Wicked Questions, /confusiasm/ and diverse richness at their best

Wicked Questions is one of the original Liberating Structures.

It’s not as straightforward as 1-2-4-all

It’s not as directly productive as Troika Consulting or 25/10 Crowdsourcing

It’s not as deep and complex as Ecocycle Planning or Panarchy

It’s not as creative as Drawing Together, Improv Prototyping or Tiny Demons

So what is it?

Life, the wicked questions way

Wicked questions is a lens for life. And not just any lens: it is a confusiastic lens. A lens that invites the rich diversity of our myriads of ways of being and doing…

It builds upon the assumption that in complex work, there is no silver bullet, and putting all your eggs into one basket is the surest way to fail. Wicked Questions, instead, invites us to consider the paradoxes we are facing, however uncomfortable these make us.

So indeed it is actively enthusiastic about the confusion it may breed.

It puts us in front of our complexity, in front of our choices, and it encourages us to hold the confusion there. It does not rush us to a response, a solution. It asks us to pause and think, feel, acknowledge: our reality is richer in hues than we tend to admit to ourselves…

Why (and when) is it helpful?

Wicked Questions is logically a helpful reflex to get at the start of something, for a group to realise and process the complexity of its agenda or reality and of itself as a group.

As to why it is helpful, Wicked Questions addresses many issues:

It helps everyone understand the diversity of perspectives in the room. As such it’s a non-threatening way to introduce non dominant perspectives. I’m thinking here of the specific perspectives of e.g. women, youth (or elderly), specific ethnic groups, specific functional groups, partners (vs. project team) etc. etc.
It goes beyond that by quelling the either/or thinking to embrace more of a both/and approach that not only recognises but actually invites more diversity in the conversation, thus more ‘data’, more brainpower. Therefore, it potentially helps create more sustainable solutions
Already at an early stage, Wicked Questions helps be more creative by imagining more complex solutions based on more options…
In its very process, it reveals many other nuances that, even though they may not be factored in the top Wicked Questions here and now could prove helpful to channel further down the line
Individually, Wicked Questions invites us to bring our whole personality, rather than just one facet of ourselves (e.g. the manager in us, the worker/colleague rather than the person we are etc.
Perhaps most importantly, it gets us more confusiastic. As human beings, we tend to like putting things, ideas, people, in neatly labelled boxes. Wicked questions forces us to hold combining opposites, to withhold the confusion that this creates and to stretch our mental elasticity… This allows us to accept more easily the messiness of life, and of people. So it also helps us accept more confusion and frustration in dealing with each other
With this confusiasm, it brings in another creative feedback loop: our acceptance of confusion makes us more likely to go beyond business as usual and beyond our first-draft ideas. It helps us rack our brains together and imagine even bolder, more daring, ambitious, off-the-wall, downright insane ideas that could be the next game-changer…
Finally, in holding that diversity and stretching the limits of our patience and tolerance for confusion, Wicked Questions even holds an element of relationship and community building. If I am able to see the importance of an opposed view point, I can value the inputs of anyone else in the group and appreciate their contribution to making our collective work more robust…

Doesn’t it feel inviting enough to use Wicked Questions then?

How does it work?

Actually, I don’t find Wicked Questions a very graceful structure.

It always feels a bit clunky and leaves me wanting for more, but for whatever it’s worth, here are the standard steps…

Introduce the concept of Wicked Questions and give a few examples e.g. “How is it that we want our conversations to be liberated from conventions and simultaneously we want to make sure we introduce structure in our conversations to make them productive?” (5 minutes)
Individually:
- List all the activities that you do or realities of your work (5 minutes). In the original instructions this step is skipped
- Identify in your list some activities or realities that seem to be opposed or in paradox and alone formulate a Wicked Question in the form of “How is it that… And at the same time…” (5 minutes)
In groups: sharpen the Wicked Questions and select the most wicked questions of them all (if focusing on collective Wicked Questions) (5 minutes)
All together: Share your best Wicked Questions in plenary, agree on the most Wicked Question and further refine it/them (10 minutes). The idea at that stage is to discuss, compare, sharpen the questions to make them perfectly wicked.

Notes from my practice – how to make Wicked Questions work even better?

Embracing paradox isn’t easy, that’s why Wicked Questions don’t always come easy, especially the first time around. So here’s a couple of tips that could help make the process easier and more effective, based on my own observations:

When listing realities / activities / intentions, either restrict yourself to one of these (indeed choose either realities, activities, intentions, attributes) OR when getting items into paradoxical pairs, pair up similar types of items. e.g. pairing intentions ‘How is it that we want to help everyone individually to become more comfortable at voicing their opinions and at the same time we want to help groups thrive as self-facilitating and collective-focused groups’ . Although I realise that this might be constraining too much, but perhaps for a first attempt it may prove handy?
Spend more time in helping each other refine the questions and make them wicked – this could be made even more helpful by introducing a prior step of ‘helping heuristics’ to help everyone find their preferred style of receiving help/advice and of giving it. You can find other ways to combine it with other structures following this post by the Liberators.
Revisit the Wicked Questions you selected as ‘most wicked’, even during the same workshop/session. It’s a way to test out whether we have already reached the optimal level of ‘wickedness’ or we can bring in some more… The Agile process applied to WQ!

Now you just have to try it and apply it in your work!

My friend Nadia already offered some very concrete ideas about this.

And for that matter, when it comes to trying, you can put both feet in the same direction 😉 Or perhaps you prefer to ponder this Wicked Question at this stage: “How is it that I am keen on releasing the power of paradoxes with Wicked Questions and at the same time I am afraid of being overwhelmed with paradoxes?”.

The LS gospel (based on principles) would say: “believe it before you see it”.

Fear not, jump and happily fail forward, we have many more (interesting) paradoxes to deal with further down the line! And you’ll see that we already embrace Wicked Questions in many aspects of our life and work 😉

And if you want to experience it first-hand with some help, join our Liberating Structures Immersion workshop (June 14-15, July 5-6)

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