The Art of Strategy: Mastering Strategic Thinking Skills

Ever been told you need to think more strategically?  It can be both blessing and curse, especially if your boss is less then clear on what that means at your organization (or for your role).  I’ve been given this nugget of advice in my career many times, and what I’ve learned is you can’t assume everyone one defines “strategic thinking” the same way, nor that your boss/organization is ready for your strategic thinking (even when they asked for it).
 
Here's my proven 8-minute primer on what to do if you’ve been asked to be more strategic at work, so you can master this skill.
 
First Steps to Empower Your Strategic Thinking
 
Define to align
Strategic thinking is a big phrase, not everyone defines it the same way, based on their values, risk tolerance, organizational culture and internal politics. Ask others in your organization how they define strategic thinking.  Make notes of their definitions (or if they have none) and work to align your understanding of this critical phrase (beyond the “Google” definition) – this may take several conversations. Don’t rely only on your manager’s definition, ask several leaders in your organization how they define this key phrase.
 
“Strategic thinking means being able to look at complicated problems and situations in a big-picture way. It involves figuring out what solutions or opportunities could help someone or a group of people reach their goals. This requires gathering information, predicting what might happen in the future, and considering different options before making a choice.” – Chat GPT
 
Understand the how
Once you have a feel for what strategic thinking is (and is not) in your organization, begin building a picture of what you need to exercise it more often in your work.  As an example, here are some of the key skills involved in strategic thinking:

• Being good at analyzing data to find patterns and trends
• Being able to think of new ideas and ways of solving problems
• Being flexible and able to change plans when needed
• Being able to communicate well and explain complex ideas to others
• Being good at making choices based on information and analysis.

Based on how your organization defines strategic thinking, what is the priority order for developing/exercising these skills?  Are there any skills missing from this list?
 
“Strategic thinking is important for leaders, managers, and anyone who makes decisions. It helps them to set goals, decide what's most important, and adjust their plans when things change. Being strategic also means being creative and coming up with new and better ways of doing things.” – ChatGPT
 
Discuss your needs
As you begin to think more strategically, involve your manager (particularly if they highlighted this as an area of development for you).  You may need to ask for access to specific data, or to sit in on meetings you’re not currently invited to.  As you continue to practice strategic thinking, keep your manager aware of your learning journey so they can support what you need to build your strategic thinking skills.  This has the added bonus of demonstrating to them how you’re making changes to think more strategic in your role.
 
Celebrate your successes
As you continue to build and practice your strategic thinking skills, help your manager to understand the positive outcome for your team and organization.  Don’t have any tangible results?  Don’t be put-off, strategic thinking takes time, and it’s often difficult to pin point a specific result.  Sharing with your manager what you’re seeing and thinking can demonstrate your ability to think strategically, even when there are no tangible outcomes, yet.
 
Be provocative
As your strategic thinking skills grow, you’ll find you see things others don’t, and you may doubt the importance of what you see because others are not seeing it too.  Be provocative, ask a question to support your exploration of strategic thinking.  As an example, asking the opposite of something can support critical thinking that leads to a more strategic outcome: “Looking at this from all angles, what if we don’t do this, what would be the impact?” is one way to do this.  Be mindful of your timing, and audience.  Pursuing these types of queries one-on-one may have a better impact then in a group meeting (and vice versa).
 
Be politically savvy
Every organization has internal politics. Strategic thinking involves considering the bigger picture and making decisions based on long-term goals and objectives. In order to do this effectively, it is important to understand the internal politics of your organization, including the power dynamics and relationships that exist between different departments, teams, and individuals.  You’ll need to develop strategies for building relationships, gaining support, and navigating decision-making processes in a way that aligns with your long-term goals and objectives.
 
“Strategic thinking may involve identifying key stakeholders and building relationships with them to gain support for your initiatives. It may also involve navigating complex decision-making processes, which may be influenced by internal politics.” – ChatGPT
 
Strategic thinking isn’t always easy.  Often it means de-personalizing solutions for the best outcome, which can have an impact on your work and the work of others.  However, strategic thinking is fast rising as an important skill, particularly for anyone pursuing an executive role. 
 
Strategic Thinking for Career Success
 
If your career trajectory takes you to the C-suite (i.e., CEO, COO, CFO, CHRO, CMO, etc.) strategic thinking is a must, not a nice-to-have. If you’re ideal position is supporting the C-suite (Director, line manager, project manager, etc.), then strategic thinking is key for you too.  Here’s why:

• Improved decision-making: When you’re able to think strategically, you’re better equipped to make (suggest, implement or support) informed decisions. Your ability to analyze information and weigh the pros and cons of different options supports good leadership and decisions making.  It can also help you to make better choices in your career.

 

• Goal setting: Being strategic means setting goals that are aligned with your values and long-term vision. This can help you stay focused on what's most important and empower progress in your career.

 

• Problem-solving: Strategic thinking can help you identify problems and develop solutions that are both effective and efficient (for you and many others). This can be a valuable skill in any job or industry.

 

• Innovation: Being able to think strategically means being open to new ideas and approaches. This helps you innovate and find new ways to add value to your team, organization or industry.

