Short-Sighted Strategy: The Truth

Hi friends,

What does “strategic thinking” mean to you?

This question might sound straightforward, but here's a little fill-in-the-blanks exercise:

“Strategic thinking is a ____-term thought process to achieve ______. It means having the capacity to anticipate, prepare for possibilities, and position yourself to succeed in the future.”

The first blank is easy enough to fill—we all associate strategy with big, long-term thinking. But what about the second blank? What did you fill it with? 

“A successful product?”

“Annual targets?” 

“Quarterly goals?”

I ask because it’s always good to stop and reflect. Even when we aim to think far ahead, it’s often possible to be short-sighted when it comes to strategy. 

I’ll explain.

Strategy vs. Planning

As leaders, many of us are under continued pressure to deliver measurable results.

You may have felt like you’ve wasted time, walking away from a dedicated strategy session without a foolproof blueprint for success. Or actionable steps to take your team toward a tangible outcome.

Subconsciously, that’s the mindset that sometimes leads us to fall short of our full capabilities:

Instead of truly strategizing for what we could truly accomplish, we end up simply “planning” for what we know we can achieve.

Does it sound familiar?

Here are a few well-known examples illustrating the different outcomes you get from “strategizing” for the future and “planning” based on what may have worked previously. 

I’m sure some of these will ring a bell:

• Blockbuster vs. Streaming Services: Remember when Blockbuster was the video rental industry giant? Then they failed to foresee (or chose not to act on) the disruptive potential of streaming. While they were doubling down on physical stores, Netflix was busy positioning itself as the future of entertainment. That’s how Blockbuster became a relic, while Netflix became our go-to for nightly viewing.
• Kodak’s Reluctance to Go Digital: Another frequently brought-up example is Kodak. Did you know they actually invented the digital camera, but feared it would cannibalize their highly profitable film business? So they opted to stick with their traditional model instead of embracing digital technology. By the time they pivoted, it was too late—the market had moved on, and Kodak had lost its edge.

These are classic examples of strategic short-sightedness: companies that shied away from risk and uncertainty, opting instead for what felt like a safer, more predictable path. 

But as we’ve seen, strategy isn’t about staying comfortable; it’s about preparing for change, even when the future is murky.

Understanding Strategic Short-Sightedness

To keep it short and sweet, strategic short-sightedness is when leaders choose certainty over possibility, falling back on tried-and-true methods rather than exploring new avenues. 

It’s an approach that leans into the familiar, thus avoiding (or procrastinating!) the discomfort of the unknown. It’s essentially an excuse to keep doing the same thing, but it gives us some temporary peace of mind—we “have a plan!”

To genuinely strategize, you need to:

• Acknowledge that there will always be unknowns. 
• Be willing to evaluate problems, consider opportunities, and make collectively intelligent decisions that serve long-term goals. 
• Accept that there are no guarantees, and not every idea will pan out, but still
• Be ready to take thoughtful risks. 

Avoiding Short-Sighted Strategy

Because many executives quickly appreciate this distinction, our workshops mainly focus on the next step: cultivating openness to risk and a clear long-term focus. 

Our workshop exercises are based on best practices that you, too, can try to emulate:

1. Divorce Perfectionism from Strategy

It’s easy to fall into the trap of aiming for the “perfect” solution that pleases everyone, but the reality is, that’s rarely possible.

Some might argue that this perfection is a form of procrastination—a distraction from real strategy, and a sophisticated way to avoid facing the discomfort of possible failure. So we create more easily achievable plans, instead.

DON’T: Aim to strategize for an “ideal solution”

DO: Docus on solving a critical problem extremely well for your target market. 

Just An Example… Identify the smallest viable market you aim to serve and home in on a specific need you can solve for them. Truly empathize with them, let their needs guide your strategy, and don’t waste time trying to make a one-size-fits-all solution. Trust that as your initial solution gains traction, you can always expand from there.

2. Embrace Adaptive Planning

The most successful leaders understand that while they can set a direction, they must stay adaptable along the way. They are not scared of periodically revisiting and adjusting their strategy based on evolving circumstances, new insights, and shifting goals.

DON’T: Aim for a rigid X-year or X-month plan by default. 

DO: Take inspiration from companies that pivoted successfully. 

Just An Example… Look at Instagram, for instance. They began as a check-in app before realizing their users were more interested in photo-sharing. By being open to change, they adapted and ultimately thrived in a highly competitive social media landscape. 

3. Build a Culture of Experimentation

Strategic thinking isn’t just about executives making plans in a boardroom; it’s about cultivating a culture where new ideas are welcomed and tested regularly. Encourage your whole team to think creatively and embrace experimentation, and try to involve as many diverse insights as possible to feed into your strategizing sessions.

This allows for small, manageable risks that can offer big insights.

DON’T: Think of your strategy sessions as “leaders only” spaces.

DO: Create systems by which all members can contribute their thoughts and ideas. Experiment with inclusive strategizing sessions to involve everyone in forward thinking!

Just An Example… Implement low-stakes experiments or prototype programs to test new ideas on a small scale before committing fully. These “safe” experiments can yield data and insights that inform larger strategic shifts over time, without the need for immediate, sweeping changes.

Over to You

It’s easy to distinguish between quick wins, immediate gains, and long-term goals in theory. 

The real challenge is staying vigilant about your daily decisions and attitude, and noticing when your mindet “slips” into easy shortcuts or ingrained unhelpful patterns. 

I suggest quickly looking at your current strategy now. Ask yourself these questions while the concepts are still fresh in mind:

• How much of your strategy is focused on immediate gains? How much considers where your organization COULD be in a realistic future?
• What “safe” plans do you have that might be stifling innovation? What plans might leave your organization vulnerable to disruption?
• How can you encourage experimentation in your team and promote risk-taking at a small, manageable scale?
• When was the last time you adjusted your strategy based on new insights? Could it be time for a reassessment?

I’m curious to hear any thoughts these questions trigger. Shoot me a DM and let’s chat about them!

— Govert