Image of three people in a circle with a question mark in the middle

Wicked Questions

R&D, Design & Innovation


This activity challenges people to explore tensions between a strategy and on-the-ground circumstance to discover new ideas. It generates questions without the intention finding answers for these questions. This activity can be used to set up other prototyping and design activities.

Wicked Questions engage everyone in sharper strategic thinking by revealing entangled challenges and possibilities that are not intuitively obvious. They bring to light paradoxical-yet-complementary forces that are constantly influencing behaviors and that are particularly important during change efforts. 

Wicked Questions make it possible to safely expose the tension between espoused strategies and on-the-ground circumstances and to discover the valuable strategies that lie deeply hidden in paradoxical waters. You can spark innovative action while diminishing “yes, but…” and “either-or” thinking. 

Examples of Wicked Questions:

  • How can we give our people room to innovate while also keeping focus on getting work done?
  • How can we scale our engagement with the community to a global level while remaining a small company of two simultaneously?
  • How is it that we are dedicated to our work and being fully present for our families simultaneously?

Wicked Questions are not something you can ‘solve’. Both sides represent an undeniable reality. Still, our thinking often makes us look for either/or solutions — solutions that affect only one side of the Wicked Question.

The purpose is not to find a single answer to a Wicked Question, but to create transparency about seemingly paradoxical realities that exist side-by-side. By accepting both realities, we can engage in deeper strategic thinking and explore new possibilities.

  • Describe the messy reality of the situation while engaging collective imagination
  • Develop innovative strategies to move forward
  • Avoid wild swings in policy and action
  • Evaluate decisions: are we advancing one side or the other or attending to both?
  • Ignite creative tension, promoting more freedom and accountability as the discovery process unfolds

Time: 25 minutes 

Materials and Set Up:

  1. Structuring Invitation
  • Ask, “What opposing-yet-complementary strategies do we need to pursue simultaneously in order to be successful?”
  • Select a topic to focus on
  1. How Space Is Arranged and Materials Needed
  • Groups of 4 to 6 chairs with or without small round tables
  • Paper for recording
  1. How Participation Is Distributed
  • Everyone involved in the work or topic is included
  • Everyone has an equal opportunity to contribute
  1. How Groups Are Configured
  • Individually
  • Small groups (6 people or smaller)
  • Whole group
  • Explain the overall purpose of Wicked Questions: articulating the paradoxical challenges that a group must confront in order to succeed. 2 min.
  • Introduce the topic that you’ve chosen to focus on. First alone, then in small groups make a list of everything you know is true about this topic. 5 min.
  • Introduce the concept of Wicked Questions and give some examples. 2 min.
  • First alone then in small groups, each participant generates pairs of opposites or paradoxes at play in this topic. 5 min.
  • First alone, then in small groups, create potential Wicked Questions out of the pairs by using the template: “How is that we are [Side 1] and [Side 2], simultaneously?”. The best Wicked Questions have positive, worthy goals on both sides. 10 min.
  • Each group selects its most impactful and wicked Wicked Question. All selected Wicked Questions are shared with the whole group. 5 min.
  • Whole group picks out the most powerful ones and further refines the Wicked Questions. 10 min.

Tips and Traps

  • Make sure that participants express both sides of the paradox in an appreciative form: “How is it that we are ____ and we are ____ simultaneously?” and not in opposition of each other.
  • Use a variety of examples to make the paradoxical attributes accessible.
  • Work in quick cycles, failing forward as you make the questions perfectly wicked.
  • Avoid nasty questions that appoint blame or are unbalanced on one side. Here is an example of a nasty question: “How can we focus on our customers when we are forced to spend more and more time on the headquarters’ bureaucracy?”
  • Avoid data questions that can be answered with more analysis.
  • Invite participants to include others in making their questions more wicked.
  • Draw on field experience; ask, “When have you noticed these two things to be true at the same time?”
  • There are no quick fixes to Wicked Questions and you may need to return to the challenge periodically with additional rounds of Wicked Questions.
  • Often a handful of people are very skilled at generating Wicked Questions: let them shine and inspire the rest of the group!