3 Key Strategic Behaviors to Apply to Your Next Decision

Posted by
May 25, 2021

Topic: Strategic Thinking

Written by Karin Blair


I have a question for you: What strategic decision are you facing? You might want to take a minute to write down your question before reading on.

Got it? Great. You have officially entered the realm of not knowing. Your strategic question is staring back at you from the page. Piercingly. Annoyingly. 

A few possible questions:

  • Should we enter the diagnostics market?
  • How should we enter that market?
  • Should we acquire this company?
  • What should our go‑to‑market strategy be for this technology?

The Difference Between Strategic Questions and Strategic Rationale

Quite possibly your question has been rattling around in the back of your head for weeks, months – even years. You recognize that coming up with the answer may be easier than clarifying the strategic rationale to support your recommendation. 

Question: Should we xxx? Yes or no. No doubt you have a hunch about the answer.

Rationale: But why should you enter the market? And when the strategic question shifts from if we should, to how we should – the complexity increases, and it can start to feel overwhelming.

You are left staring at that question without any ideas about what you should be doing to make the strategic call, or recommendation to the ultimate decision‑maker.

YOU may be thinking:

  • “Heck if I know.”
  • “I don’t know where to start.”
  • “I’m not strategic.”

For many of my clients, the strategic question is clear. It is how to go about answering it, strategically, that isn’t. 

In the realm of not‑knowing, the obstacle to the decision often has to do with a self‑identified lack: 

  • lack of skill
  • lack of knowledge
  • lack of understanding
  • lack of strategic ability

Clients feel something is missing that would enable them to make that high‑stakes call.

Recognizing Your Key Strategic Behaviors in Action

But what if you are more of a strategic thinker than you realize? What if you haven’t recognized behaviors you can leverage to help answer your strategic question?

For example, when you think about your strategic question, what variables might inform your decision? I encourage you to take a minute to reflect before reading on.

Maybe you are considering or wondering:

  • Is the market large, growing, profitable?  
  • Are we well‑positioned to serve this market? Do we have distinct capabilities?
  • Do we know enough about these customers’ needs and challenges to create a winning value proposition relative to the competition?
  • How might competitors react to our market entry?
  • What is the cost of not expanding to this new market? Is status quo an option? 

As you create your list, it is likely you are anticipating questions that your boss, executive leaders, or board of directors might ask before deciding to support your recommendation.

You are also anticipating how the future may unfold. No, really. 

Whether you realize it or not, you have specific beliefs or assumptions, that if the future played out this way, would make your recommendation brilliant! You are envisioning a future that supports your recommendation. 

The key challenge is that if . . . If the future plays out this way. The uncertainty of predicting the future can majorly derail robust strategic thinking.

The quality of strategic decisions is a function of your capacity to:

  • think strategically AND
  • effectively lead through the discomfort of complexity and uncertainty.

If you notice you are getting derailed by that second point, check out this article to help you orient in that discomfort.

Otherwise, hang with me to tap into key strategic behaviors that will enhance your thinking as you make decisions.


We all have the capacity to anticipate. To foresee, predict, or expect something in the future to happen. 

Can you think of an instance recently where you said, “I saw that coming!” Like when my son filled his glass to the rim and then spilled his drink on his way downstairs. Or when a colleague kept resetting their deliverable timelines, resulting in the whole project timeline being delayed. 

Strategic thinking ups the stakes on our ability to anticipate, no doubt – increasing the level of complexity and uncertainty we must navigate. AND, you just demonstrated that you already have a foundational ability to anticipate. Where else does this ability show up? 

Any Queen’s Gambit fans out there? Chess is the quintessential example of an ability to anticipate and then act now in a way that advantageously positions you for two, three, four competitive moves down the road. 

Our ability to anticipate only requires a curious, creative, and imaginative mind. The biggest obstacle to being good at anticipating is our desire to "get it right" – for the future to unfold just as we imagined.


This takes us to another core behavior of strategic leaders. The ability to interpret data, connect dots, make meaning. To decide what to pay attention to and what to disregard.

