How to Improve Your Strategic Thinking

One of the many challenges for large, publicly traded companies is that they tend to run their businesses on a quarterly basis. They, of course, will deny this forever, but for many publicly traded companies, the most important quarter in the history of the company is whatever quarter they are currently in.

They have to “make the numbers,” or Wall Street will crush them.

That causes them to jettison a lot of long-term strategies in favor of short-term programs designed to achieve whatever quarterly results they had committed to achieving.

Surprisingly, the need for short-term programs at the end of a quarter most often comes from flawed long-term strategies developed earlier in the year. And better long-term strategies can only come from better strategic thinking.

Strategic thinking can be defined as the ability to analyze complex situations, anticipate future challenges and opportunities, and develop long-term plans to achieve specific goals. It involves a combination of critical thinking, problem-solving, and vision casting to make informed decisions that align with broader, long-term objectives.

Key elements of strategic thinking include:

Vision-Oriented – Focusing on long-term outcomes rather than just immediate problems.

Systems Thinking – Understanding how different elements interact within a larger system.

Analytical and Creative Thinking – Using data-driven insights while also considering innovative approaches.

Proactive Approach – Anticipating risks and opportunities before they arise.

Decision-Making Under Uncertainty – Navigating ambiguity with calculated risks.

Strategic thinking is a must for leaders, businesses, and even individuals who want to remain competitive, adaptable, and successful in achieving their objectives.

Leaders can improve their strategic thinking by developing a mindset that balances big-picture vision with practical execution. Here are key ways you can enhance your own strategic thinking.

1. Expand Your Perspective

Stay informed about industry trends, global developments, and emerging technologies.

Read widely—books, reports, and case studies—to gain diverse insights.

Engage with people outside your immediate industry to understand different viewpoints.

2. Ask Better Questions

Challenge assumptions by asking, “What if?” and “Why not?”

Use first-principles thinking to break down complex problems.

Regularly reflect on long-term goals and whether current actions align with them.

3. Develop Pattern Recognition

Analyze past successes and failures to identify trends.

Observe competitors and market shifts for early signals of change.

Use scenario planning to prepare for multiple possible futures.

4. Think in Systems, Not Silos

Understand how different parts of your organization interact.

Recognize bottlenecks, dependencies, and leverage points for impact.

Align resources and efforts to maximize synergy.

5. Make Time for Strategic Thinking

Block out time for deep thinking, away from daily firefighting.

Engage in brainstorming sessions with your team to explore long-term strategies.

Schedule regular reflection periods to assess progress and refine strategies.

6. Test and Iterate

Implement small-scale experiments to validate strategic decisions.

Use feedback loops to adjust course quickly.

Balance bold vision with flexibility to adapt to new realities.

7. Develop Decision-Making Discipline

Avoid analysis paralysis—focus on key priorities and take calculated risks.

Use data-driven decision-making while keeping intuition in check.

Learn from past decisions to refine future strategies.

All of this takes time. That’s where your mindset comes in. If you consider it a waste of time to block time on your calendar to think, then it’s unlikely you’ll do much, if any, of this. You will instead constantly be congratulating yourself for putting out one fire after another. If your mindset tells you that setting aside time to think and plan is a great investment of time, then you’ll likely prevent the fire in the first place.

Imagine what you can accomplish in the time you would have been firefighting. Whatever those accomplishments might be, I’ll bet they won’t include scrambling to achieve some goal at the end of a quarter or the end of a year. Because those goals will have already been met.

That’s a whole lot more productive and a whole lot less stressful way to lead an organization. But of course, as always, it’s your choice to make.

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Thinking Strategically

I’ve always found thinking to be a good thing to do. That’s especially true before you say something. Our thoughts create our words and our words frequently become our actions. We need to think about that in particular. 

But I sometimes think that “overthinking” causes as many problems as not thinking. Different problems for sure but problems all the same. I often marvel as I watch people prepare a presentation. They think and rethink every word as they put it in their PowerPoint. I’ve seen people make literally dozens and dozens of changes to the wording on their slides. All the while giving almost no thought as to how they were going to say those words. 

They fail to realize that when it comes to presenting effectively how you say something is roughly 5 times more important than the something you say. Overthinking tends to paralyze us. It prevents us from taking action until everything is perfect and since everything is rarely perfect… you see what I mean. 

But there is also what I would call an elevated level of thinking. This is the level we want to strive for when thinking about the big stuff in our lives and careers. It’s known as Strategic Thinking.

