10 strategic questions you need to ask in a strategy workshop

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At Strategic Facilitators, we help our clients build purposive engaging agendas and session plans to ensure workshops have the desired results.

We have built strategic questions into these agendas for nearly two decades. We offer the following ‘top ten list’ of strategic questions, inspired by Chris Bradley and colleagues (2012), Roger Martin (2014), Ken Favaro (2013), Richard Rumelt (2011), Jack Welch (2005) and Dana O’Donovan & Noah Rimland Flower (2013), and our own work with more than 100 organisations.

  1. Why do we do what we do? What’s the problem or opportunity in the world with which we are engaging?
  2. Who are our primary customers?
  3. What do we want to be famous for?
  4. Where will we compete, specifically?
  5. What is our winning move/s?
  6. How will we add value to our stakeholders?
  7. How does our strategy rest on insight that only we have?
  8. How does our strategy put us ahead of the market?
  9. What capabilities do we need to be successful in the future?
  10. What could a competitor do to hurt us?


Bradley, C, Hirt, M, Hirt, & Smit, S 2011, ‘Have you tested your strategy lately?’,
McKinsey Quarterly, January
Favaro, K 2013 ‘How leaders mistake execution for strategy) and why that damages both)’, Strategy + business, February
Martin, R 2013, February 5 2013 ‘Don’t Let Strategy Become Planning’, HBR
blog post https://blogs.hbr.org/2013/02/dont-let-strategy-become-plann/
O’Donovan, D & Rimland Flower, N 2013 ‘The Strategic Plan is Dead. Long Live Strategy.’, Standard Social Innovation Review https://www.ssireview.org/blog/entry/the_strategic_plan_is_dead._long_live_strategy
Rumelt, R 2011 ‘The perils of bad strategy’, McKinsey Quarterly, June
Welch, J 2005 Winning, Harper Business, New York

To download PDF click here.