Ironically, another obstacle to anticipating the future appears when we unconsciously anticipate how hard it will be to interpret those variables. To create all the potential scenarios that could unfold in the future. Wait, what? I know. That was a mouthful. Let’s break it down. 

Return to your list of variables – when the creative juices get flowing, more and more variables tend to emerge. Which creates more and more dots to connect – more scenarios and potential outcomes to piece together. It is like the mind‑blowing capability of Tesla software. Artificial intelligence anticipates an unfathomable number of potential scenarios based on a seemingly infinite number of combinations and conditions for each variable.

In creating strategic futures, we anticipate this complexity and interpret its outcomes, causing our minds to shut down before we even start.

Yet we all have the capacity to interpret and make meaning of data. We do it every day. We are fundamentally wired to make meaning. If you got stuck in the “I’m not strategic” mindset, guess what: you have just demonstrated your ability to interpret.

Consider: How did you decide that you aren’t strategic? Based on what data? How are you interpreting and making meaning of various data and inputs to come to this conclusion? Would someone else have a different perspective, or would they come to a different conclusion as they interpret your data? 


In a recent coaching session, a client was firmly rooted in her belief that she was “not strategic.” By the end of our session, she was surprised to have revealed several strengths she had had all along to leverage toward amplifying her impact as a strategic leader.

I interpreted her 360 data differently and challenged her firmly held belief. She had focused on her strengths as a results leader and people leader. I focused on the abilities that made these strengths possible AND are hallmarks of a strategic leader—decisive, courage to stand alone, dealing with ambiguity, and seeing the big picture. 

Same data. Different interpretation. Different belief.

Six Behaviors of Strategic Leaders

As you look at key behaviors of strategic leaders, can you see any of these in action in your life?  Particularly those top three that you can apply to your current strategic decision.

  • Anticipate – scan the environment for signals of change
  • Challenge – question the status quo and existing paradigms and assumptions
  • Interpret – see connections and patterns and create new insights
  • Decide – evaluate options and consider trade‑offs, balancing short and long term
  • Align – achieve buy‑in among stakeholders who have disparate views and agendas
  • Learn – adapt based on dis-confirming evidence, even after a decision has been made

The specific situations in which those behaviors show up matter less right now. You may not have applied them to anything "strategic" yet. What’s important is, can you see that these behaviors are familiar to you? That you have experienced them, maybe even practiced them regularly in certain situations. 

Have I managed to challenge your assumptions and beliefs about your capabilities as a strategic leader? As you realize that you are even just 2% more strategic than you thought moments ago, what might be possible? 

Putting It Into Practice:
Applying Strategic Behaviors to Your Strategic Question

Strategy is ultimately high‑level decisions about what you will do, won’t do, and why

And, to operate strategically, you must start with the end in mind. An end, a future, that is inherently unknowable. An unavoidable truth. 

On top of that, there is no one right way to achieve your desired outcome. So, strategy is also about options and trade‑offs that help you understand and evaluate the strategic possibilities to achieve your strategic objective. 

To put those strategic behaviors in practice and make progress on your strategic question:

Step 1: Make time for strategic thinking.

Step 2: Frame options to your strategic question. 

What are you deciding between? Regarding the acquisition, three options to achieve your strategic objective might be:

  • Acquire this (or similar) company.
  • Partner with this (or similar) company. 
  • Build internal capabilities.

Step 3: Experiment with the first three strategic behaviors – Anticipate, Challenge, Interpret. 

Create a robust point of view about the future, about the market and your position in it. 

We can make thoughtful strategic choices by playing with different scenarios and beliefs about the future. Often, the most transformational strategies bet on a future few would dare to conceive. 

As you evaluate each option, consider “what would have to be true” to make this a winning strategy. Capture your assumptions. Then challenge them. Inform those scenarios with analysis. Collaborate with colleagues. Seek other interpretations of the future. And have fun, as you engage in the creative process of developing strategy and making strategic calls.

Step 4: “Learn by doing,” and adapt as you go. 

How might your assumptions and beliefs be changing as the future unfolds?

As you practice these strategic behaviors, you will strengthen your strategic thinking and your ability to bet (aka decide) on the strategic option that increases the odds of success for your business, market, and context.

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