 

• Leadership: Strategic thinking is a key skill for effective leadership. By thinking strategically, you help your team or organization navigate complex challenges and achieve goals.

 
Strategic thinking can help you to be more effective and successful in your career (no matter what role you’re in). It helps you identify opportunities, make better decisions, and lead with confidence.  
 
Overcoming Common Barriers to Strategic Thinking
 
Strategic thinking isn’t a “magic bullet”.  You’ll need to overcome every-day barriers to successfully adopt strategic thinking into your ways of working.

• Lack of time: Strategic thinking requires time and effort to gather information, analyze data, and consider different options. When you’re are busy with day-to-day tasks or working in a fast-paced environment, you may not have the time or mental bandwidth to engage in strategic thinking.  Protecting time each day (from 15 minutes of thinking time to something longer) is key to overcoming this barrier.

 

• Lack of information: Strategic thinking depends on having access to accurate and up-to-date information. When you don’t have access to the information you need, or when the information you have is incomplete or inaccurate, it can be difficult to engage in strategic thinking.  Asking others to share information with you (letting them know why and how you want to use it) can remove this barrier.

 

• Narrow-mindedness: Strategic thinking requires yourself and others to consider different perspectives and possibilities. When you’re narrow-minded or closed off to new ideas, you may struggle to engage in strategic thinking.  Staying in touch with your resistance to thinking more globally, to risk-taking and to being innovative can help you understand when something’s in the way of being able to think strategically (like fear, doubt, cynicism, etc.) allowing you to work with those concerns, overcoming this barrier to strategic thinking.

 

• Fear of failure: Strategic thinking involves taking risks and making decisions that may not always lead to success (but will lead to learning). When you’re afraid of failure, you may be hesitant to engage in strategic thinking and instead stick to what works.  Presenting new ideas as something to try (a pilot, for example), or taking them in small steps to start, (i.e., rather than doing it as a whole program) can help you test your assumptions, and make iterative changes as needed to see the viability of your strategic initiatives, removing this barrier (for yourself and others).

 

• Groupthink: Groupthink occurs when you prioritize conformity and consensus over independent thinking and analysis. When you engage in groupthink, you may not consider all the available information or alternatives, which can hinder your strategic thinking.  Asking yourself provocative questions, like “Why do we do this”, “Why do we do this in this way?”, “What would happen if we stopped doing this?” or “What are the ways our competitors do this?” can help you step away from groupthink (and you can use these questions to support others in thinking more strategically too).

 

• Lack of expertise: Strategic thinking requires a certain level of expertise and knowledge in a particular field or industry. When you lack this expertise, you may struggle to engage in strategic thinking and make informed decisions.  Experience and expertise development may need to become part of your strategic thinking development plan to overcome this barrier.

 
Overall, these barriers can hinder strategic thinking and prevent you from making the best decisions for yourself or your organization. It’s important to be aware of these barriers and work to overcome them to engage in effective strategic thinking.  
 
What to Do When Your Boss Resists Your Strategic Thinking
 
Another barrier can come in the form of your bosses’ limitations when it comes to strategic thinking.  While your manager may have asked you to build this capacity, they may not have it themselves, or may become intimidated by your insight and suggestions.  Here are some things to do if your boss is not on board:

• Clarify expectations: It may be your boss is not opposed to strategic thinking per se, but has different expectations about your role or responsibilities. Clarify expectations by asking your boss about their priorities and how they see your role in the organization (and where strategic thinking fits in). This can help you to better understand their perspective and tailor your approach to better align with their expectations.

 

• Build a case: If your boss doesn't understand the value of strategic thinking, you may need to build a case for it. You could to present evidence (anecdotal, etc.), data, or examples of how strategic thinking has benefited other organizations or individuals. You can also explain how your strategic thinking can benefit your team or organization in concrete terms.

 

• Find allies: If your boss is resistant to your strategic thinking, find allies within the organization who share your perspective. This could be colleagues who have similar goals or values, or individuals who have successfully used strategic thinking to drive results.

 

• Be flexible: It may be that your boss has a different approach to problem-solving or decision-making. Try to be flexible and adapt your approach to better align with their preferences. This could mean being more collaborative, focusing on short-term goals, or using different communication strategies.

 

• Consider other options: If your boss is completely opposed to strategic thinking and you feel that it’s hindering your growth or effectiveness in the organization, you may need to consider other options. This could mean looking for a different position within the organization or exploring opportunities outside the organization.

 
It’s important to be proactive and (ah-hem) strategic in your approach to engaging with your boss. By clarifying expectations, building a case, finding allies, being flexible, and considering other options, you can work to overcome their resistance to your strategic thinking so you continue to add value to your organization.
 
These are the key strategies I’ve used successfully in the past to support building my own strategic thinking skills (and those of my clients).  This isn’t always an easy journey; truthfully, sometimes I was told to think more strategically because my boss couldn’t think of anything more concrete to offer as constructive criticism (and their lack of leadership became my career game-changer).
 
Don’t let vagueness stop you from building this key skill.  By understanding the steps and skills to being more strategic, identifying how strategic thinking supports your long-term career goals and overcoming barriers and resistance to strategic thinking (for you or your boss) will ensure you master this critical skill BEFORE you need it.

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