Winning the Long Game: Developing a Strategy Mindset

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This article was originally published in Real Leaders magazine.

Winston Churchill famously said, “It’s always wise to look ahead… but difficult to look further than you can see.”

Difficult? Yes. But even in times of disruption, uncertainty, and challenge it is undeniably possible to see the future…or more accurately, the “futures.” I’m not talking about an apocryphal, crystal ball vision of the future, or even a linear prediction model, but rather the type of strategic foresight that gives a glimpse into what could be so that companies and their leaders are better prepared to respond to and/or shape the future.

This kind of foresight, gained through structured methodologies like scenario planning, requires a strategy mindset – a belief that optimism, integrated and holistic thinking, peripheral vision, outside-in analysis, and team alignment creates exponential opportunity – and thus, it’s worth the effort.

Why is a Strategy Mindset so Important?
Leaders with a strategy mindset believe they have agency over the future despite, or maybe even because of, all of the ambiguity they face. They see around corners. They see possibilities and choices where others see problems and constraints. They place smart bets when others are fighting, flighting, or stalling.

To manage the influx of disruption, seize opportunities, and even create the next unicorn, executives need to systematically expand the boundaries of their understanding, gather more insight, and ultimately synthesize faster so they can integrate risks and opportunities into courageous strategies. Of course, they need to do all of this while making smart short-term and operational choices.

A strategy mindset starts with asking the right questions:

  • In what multiple ways could the future unfold?
  • Which forces are in our control and which are not?
  • What is the full range of choices our company faces?

Rather than driving immediate and actionable solutions, addressing these questions sparks depth, exploration, strategic dialogue, and transformative thinking. It demands that leaders flex a different set of muscles than they are used to.

That’s why strategy today is more than a skillset. Strategy is a mindset – a set of beliefs about how to find and execute on opportunities, supported by a way of being that enables expansiveness, accountability, and engagement.

The 5 Elements of a Strategy Mindset

Often when a leader achieves short-term results repeatedly, they balk against long-term planning. Why fix it if it isn’t broken? A strategy mindset doesn’t negate the need for both nimble thinking and focusing on this quarter’s results…it simply enhances your ability to approach all planning with a more strategic lens. Understanding the five key elements is the first step in being able to nurture and adopt a strategy mindset.

  1. Taking the long view – While the past offers critical lessons and the present is where decisions get made, a long-term future orientation opens up choice and possibility because it is unimpeded by all of the limitations of the present reality. In making decisions, do you start from the unconstrained opportunities the future offers and work backward to determine your choices or begin with a more confined and “realistic” set of options?
  2. Starting from the context – Outside-in thinkers look for opportunities and threats in the contextual environment (social, technological, political, economical, and increasingly epidemiological forces), before narrowing in on the decisions they do control. Do you systematically consider the impact of forces you don’t control or focus more directly on those forces you do control?
  3. Challenging the conventional wisdom – Long-established, familiar ideas and routines breed predictability, certainty, and often times unrivaled rigidity. They are the enemy of innovation and disruption unless they are challenged by multiple competing plausible scenarios. Do you depend on an implicit understanding of your core business assumptions or do you explicitly surface and interrogate the assumptions to determine which ones are based on habits and which are well-grounded?
  4. Making sense through synthesis – There’s generally more data, information, and insight to process than time available to interpret or act on it. This creates a need to separate the signal from the noise in order to rapidly infuse a broad range of information without ignoring key information. Do you rely on a small set of credible and dependable sources to inform your view or do you systematically scan, synthesize, and process information from a broad array of inputs?
  5. Being purposefully optimistic – Positivity and an optimistic outlook transform challenges into opportunities and victims into responsible leaders. It is the foundation of a solution orientation, offering a wide range of viable and attractive choices. Are you generally focused on risks, concerns, and the threat of loss or opportunities, upside, and potential wins?

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The idea of a strategy mindset is easily understood but learning how to cultivate one is the journey all great leaders must go on. Take this short quiz and instantly get feedback on what kind of mindset you currently have and how to nurture it for best results.

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