You Can Be a More Strategic Thinker, Starting Right Now

Here’s what I learned in my time as a chief strategy officer

Shane Kinkennon
Jul 14, 2020 · 5 min read
Photo purchased on Shutterstock

Just about everyone could benefit from taking a moment to think big picture when making daily choices that are rarely as inconsequential as they seem. And there’s no doubt that most employers would benefit if their people practiced a little more of this kind of thinking. Strategic thinking.

So what do you do? In fact, opportunities are all around. Think about your work. Perhaps there is a program offering with shrinking margins, a customer experience that’s clunky, an internal process that’s been outgrown, or simply a low-value group habit that has hardened over time. Any of those might benefit from questions like:

  • What ultimate aim is this serving?
  • To what degree is it effective?
  • How does it advance goals we’ve agreed to?
  • Is it causing any unwanted side results?
  • Might there be a better / more efficient / more elegant / more lucrative way?

To pose these kinds of questions and see them honestly explored, while (at least temporarily) withholding fear of change, is to think strategically. And the behavior is available to people at every level of your organization. Most executive leaders could stand to do more of it. In a study by the Strategic Thinking Institute, described by Ron Carucci in this article in Forbes, a whopping 96% of leaders say they lack time to think strategically.

Yet thinking strategically is in no way the sole responsibility of people in leadership roles. Managers and others who are closer to the front lines often are in an optimal position to spot the possibility of a better way.

But how exactly do you put strategic thinking into daily practice? I spent time as a chief strategy officer for a diverse global business. Here’s what I learned:

1. Ask little-kid questions. Take a lesson in unadulterated curiosity from children. Be the person on your team who asks, “Why?” Or “How do we know?” Or “Why not?” Ask such questions as ideas gain traction, and ask them about things that are long established. You don’t need to sound lawyerly or be negative. Ask with respectful curiosity and be genuinely eager to see where the conversation goes. Nina Bowman in Harvard Business Review writes, “Questions are the language of strategy.” Strategic conversations are begun by people who are willing to leave no question unasked.

2. Seek patterns. Pursue and find what might be revealed in data and trends, both internal and market-wide. Key relevant insights can lurk in all manner of performance indicators — think utilization rates, engagement levels, average donor contribution, or average order value. Or they are available for detection out on the marketplace horizon. Paul Schoemaker advises , “Look for game-changing information at the periphery of your industry.” Data-born insights and trends don’t often hold the complete answer to strategic questions. But they tend to serve as terrific clues.

3. Think in terms of dominoes . When approaching a decision, take the time to game out all that might result from it, including well down the road. Might a product-feature adjustment that seems straightforward and opportune today set in motion a customer expectations that in time would be difficult to meet? You need not become preoccupied with what could go wrong, necessarily. And no one has a crystal ball. You just want to contribute to a sense of confidence that the possible implications of today’s choice are understood and accounted for as best as they can be.

4. Keep your eye on what could be. Be optimistic that ideas that seem farfetched today may well be feasible three years from now. So, indulge in ideas. Challenge yourself and others with questions like, “What’s the most creative thing we could possibly do in this moment?” Embolden yourself by opting for confidence that your team is responsive, innovative and capable. Practice the mindset and repeat the behavior as often as you can. Plant the seeds of routine strategic inquiry.

5. Be an ambassador for strategy. Raise your hand to share the news of strategic direction shifts. Take some responsibility for interpreting what strategy means for your team’s or department’s work. Be the individual who constantly reminds others around you of strategic decisions made. Be generous in helping others see how their responsibilities or projects might be shaped by such decisions. Help managers and frontline workers think through and articulate how their work might adapt based on new strategic change.

Two more insights

I learned that most of the above behaviors require suspending the fear of change that we all share to some degree. Or at least trying. Unacknowledged distaste for change is a real obstacle to thinking big. So if you’re someone who is made uneasy by the thought of change, try practicing simply suspending it from time to time. First on small things in your daily work, and then on larger things. By and by, it’ll open the gate to strategic thinking more routinely.

Another thing I learned: when the strategy-setting is done, put yourself in the thick of interpreting the strategy, facilitating aligned action, and executing in a way that is on point. As everyone who reads business books knows, strategy is ultimately only as good as its follow-through implementation. And you can learn a lot about strategic thinking by getting your hands dirty in the execution of big ideas.

Terina Allen puts it this way in Forbes: “Strategic leadership is what happens when leaders move beyond the role of having and communicating a vision to fully understanding, thinking about, planning and executing the necessary strategies to realize it.”

Let go of the idea that strategic thinking is someone else’s job. It needs more good people! People like you. There’s a good chance you’re more capable and ready than you think.

Originally published at on July 14, 2020.

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Shane Kinkennon

Written by

Plan | Lead. I help senior execs make plans and lead accordingly.

The Startup

Get smarter at building your thing. Follow to join The Startup’s +8 million monthly readers & +724K followers.

Shane Kinkennon

Written by

Plan | Lead. I help senior execs make plans and lead accordingly.

The Startup

Get smarter at building your thing. Follow to join The Startup’s +8 million monthly readers & +724K followers.

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