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How to Master Strategic Thinking Skills in 7 Simple Steps

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Are you a strategic thinker? Strategic thinking skills can often mean the difference between:

  • A small bonus vs. a large salary raise
  • Getting rejected vs. getting accepted
  • Making the same mistakes vs. learning from them

Here’s how to do it.  

Helping with this article is the amazing Dorie Clark, a professional communication coach and world-class speaker. Her book, The Long Game: How to Be a Long-Term Thinker in a Short-Term World teaches how to strategically and smartly think.

What is Strategic Thinking?

Strategic thinking is the ability to focus deliberately on long-term projects. Strategic thinkers often use a combination of analyzing situations, coming up with a viable plan, implemnenting their plan, and overcoming possible obstacles in order to effectively navigate a decision.

97% of leaders identified strategic thinking as a key to their organization’s success. Yet, 96% said they don’t have time to do strategic thinking at all.—Dorie Clark


Because just like exercise, we know it’s good for us, yet we sometimes procrastinate. In fact, we often use busyness as a means of avoiding things we don’t know about or are emotionally hard to think about.

Sound familiar? But instead of being busy for the sake of busyness, let’s learn how to be a truly long-term thinker and work smarter.

7 Strategic Thinking Tips to Boost Your Long-Term Thinking

4 questions to ask yourself

Workers spend an average of 41% on tasks that offer little personal satisfaction and could be delegated to others, according to Harvard Business Review. So how do you maximize your time?

Ask yourself these 4 questions before doing ANY task:

1. Should I be doing this task at all?

2. Could I delegate it to someone else or stop doing it altogether?

3. Where should I focus my effort in order to get the biggest return?

4. If I were starting fresh today, would I still choose to invest in this project?

For example, let’s say you write a weekly newsletter with 1,000 subscribers. Here’s an example set of answers:

  1. Yes, I should be doing this task for my 1,000 newsletter readers.
  2. I could benefit by saving time and delegating the weekly email to someone else to write.
  3. To get my biggest return, I should spend time writing on my blog rather than on newsletters.
  4. If I were starting fresh today, I would not invest in newsletters, but rather grow my blog more.

Action Step: Go through the 4 questions with your daily or weekly tasks you’re spending the most time on or you think might be able to be delegated. You might be surprised at how much time you can save. For further goal-conquering tips, check out our article: Goal Setting: 5 Science Backed Steps to Setting and Achieving Your Goals

Take one step at a time

Got a goal you MUST accomplish?

News flash: you don’t have to know how to reach your goals, but take one step at a time. 

Decide what to be “bad” at

Very few companies refuse to choose what to be strategically bad at. But choosing what to be bad at is key.


Because people often refuse to be bad at things. NOBODY likes to be bad, right?

But once you choose what to be great at, you’ll HAVE to be bad at some things by default. For example:

  • If you value speed, you might suffer in quality.
  • If you’re great at customer service, you might suffer with too much people pleasing.
  • If you prioritize finding only the best clients, you might be bad at gaining broad exposure.

Makes sense?

In order to avoid an overall average experience, you need to choose what to be bad at. 

Action Steps: List down the things you KNOW you’re bad at. Hate email? Write it down. Want to spend a majority of your time on small details, even if it takes a lot of time? Write that down.

Whatever your “bad” things are, consciously be aware of those things and find someone who is good at them! Having trouble finding what you’re not-so-great at? Check out the video:

Optimize for interesting

In life, we’re often taught black or white:

  • Optimize for wealth and become a banker or doctor, OR
  • Optimize for meaning and work for a non-profit or charity.

However, neither of these frameworks quite fit for most of us. Instead, try optimizing for interesting.

What’s interesting to you? What do you crave knowledge about? What are you excited to do during your free time?

Action Step: Let’s get back to the career drawing board. Write down the things you are interested in doing. This doesn’t mean you have to totally quit your job—but if you HAD to suddenly start a new job tomorrow, what would you want to be doing?

