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The Jester — Agile Management Hack №5

Maggie Sun
3 min readFeb 10, 2022

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Do you feel you and your team are trudging in the mud? You know there’s an issue to be addressed, but you can’t find the fix, or worse — you may be working on the wrong problem based on old assumptions and habits. More often than not, you tried all the traditional techniques to figure out the solution, but only ended up in a politically correct situation where bad compromises were reached and no one dared to tell the truth.

Try the agile management hack — the Jester — which is designed to save you out of this kind of dilemma. The Jester is a role that can be taken by anyone in an activity during which this person is empowered to use humorous and provocative language to raise powerful questions in order to disentangle a situation through:

  • revealing the true intentions behind politically correct business talks;
  • bypassing the traditional chain of command to avoid bureaucracy;
  • breaking analysis paralysis or overcoming indecisiveness and procrastination.

For example (see linked video for clarity):

- In a meeting, when everyone echoed a new VP’s speech about continuing the “great work” together, the jester asked: “Our previous VP lasted only three months. How continuing to do the same will play out?”

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Maggie Sun
Maggie Sun

Written by Maggie Sun

MBA, certified agile coach and experienced strategy analyst, specializing in business agility, agile leadership, Beyond Budgeting, and general management.

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