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  • Barb Bickford

How do you get people to think outside their boxes?

Updated: Nov 7, 2022


The answer: Ask Wicked Questions!

A Wicked Question is a question that poses seemingly contradictory yet equally desirable ends. Here are some examples of Wicked Questions:

-- How can we be both flexible and organized?

-- How can we be generous with our time without giving ourselves away?

-- How can we create shared experiences while we are alone?

-- How might people — even longtime enemies — transform conflicts into creative dilemmas they feel motivated to solve together?

A truly wicked Wicked Question, like the fourth one, makes people shudder or groan, because they recognize the gap between how things are and how they would like them to be.


Paradoxical questions like these invite people to step out of their box(es). They put a group into "creative tension" -- a state where discomfort ultimately gives rise to better ideas and outcomes. For example, over time, wrestling with the fourth question gave birth to Convergent Facilitation, a collaborative decision-making process that is both inclusive and efficient.


In order to resolve a Wicked Question, a group must get out of their boxes, think at a higher level and escape "either/or" thinking.


The path out of "either/or" thinking is paved with trust and willingness, and the leader needs presence, skill and commitment to keep the group on that path. (Read more on those qualities in my blog post, "What leadership qualities matter most for making collaborative decisions?")

How do you craft a Wicked Question?


-- When your group is stuck in "either X or Y" thinking, simply ask, with sincere curiosity, "how can we have both X and Y?"

-- Use “Wicked Questions” (a liberating structure) to develop and process wicked questions. Instructions for "Wicked Questions" are here.

Try using a Wicked Question in your next thorny group meeting and share how it goes in a comment below!


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