Barry Winkless, CSO Cpl Group & Head Future of Work Institute

Barry is Chief Strategy Officer of Cpl Group & head of the future of work institute. He is a thought leader on the future of work, strategic design, and business creativity. Over the past 25 years he has worked globally with some of the world’s most respected organisations and is a frequent author and speaker at numerous client and external events. As head of the future of work institute Barry leads a multidisciplinary team working globally to question, explore and design future work solutions with organisations. So, he isn’t just a speaker but is actively pushing the frontiers of the future of work every day in the real world.



As leaders in an increasingly turbulent world, the ability to see, think, and do in a more strategic way has never been more important.  There is a lot written on strategic thinking – numerous articles & books that go deep into the topic and provide all sorts of frameworks, models, and methods. From my experience of real-world application across multiple sectors there are 4 C’s at the core of any practical approach to strategic thinking – Curiosity, Creativity, Commerciality & Compellingness. All 4 are interdependent and together form a powerful mind-kit for strategic success.

  • Curiosity

When it comes to strategic thinking, curiosity is about seeking breadth, depth, variety and ‘meta-ness’ to get to richer and more innovative places. It’s not enough just to go deep on our current business or sector. In fact, curiosity often dies early when we ask and quickly answer deceptively simple strategic questions like ‘what business are we in’?  When I asked our own executive team that very question 5 years ago, they said ‘recruitment’, whereas when we got curious and looked at it from a breadth perspective (i.e. what was happening in totally different but tenuously related business arenas) and from a meta perspective (i.e. what are some meta trends that are universally fundamental to what we do) we landed on ‘we are in the business of transforming our clients through connected talent solutions & experiences’. Curiosity needs to be at the centre of your strategic practice from initiation to exploration through to execution. A powerful Japanese philosophy useful to help drive curiosity is Shoshin, which means to continuously adopt a beginner’s mindset and maintain an attitude of openness, eagerness, and lack of preconceptions when studying a subject.

  • Creativity

Creativity for strategy is not just about coming up with lots of ideas. It is about asking creative and searching questions, looking for interesting connections from unexpected places, combining & multiplying concepts, and adopting holistic perspectives to understand how systems work. One of the most powerful tools that imbues creativity into a strategic process is the classic Diverge-Converge process of design practitioners. In essence this means diverging as far as we can from our starting point of where and what we are as a business today, to what are all the things we could be and do as a business (and associated explorations) before converging on what we can & should do based on certain realities and practicalities. In over 50 strategy projects I have noticed that leaders and leadership groups often don’t give enough Divergent time to the strategic thinking process resulting in ‘Usual +’ ideas (same old ideas but with some adaptation). As a general principle if you don’t feel as though you are being mad at the Divergent part of the process then you probably need to go that little bit further. Spending time on the Divergent part of the process always feeds better concepts at the Convergent side. It also frees up time to merge and multiply seemingly unconnected questions, ideas, and concepts into more compelling places.

  • Commerciality

Any strategic approach needs ultimately to create impact or what Steve Jobs would call ‘a dent in the universe’. Adopting commerciality ultimately means a continuous focus on impact- whatever way that impact is measured. It also means testing and trialling ideas wherever possible- putting a real toe in the water and learning. One of the key goals of strategic thinking is to literally outthink and pre-think your competitors. To this end strategic ideas must be fully formed to go deep on how that idea might play out in different contexts. A very useful approach here is the initiation of one or more ‘Hero Plays’- small but focused projects that proves or moves forward (or indeed helps you rethink) a strategy or strategic concept. Sometimes this might be a simple prototype of a business model that is then played with by a group of trusted colleagues or customers. It may go even further and be a pilot developed in conjunction with a key supplier or partner. The key here is to be small, playful, low or no cost, but moves thinking forward and gives a deeper perspective on impact and commerciality.

  • Compellingness

The end goal of strategic thinking is to create a compelling tale of direction for your business, business unit or indeed for your life. As such storytelling, and more precisely the ability to use storytelling to create a narrative that excites yourself and your stakeholders is of critical importance. The concept of the ‘Show Bible’ is useful here. A show bible is an idea borrowed from the TV industry. It is a document that highlights the key plot structure, audience, characters, adversaries, mood and tone of the series and often includes visuals to get across the concept in a comprehensive fashion. Thinking about your strategy in this way forces a richer story led approach. Discussing what adversaries you are trying to defeat instead of ‘this is our competitor set’ for example, can bring you to more interesting places. Having a ‘tale of direction’ as your end goal means not just focusing on the left-brain aspect of your strategy i.e. the stats, the numbers and the trends but also the right-brain aspect too- the key plot, the feeling and the flow. It is often the right-brain aspect that is critical to sustaining a strategy or strategic concept across multiple stakeholders and ensuring a level of ownership and indeed interest beyond the executive suite.


Curiosity, Creativity, Commerciality and Compellingness- together are a powerful mind-kit for strategic thinking. Consistent application of these principles will improve your ability to look at the world in new and surprising ways and craft tales of direction that on one hand are commercial and, on the other, will excite people to meaningful and sustained action.

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