At the age of 11, Taylor Swift realised her talent for singing was not enough when she failed to get a record deal. To succeed, she decided to be strategically different. Learning three guitar chords won her a song-writing deal with Sony aged 15. Modelling for Abercrombie & Fitch increased her profile. Use of social media expanded her fan base. Writing songs from her teenage perspective produced a No. 1 album. She has made a series of ambitious, strategic moves including collaborating across genres to give her appeal beyond country pop. Despite challenges from younger rivals, and criticisms about fake authenticity, strategic thinking has taken her from karaoke competitions to become one of the world’s most powerful musicians.

It’s possible to be a strategic thinker without using any strategy tools, but it’s not possible to create brilliant strategy without being a strategic thinker. There is an important difference between creating strategy documents and creating strategy that gets you where you want to be. There’s also a valuable difference between managerial thinking and strategic thinking.

Leaders often say they want strategic thinking. They want to be prepared and they believe strategic thinking will help them prepare. They want more from less, and they depend on strategic thinking to deliver. They want people around them who see the bigger picture. They want clever solutions to messy problems. And they want to move beyond the obvious and out-think the competition.

Strategic thinkers ask different kinds of questions and look at old (and new) problems with fresh eyes. They see what other people miss – whether that’s some apparently unimportant detail or some very long-term trend as part of a much bigger picture. Part of their value is that they ask questions that are creative and custom-made for the particular situation. This book is full of questions to give you more options when you are forming your own strategic questions. But the most important questions to keep asking are: why and why not?

It’s best to focus on questions that open up thinking rather than prematurely landing in unhelpful levels of operational detail. The strategic thinker is able to open up thinking (creating lots of possibilities) and then create visions that are clear and engaging to shape the future in desirable ways.

Organisations tend to be full of people trapped by a series of constraints. Their view of the world is limited by role descriptions, departmental responsibilities and corporate processes. In addition, their focus tends to be on the short-term demands of reporting structures and performance management.

Different people are naturally interested in different aspects of the big picture. Some focus on practical aspects of what happens next while others want to understand the facts and figures to support a new direction. Some are concerned about its impact on people (the wider team) while others want to do something new and amazing whether or not it is realistic or practical.

The strategic thinker is interested in aspects of all of these concerns but is capable of a kind of mental gymnastics. Strategic thinkers are able to link ideas from different specialist areas and highlight opportunities from contradiction, tension and paradox. They work out how things can fit together better.

In times of stability or straightforward growth, bold strategic thinkers can be underappreciated. They want to do great things and when they are stopped they either give up or move on. In times of uncertainty, or when it becomes hard to grow, the organisation urgently needs strategic thinkers but may find that it doesn’t have enough of those people in positions of influence. It may also find that it’s not used to listening to them (or joining in the strategic conversation) so that they have to learn new strategic thinking habits.

Another challenge is that there is very little formal development of strategic thinking that includes the kind of creative, obsessive eclecticism that is necessary. Part of the reason is that it’s just not easy to do. You can’t just have dull, uninspired, by-the-numbers, check-box training for strategic thinking if you want to have brilliant, inspired, beyond-the-numbers, out-of-the-box behaviour.

The good news is that most people want to be creative and have a desire to understand how to improve their future. There are many sources of inspiration for strategic thinking – what people hate, what they love, what frustrates them, what captivates them. And strategic thinking can turn disconnected emotions, desire and effort into something that offers direction and purpose.

You’ll know when you’re getting better at strategic thinking when your first response to a situation is to ask open questions. You will start trying to take things apart that seem closed and then putting them back together. You will become more playful and creative with the combinations that you try. And you will look for more varied, eclectic, diverse inputs into your thinking process.

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