On Learning Strategic Thinking

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Some people, it seems, just “get it” better and faster than other people. They understand how what other people do influences their options, they consider what incentives are at work in complex situations, and they think through the possible consequences—intended or unintended—of numerous scenarios. 

They think critically. They challenge assumptions, including their own. They do all of these types of thinking, which roughly fall under the umbrella of “strategic thinking.” 

These strategic thinkers, we hope, are among those leading our organizations. 

We hope that leaders think strategically because our world is continually changing. Many argue that the pace of change continues to accelerate, and increasingly rapid technological innovation combined with globalization suggest that this is the case. 

We need leaders who think strategically because the success of their organizations in the long term depends upon it. 

Therefore, many are investing in developing the capacity for strategic thinking within their organizations. They wonder, with good reason, whether people can actually learn strategic thinking. Because if people can learn it, we might be able to teach it. If we can teach it or otherwise reliably encourage its use, our organizations should benefit. 

But first, what is strategic thinking? Numerous books and articles have explored this question, and reviewing all of them is well beyond the scope of what I’m trying to do here. Suffice it to say, however, that Jeanne Liedtka (a strategy professor at the University of Virginia’s Darden School of Business) put it well in her 1998 paper in the journal Long Range Planning

Although published a few decades ago, Liedtka identified what I think are likely five still-relevant elements of strategic thinking. At the risk of over-simplification, here they are, summarized:

  • A systems perspective—including figuring out how your organization creates value and identifying its stakeholders and how it “fits” into its ecosystem. 
  • A focus on intent. This means that strategic thinking is about finding a direction for your organization and concentrating energy toward an objective. 
  • An openness to emergent, creative options. This involves people being open to change, and having the ability to adapt to changing circumstances, taking opportunities when they arise. 
  • An understanding of the gap (and sometimes, the chasm) that separates where the organization is now and where it should go in the future. This involves a deep consideration of the organization’s capabilities and capacity, which implies connecting the past, present, and future state. 
  • An ability to make educated guesses and test assumptions. This requires leaders to balancing creativity with risk as they iterate their way ahead. 

Liedtka also makes the point that strategic thinking isn’t as much about knowing as it is about learning. And that, to me, is a central point. If an organization is to help its people be better strategic thinkers, it must encourage the mindset that comes with learning. 

Such a mindset involves curiosity and wonder. It involves candid, tough conversations in which people must feel free to challenge each other. It involves poking holes in what we think is true, what we think must be the answer. It involves gathering data about other people’s perspectives, in particular about your customers, your stakeholders, your adversaries. And it involves risk-taking, experimentation, and reflection to identify lessons learned. 

So how do you get people to do that? 

In my experience, one way is through intense, facilitated experiences that force people to practice it. 

And I’ve been fortunate to have had two recent experiences that were designed specifically with this goal in mind. 

Both of these experiences were with the U.S. military. 

The first was the Human Resources Advanced Course at the Naval Postgraduate School’s Human Resources Center of Excellence. It’s a two-week course for senior officers in the U.S. Navy’s Human Resources (HR) Community, which comprises about 850 total officers—both active duty and reserve. I’ve been a reserve officer in the community since 2010. 

A large part of the course was about knowledge acquisition. There’s always more to know about how the U.S. Navy recruits, trains, and manages its people. 

But another large part of the course was about strategic thinking. And the approach taken by our facilitators was to encourage us to think creatively about the future of our collective role as HR officers in the U.S. Navy. 

Specifically, we did this as part of a “design thinking challenge.” 

Guided by facilitators, we worked in small groups to iterate our way toward a better understanding of how we could add value to our “customers” whom we serve in the rest of the Navy. 

This project, in my opinion, was the most important part of the course. It forced us to think beyond our community (think of this as a large department, business unit, or function in a civilian organization) and to explore how we can best serve the rest of the organization now and in the future. It allowed us to frame what we do from the perspective of those whom we serve. Although difficult and frustrating at times—because it’s so different from how we normally think and act—this is exactly the type of creativity and strategic focus that’s needed for an organization of any type to stay relevant. 

And it requires a mindset in which we're helping to create the future, not simply reacting to it. That’s strategic. It also requires people to become comfortable with ambiguity, because you really don’t know where you’re headed until you get there.

There’s an old joke that gets at this to some degree. 

Question: How many designers does it take to change a light bulb? 

Answer: Does it need to be a light bulb?

Design thinking, like strategic thinking, isn’t new. But it’s useful because it forces you to think about things from new perspectives and iterate toward solutions that truly help your customer. Instead of pushing your solutions onto the rest of the organization or onto your external stakeholders, you’re involving them as much as possible in the co-creation of it. 

Imagine if your HR or finance and accounting departments (or any function, for that matter) did more of that, or something closer to it. 

The second military experience that I recently had that forced us to think strategically was the Reserve Component National Security Course, hosted by National Defense University. 

This course, which was also two weeks long, included participants from the reserve components of every U.S. military branch along with the National Guard. We also had a few international military officers and a few U.S. government civilians who participated. 

The way in which this experience fostered strategic thinking was two-fold:

First, we listened to numerous scholars give lectures on wide range of topics relevant to national security, followed by facilitated discussion in small seminar groups. This forced all of us to think about new topics and debate new ideas, which encourages strategic thinking by widening the spectrum of angles from which to consider a central topic—in this case, the national security of the United States. 

Second, we analyzed, debated, and eventually presented our solutions regarding a simulated crisis. This forced us to integrate parts of what we had learned while critically evaluating information, wrestling with ambiguity, and making sense of conflicting priorities and interests. 

It was tiring. It wasn’t always pleasant—in the moment. But learning often isn’t easy. It requires effort and concentration. And at the same time, due to their relevance and the necessity of developing strategic thinking, these courses were extraordinarily useful and valuable. 

So, how can organizations encourage strategic thinking and build the capacity for it among their people? 

I think the answer is similar to what Morgan McCall (a professor of management at the University of Southern California’s Marshall School of Business) wrote about leadership development. 

Namely, leaders develop through experience. 

To the extent that strategic thinking can be taught—be it in the military or in civilian organizations—it is likely to happen through experiences. 

Those experiences can be like the ones that I went through, ones that force people to design solutions or potential courses of action. Ideally, they could be integrated into how an organization goes about developing its talent overall. For example, an organization might include elements of design thinking, scenario planning, and other elements of strategic thinking into its formal leadership development programs.

Beyond those formal programs, however, strategic thinking is probably more likely to thrive in organizations that value it, which is easier said than done. Think about your norms:

Are people rewarded for voicing contradictory ideas? 

What happens when people fail while trying something new—are they applauded for learning or scolded for failing?

What happens when, in meetings, someone challenges assumptions or deeply held organizational “dogma?”

Overall, I think, learning strategic thinking might best be done through facilitated, focused experiences that teach ways of thinking and acting that are then actually rewarded in the larger organization. 

Without both of those components—facilitated experiences and a conducive culture and climate— it seems unlikely that people will learn how to think strategically.  


About Ben Baran
Ben Baran, Ph.D., is probably one of the few people in the world who is equally comfortable in a university classroom, a corporate boardroom and in full body armor carrying a U.S. government-issued M4 assault rifle. Visit: www.benbaran.com.

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