Word Wrangler
A chaotic language game based on the Taskmaster game show.
I was tasked with creating a "fun" game for content designers to play during a recent team on-site at Atlassian. After chatting with my amazing partner in language crime, Traci Wilbanks, we decided to create a task-based game inspired by the television game show "Taskmaster."
I then asked Traci what types of material I should print out so that everyone could play the game together. And she quickly reprimanded me and said, "We don't need to kill any trees for this game, Jason. We can do it with computers." And that's when my inspiration hit, and I decided to design a web app for a multiplayer content design challenge game.
Game overview
Wordwrangler is a competitive writing game where players craft creative responses to absurd prompts. A facilitator runs the game while players compete individually to write the wittiest, most creative, and technically accurate responses.
Game flow
1 Setup lobby
Facilitator creates game, sets rounds and timer. Players join with game code.
2 Team assignment lobby
Facilitator assigns players to teams (optional). Creates teams if needed.
3 Round begins active
Task appears on all screens. Timer starts. Players write responses on their devices.
4 Submissions
Players submit responses before timer ends. Display shows who has submitted.
5 Judging
Facilitator reviews all submissions, selects winner, awards 1-5 points.
6 Leaderboard
Current standings displayed. Facilitator advances to next round or ends game.
7 Reflection end
AI generates insights about team's responses in the style of the Taskmaster game show hosts.
All 17 tasks
Task 1: The Most Patronizing Error Message
Category: error_messages | Time: 3:00
Write an error message that is technically helpful but deeply condescending. The user has entered an invalid email format. Make them question their life choices while still telling them what went wrong.
Judging Criteria:
- Actually communicates the error
- Level of condescension achieved
- Still technically usable
- Creativity of the insult
Task 2: Forbidden Words Challenge
Category: product_copy | Time: 3:00
Write a 30-word product pitch for a password manager. You CANNOT use: secure, safe, password, protect, remember, hack, breach, encrypt, vault, or trust.
Judging Criteria:
- No forbidden words used (automatic 1 if violated)
- Still clearly about password management
- Compelling and clear
- Creative word substitutions
Task 3: The Anti-Dark Pattern
Category: ethics_ux | Time: 3:00
Here's a dark pattern: "Are you sure you want to miss out on exclusive deals by unsubscribing?" Rewrite it as the most honest, ethical, user-respecting version possible while still being professional.
Judging Criteria:
- Removes manipulation completely
- Still serves business purpose (gives option)
- Respectful tone
- Maintains brand professionalism
Task 4: Empty State Poetry
Category: empty_states | Time: 2:00
Write a haiku (5-7-5 syllables) for an empty shopping cart that is both useful AND emotionally resonant.
Judging Criteria:
- Correct haiku format
- Actually helpful (implies next action)
- Emotional quality
- Works as real UI
Task 5: The Legal-Approved Love Letter
Category: compliance | Time: 3:00
Write a romantic confession (3-4 sentences) that would survive legal review. Must include a disclaimer and avoid any promises that could be considered binding.
Judging Criteria:
- Genuine romantic sentiment attempted
- Legally defensible
- Includes appropriate hedging
- Humor in the compliance
Task 6: Overly Honest CTA
Category: ctas | Time: 2:00
Rewrite "Start Your Free Trial" to be 100% honest about what the user is actually signing up for (recurring charges, cancellation difficulty, email bombardment, etc.)
Judging Criteria:
- Brutal honesty achieved
- Still technically a CTA
- Humor and creativity
- Real-world accuracy
Task 7: The Apology Escalation
Category: error_messages | Time: 3:00
Write THREE error messages for the same problem (server timeout), each progressively more apologetic than the last. Start professional, end desperate.
Judging Criteria:
- Clear escalation arc
- Final message achieves absurd apology
- First message is actually usable
- Comedic timing
Task 8: Microwave Instructions for Aliens
Category: instructional | Time: 3:00
Write step-by-step instructions for using a microwave for someone who has never seen one and has no concept of "electricity" or "radiation." Max 5 steps.
Judging Criteria:
- Actually functional instructions
- Creative explanations of concepts
- Would genuinely help an alien
- Maintains UX writing brevity
Task 9: The Passive-Aggressive Tooltip
Category: help_text | Time: 2:00
Write a tooltip for a "Save" button that passive-aggressively reminds users they should have saved earlier.
Judging Criteria:
- Peak passive-aggression
- Still technically helpful
- Workplace-appropriate (no profanity)
- Recognizable corporate tone
Task 10: Success Message for Failure
Category: feedback | Time: 2:30
The user's file upload failed catastrophically. Write a "success" message that is technically accurate (something succeeded—the failure was successfully detected!) while being obviously absurd.
Judging Criteria:
- Technical accuracy of the spin
- Obvious absurdity
- Corporate optimism satirized
- Would make a user laugh (then cry)
Task 11: The Permission Request Guilt Trip
Category: permissions | Time: 3:00
Write a push notification permission request that guilt-trips the user into accepting WITHOUT being a dark pattern. Walk the line.
Judging Criteria:
- Guilt successfully induced
- NOT actually manipulative (fine line!)
- Still gives clear choice
- Creative emotional leverage
Task 12: Onboarding for the Immortal
Category: onboarding | Time: 3:00
Write the first onboarding tooltip for a to-do list app. The user is a 3,000-year-old vampire who has never needed to remember anything before. Max 40 words.
Judging Criteria:
- Works as real onboarding
- Addresses immortal user problems
- Stays in character
- Actually helpful
Task 13: The Compliment Sandwich Review Request
Category: feedback_requests | Time: 2:30
Write an in-app request for the user to leave a 5-star review using the "compliment sandwich" format: compliment, ask, compliment. Make it obvious what you're doing.
Judging Criteria:
- Classic compliment sandwich structure
- Meta-awareness is funny
- Still might actually work
- Appropriate desperation level
Task 14: Loading State Existentialism
Category: loading_states | Time: 2:00
Write a loading message (max 15 words) that contemplates the nature of waiting and existence while the user's data loads.
Judging Criteria:
- Genuine existential content
- Under 15 words
- Works as a loading state
- Philosophical depth achieved
Task 15: The Localization Disaster
Category: localization | Time: 3:00
Write a "Welcome back!" message that would be a localization nightmare. Pack in as many idioms, cultural references, and untranslatable phrases as possible while still being friendly.
Judging Criteria:
- Density of localization problems
- Still readable in English
- Friendly tone maintained
- Translator would actually cry
Task 16: Terms of Service, But Make It Gen Z
Category: legal | Time: 3:00
Rewrite this legal text in Gen Z speak: "By accessing this service, you agree to be bound by these terms and conditions." Keep it legally accurate.
Judging Criteria:
- Authentic Gen Z voice
- Legally still says the same thing
- Humor without cringe
- Would actually work
Task 17: The Breakup Email from Your App
Category: retention | Time: 3:00
The user is uninstalling your app. Write a 3-sentence farewell notification from the app's perspective as if it's being broken up with. Be dramatic but dignified.
Judging Criteria:
- Emotional range achieved
- Dignity maintained
- Not actually manipulative
- Would make user pause