Here’s How To Train Strategic Thinking The Right Way [Guide]

Are you an individual contributor who needs to make decisions about project priorities and how much time to devote to different tasks? Or maybe you’re the director of a marketing group who must decide on various funding levels. 

You might even be a corporate executive tasked with establishing future strategies for your firm. These are all examples of activities where strategic thinking is required.  

Strategic thinkers are guided by clear business concepts that are grounded in the economics of their companies and the success factors of their industry.

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The concept can be traced as far back as 400 B.C., with the Greek theorist Xenophon who highlighted the importance of knowing the purpose of your business.  

Training and organizational development professionals have dual uses for strategic thinking. On one hand, they must use it to make decisions. On the other, they are required to teach or train others in their organizations how to think strategically.

Today, I’ll show you how to train strategic thinking the right way.

What is Strategic Thinking?

professional training manager in strategic thinking

According to Professor Collis of Harvard Business School, strategic thinking occurs when individuals analyze opportunities and problems from a broad perspective and understand the impact their actions might have on others. 

Nathan (2015) argues that it involves forwarding unconventional perspectives, questioning the obvious, and encouraging contrasting thinking and creative solutions. Practitioners view it as one of the most valuable executive and management skills.

"Strategic thinking occurs when individuals analyze opportunities and problems from a broad perspective and understand the impact their actions might have on others." – Prof. Collis Share on X

Great strategic thinkers have exceptional analytical and creative thinking skills. They are able to look at current, past, and future realities through a lens that allows to pick out patterns which may have gone unnoticed. 

And the best part, they are able to apply this learning to make real-life decisions. True strategic thinkers have the ability to effectively prioritize and make trade-offs in deciding what to do and where to go next.

The Fundamentals of Strategic Thinking

Paloma Cantero-Gomez states there are seven fundamental skills associated with becoming a strategic thinker:

  1. Vision
  2. Framework
  3. Perceptiveness
  4. Assertiveness
  5. Flexibility
  6. Emotional Balance
  7. Patience

Let’s take a look at each of these fundamentals…


Strategic thinkers create and stick to a clear visioning process. They use both logic and creativity to define an ambitious and rigorous picture of what must be accomplished—one that enables commitment and moves the needed energy to make it happen.


Successful strategic thinkers define their objectives and develop an action plan with goals that are broken down into tasks specifically measured in terms of timeline and resources. They set up deadlines and commit to them.

They’re conscious of their own biases and factor their own circumstances and perspectives within a framework that includes contingency plans.


Strategic thinkers are able to look around and understand the world from all the different points of view. They listen, hear, and read between the lines.

They observe before forming a judgment and absorb and make use of the different angles that are helpful for better guidance. 


Strategic thinkers are good decision-makers. They conduct comprehensive evaluations, choose the way to go, and walk firmly into it without hesitation.

They do not let the doubts fog their vision.

Communicating what they want and need effectively by using clear orders while simultaneously respecting the thoughts and wishes of others, they defend their points of view without harm or hostility.


Strategic thinkers know their weaknesses and are committed to seeking the advice of others. They are humble enough to be flexible and adjust their ideas and framework to achieve the desired results, not confusing flexibility with lack of structure. They shift gears and think about different ways, developing multiple strategies.

Emotional Balance

Strategic thinkers are cognizant of their emotions, they don’t react to them as an important element of accepting a position or making a decision. 

They are able to accept both positive and negative feedback and respond in a way that protects and progresses toward their desired outcome. 

They think positively and look for different opportunities. Kind, compassionate, and optimistic, strategic thinkers interact passionately with their surroundings.


Strategic thinkers have the ability to be patient. They do not rush to conclusions and they invest their energies in a way that is sustainable and led by a long-term vision.

In other words, they have learned to wait.

Why Managers Should Learn How To Think Strategically

Strategic thinking is essential for managers as they seek to help their organizations succeed in an environment of constant change:

  • Strategic thinking results in the creation of unique business insights;
  • Individuals who use this approach raise their thinking to see beyond the fundamental elements of their organizations;
  • This helps them determine how to use their resources more effectively so that they are better positioned to assist their businesses achieve their objectives, and;
  • It focuses the management team on markets that are likely to succeed.

So, training managers on how to think strategically is essential for companies trying to obtain or maintain a competitive advantage.

Training Managers in Strategic Thinking

coach training a manager in strategic thinking

Full disclosure, using the term “teach or train strategic thinking” is in some ways a misnomer. “Training” strategic thinking requires a holistic approach:

  • Providing managers with the appropriate information;
  • Assigning a coach or mentor;
  • Crafting a philosophy;
  • Inserting the appropriate rewards system, and;
  • Teaching them how to ask the right questions.

While training organizations participate in each of these activities, and should certainly take the lead on some (like ensuring that managers have the appropriate information, teaching leaders how to craft a philosophy, and training managers how to ask the right questions), the role of L&D for inserting the appropriate rewards system and assigning mentors is one of influencing, coordinating, and collaborating.

Here’s The Right Way To Teach Strategic Thinking…

Based on the framework discussed above, there are specific steps you can take to teach strategic thinking and help managers achieve better results:

» Provide managers with the appropriate information 

To think strategically in business, you must understand the company’s industry, market, customers, competitors, and emerging technologies. 

