How to navigate paradoxical challenges as a team with Wicked Question from Liberating Structures

Do you recognize this?

In your daily work, you must proceed quickly and in an agile way so that you can deliver your work. At the same time, you must take the time to think slowly and deepen your understanding of the challenges you face.

Both are needed, fast acting and slow thinking.

But it is not always easy or obvious.

Two poles or truths competing with each other pull you in opposite directions. As an individual, you probably face more of these kinds of paradoxical challenges.

Only you can take responsibility for your happiness… but you can’t do it alone. It’s the great paradox of being human.
Simon Sinek

Stuck in either/ or thinking

The same is true for a team, a group, a network or a community. It is possible that your team faces some tensions and frustrations because it is dealing with paradoxical truths. It might be that your team is stuck in either/ or thinking.

par·a·dox | \ ˈper-ə-ˌdäks , ˈpa-rə- \
1: something (such as a situation) that is made up of two opposite things and that seems impossible but is actually true or possible
2: someone who does two things that seem to be opposite to each other or who has qualities that are opposite
3: a statement that seems to say two opposite things but that may be true
Merriam-Webster

Being precise and generous at the same time are opposing truths. The same is true for planning and preparedness versus flexibility and agility. Or working the networked way in a hierarchy.

These opposing forces create tensions and can lead to misunderstandings and arguments. The trouble is often that it is difficult to see the presence of a paradoxical challenge.

Uncover paradoxical challenges

With Wicked Questions from the Liberating Structures repertoire, you uncover these paradoxical situations and trigger discussions with your team to create new possibilities.

You ask: How is it possible that… and that… simultaneously? That’s a wicked question.

How is it possible that… and that… simultaneously?

For example, how can we be fully professional, engaged, and passionate and at the same time be fully present for family and friends?

Or, how is it possible to develop some habit and rhythm in our daily work life and that we must be ready to embrace change simultaneously?

Wicked Questions brings some relief.

You can already do it with two people.

What you need

Paper and pen and around 20-30 minutes.

That’s all.

How it works

For 2-3 minutes, generate a list of truths & realities about your work these days (or any other issue you want to explore). Do this on your own.
Then, still on your own, for 2-3 minutes, review your list and select two items that are paradoxically opposed or in creative tension with one another.
During the next 10 minutes work in pairs, trios, or groups of four. Share your opposing truth and formulate these as Wicked Questions: How is that we are …. and we are …. simultaneously? Select the most impactful and relevant wicked question and refine it in the group.
With the whole group share Wicked Questions (5-10 minutes).
Then debrief your insights.

In Barry’s blog post, you find some inspiration on how to combine Wicked Questions with other Liberating Structures.

Learning Moments