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Make The Wicked Question Of Your Scrum Team Transparent

November 28, 2020

"I see Wicked Questions everywhere now", confided a Scrum Master in us when we helped her become aware of them. 

One of the characteristics of complex work is that it is full of contradictory and competing goals. Although each is equally valid and worthy of pursuit, they create tension or open conflict when they are pursued together. In a simple world, we can resolve this tension by letting go of one goal over the other. But that luxury doesn't exist in complex work. Wicked Questions really are everywhere once you start looking for them. Also in how teams and organizations work with Scrum. For example:

A question they often struggle with is:
> “How can we encourage autonomous Scrum Teams while also moving towards a shared Product Goal with other teams?”


> "How can we accept the unpredictability of complex work on the one hand while developing a clear strategy towards the future on the other?"

When organizations launch initiatives to start with Scrum, XP, or Kanban, Wicked Questions inevitably emerge and create tension. Unfortunately, organizations either don't address these questions, and their tension, or they pretend they don't exist at all. But under the surface, the tension festers.

The purpose of this do-it-yourself workshop is to help your Scrum Team articulate the paradoxical challenge they must face in order to succeed. And to help your team(s) move from either/or- to yes/and-thinking, and find solutions that address both sides of the Wicked Question.

Wicked Questions

How does it work?

The PDF outlines a detailed 5-step tried-and-tested 90-minute workshop that relies on Liberating Structures to engage and unleash your team. The string is designed with virtual teams in mind and includes:

  • Wicked Questions
  • Integrated~Autonomy
  • 15% Solutions

What do you receive?

  • A 10-page full-color guide (PDF).
  • We take you through the flow of the string in great detail. Not only do we explain all the steps involved, but we also explain why they are happening. This should make it easier to design your own strings in the future.
  • The instructions support all virtual collaboration tools where you can create breakouts or separate channels occasionally (such as Zoom, GotoWebinar, and Teams). You can set up an additional virtual whiteboard in a tool like Mural, Google Slides, or Miro if you prefer.
  • The PDF outlines additional resources and useful reading, both to prepare and to distribute afterward.


- Get the do-it-yourself workshop:
- Run the workshop with your team
- Let us know how it went!

Let's learn and grow, together! 


We give away most of what we do for free. That is not very clever from a commercial perspective, but we wouldn’t have it any other way. We rely on community support to make this possible. See how you can support us too at

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