3 Ways to Improve Your Strategic Thinking Skills

Do you remember a game from your childhood where you started with an unrecognizable collection of dots on a page, drew a line between them in just the right way, and an image emerged?

Connect-the-dots may be a simple pastime from your youth, but it’s also a metaphor for one of the most powerful capabilities of all successful leaders: strategic thinking.

Stop and think about a time you faced a situation where things were unfamiliar, disorganized, even chaotic. By carefully connecting the dots in all the right places – between people, ideas and resources – you created clarity and opportunity. Your strategic thinking skills carried the day.

Making meaningful connections that allow you to make smart moves is a beautiful thing, especially when it leads to “Eureka!” moments like finding the perfect solution to a pressing problem or developing a creative approach to a new initiative.

Why we don’t think more strategically

One of my coaching clients recently told me that connecting the dots was one of her greatest strengths. Her face lit up as she talked about an interesting new trend she had observed and how she enjoys tackling challenges that seem to stump others.

Then, with a deep sigh, she explained her most daunting leadership dilemma: Not having enough time to think like this.

“I’m too much in the weeds,” she told me, leaving precious little time to think about bigger issues and opportunities.

It’s not just lack of time. Leaders face many other challenges when it comes to thinking strategically:
  • Constant distractions such as meetings, phone calls and unexpected problems that you feel you must respond to.
  • Reasoning and analytical skills that have gotten a little rusty, making it that much harder to come up with solid solutions.
  • Lack of information or adequate resources to help fully understand the landscape when making critical decisions.

You can have a bigger impact

You don’t want to shirk your day-to-day responsibilities, of course, but you want to be more than a tactician. Most leaders want to be strategic thinkers and trusted advisors. Holding this kind of sway gets you invited to the table to work on the big stuff. As a result, your impact on your team, your organization and your industry can be far greater.

Strategic leaders know what matters most and focus on delivering high value. In a practical sense, they have the ability to:
  • See across the total enterprise and thinking collaboratively, not just about one team or business unit.
  • Focus on problems that have the greatest impact on key business goals and initiatives.
  • Spot important trends and know which ones will impact the organization.
  • Understand the competitive landscape and develop a strong positioning that attracts the best customers.
  • Envision where the business needs to go in a rapidly changing environment.
  • Develop plans to lead the organization into the future.

How to think more strategically

To lead at this level, let’s start with some learnings from neuroscience research and how you can optimize your prefrontal cortex, which is the part of your brain responsible for working through complex issues. Then we’ll take a closer look at some ways you can broaden your perspective and challenge status-quo thinking.

If you’d like to dig a little deeper, I’ve created a detailed guide that expands upon this blog post. “Improve Your Strategic Thinking Skills” includes a comprehensive checklist of more than 30 questions to help yourself and your team take a deeper look at the factors impacting your business now and in the future. I hope you’ll take a look. 
1. Optimize Your Brain

It’s virtually impossible to think strategically when you multitask. Distractions such as email, phone calls, and visitors require us to shift gears too frequently to allow us to peel back the many layers of a challenge. To counter these distractions, find at least one two-hour block a week when you can work on a single pressing item without interruption. Literally, schedule it on your calendar.

When possible, especially on bigger projects, it’s best to leave your office. You will make more connections and have more of those coveted “Eureka!” moments when you can put yourself in a stress-free environment, not bound by time or place. Where is your “happy place” — a favorite room in your house, a cabin on the lake, a quiet spot in your local library? Go there when you need to think deeply.

You also will have more success solving difficult problems by putting yourself in a positive state of mind. Carol Dweck’s TED talk on how students overcome challenges underscores the value of a positive mindset. As you approach situations where you need to think strategically, remind yourself an answer is within reach.

Another way to optimize your mental performance is by engaging in creative, stimulating activities outside of work such as hobbies or working out. This puts your prefrontal cortex into a high-performing state often referred to as “flow.” This is because your brain releases just the right amount of adrenaline and dopamine – not too much, not too little. During these times, the brain often works subconsciously on solving problems. Be sure to make regular time in your life for hobbies and “flow” so you can encourage these connections to happen and allow new ideas to surface.

2. Broaden Your Perspective

If you keep listening to the same things or talking with the same people, you’ll find it much more difficult to be strategic when it comes to tackling your organization’s bigger issues. Remember, new thinking comes when you connect the dots in new ways.

Start by thinking about the information you access now. How can you broaden your perspective by mixing it up, adding new resources or meeting new people? Here are some things to consider.

Resources — Look at the blogs, e-newsletters, research reports, websites and other things you read to ensure you have a blend of:

General business news locally, nationally and internationally.
Political, social and economic trends.
Industry-specific information.
Leadership advice, tools and techniques to develop yourself and those you lead.
Creative inspiration – poetry, novels, humor pieces, or anything that sparks a few “wows” and “cools” in your heart and mind.

Insights — Subscribe to an insights service that can provide trends about the attitudes and behaviors of your customers and stakeholder groups, as well as thoughtful analysis about the future of your industry.

Conferences – Rethink the conferences you are attending. Consider swapping out for – or adding — something outside your normal that offers:

Speakers on innovation.
Futurists who can give you a better sense of how business and society are evolving.
Case studies on new business models.
Best practices on leading through change.

Competitors — Pick three competitors to benchmark and do a deep dive on what’s working. Study their websites; get on their email distribution list; download and study their whitepapers. Don’t copy what they do. Instead, look at the unique way they solved a problem or acted opportunistically. What do you observe? What lessons can you learn from their approach? How could this inform your thinking?

Other industries — You can learn a great deal from other sectors. Join a local or regional business group that includes leaders from outside your industry. By broadening your network, you’ll gain fresh perspectives on business challenges others are facing and addressing in different ways. Consider joining a national peer-to-peer organization such as Young Presidents’ Organization, Women Presidents’ Organization or Vistage that offers advisory boards, business research and speakers.

3. Challenge Your Thinking 

In addition to looking outward, you need to take stock of some critical internal business issues including:

  • Products and services 
  • Positioning 
  • Growth
  • Talent 


If you’re ready to think deeply about your business, I’ve created a list of more than 30 questions to challenge your thinking in all four of these areas. You can find this list plus much more in a comprehensive strategic-thinking guide:“Think Bigger. Lead Better.” 


I think you'll find this guide invaluable for helping you and your team think through many of the factors impacting your business now and in the future.  It's available in a fully digital format with space available for you to write your answers and capture your thinking for each question. This format also makes it easier to share with team members/colleagues and capture their thinking as well.


When you played connect-the-dots back in the day, it probably didn’t take long for you to begin seeing a pattern. It’s not always that easy or that clear for a leader. But seeing patterns and creating strategy for the future is one of the most rewarding parts of the job. 


So, optimize your brain, broaden your perspective, and challenge your thinking. Then see what emerges.


Copyright (c) 2018 Velocity Collective, LLC. All rights reserved.

Written By

Elise Mitchell

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