Thinking strategically involves adopting a holistic and long-term perspective to make informed decisions that align with your goals and objectives. I hope you paid attention to that previous sentence. If you did then you understand that absent goals and objectives there will be no strategic thinking either. So if you have no goals and objectives for your life, or you have no interest in developing any, you can quit reading now. But if you are goal oriented then here are some ideas to help you think more strategically. 

While we are looking at strategic thinking in terms of business in this particular post understand that thinking strategically can have a huge impact on your personal life as well. 

  • Define your goals: Clearly identify your short-term and long-term objectives. What do you want to achieve? Having well-defined goals will guide your strategic thinking and decision-making process.
  • Understand the bigger picture: Develop a deep understanding of the internal and external factors that can influence your goals. Analyze market trends, industry dynamics, competitive landscape, and any other relevant factors that can impact your success.
  • Conduct a SWOT analysis: Assess your strengths, weaknesses, opportunities, and threats to gain a comprehensive understanding of your current situation. This analysis will help you identify areas where you can leverage your strengths, overcome weaknesses, exploit opportunities, and mitigate threats.
  • Think long-term: Strategic thinking requires a focus on the long-term implications of your decisions. Consider how your choices today can impact your future outcomes. Avoid short-sighted thinking and prioritize sustainable strategies that can provide lasting benefits.
  • Analyze risks and uncertainties: Recognize that strategic decisions involve inherent risks and uncertainties. Identify potential risks, evaluate their likelihood and potential impact. Develop contingency plans to address them. Be prepared to adapt your strategy as new information emerges.
  • Embrace creativity and innovation: Strategic thinking often involves exploring new ideas, approaches, and perspectives. Encourage creativity and innovation within your thinking process. Challenge conventional wisdom. Be open to unconventional solutions that can give you a competitive advantage.
  • Consider different perspectives: Engage in critical thinking by considering various viewpoints and alternative scenarios. Avoid confirmation bias and actively seek out dissenting opinions. This practice helps you anticipate challenges and make well-rounded decisions.
  • Prioritize and allocate resources: Strategically allocate your resources, including time, money, and manpower, to areas that have the highest potential impact on your goals. Make informed trade-offs and invest in initiatives that align with your strategic objectives.
  • Continuously learn and adapt: Monitor the outcomes of your strategic decisions and be willing to learn from both successes and failures. Adapt your strategy as necessary based on new information, changing circumstances, and emerging opportunities.
  • Communicate and collaborate: Strategic thinking should not be confined to an individual endeavor. Foster a culture of strategic thinking within your team or organization. Encourage open communication, collaboration, and the exchange of ideas to collectively contribute to strategic decision-making.

Strategic Thinking is a skill that develops over time with practice. By consistently applying these ideas and reflecting on your decisions, you can improve your ability to think strategically. Strategic Thinking is a life skill and it’s one that the most successful people never stop working on. 

Think about that!

Thinking is a Pretty Good Thing to Do

My first job out of college was working for an electronics company designing new to the world products. I was at my desk one day staring at a circuit board when my boss walked up and asked what I was doing. 

I said I was struggling with how I was going to move electrical current between two large capacitors without burning up the transistors in between. I added that I was thinking about the best way to go about it without adding unnecessary complexity to the circuit board.

His reply was instantaneous and abrupt. He told me “you’re not paid to think, you’re paid to work.” 

I guess he wasn’t all that familiar with how the design process worked. But thinking is actually a good thing to do no matter the situation. Most people know that. Most people also invest very little time in actually thinking. They claim to not have time. 

We live in a time where information is coming at us at all times from every source and direction imaginable. It never stops. We’re also told that successful people maximize every second for the sake of productivity. 

But we’re seldom told what the absolutely most successful people do. The most successful people set aside time almost every day to sit and think. Sit quietly and alone to just think. 

They know that life is cause and effect. They know that their decisions are their keys to success. So they make “think time” a priority. They think through all big decisions, they consider the consequences of the consequences of the consequences of their decisions. 

Highly successful people outthink the average person. It’s not necessarily because they are smarter it’s because to set aside time to truly think. They don’t care if some average person calls it daydreaming. They don’t care if someone calls them a slow thinker. They will not be deterred by people less successful than them. 

Maybe you need to think about thinking a little more because thinking is a pretty good thing to do. Block time on your calendar for thinking. Do it every single day. It’s okay if your mind wonders a bit, don’t limit what you allow yourself to think about. Some of your time will be very strategic thinking and some of your time will be “what if” and “why not” thinking. All thinking is better than no thinking. 

Think about that!