top of page
  • Writer's pictureDanielle Terranova

How to Think Strategically

Pad of paper with New Year's Resolutions written across the top.

In professional life, we often hear about the crucial importance of strategic thinking. It’s a buzz-term that gets thrown around in boardrooms and professional development meetings, but what does it really mean think strategically?

When you delve a little deeper, you soon discover two things: one, strategic thinking means something different to everyone and two, it's a term used to describe a very wide range of workplace thinking and behavior. If we cant agree on the definition and behaviors associated with such a critical professional competency, how can we hold each other accountable to thinking strategically when performance review season rolls around?

In this lesson, we’ll unpack what it truly means to think strategically, explore best practices for honing strategic thinking skills, examine the barriers to strategic thinking, and discuss methods to develop strategic thinking in others. Let's dive in.

Defining Strategic Thinking

Looking up the definition of “strategic thinking” does very little to clarify a relatively ambiguous term. In a nutshell, thinking strategically involves acting in a way that maximizes your ability to achieve long-term goals and effectively navigate complex situations. While this description is technically accurate, It’s helpful to break down the concept into more simplistic terms.    

When it comes to strategic thinking skills, those who are good at it have three things in common.

(1) They identify long-term organizational goals, otherwise known as “the big picture” and keep them at the forefront of decision making.

(2) They know how to determine the key projects, initiatives, and programs (a.k.a. strategies) required to achieve the company's long term goals.

(3) They avoid getting bogged down in the details of execution and maintain focus on the crucial strategies necessary for long-term goal achievement.

While most professionals are either good at seeing the big picture or focusing on the details of execution, talented strategic thinkers know how to do both. They understand the goals of their organization, know their role in achieving those goals, and keep their attention on the best ways to get the company from where they are to where they want to be.

When someone is described as not strategic enough, it often means they’re too immersed in transactional-level work; concentrating on execution, immediate solutions, and ensuring a smooth workflow. They get lost in tasks and deliverables, and neglect opportunities to influence the methods by which goals are achieved. While occasionally digging into details and managing particulars of workflow is essential for running a successful team, strategic thinkers resist getting stuck at this level of management. Strategic thinkers know to lift their heads from the spreadsheets, periodically survey the broad landscape of organizational goals, and consistently work to align their efforts with the best strategies to achieve long-term objectives.

Keys to Being More Strategic

If we understand that strategic thinking is important, it naturally begs questions about how one can become more strategic at work. Here are seven key strategies to bolster strategic thinking skills and support a strategic perspective when making decisions.

1️⃣ Maintain a Visionary Perspective: Possess a clear understanding of the company's mission and long term goals, and be very clear about your role in achieving those objectives.

2️⃣ Create Goal Alignment: Ensure all strategies, including projects, initiatives and programs, align with a specific and measurable goal the company is trying to reach. Resist any projects that do not ladder up to a specific long-term goal.

3️⃣ Do Your Homework: Conduct critical analyses to support strategic decisions with facts, data and research. Explore solutions from multiple perspectives and play devil's advocate to ensure the best strategies are adopted.

4️⃣ Be Creative: Think outside the box, seek inspiration from unlikely sources and avoid exclusive use of standard responses or well-worn pathways to success. Expand your sphere of influence to include those outside your industry who may provide ideas about unconventional paths to success.

5️⃣ Preserve Adaptability: Don't make strategic planning a "set it and forget it" exercise. Evaluate and reevaluate strategic plans to ensure continued alignment with big picture goals. Pivot when strategies fail and see unintended consequences as opportunities to correct course.

6️⃣ Communicate Strategically: Always start strategic communication with big-picture common goals, then explain how your strategic plans will make goal achievement possible. Connect strategic ideas to a powerful reason "why" to show your commitment to your company's long-term goals.

7️⃣ Plan to Execute: Strategic plans are just ideas if they aren't tied to deliverables and attached to measurable performance indicators to track progress. Pay attention to plans for strategic execution - just don't get stuck at that level of attention for too long.

Obstacles to Thinking Strategically

It would be a mistake to assume that our ability to think strategically operates in a vacuum, detached from the organizational context in which we function. There are significant factors that can limit our strategic thinking capacity on behalf of the organizations we serve.

❌ Bandwidth Constraints: Expecting leaders to think strategically while burdening them with limited resources, shrinking teams, and growing demands is unrealistic. Evaluating work from a strategic perspective requires mental space, a luxury that only a few companies can afford.

❌ Tunnel Vision: During times of uncertainty, crises, and high-pressure situations, we often succumb to tunnel vision. Evolution has primed us to focus intensely on immediate problems, leaving long-term strategic planning on the back burner. We become engrossed in resolving immediate issues and lose sight of the broader strategic perspective.

