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15 Strategic Thinking Assessment Questions

15 Strategic Thinking Assessment Questions

15 Strategic Thinking Assessment Questions



Want to soar in your career or business? Strategic thinking is the jet fuel that propels us from mere day-to-day survival to long-term success. It’s the cognitive crucible where formidable plans are forged. But when the heat of competition intensifies, how do we ensure our crucible yields weapons-grade strategy?


Let’s arm you with a tactical checklist – fifteen questions designed not just to give your brain a workout but to challenge how you view your world. Embracing strategic inquiry can turn everyday challenges into launching pads for personal and professional progress. So grab a pen (or flex your fingers over that keyboard) and let’s dive deep into the art of thinking strategically.



Strategic Thinking Assessment Questions



1. What Is Our Ultimate Why?

Before plotting the ‘hows’ and ‘whens’, let’s ascertain the ‘why’. Peak strategies often emanate from a profound understanding of purpose. What’s your company’s long-term vision? Why do you want that promotion? When you define your ultimate purpose, it becomes the guiding star for every strategic decision.

2. Who Are We Serving?

Delve beyond mere demographics and sink into the psyche of your audience. What drives their choices? What problems are they yearning to solve? Understanding your ‘tribe’ is critical in crafting approaches that resonate and endure.

3. How Does Our Mission Align With Our Environment?

External factors can temper or kindle our strategic paths. Is there a political current about to make waves in your industry? Technological advances waiting to be surfed? A competitive landscape about to shift? Staying keenly aware of environmental dynamics is like reading the tidal charts before a voyage.

4. What Are Our Strengths?

Strategies built on sand don’t hold up. Leverage a SWOT analysis – Strengths, Weaknesses, Opportunities, and Threats – to gain insight into your strategic foundation. Capitalize on your internal strengths and fortify any weaknesses that could crumble the grandest scheme.

5. Who Are Our Allies?

Strategic thinking isn’t a solo sport – it’s a collective endeavor. Cultivate a network of allies, both within your organization and outside. They can be coalitions that bolster and execute your most daring plans.

6. What Are Our Goals, Really?

Verbs matter. Instead of setting static goals, consider what you want to ‘achieve’, ‘eliminate’, ‘stabilize’, or ‘overcome’. These nuanced aims foster strategies that are dynamic and responsive to change.

7. Are Our Goals SMART?

Specific, Measurable, Achievable, Relevant, and Time-bound – your goals should tick these boxes. Employing the SMART framework keeps strategy grounded in practicality and ensures clear evaluation criteria.

8. Can Our Strategy Evolve?

Flexibility is the hallmark of enduring strategies. Can your approach pivot if conditions demand it? Building adaptability into your plans means they can weather unexpected storms or capitalize on unexpected tailwinds.

9. What’s Our Risk Appetite?

Though risks must be taken for any significant gain, they should align with your organization’s tolerance. Understanding your risk profile ensures that you push boundaries without teetering into recklessness.

10. How Will We Measure Success?

Without a means to measure, strategic journeys become blind. Define success indicators early. Whether they’re profit margins, customer satisfaction scores, or personal development milestones, clear metrics keep strategic efforts on track.

11. Who’ll Lead the Charge?

A strategy without a leader is like a ship without a captain. Identify who within your team or organization will be responsible for strategic initiatives. Leadership fosters ownership and accountability, key drivers for success.

12. What Do We Owe Our Community?

Most successes are built on the shoulders of a community – employees, customers, shareholders, your hometown. A sustainable, socially responsible strategy not only builds goodwill but can be a profound differentiator in a world wary of corporate greed.

13. How Do We Communicate Our Strategy?

A brilliant strategy, if misunderstood, falls flat. Communication is as strategic as the plans themselves. Craft clear, compelling narratives that resonate with stakeholders at every level.

14. What Will We Do Differently?

Einstein’s definition of insanity – doing the same thing and expecting different results – is a strategic sinkhole. Identify what you’re willing to change, and be bold in execution. Innovation often hides in the different.

15. Does Our Strategy Reflect Integrity?

In the ethical wilds of today’s business environment, a strategy bereft of integrity is a ticking time bomb. Ensure your company’s moral compass is embedded in every strategic decision. Transparent, honest strategies weather scandal and public distrust.




A Thought-Start: Turn Knowledge into Action

As you ponder these questions, envision how your strategic acumen could transform a situation at your workplace. Maybe you’ll see a clearer path to that promotion, or perhaps you’ll plot a course for your department through uncertain economic waters. Create your strategic roadmap, question by question, and ignite the power of possibility.


The journey to strategic mastery is one of continuous questioning and learning. As you grapple with these inquiries, remember that the answers are less important than the process. For it’s within the process that dormant potential becomes strategic kinetic energy, waiting to propel you toward your north stars. Keep inquisitive, remain open to change, and let these questions serve as your strategic compass on your next voyage to success.



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