One company I worked with mandated industry presentations at their monthly officer’s meeting by instituting a “lunch and learn” business program.

The L&D team assisted in this effort by teaching the managers how to create concise presentations and facilitating the conversational sessions.

» Assign a coach or mentor

Robert Kabacoff, the vice president of research at Management Research Group, argues that the most effective way to develop strategic thinking skills is to be coached by someone who is already a strategic thinker. 

The perfect candidate for this role is someone who has the ability to keep individuals focused on strategic objectives and their impact. 

A company I helped accomplished this by assigning a “success coach” to every new manager from the executive level down to the line supervisors. L&D coordinated the assignment of the mentors and trained them on coaching techniques.

» Craft a philosophy

Strategic thinkers have the ability to communicate their philosophy through well-crafted vision and mission statements with clear goals throughout the company. 

This type of communication helps employees understand the broader organizational strategy and helps them stay focused, incorporating it into their own plans. 

An organization of over 100K members I worked with accomplished this by investing in a “leadership academy” that taught the heads of international programs how to craft and deliver their vision and mission statements.

» Insert a rewards system

If you want your managers to become strategic thinkers you must reward them when they demonstrate that they are thinking and not just reacting.

While inserting a rewards system is typically not the responsibility of the L&D team, training managers should use their influence to encourage executives and line managers to develop and insert such a system.

In one organization that I supported, the L&D group coached the company’s executives on how to identify the desired behavior and how to reward it.

» Teach managers how to ask the right questions

Kabacoff says you need to promote a “future perspective” in your company. If a manager suggests a course of action, you need to ask them two questions: 

  1. First, what underlying strategic goal does this action serve, and why?
  2. Second, what kind of impact will this have on internal and external stakeholders?

Constantly asking these two questions whenever action is considered will go a long way towards developing strategic leaders. The role of L&D here is to teach managers how to incorporate these questions into their daily activities. Supervisors must reinforce this behavior through feedback and coaching.

… And Here’s The Wrong Way

I once did some work for a medium-sized Human Capital Management (HCM) Firm. The managing partner felt that the company was missing out on business opportunities because the employees weren’t “thinking strategically”.  

As I started interviewing the team, I uncovered two core problems:

  1. First, the organization had a vision and mission statement but no one in the organization was aware of it (with the exception of leadership); 
  2. Second, when leadership interacted with the team, they would ask technical questions specific to an individual project. The employees considered themselves technical experts and didn’t see the value of understanding business trends.

None of the employees had mentors and the team members only received financial rewards by working more hours. This is the exact opposite of teaching how to be strategic in a business environment.

Misconceptions of Training Strategic Thinking

My experience with the HCM firm dispelled two common misconceptions about strategic thinking that are damaging to a company’s overall culture:

  1. Strategic thinking cannot be taught, and;
  2. Not everybody can think strategically.

Strategic Thinking Cannot Be Taught

A number of learning strategies were introduced that proved this statement is false:

  • We disseminated information about the company’s mission and vision;
  • We implemented lunch and learn sessions where corporate leadership provided information about the company and the HCM industry to employees;
  • Leadership was coached to ask questions that forced employees to investigate their rationale for making decisions and to consider their impact;
  • And, we assigned each employee a coach to help them identify and work toward their own strategic goals, effectively “teaching” this practice.

The results of these efforts disproved the second misconception…

Not Everybody Can Think Strategically 

Six months after we introduced the learning intervention, the HCM firm’s revenue was up 30% YoY as a result of business generated by implementation consultants.

Prior to the intervention, only sales personnel generated business.  

While some employees became better “strategic thinkers” than others, every member of the team demonstrated the ability to think strategically.

Helping Organizations Grow More Strategically

manager trying to think strategically

Great thinkers are everywhere, they just need to be taught how to think in a contextual environment such as a business or organization.

That’s where strategic thinking “training” comes in. And it’s one of the more powerful tools for organizations to grow their assets faster.

With only a handful of strategic thinkers sitting at the top of the hierarchy, a company will always be stuck dealing with constant handholding.

But when an organization invests in the mental and contextual ability of managers at the lower levels, everyone involved benefits.

That’s how companies grow big: they trust their managers and employees to think for themselves so that they can bring real value to the table.

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Originally published Aug 14, 2020

Frequently Asked Questions

What is meant by strategic thinking?

Based on a definition from Professor Collis of Harvard Business School, strategic thinking occurs when individuals analyze opportunities and problems from a broad perspective and understand the potential impact their actions might have on others.

What is an example of strategic thinking?

One example of strategic thinking is the director of a marketing group who decides on funding for various campaigns with different target audiences.

Can strategic thinking be taught?

Yes, strategic thinking can be taught, but helping managers become strategic thinkers requires a holistic approach rather than a specific training session or workshop.

How do you train strategic thinking?

Training strategic thinking requires: 1) providing managers with the appropriate information; 2) assigning a coach or mentor; 3) crafting a philosophy; 4) inserting the appropriate rewards system, and; 5) teaching them how to ask the right questions.