger Things: The Upside Down retrospective format

The Real World

What went well and kept us grounded this sprint?

This topic represents Hawkins in the normal world — the bright, positive side where things are working as they should. Encourage participants to celebrate wins, smooth processes, and moments of success. Setting a positive tone first helps build the psychological safety needed before venturing into the Upside Down.

The Upside Down

What problems dragged us down or felt darker than expected?

The Upside Down is the shadowy mirror world where things go wrong. Use this topic to surface blockers, frustrations, and issues that quietly drained energy. The theme makes it easier to name problems without blame — frame them as dark forces to be understood and overcome.

The Demogorgons

What monsters, risks or threats are lurking ahead?

Demogorgons are the dangers that could strike if left unchecked. Ask the team to identify emerging risks, looming threats, and warning signs on the horizon. Naming these monsters early gives the team a chance to prepare and defend before they attack.

The Party's Arsenal

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

Just as the kids gather weapons, friends, and plans to battle the monsters, this topic focuses on solutions and support. Encourage actionable ideas, resources, and allies the team can rally to defeat the problems and risks identified. Turn these into concrete next steps and owners.

When to use this retrospective

  • Around Halloween or whenever you want to add a fun, themed twist to your regular sprint retrospective.
  • After a particularly tough or chaotic sprint where naming problems feels emotionally charged — the playful framing makes hard topics easier to raise.
  • When team energy is low and you want a creative format to boost engagement and participation.
  • To help newer or quieter team members open up by lowering the seriousness of discussing risks and blockers.

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?

Ideas and tips for your retrospective meeting

  • Set the scene with a quick intro to the theme so everyone understands the metaphor — the Real World, the Upside Down, the Demogorgons, and the Party's Arsenal.
  • Keep the fun light but the insights real — make sure themed language doesn't trivialise genuine concerns or dismiss serious risks.
  • Use voting to prioritise which Demogorgons (risks) and Upside Down problems to tackle first, so you focus on what matters most.
  • Always close by converting the Party's Arsenal ideas into clear, owned action items with due dates.
  • Encourage equal participation by timeboxing brainstorming and inviting quieter members to share their monsters and wins.
  • Consider a themed background or playing the Stranger Things soundtrack to set the mood for an in-person or video session.

Frequently asked questions

What is the Stranger Things: The Upside Down Retrospective?
It's a fun, themed retrospective inspired by the Netflix series that guides teams through celebrating wins (The Real World), surfacing problems (The Upside Down), identifying risks (The Demogorgons), and planning solutions (The Party's Arsenal).
When should I use this themed retrospective?
It's ideal around Halloween, after a difficult sprint, or any time you want to boost engagement with a creative format while still driving meaningful improvement.
How long does it take to run?
A typical session runs 45 to 60 minutes depending on team size, with time for brainstorming each quadrant, grouping and voting on ideas, and agreeing on action items.
Does the theme make it harder to address serious issues?
No — when facilitated well, the playful framing actually lowers barriers and makes it easier for people to raise difficult problems and risks they might otherwise avoid.
How is it different from a standard sprint retrospective?
It covers the same goals as a classic Start/Stop/Continue or What Went Well retro but adds a forward-looking risk quadrant (The Demogorgons) and a fun narrative that increases participation and energy.
Can I run this retrospective remotely in TeamRetro?
Yes — you can run it live or asynchronously in TeamRetro, with team members adding ideas to each themed quadrant, then grouping, voting, and converting insights into tracked actions.

New to retrospectives? Read our guide on how to run a retrospective →

Related templates

WWE Smackdown Showdown Retrospective

Tag-team your sprint reflections with wrestling-themed flair.

Working, Not Working Retrospective

A clear-cut way to identify successes and improvement areas

Quarterly Retrospective

Reflect, realign, and recharge your team every quarter.

Baby Steps Retrospective

Drive continuous improvement through small, achievable changes.