❌ Analysis Paralysis: While making data-driven decisions is crucial, strategic thinkers also recognize the value of making decisions and learning from unforeseen consequences. Leaders who become overly entangled in exhaustive research and analysis to identify the "perfect" strategies may never move beyond the starting point.

❌ Vision, Mission and Goal Ambiguity: Leaders can only align their strategies when they understand the organization's vision, mission, and goals. If companies fail to define these core elements clearly, how can they expect their leaders to think strategically? Organizations must convey their goals clearly, establish clear priorities, breathe life into their mission, and paint a vivid picture of what can be achieved with a compelling vision. Companies must also resist a reactionary approach to shifting goals and priorities, understanding the corresponding chaotic impact on the entire ecosystem. 

❌ Cultural Barriers: To nurture strategic thinking leaders, companies must foster a culture that celebrates change, innovation, and learning from mistakes. They need to reward vulnerability, which often accompanies setting strategic direction and challenging norms that penalize leaders for taking calculated risks.

❌ Groupthink: (OK, last buzz-term!) It's all too easy to conform to the consensus within a group, particularly in companies where questioning collective wisdom is discouraged. When consensus drives strategic planning, it stifles strategic thinking. Instead, companies should actively seek diverse perspectives and encourage devil's advocacy when shaping strategy.

❌ Micromanagement: When leadership fails to trust their teams and engage in managing the details of execution, they focus attention away from strategic ideas. While micromanagers believe they are helping when they control the nuances of work, they hinder team effectiveness when they insist on being informed of every decision and second-guessing the talent on their teams. Micromanagement also means leaders are taking their eye off the prize. If the leaders in an organization aren’t thinking strategically, who will?

Barriers to strategic thinking are inevitable, however they present an opportunity to course correct, instigate change, and connect with the part of ourselves that knows how to do hard things. By actively addressing these barriers, we become architects of a corporate culture that nurtures strategic thinking. In this environment, teams are not just encouraged but emboldened to challenge conventions, critically analyze information, and design the best path forward. As a result, organizations become more agile, adaptive, and prepared to thrive in the face of uncertainty, ultimately securing their long-term success.


Unlocking Strategic Potential in Others

If we've fulfilled our roles as competent professionals, ensuring that we think from a strategic perspective and holding our organizations accountable for creating environments, the next frontier involves cultivating strategic thinking in others. In addition to sharing this article with your team 😊, here are a few more tips to unlocking strategic potential with colleagues.

👉 Share meaningful, long-term goals: Share objectives that reflect your team's impact on the organization's overarching goals. Connect these goals to the fulfillment of the company's mission and look beyond purely financial expectations. While financial targets are crucial, expanding the scope of goal achievement beyond revenue can stimulate a strategic perspective in those less motivated by financial gains. 

👉 Adopt a Consultant Approach: Encourage your team to think like external advisors unburdened by historical baggage, politics, and resource constraints. Challenge them to develop 3-5 short-to-mid-term strategies that resemble recommendations from an external party to achieve each team goal. Shifting perspectives from what's probable to what's possible can trigger strategic problem-solving that may otherwise remain untapped.

👉 Plan for Strategic Thinking: Dedicate specific meeting times, at least once a year, to strategic planning with your team. Recognize that it can be challenging for managers to shift focus from day-to-day operations to the big picture. Allocating dedicated meeting time to focus on the broader context for organizational decisions can significantly enhance the quality of strategic ideas.    

👉 Include Everyone: Involve as many team members as possible in strategic planning. A few times a year, those with direct reports should set aside time to outline company and departmental goals and brainstorm strategies with their teams. This not only sets a positive example for strategic thinking processes but also leverages the opportunity to secure buy-in for strategic ideas.

👉 Continuous Review:  Understand that strategic planning is an ongoing process. After plans are set, regularly evaluate their effectiveness in achieving goals and be ready to pivot as needed. Encourage your team to demonstrate strategic agility by reevaluating and adjusting plans at least once per quarter.        


In this article, we’ve navigated the ambiguous landscape of strategic thinking practices by illuminating the barriers and challenges that stand in the way of strategic thinking and identifying best practices for cultivating strategic thinking in ourselves, our teams, and the organizations we serve. Let's remember that strategic thinking is more than a professional buzz word or a necessary once-a-year activity; it's the compass that guides us in steering our organizations toward long-term success. By fostering a culture that celebrates innovation, embraces change, and empowers individuals to think strategically, we help our teams to translate goals into reality and thrive in complex and dynamic environments.  

Headshot of Danielle Terranova

Danielle Terranova is the voice behind Leadership Lessons with Danielle.

She has been an executive coach since 2015 and owner of Terranova Consulting, LLC since 2019.


Commenting has been turned off.
bottom of page