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Tip 249 - Strategic Insights and Questions




Strategic thinking involves identifying, imaging, and understanding plausible future operating environments. Strategic thinkers ask questions in purposeful ways to inquire about the past, present, and future, as well as organizational capacity and environmental factors. Consider the following questions to gather organizational insights:

  • Do we understand what environmental factors-internal and external-are likely to impact our desired future?

  • How deeply are we questioning our ways of operating?

  • Do we operate from our interpretation of the past or anticipation of the future?

  • Are our existing assumptions valid when considering the future?


Identifying the right information needed to generate insights is challenging. Reflect on how you might apply these strategies:

  • Identify and clarify the right questions by asking key stakeholders and experts their thoughts on what is needed and why.

  • Explore what relevant and quality information is known and currently available.

  • Consider what key stakeholders expect the results to be in order to test their assumptions and convey findings in audience-relevant terms.

  • Focus on the big story before delving into the weeds.

  • Us the power of storytelling to seek and deliver information. 

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