Sideway Learning – Questions Toolkit

Thoughtfully questioning helps understanding a problem from multiple positions


Questions help get “unstuck” when we need to understand a problem from multiple positions. Asking questions leads to different starting points, different people, and different sectors. You can use the Question Worksheet, provided within this Questions toolkit, to create questions which are increasingly complex, representing more and more complex thinking.


Use this thoughtful questioning tool not to look for answers, but try to understand issues from multiple points of view.
When using this tool be aware that:
(1) Unlimited questioning may prevent projects from moving forward.
(2) Questions rub against power and some people maintain power by refusing to ask and answer questions. Therefore, there can be repercussions when questioning challenges power.


Marquardt, M. (2005). Leading with questions: How leaders find the right solutions to knowing what to ask. San Francisco, CA.
Jossey-Bass. Westley, F., Zimmerman, B. & Patton, M. Q. (2006). Getting to maybe: How the world is changed. Vintage Canada.