A CEO client of Brainzooming was matter of fact in supporting a more innovative organizational culture: “We’re not going to have winning or losing. We’re going to have winning or learning.”

That’s a great ambition.

Creating a culture that values both winning and learning from setbacks boosts performance and morale. Achieving it, though, takes work and many executive actions consistent with this ambition.

One essential aspect of this type of innovative, winning or learning culture involves asking insightful strategic thinking questions. Ask them about every initiative to encourage; they will encourage reflection, celebrate successes, and extract lessons from every challenge that you face.

Strategic Thinking Questions for Winning and Learning

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Here’s the Brainzooming perspective to started incorporating strategic thinking questions that maximize repeated winning and learning how you can innovate and develop whenever you face challenges.

When You're Winning, Ask:

  1. What specific actions or strategies contributed to success?
  2. Which strengths did the team display?
  3. How did our preparation influence team performance?
  4. What did we do better than our competitors (or better than previous efforts)?
  5. How can we replicate (and adapt) our success to repeat it and/or bring it to other efforts?
  6. What feedback was available during the initiative, and how did we incorporate it to improve success?
  7. What challenges did we overcome? How did we manage those?
  8. How can we continue to improve even in successful areas?
  9. What did we discover about team dynamics?
  10. How can this success motivate and inspire our team and stakeholders?
  11. Who displayed unexpected talents, capabilities, or effort that we can celebrate?
  12. How will we document and share this success as a learning tool for others?

When You're Not Winning, Ask:

  1. What were we trying to achieve? What factors stood in the way of reaching our goals?
  2. Which areas did not perform as expected? What are potential reasons behind whatever gaps emerged?
  3. What unforeseen challenges did we encounter? How did we respond to them?
  4. What assumptions or initial expectations, if any, later proved incorrect?
  5. What did we learn about our processes, tools, and/or resources that needs improvement?
  6. Where were our communication efforts successful and unsuccessful?
  7. How did we do at making decisions under pressure?
  8. What feedback did we receive throughout, and how can we use it constructively?
  9. Where do we need additional skills, knowledge, or resources to overcome comparable future challenges?
  10. What can we learn from this experience about resilience and perseverance?
  11. How can we, as a team, support each other through recovering and moving forward?
  12. What specific steps can we take to avoid similar future outcomes?
  13. What steps could turn these learnings into growth and innovation opportunities?

Strategic Thinking Questions are Vital for a Winning and Learning Environment

Winning or learning demands great strategic thinking before, during, and after any initiative. Select from these and other question sets to foster an organization that is continually moving ahead smarter with a higher probability of future success all the time.

If you want to create the safe space that’s needed for your team to share their perspectives on these types of questions, our online collaboration platform, Blast!, is the ideal environment. Let’s grab thirty minutes to discuss how Brainzooming can help you advance both winning and learning! Mike Brown

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