No matter the time of year, it’s ALWAYS a good time for strategic thinking and considering innovative strategic planning questions. You can depend on great questions to push your strategic thinking and move you into increasingly smarter, more differentiated, and successful market strategies.

Strategic Thinking Questions for Next Year

Reviewing conference tweets, Brainzooming strategic planning engagements, and leftovers in our strategic thinking exercise R&D lab, here are fifteen innovative strategic planning questions (plus a bonus ice breaker question) to move to the top of your strategic planning questions list – whether you’ve started planning or not!

Strategy & Purpose Questions

  • When we say our purpose and messages aloud to someone outside our business, do these statements make sense? (Evan Conway, president of OneLouder, a Kansas City-based mobile app developer)
  • What would you do differently if you HAD TO get 10x better / bigger in the next 12 months? (An incredibly challenging question was inspired by Chuck Dymer - Brilliance Activator)

Strategic Marketing Questions

  • How can we shift more value to the front end of a customer relationship, not charging anything until later when the customer fully realizes the benefit? (Inspired by TEDxKC presenter, Shai Reshef)
  • Have we set a pace for our brand experience to allow a customer to get the maximum value from our brand? (Inspired by Julian Zugazagoitia, Director of the The Nelson-Atkins Museum of Art at TEDxKC)
  • What are our organization’s passion and purpose, and how are we effectively and innovatively marketing them? (From BigIdeas12 conference tweets)

Strategic Innovation Questions

  • How can we get more ideas at early stages when it’s easier and less expensive to incorporate great ideas? (Inspired by Rob Grace of Bazillion Pictures)
  • What can be removed from what we do / produce? (A variation on a Steve Jobs question to drive simplicity, via Ken Segall, author of “Insanely Simple” affiliate link)
  • In what ways can we innovate to offer “more for less”? (Michael Raynor, author of “The Innovator’s Manifesto” affiliate link)
  • To identify potential innovation opportunities, what are the most frequent workarounds customers are asking our sales, customer service, and other representatives to perform?
  • How can we break up big change into pieces too inconsequential to fail (i.e., no matter what happens, we’ll either meet our objectives or learn so much when we don’t, we still win)?

Customer and Market Questions

  • Who specifically is representing the customer 24/7 in our business?
  • What benefits are our customers seeking when they buy from us, and who else is poised to deliver those benefits to them?

Learning Organization Questions

  • Who are our rising stars two jobs away from ever being included in strategic planning that need to be included starting right now?
  • What makes the work our organization does worth it for our employees? (From author of “The Commitment Engine” author, John Jantsch at TEDxKC affiliate link)
  • How are we learning (individually and as an organization) by doing, failing, collaborating, creating, and teaching? (Danya Cheskis-Gold of Skillshare at BigIdeas12)

And a Bonus 16th Strategic Thinking Question - My New Favorite Ice Breaker

  • If you could have the characters in any painting come to life, which painting would you choose? (A wonderful ice breaker from Amy Dixon of on Twitter that elicits very diverse and insightful answers)

Still Need to Get Your Strategic Planning Set for Next Year?

If you’d like help in developing your annual plan done faster than ever, contact us at 816-509-5320 or email

Our Brainzooming name means what it says: we’ll stretch your brains through strategic thinking exercises to consider new opportunities and quickly zoom them into a plan that’s ready for next year when next year starts! We’d love to help you hit next year zooming!   – Mike Brown

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If you’re struggling to create or sustain innovation and growth, The Brainzooming Group can be the strategic catalyst you need. We will apply our  strategic thinking, brainstorming, and implementation tools to help you create greater innovation success. Contact us at or call 816-509-5320 to learn how we can help you figure out how to work around innovation and implementation challenges.

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