QUESTIONNAIRE: Strategic thinking self-assessment

This self-assessment is designed to show you how you’re operating across the three dimensions of strategic thinking: being proactive, focusing on what matters and seeing the bigger picture.

The three dimensions are a framework I came up with to explain what strategic thinking looks like—at least, in my mind—and how you could use it to be more effective at work.

If you’re looking for a fun way to engage with the underlying concepts, check out the leadership novella on four fictional leaders—Claire the Control Freak, Rob the Rebel, Quinn the Quiet Achiever and Gene the Chaotic Genius—who are also looking to be more strategic (and less annoying to themselves and others). The concepts are also explained in a series of articles, along with practical tips on how to apply them. The link to these is at the bottom of this page.

But you don’t need the novella or the articles to complete the self-assessment. This is a fun diagnostic tool, so don’t take your results too seriously. It’s just here to prompt you to examine your current mindset in a different way.

In the novella, the characters use a simplified Low/Medium/High version of this assessment. The scored version below gives you a more detailed picture.

To complete the questionnaire, rate each statement from 1 (rarely true) to 5 (almost always true), then add your five scores in each dimension. Be honest rather than aspirational as the goal is to get a clear view of where you are today.

Note: This is a free, low-tech tool that requires a pen and paper. Feel free to use an AI tool to tally your answers, if you prefer.

DIMENSION 1: BE PROACTIVE

Acting with purpose rather than reacting to whatever arrives

  1. I translate my goals into a realistic plan and adjust it when circumstances change.

  2. I anticipate problems and address them before they escalate, rather than waiting until they land on my desk.

  3. I have systems in place to keep routine work flowing without constant attention.

  4. I build buffer time into my calendar so I'm not running at capacity and have room to respond when things change.

  5. I know my own strengths and weaknesses and plan around them.

DIMENSION 2: FOCUS ON WHAT MATTERS

Choosing what counts and letting go of what doesn't

  1. I am clear on the purpose of my role and use that clarity to decide what is and isn't mine to take on.

  2. I prioritise based on genuine risk and impact, not on who's asking loudest or most recently.

  3. I let others solve problems they're capable of solving, even when I could do it faster myself.

  4. When I delegate or step back, I treat it as a development opportunity for others rather than just offloading work.

  5. When planning or prioritising, I consider whether the right people and perspectives are heard, even when that makes things slower or messier.

DIMENSION 3: SEE THE BIGGER PICTURE

Thinking beyond your immediate work and building for sustainability

  1. I consider how my deadlines, requests and working style affect my colleagues' workload.

  2. I look for root causes and patterns rather than just addressing surface symptoms.

  3. I build systems and develop others so that things work well even when I'm not available.

  4. I actively consider how my work connects to other teams, stakeholders and the organisation's broader goals.

  5. I model sustainable work habits that protect both my wellbeing and my team's.

SCORING AND INTERPRETATION

Important: Think of your scores as a snapshot of how you’re operating right now, under current conditions. Low scores don’t mean you’re failing; they just mean there may be something worth adjusting.

Scores by dimension

For each dimension, add your scores (5-25 possible).

21-25: Strong. This is your strength area and you could consider helping others develop similar habits. Your only challenge will be maintaining them when work gets busy.

16-20: Solid. You have good instincts here but may not always follow through. Look for one small system or habit that could make this more consistent.

11-15: Developing. This dimension may need some attention. Revisit the article on the three dimensions of strategic thinking and choose one suggested practice to focus on for the next thirty days.

5-10: Growth area. This is likely where small changes could have the biggest impact. Start with just one statement from this dimension and focus on it for the next ninety days.

Overall score

Add all fifteen scores (15-75 possible).

60-75: You're operating strategically across the board. Your challenge now is sustaining this under pressure and noticing early when you start to slip.

45-59: You have good strategic habits in place, with room to build further. Pick your lowest-scoring dimension and focus there for the next thirty days.

30-44: You have good strategic instincts, but day-to-day pressure is likely outweighing your current systems. Start with one change in your lowest-scoring dimension and give it ninety days.

15-29: You're likely in extended reactive mode and that’s useful to know. Consider what support, boundaries or changes would help create space for more strategic work. Start with just one dimension and revisit the articles for practical tips on where to begin.

Other resources

Check out the novella page for the fictional leaders' full stories, a five-part article series and a quick quiz to find out which character you're most like.

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