Author: George Liacos
How to think more strategically: Constructive Scepticism: Example (Part 2)
There are multiple actions you can take to build your strategic thinking muscle.
We build our strategic thinking muscle using a range of techniques and tools as outlined in my book Spark Change.
The fourteenth Spark I’d like to introduce you to is Constructive Scepticism. Let’s share with you an example.
How to think more strategically: the mental approach
This approach forces us to ask questions. This asking is especially prudent in the resource-constrained for-purpose sector. It forces us to squeeze every thinking drop out of ourselves in our strategic thinking, which in turn leads to more effective, sustainable and mission-aligned outcomes, crucial for nonprofit success.
Here is the mental approach I use when wanting to deploy this Spark. It is based on the sceptic method and rooted in philosophical scepticism:
- Identify and question key assertions: Begin by breaking down what is in front of you and looking for pivotal assertions or facts. Question the validity of these assertions. Especially organisational sacred cows.
- Get to the evidence: Once you have picked your target ‘fact’, seek out the evidence. Analyse the evidence supporting these facts. Scrutinise the quality, source and relevance of the evidence presented. I can’t tell you how many times I find that the ‘fact’ is really a long-gone team member’s opinion.
- Identify assumptions: Uncover and challenge the assumptions supporting these facts. This helps in understanding the foundational beliefs that need re-examination.
- Suspend judgement: Maintain a stance of suspension of judgement in the absence of conclusive evidence. Avoid jumping to conclusions based on insufficient information.
- Develop your view: Confirm the fact or re-organise the evidence and assumptions into a new ‘fact’ or insight.
- Evaluate logical consistency: Assess the logical coherence of the new or validated insight. Identify any fallacies or inconsistencies in reasoning.
- Practice intellectual humility: Recognise the limits of your knowledge and remain open to new information and correction.
Constructive scepticism is a powerful tool in strategic thinking, encouraging a thorough and critical evaluation of information, leading to more-informed and rational decision-making.
How to think more strategically: six tools to guide you
For those looking to amplify their skillset in this domain, here are six tools that, when embraced, can foster a more profound grasp of this concept:
- Red team strategy exercises: Adopted from military war games, this involves creating a team whose sole purpose is to challenge an organisation’s strategy or plan. By actively seeking to find holes or vulnerabilities, it forces the primary team to think critically and defend its choices, promoting a sceptical mindset.
- Futures thinking workshops: Engage in workshops that delve into speculative futures. By contemplating multiple potential scenarios for the future, one learns to question the present. Organisations like the School of International Futures offer such workshops.
- ‘Kill the company’ brainstorming sessions: Popularised by innovation expert Lisa Bodell, this exercise involves teams brainstorming ways in which they would put their own company out of business. This reverse psychology approach helps identify blind spots in current strategies and cultivates a questioning approach.
- Deep dive immersions: Sometimes, stepping out of your environment can foster scepticism. Embark on immersion trips into entirely different industries or cultures. The exposure to different ways of thinking and doing can spark a questioning mindset when you return to your domain.
- Digital detox retreats: In our information-saturated age, taking time to disconnect can sharpen critical thinking. Retreats that emphasise reflection, devoid of technology, can allow you to sift through information more sceptically when you reconnect.
- Devil’s advocate debates: Regularly organise debates where participants are randomly assigned positions, even if they don’t personally believe in them. Defending or arguing against a particular stance hones the skill of looking at issues from multiple perspectives and encourages questioning of commonly held beliefs.
Embracing these unconventional methods and tools, challenging though they may be, can undoubtedly amplify your constructive scepticism skills. They compel us to step out of our comfort zones, question our beliefs, and foster an environment where strategic thinking thrives on a mix of trust and enquiry.
Resources & Support
This is why I wrote the book Spark Change, developed the Strategic Thinking Masterclass, and have released The Spark Strategic Leader ™ Subscription Program – all to help our sector’s leaders build the strategic thinking muscle.
Contact us at info@sparkstrategy.com.au to find out more.
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Want to read more about each Spark? Check out all our blogs and resources.

