Wicked questions

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This microstructure wraps a workshop activity around the concept of “wicked questions” — the paradoxies of complex realities — to shine a light on their existence. This will help us acknowledge them as the first step towards doing something about it (or not).

In practice

Articulating good questions is hard. I’ve built up a ton of experience designing inquiries for user research projects and with the classic design thinking “How Might We” method. However, wicked questions is a different muscle, and I can see that working on it would improve my range. There are beautiful examples in the Liberators publication that show the way.

I will increase my ability before attempting to run this activity for other people. To bring value beyond giving instructions, a facilitator needs “editing” expertise.

Facilitation notes

There will be groups that have already bought into the idea that we need to grapple with complexity head-on. Perhaps they are resigned that it’s unavoidable; that it’s what’s required to get unstuck. Some even relish the idea. Wherever that energy comes from, this kind of audience is primed for Wicked Questions.

If not, I would be especially careful in my language in introducing the purpose of this activity. People may have difficulty understanding why we’d work so hard on forming questions , especially when we “only” move on with one or two.

This line of thinking goes for ideas, too. Sometimes people are confused as to how we can casually leave so many ideas on the cutting board. “There’s so much treasure there! ” they cry.

Seeing the questions as problems to be solved would also take away the strength of a wicked question. Showing and discussing examples to understand the nature of “wickedness” would help to align understanding before we start listing up the truths.

Workshop design notes

Identifying a question, even if it’s critical to unlocking a new line of thinking, is not always recognized as a meaningful workshop activity in itself. People need some degree of resolution or at least a facilitated space to chew on potentials actions to take on this “ now what? ” situation. It’s our natural arc, and most of us simply don’t have the resources at hand to do that independently after the workshop, whether it be time, tools or support.

So it flows more naturally (and leads to bigger impact and satisfaction of the workshop experience) if we segue into a generative activity and indeed, that’s what the LS website recommends:

Use Wicked Questions to evaluate and launch Improv Prototyping, Ecocycle, and 25/10 Crowd Sourcing

When you have a strong Wicked Question, don’t stop there! Follow with 15% Solutions and 1-2-4-All to generate and sift ideas. Making progress on any one Wicked Question can shift what is possible.

This entry is part of Liberating Structures Field Notes, my collection of stories and reflections from the field. It's written for people who already know LS and are deepening their practice. If you're just getting started and looking for activity instructions, you'll find them at liberatingstructures.com..