Short Story: Strategic planning questions that allow people to challenge conventional norms are fun and lead to disruptive thinking, so employ questions to harvest ideas from the wild possibilities.

The other day, someone reached out looking for short, funny, strategic planning questions. We have tons of strategic planning questions, including a few we have singled out as more fun than others. We also have quite a bit on fun strategy planning, including one of our most popular new eBooks, 11 Fun Ideas for Strategic Planning.

The question got me thinking about specific strategic planning questions we use to liven up strategic thinking.

3 Short, Funny Strategic Planning Questions

Thumbing a group’s collective nose (or perhaps raising a prominent finger) toward someone or something standing in the way of pursuing new, innovative strategies always adds fun to a strategy workshop. Here are three opportunities to challenge typical roadblocks to innovation and new strategic ideas:

1. Stick It To Authority Figures

What completely outrageous thing could we do that would be incredible, yet get us into big trouble with the boss?

This is the core creative thinking question for our Shrimp exercise. We have mentioned previously using it to revive a group’s energy. This creative thinking question also helps them move beyond ideas they would typically self-censor in almost any situation.

2. Give Conventional Expectations the Heave Ho

If we did exactly the opposite of anyone’s expectations, what would we do?

This strategic thinking question is on our extreme creativity list. It does a great job of giving people permission to change everything, even if it’s only hypothetical at first.

3. Get around Expectations Because of Who You Are

If characters from The Big Bang Theory were solving this problem, what would they do?

This strategic planning question is an updated, hipper version of one of our favorite creative thinking questions: How would the castaways from Gilligan’s Island solve this issue? Both versions of Change Your Character exercises, they free a group’s perspective and energy to imagine how others would tackle daily issues around your organization.

Wait, There’s More!

These types of questions typically generate a higher percentage of ideas that, on the surface, seem completely ridiculous. That’s why you want to couple them with questions to help mine the ideas for possibilities that you CAN implement. These are a follow-up questions to consider using:

  • What could we take from these ideas (and modify) to apply to our situation?
  • How could we take this idea just as it is to challenge how we do things now?
  • How can modify this idea as little as possible to be able to move on it quickly without losing how outrageous / special / disruptive it is?

Granted, we don’t use each of these funny strategic planning questions in every client workshop. When we do use them, they definitely boost the energy level dramatically. - Mike Brown

New call-to-action

If you enjoyed this article, subscribe to the free Brainzooming blog email updates.