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Wicked Questions

TTool · Wicked Questions

By , Editor · · What’s Next

The same debate surfaces every quarter. Someone argues for speed, someone argues for quality. It never resolves because it was never meant to.

Wicked Questions is a facilitation technique that surfaces paradoxes through questions structured as "How is it that we are X and Y simultaneously?" — where X and Y seem contradictory. The technique opens both/and thinking rather than forcing false either/or choices.

A large quoted prompt template - "How can we X and Y at the same time?" - above a three-step numbered row: 01 FRAME, 02 OPEN and 03 NAME. A caption reads "name the paradox; stop pretending it resolves."
Method visual — Wicked Questions
A move inside a Playbook

“Someone senior is going to try to hijack the next meeting.”

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