Fun Retros - Liberating Structures - Wicked Questions

Articulate the Paradoxical Challenges That a Group Must Confront to Succeed (25 min.)

The aim is to find one or more paradoxical questions in roughly the form of “How is it that we are ____ and we are ____ simultaneously?”. (put this template at the top of your jamboard)

It’s important that both sides of the question are appreciative, otherwise this exercise can quickly turn into finger pointing.

Once we’ve found some wicked questions, we’re not actually aiming to solve them. A really good wicked question just represents an undeniable reality.

An example to help explain it, without anchoring thought processes:

  • “How is it that we are raising our children to be very loyal and attached to the family and also independent individuals?”

[5 mins] on the jamboard, add post-its of positive traits of the team.
[5 mins] go through each post-it, see if there is already an appreciative opposite or paradox elsewhere on the board. If not can you think of one?
[10 mins] pick out the most powerful wicked questions, further refine them, and discuss.

Some more examples:

  • For teams that are split across workstreams: "How is it that we are both integrated and autonomous?"
  • For teams with a dedicated scrum master and product owner "How is it that we build leadership teams within our Agile transformation and simultaneously expect self-organization and responsibility?” /

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