The Strategic Thinker-Leader

by Ami Nahshon 

The Thinker PicFor those who read my recent piece titled “5 Reasons Why ‘Strategic Doing’ Beats Strategic Planning”, 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 a creative art and less a science, despite what the bean-counters and McConsultants would have you believe.

Like other creative arts, great strategy springs from inspiration. And inspiration comes in its own good time rather than during scheduled meetings: while we’re arguing with a friend, thinking about a problem, noticing something we missed before, sometimes even when we sleep. (OK, maybe that last one is just me…)

And, perhaps more to the point, strategy isn’t a thing, a plan, a committee, 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 to 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 definitive answers, sorry to disappoint. Then again, maybe great strategy is like pornography: you know it when you see it, to paraphrase the late Justice Potter Stewart. But let me nonetheless share a few observations from my years in the trenches about the what and how of strategy.

If, as I would argue, strategy is nothing more than an organized way of thinking about change, then “doing strategy” should be built on a sequence of cognitive steps. A disciplined intellectual approach to transforming what is to what could be. A reasoning process built on a clear and compelling end-state vision.

So what’s it look like, that disciplined and orderly thought experiment that I call strategy? Like any other disciplined intellectual process, strategic thinking is built around a sequence of questions that, for purposes of this discussion, I’ll group into four:

  • QUESTION 1: What is your end-state vision? How do you imagine that one 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 8-year-old? (If not, go back to the beginning and start again.)
  • QUESTION 2: What needs to change in order to get from here to there, to transform that specific piece of the here-and-now world into your desired end-state? And 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?)
  • QUESTION 3: What are the tools/resources/knowledge you’ll 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, more challenging and interesting, for how to rearrange, redeploy or reprioritize existing assets to bring about the desired change?
  • QUESTION 4: What’s your change management action plan that describes in detail the ‘what, how, where and when’ of planning and executing the initial steps toward achieving your end-state vision? Why focus on initial steps? 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 will have the humility to acknowledge that fact and the tools and creativity to lead and manage in a fluid environment.

“Of course,” say 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’ maybe 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 herein lies the art. Every winning strategy – and, for that matter, every successful organization – is built on the ability of leaders to respond adaptively and creatively to change. And 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. For more information, contact him at



About Ami Nahshon

Ami serves as principal consultant and managing director of Ami Nahshon Strategic Consulting, working with nonprofits, foundations, social businesses and their leaders to optimize organizational strategy and performance.
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