Key Activities to Boost your Strategic Thinking Skills

Posted by
October 19, 2021

Topic: Strategic Thinking

Written by Karin Blair


Has someone ever told you to “be more strategic”? 

It can be maddening feedback, because, like strategy itself, it’s rather intangible.  

One of the more tangible expressions of strategy is the logic behind resource allocation decisions—the “why” that supports where you choose to focus and invest and, equally important, where you don’t.  If you want to “be more strategic,” a good place to start is to think more strategically about those decisions and investment recommendations. Strategic thinking informs decisive action today that creates the business of tomorrow.

Ideally, you are building a business that is built to last, sustaining growth and competitive advantage for years to come.

Unlike strategic planning that may only occur annually with limited participation, strategic thinking can occur at any time and at any level of the organization. There are many opportunities to apply strategic thinking to your day‑to‑day actions.  

What Is Strategic Thinking?

At its foundation, strategic thinking is a particular lens or mindset with which to view the business and decisions you face each day. Decisions on where to focus and how to effectively allocate limited resources:

  • through a unique set of activities 
  • to outperform the competition 
  • in serving targeted customer needs (of today AND tomorrow). 

The quality of those decisions is directly linked to the quality of your strategic thinking.  

Strategic thinking involves generating and applying strategic insights to sustain competitive advantage.  

Strategic insights are new ideas or perspectives that combine two or more pieces of information (aka synthesis) to positively affect the strategic position, and growth, of the business. The more distinct the insight, the more opportunity for competitive advantage.  And the greater the risk. Because fewer people see the opportunity or possibility that you see.  

Which means you are either a genius or a fool!

Strategic Thinking Activities—What Should I Be Thinking About?

Strategic thinking involves seeing the world as it is, and as it could be. There’s no formula for strategic thinking. No predictable process to derive strategic insights.  Generating insights is a creative process, and you will need to accept the unsettling feelings associated with not being able to control when these insights emerge.  

The quality of strategic thinking ranges from brilliant to nonexistence, and it is easiest to recognize in these two extremes:

  • No sense of direction, and no sense of the longer‑term or the broader context of decisions; or
  • Disruptive, revolutionary, and mind‑blowing—“Why didn’t I see that?”  

We can strengthen our strategic thinking by practicing repeatable activities that lay the foundation for strategic insights. The next time you take some time to think strategically, grab a verb from the list below and see where it takes you.

1. Scan. Explore your external and internal landscape to identify shifts underway and see an issue or opportunity through a broader perspective. Practice observing and noticing what is true of your capabilities, customers, competitors, markets. 

    • What are the key trends and patterns in the broad market landscape?
    • How are industry and competitive dynamics evolving?
    • How is the basis of competition shifting?
    • How are customers’ needs and consumption patterns evolving?
    • Who (or what) is positioned to disrupt the industry?

2. Discern. As you scan your context, the sheer volume and complexity can be overwhelming. You must find the signal in all that noise and discern what matters most to the future of your business. Of all that data, what is relevant to inform your strategic decisions? The answer usually emerges over time with reflection and rumination.

    • What are the priority threats and opportunities before us?
    • What requires a strategic response (in essence, a shift in how you may be allocating those limited resources to continually create advantage)?

3. Interpret. This activity is where you make meaning of all that data. Where you make connections, identify patterns, and see how multiple variables can, or do, interrelate.  Your job is to see the same data available to your competitors in new and distinct ways.

      For example:
    • What you choose to focus on or discard
    • What meaning you make of it—for example, what you assess as opportunity or threat 
    • How you make connections across seemingly disconnected dots—particularly in ways others fail to see   

Interpreting is the least predictable or controllable of these activities, but a tangible action is spending time considering the various ways you can see and make meaning of the same data differently. Like looking through a kaleidoscope and seeing a seemingly infinite number of patterns being created from a fixed set of colorful objects. Or to use another metaphor to make this abstract activity just a little more tangible: How many different meals can you make from the same base ingredients?  

4. Challenge. Strategic thinking demands that you consider all assumptions, beliefs, and information from a fresh perspective. Like the way Cirque du Soleil challenged what it means to be a circus. A circus without animals was unheard of at one time. And at one time, a mobile phone was unimaginable.

To experiment here, plan a meeting with your team where you challenge three to five beliefs you hold to be true. For example, "Our company cannot deliver customized solutions cost‑effectively."

    • Where do we find ourselves saying, “that’s just the way it is?”
    • What do we believe to be true, and how might it not be?
    • What could be possible if that weren’t “just the way it is?”
    • What would have to be true to make the impossible possible?

5. Envision. This strategic thinking practice involves spending time walking around in the future. Stretch your imagination and play around with different scenarios.

    • What do you anticipate will be true about your customers and competitors?  For example, how will the practice of medicine change?  
    • How will market dynamics be different than today?
    • What will be possible that isn’t today?

6. Ideate. This is time spent creating new possibilities—possibilities that may become requirements to be well‑positioned in the future you envision. It often involves brainstorming new ways of …. [fill in the blank]:

    • Creating value for your customers (through products, services experiences)
    • Creating advantage relative to the competition
    • Making an operational process more scalable 

7. Frame Your Options. The ultimate impact of strategic thinking appears in your decisions.  Decisions that involve trade‑offs—in terms of where you will or won’t focus resources. Spend time framing trade‑offs into different options to help you think through the supporting logic and beliefs behind your ultimate recommendation or decision.

    • What do I lose and what do I gain in these different options? For example, an option that optimizes for speed versus another that optimizes for quality.
    • What are my driving beliefs and assumptions that make this the right trade‑off for my current context?
Keep in mind, trade‑offs should be equally viable alternatives. The decision will be uncomfortable as you cut off certain possibilities in favor of others. I used to say to my team, if the decision was easy, it didn’t belong in the room with us.    

Each of these activities represents a point of entry or focus for your time to think.  A mix of time spent seeing what is (from as many perspectives as possible) and creating what could be. These activities are interrelated, and as you practice them, you will strengthen your ability to generate high‑impact strategic insights.  

And remember: The more your strategy is based on data and trends in plain sight, the less unique it will be. The most valuable insights are new and distinct and lead to a highly differentiated strategy required to gain competitive advantage. The deeper the insight, the higher the impact. 

Working Through the Practice of Strategic Thinking

Mastery is built through practice and experimentation.  

The quality and impact of your insights will increase over time. The first step is to increase the frequency of time spent thinking strategically and creating the conditions for strategic insights. Steep yourself in data, look at things from multiple perspectives, challenge conventional wisdom, and play around with options for the future. 

Don’t be surprised if some resistance or discomfort arises—keep going. Remember that fine line between genius and fool: The deeper the insight, the higher the impact AND the higher the risk. 

In game‑changing strategic leadership, risk is unavoidable. And the risk is well worth the reward. 

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