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  • Writer's pictureBarb Bickford

Leading with Paradox

Updated: May 2

How Leaders Can Embrace Contradiction to Drive Innovation


Today, I want to talk about a specific type of question: paradoxical questions. These questions can be a bit tricky, but they can also be incredibly valuable in helping groups think outside the box and come up with creative solutions. Want innovation? Make friends with paradoxes!


What are paradoxical questions?


Paradoxical questions are those that seem to contradict themselves, and the contradiction invites the listener to consider how both might be true at the same time or might express equally desirable ends.


Paradoxical questions can help us to think more creatively and find solutions that may have seemed impossible before. Here are some examples:

  • How can our decision-making process be both efficient and rigorously inclusive, simultaneously?

  • How is it that we can be natural leaders and respectful followers at the same time?

  • How might we both provide better care for our children while also challenging the status quo of the systems that keep them stuck?

  • What if we stopped trying to fix this problem and embraced it instead?

  • How can you be generous in your time without giving yourself away?

Did any of those questions make you groan? A truly paradoxical question will do that.


As a meeting facilitator, I have found that using paradoxical questions in meetings can be an effective way to challenge assumptions and invite people to think outside the box. They require groups to think deeply and critically and come up with truly fresh ideas that achieve both goals.


A quote "How wonderful that we have met with a paradox.  Now we have some hope of making progress." -- Niels Bohr

How do you solve a paradoxical question?


The only way for group members to “solve” a paradox is to change their perspective and get really curious and creative. When you want your group to be innovative, ask a paradoxical question!


For example, here is one: "How can we have both speed and quality in our work?"


To answer this question, we might need to approach the problem from a different angle. We might need to question our assumptions about what "speed" and "quality" mean and consider whether there are other factors that could be influencing our work. We might need to experiment with new processes or technologies or find ways to better balance our workload.


By asking a paradoxical question, we can break out of our usual patterns of thinking and find new solutions to old problems.


How can you develop paradoxical questions?

Option 1: Change an “either/or” question to “How can we have both X and Y?”


The easiest way to create a paradoxical question is to notice where your group is stuck in “either/or” thinking. Framing a question as a paradox can be very valuable in this situation. Simply change the “either X or Y” polarity to “How can we have both X and Y?”


For example, your community might be in conflict over how to spend a grant. One sub-group wants to create programs for young people and another sub-group wants to support the elderly. You can shift the group into solving the problem together by asking, “How can we both serve the youth and the elderly in our community?”


This puts the group in “creative tension”— a state where discord ultimately gives rise to better ideas and outcomes.


One group I know faced this very question. They resolved the paradox by creating a mutualy beneficial mentoring program where able-bodied youth help the frail elderly and elders serve as "grandparents" to youth. Voila!


Option 2: Engage everyone in creating the questions


Another way to develop paradoxical question is to use an activity called "Wicked Questions". A "wicked question" is another term for paradoxical questions, because they can be wickedly difficult to resolve.


Wicked Questions is one of 33 activities called “Liberating Structures.” Liberating Structures (LS) were developed by Keith McCandless and Henri Lipmanowicz to help change how groups work together in inclusive and engaging ways. They are easy to learn and very adaptable. You can learn more about Liberating Structures here and find the instructions for Wicked Question here.


“Wicked Questions engage everyone sharper strategic thinking by revealing entangled challenges and possibilities that are not intuitively obvious...[They] 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.” -- the LS website.

How can you start using paradoxical questions in your own meetings?


Here are a few tips:


1. Encourage creativity by creating safety. Paradoxical questions can be a bit intimidating, so it's important to create a safe and supportive environment where people feel comfortable sharing their ideas and question their deeply held assumptions and beliefs. Encourage creativity and open-mindedness and avoid dismissing ideas too quickly.


2. Use humor. Paradoxical questions can be fun and playful, so don't be afraid to inject a bit of humor into the process. This can help to lighten the mood and make people more comfortable with the idea of thinking outside the box.


3. Be patient. Paradoxical questions can take a bit of time to answer. Don't rush the process. Allow people to think deeply and critically about the question and to challenge their assumptions. The extra time and effort will be worth it when you come up with truly innovative solutions.


In conclusion: dive in and innovate!

Using paradoxical questions can be a powerful tool for generating creative solutions in meetings. By challenging our assumptions and thinking outside the box, we can come up with truly innovative ideas.


Of course, answering a paradoxical question is not always easy. But the rewards can be significant. By answering a paradoxical question, we can find solutions that are more creative, more innovative, and more effective than we might have thought possible.


Take your leadership of discussions to a new level! Craft and use a paradoxical question and see where it takes you. Who knows – your group might just come up with the next big idea!

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