When you’ve got your list down, let’s take it into action overdrive: How to Get a Job You Really Want: From Resume to Interview

Network with a “friend” mindset

Have you ever been to a network event with the sole mission to connect with as many people as possible?

But here’s the kicker: simply going in with that mindset isn’t enough. In fact, going into a networking event with the goal to meet the most people is actually counterproductive.


Studies show us that even the most well-intentioned executives, who expressed a desire to meet new people, actually spent half their time at a networking event with the people they knew. That’s because we’re creatures of our comfort zone. We love to stick with the familiar, and we have a fear of the unknown—including people (yes, even extroverts!).

Action Step: Let’s switch on our “friend” mindset:

  • Treat everyone at a networking event as your friend. Reach out to truly random people you don’t know and talk to them. If this is too hard, Approaching with warmth is key—use open body language and act as if you’re already friends.
  • Play it casual. Have you ever been to a networking event where you meet someone who’s all-business, dressed to impress? (Or maybe you’re that person). Networking events are great because they CAN be a little more informal (depending on what event you’re at). Instead of going in business-minded, use this opportunity to play it casual—brush up on your jokes, strike up a nice conversation starter, and use this opportunity to use your natural curiosity to get to know people.

Pro Tip: Use confidence. When you say things confidently, every word seems to just “stick” better. Take a look at the funny video below and how non-threatening and confident he approaches people:

Use your next networking opportunity to say it with confidence!

Avoid people pleasing

It’s no surprise that people tend to do things that others are doing. For example, if we’re walking down the street looking for a grocery store, we might choose the one with people shopping there than the empty one.

When it comes to strategic thinking, avoiding people pleasing is essential to minimize external influence on your own thoughts. People pleasers tend to:

  • Prioritize other people’s desires over their own
  • Apologize for small mistakes
  • Worry about other people’s reactions
  • Laugh a lot (even when it’s not funny)
  • Do most or all favors from friends
  • Break their values for their friends
  • Want others to be happy around them

While independent-minded strategic thinkers tend to:

  • Make smart decisions when it comes to others’s desires
  • Make every apology count
  • Not worry about other people’s reactions
  • Laugh only when they think it’s funny
  • Do favors for others if it’s not too troublesome
  • Keep their values
  • Want others to be happy, but don’t stress about it

Action Step: Are you a people pleaser? Find out by heading over to the article and taking the quiz: 11 Expert Tips to Stop Being a People Pleaser and Start Doing You

Become a lifelong learner

Learning is a critical skill to master strategic thinking.

And it’s not just stuffing in as much content in your brain as possible…

Strategic thinkers are also lifelong learners.

Whether you’re into:

  • Giving presentations
  • Traveling
  • Dancing
  • Music
  • History
  • Pickleball
  • Cooking
  • Board games
  • …Or anything else, really

Learning how to learn can teach you how to connect concepts in a much more efficient way. For example, have you tried the “learn stacking” technique?

If you’re learning about cabinet making, you might also want to learn about the types of paints that are used to paint cabinets, the types of trees cabinets are made from, the various types of cabinets commonly used throughout the world, etc.

Learn stacking is about building relational knowledge. Expanding your knowledge will help you “connect” what you’re learning better and better integrate it into long-term memory.

For more great learning tips, head on over to 15 Effective Ways You Can Learn How to Learn

The One Thing

That’s a wrap!

The most important takeaway: What’s the one strategic thinking tip in this article you will add to your life that will benefit you the most? Think strategically—not only in terms of days or months, but years or decades.

Whether it’s delegating your “bad” tasks or implementing new strategies for learning, take these habits with you, go out, and conquer.
I think KNOW you’ve got this!

How to Deal with Difficult People at Work

Do you have a difficult boss? Colleague? Client? Learn how to transform your difficult relationship.
I’ll show you my science-based approach to building a strong, productive relationship with even the most difficult people.

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