🏆🇬🇧 Taskmaster Challenge

Step into the whimsical world of Taskmaster! Let's review the last sprint as contestants taking on epic tasks. Celebrate clever solutions, laugh at glorious mishaps, and brainstorm winning strategies to outsmart the Taskmaster in future rounds.
50–65 min
4-10 people
Based on: What Went Well, What Went Wrong, What We Want to Improve
🏆🇬🇧 Taskmaster Challenge

Template Columns

🎉 Prize Winning Tasks

Celebrate the brilliant tasks and clever moves that earned the Taskmaster’s praise this sprint.

Base column: What Went Well
⏳ Time-Busting Blunders

Reveal the hilarious or troublesome moments when things didn’t go to plan and left us in a fix.

Base column: What Went Wrong
💡 Champion’s Tactics

Suggest fresh strategies and wildcard ideas to win future tasks and impress the Taskmaster.

Base column: What We Want to Improve

About this template

The Taskmaster Challenge retrospective invites your team to reflect on the last sprint with creativity and humor, celebrating clever wins, laughing at setbacks, and brainstorming new strategies in a playful, contest-style format.

When to use this template

Choose this format when your team needs an energy boost, wants to add some fun to regular retros, or could benefit from a fresh approach to learning from success and failure.

How to facilitate

1

Set the playful tone by briefly introducing the Taskmaster theme and encouraging a lighthearted mindset.

2

Invite everyone to add their 'Prize Winning Tasks'—highlight moments where smart thinking, teamwork, or clever moves led to success.

3

Reveal and discuss 'Time-Busting Blunders'—share unexpected setbacks, funny mishaps, or challenges faced along the way.

4

Brainstorm and capture 'Champion’s Tactics'—collect new ideas, wild solutions, or tactics for outperforming old routines and future obstacles.

5

Vote on the most creative or valuable Champion's Tactics to prioritize for your next sprint.

6

Wrap up by recognizing fun moments and giving out a virtual ‘Taskmaster Award’ to a standout contribution, reinforcing appreciation and team spirit.

Pro Tips

Encourage storytelling to bring both successes and blunders to life—it builds empathy and makes learning memorable.

Mix up who plays the 'Taskmaster' role each sprint to keep facilitation fresh and give everyone a chance to lead.

Add small challenges or polls between sections for extra engagement and light competition.

Document the best tactics in a shared playbook so the team can refer back and measure progress over time.

FAQ

How do I keep the session fun without losing focus?

Set expectations early and use the Taskmaster theme to break up discussions, but gently refocus on learning and action items between laughs.

What if some team members are uncomfortable sharing their mistakes?

Model candor by sharing your own blunders first and remind the team that the session is a safe, blame-free space for growth.

Can this template work for non-software or cross-functional teams?

Absolutely—Taskmaster Challenge is flexible and fun for any team looking to celebrate wins, dissect setbacks, and brainstorm improvements.

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At a glance

  • Duration

    50–65 min

  • Team Size

    4-10 people

  • Columns

    3 columns

  • Base Format

    What Went Well, What Went Wrong, What We Want to Improve

Tags

creative
engagement
reflection
team building
fun
action-oriented

Ready to get started?

Use this template to run your next retrospective