While the year is winding down, it’s an ideal time to use strategic thinking questions to think about what you need to change for next year.

And what better way to get started than with a new batch of strategic thinking questions.


15 Strategic Thinking Questions to Explore

Some of these strategic thinking questions may seem reasonable; others may seem so outrageous that you wouldn’t ever considering using them. Our recommendation is to start with all of these ones that seem unbelievably outrageous.

In fact, the more outrageous, the better when it comes to applying these strategic thinking questions to your aspirations for the year ahead!

  1. How can we educate and cajole customers to raise their standards about the product / service we deliver? Then how can we more overtly encourage them to proactively point out when we aren't meeting their high standards?
  2. What steps can we take to lower our brand's tolerance for creating products and service that aren't perfect?
  3. How can we reduce the barriers to starting new initiatives for our people who are most likely to do great things and deliver incredible value?
  4. How can we enable talented and less experienced people to get the backing for new initiatives early in their work histories before they've had a chance to imagine their ideas won’t work?
  5. How do we design new products or services for the potential customer who could be the most outrageously important and critical customer we could ever serve (as opposed to designing it for the lowest common denominator)?
  6. What would our brand look like if we deliberately tried to break every rule we can imagine that's defined our industry and business until now?
  7. Where does our company move the slowest, and what steps can we take to dramatically speed things up by next week, at the latest?
  8. How would it improve our organization if we only paid people based on delivering the specific results we need for customers?
  9. In what ways would only paying people based on delivering the specific results we need for customers make things worse?
  10. What steps could we take to turn the craziest good idea we have into reality as soon as possible?
  11. Before we start deciding how we're going to do something, what are all the ways we could decide to measure success or failure as early and often as possible during development?
  12. What are all the little pieces we need to break a "too big to start or even imagine how to start" project up to finally get it started?
  13. What will it take to blow up every reason why our organization fails to start tackling the important challenges we've become too accustomed to accepting?
  14. If we ruled out the belief that ANYTHING is impossible to accomplish, what would we start trying to accomplish RIGHT AWAY?
  15. What are nine other projects we could start that are related to our organization's biggest project to help us move it ahead more quickly?

Are there enough strategic thinking questions on this list that make you squirm?

If so, be sure you start asking those first! – Mike Brown

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