The Strategic Thinker-Leader

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By: Ami Nahshon

For those who read my “5 Reasons Why ‘Strategic Doing’ Beats Strategic Planning” post, it will come as no surprise that I spend a fair amount of time thinking about, critiquing, and doing strategy. Truth be told, strategy is a bit of an obsession for me, more creative art and less a science, despite what the bean-counters and McConsultants would have you believe.

Like other creative arts, truly great strategy is the product of inspiration. And inspiration comes to us in its own good time rather than during scheduled meetings: while we’re arguing with a friend, thinking about a problem, noticing something we’d missed before, even while we sleep. (Okay, maybe that’s just me…)

More to the point, strategy isn’t a thing, a plan, a committee, or a document. It’s a way of thinking about change — a way of imagining that demands action. Because, at the end of the day, strategy is nothing more than a language for translating ideas into outcomes.

So what makes for great strategy, and how do you get there? When do you know you’ve nailed it? And, perhaps most challenging, can the art of strategy be taught? I don’t have the definitive answers to those questions. Maybe great strategy is like pornography: you know it when you see it, to paraphrase the late Justice Potter Stewart. That said, allow me to share a few observations from my years in the trenches about the what and how of strategy.

If strategy is nothing more than an organized way of thinking about change, then “doing strategy” should be built through a sequence of cognitive steps — a disciplined intellectual process that transforms what is to what could be and leads to a clear, compelling end-state vision.

So what does that disciplined and orderly thought experiment I call strategy look like? Like any other disciplined intellectual process, strategic thinking is built around a sequence of questions:1. What is your end-state vision? How do you imagine your particular corner of the world looking different than it does today? Can you formulate a clear and actionable vision that is neither so broad as to be unhelpful nor so narrow as to blur the distinction between ends and means? Does the vision have sufficient power to inspire and activate those both within and outside the organization to think big, do big, and invest big? And, no less important, can you make the vision understandable to an average eight-year-old? (If not, go back to the beginning and start again.)

2. What needs to change in order to get from here to there and transform that concrete piece of the here-and-now world into your desired end-state? What’s the logical construct — the change architecture, the rationale — behind how you intend to achieve that changed state? What are the relevant levers of power — institutions, people, policies, resources — and how will you rearrange and manipulate them in order to achieve your desired end-state? (In today’s lexicon, what’s your theory of change?)

3. What tools/resources/knowledge will you need to engineer the desired change, both those currently available to you and those required? What’s your plan for how to acquire the missing pieces or, perhaps more challenging and interesting, how to rearrange, redeploy, or re-prioritize those pieces to bring about the desired change?

4. Does your change management action plan describe in detail the “what, how, where, and when” of planning and executing the initial steps toward achieving your end-state vision? And why focus on initial steps? Answer: because unlike conventional strategic planning that purports to anticipate every step from beginning to end, real-world change dynamics are fluid and often unpredictable, and the strategic thinker-leader must have the humility to acknowledge that fact, not to mention the creativity to lead and manage in such an environment.

“Of course,” write Loch and Kavadias in the European Business Review (January 19, 2015), “senior managers need to plan, but they also need to realize that large pieces of ‘the plan’ may be no more than hypothesis. Evolving the strategy is a journey where planning helps you to diagnose where you are and to understand the direction of travel, but it is not an ‘optimized planned change’….

“When you look at the strategy journey through this lens, the cauldron…suddenly changes from a hard-to-control mess to a great opportunity to generate the inputs for good strategic decisions.”

And therein lies the art. Every winning strategy — and, for that matter, every successful organization — is built on the ability of its leaders to respond adaptively and creatively to change. That is precisely why strategic thinking and leading is the sine qua non of effective executives, and why those organizations led by people who embrace the “hard-to-control mess” as opportunity will come out ahead every time.

So, can the art of strategic thinking-leading be taught? My answer is an unequivocal “maybe.” But cultivating the ability to imagine alternative futures, to think big, to never be fully satisfied with “what is” certainly constitute a good place to start.

Ami Nahshon offers a portfolio of coaching and consulting services to help nonprofits and their leaders optimize philanthropic mission, strategy, and performance. In his last post, he wrote about the empowered leader. For more information, contact him at

Author: Ami Nahshon

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