The Strategic Thinker's Playbook: My Journey from Weakness to Growth

Once upon a time, I thought I lacked strategic thinking, thanks to an early performance review at Google, where it was flagged as my “area of development,” which is corporate-speak for weakness. I found the concept of strategic thinking nebulous; what does it even mean? Being a dutiful problem solver, I sought help from someone who pointed out that instead of viewing this gap as a deficiency, I could approach strategic thinking as a buildable skill, which is how I was introduced to the concept of a growth mindset.

Once strategic thinking felt attainable, I searched for resources and realized that not only was I capable of it, but I was already using it in my life. I just needed to figure out how to apply it in the workplace. I found training materials that provided a framework to help me with my self-development.

That initial feedback from Google—that I lacked strategic thinking—became the catalyst for a 10-year journey that has proven invaluable. This process has not only helped me, but after sharing the framework in talks and with coaching clients, I've seen how it can help anyone build this crucial skill.

What is Strategic Thinking and Why Does It Matter?

Strategic thinking involves analyzing opportunities and problems from a broad perspective and understanding the potential implications of each choice you make, a process for accomplishing goals and generating unique insights to solve problems. When you embark on a new task, rather than just thinking about a checklist of things to do, strategic thinking takes external factors and unexpected occurrences into account, as well as the broader impact of what you’re trying to accomplish.

Consider the role of strategy in a game like checkers, which I played with my son when he was only six years old. When you first start to play, you learn the rules (like which direction and how many spaces you can advance each piece) and can then make a move. Playing strategically means that in addition to picking your next move, you picture where you want to be several moves from now and anticipate your opponent’s moves. Even my then six year old could do this. Sometimes you choose moves with the long game in mind – I might let my opponent take one or two of my pieces early on to give them a false sense of security while I execute my long-term strategy.

Strategic thinking helps leaders make better decisions, motivate and influence diverse teams, and innovate. From a professional development standpoint, it’s a means to increase your scope, impact, leadership, and influence, all of which are critical for advancement.

Practical Tools and Tactics to Foster Strategic Thinking

Grow Your Network

I’ll be honest—my gut reaction to the idea of networking used to be sheer dread. Going to networking events and schmoozing with strangers sounded terrifying to me as an introvert. But it’s such an important skill to develop because it exposes you to new opportunities and diversity of thought and experiences. By definition, it increases the number of relationships you have to help you get your job done, advance professionally, and provide personal and professional support.

First, start by understanding the relationships in your existing network and ask yourself which of these roles they play:

• Professional support through direct guidance or making connections

• Sponsorship from individuals with decision-making power and significant influence in your organization and who advocate for your career advancement

• Personal support from those you can share with and consult about decisions or concerns

Within your network, you can have more than one kind of relationship with a person and varying levels of trust and closeness.

Then, focus on expanding beyond your current network. The key to this is identifying the brokers. In a typical social network, you find clusters of people with similar interests and characteristics that are independent of each other. When there is a broker, these specialized, independent clusters become linked to each other, creating access to diverse backgrounds, expertise, and styles. 

The role of brokers in networks

Brokers create opportunities and introductions, and an expanded network gives you access to more perspectives, which open up a deeper understanding of the organization or system in which you are operating. So it’s wise to either connect to a broker or act as one.

To me, thinking of networking as connecting with people you already know and creating new connections for other people feels a lot more natural and enjoyable than schmoozing with a room full of strangers.

When it comes to expanding your network, start with activities related to your interests, so it’s easy to find common ground with new contacts. When you meet new people, approach the conversation with an open mind and don’t worry about having a detailed agenda. It’s perfectly fine to engage in small talk, asking simple open ended questions, like “what do you do?” or “how long have you been part of this class/club/group?” For example:

• Join an organization or activity related to your hobbies and interests. If you take fitness classes or participate in a sport regularly, strike up conversation with the people you become familiar with.

• Get to know people in different teams or roles or keep in touch with former colleagues. Set a small goal like inviting one person to lunch or coffee every week.

• Volunteer for an organization or project that is aligned with your interests outside of your normal work

• Attend industry conferences

• Attend team functions and social events

• Use professional networking platforms like LinkedIn to find people in areas that interest you to learn more or get introductions

Embrace a Learner Mindset

Having a growth mindset means you believe most abilities can be developed through hard work and dedication, you embrace risk and challenges, and you view failures as learning opportunities. The opposite of this is having a fixed mindset, a helpless and passive perspective: you believe that intelligence and talent are fixed traits and spend time documenting them instead of developing, you rely on existing talent instead of effort, and you see failures as a reflection of your innate deficiencies. The good news is, fixed mindsets are not truly fixed – you can choose to shift to a growth mindset.

Tips to exercise your learner skills:

• Attend company meetings to learn about what other teams are doing 

• Subscribe to or follow trade journals, business updates, and podcasts.

• Take advantage of training programs at work, sign up for continuing studies courses at local universities, or use online learning platforms like Coursera

• Talk to peers to get fresh ideas and request feedback on your ideas

• Review other team’s OKRs

• Carry a notebook or use your virtual notepad to jot down learnings or observations that come from your successes and failures

• Create news alerts for your company, your product, and your competitors

• Pursue interests outside of work (see networking above!)

Cultivate Curiosity

In a study of executives who were considered top strategic thinkers in their industry, Professor Ellen F. Goodman at George Washington University sought to understand how their expertise was developed. The data showed that executives followed one of three processes:

1. Tackling increasingly difficult challenges over several years.

2. Being driven by natural curiosity to repeatedly use past experiences to look at a problem from different angles.

3. Following a process of asking and reflecting on three questions related to vision, strategy, and implementation, respectively:

4. Where are we going?

5. How will we get there?

6. How well are we executing?

What did the leaders who used the second and third processes have in common? They had a curious, inquisitive mentality. To put this in practice, carry a notebook or virtual notepad to take notes on the go, or use a voice recorder. I personally find that handwriting my notes fuels my creativity, but digital notetaking can be faster and more convenient. Set aside time and space for reflection and synthesis; consider blocking time on your calendar regularly and going away from your usual workspace. Then, start by asking yourself the three questions above, or check out my articles on self-reflection for additional prompts. If you get stuck trying to find answers, don’t be shy about talking it through with other people and asking for input.

Be Proactive

Learning to excel at strategic thinking won’t happen overnight. Like any other skill, it improves with practice and consistency. Research shows that it takes approximately ten years or 10,000 hours of practice to become an expert at anything.  

Here is an image of bakasana, or crow pose. I’m a dedicated yoga practitioner and yoga teacher, and it took me about 7 years of regular yoga practice to be able to balance on my arms. If I think back to the first time I tried it, it felt impossible. But I just kept trying it over and over, getting different form tips from each teacher and class. I’d see small gains over time, like being able to lift one foot off the ground, then to lift the other for a split second, until one day, I was able to balance and hold it. And if I don’t practice it for a while, it may take some time to relearn the pose.

The best strategic thinkers are able to combine a broad base of diverse experiences and contacts with a willingness and ability to reflect, synthesize, and ideate. You can be proactive by taking control of your development and making things happen rather than passively reacting to situations or waiting for something to happen. Create opportunities for yourself to stretch and learn and practice your strategic thinking.

And be persistent! Just because something doesn’t work or feels too difficult doesn’t mean it will always be that way. It’s normal to have doubts early on in your learning process – that’s just part of the conscious incompetence phase.

What It Looks Like in Action

To get really practical and concrete, here are some examples of how you can use strategic thinking to boost your performance, increase your leadership and influence, and deliver better results. Think of it as going beyond excellent execution of tasks to anticipating and planning for risks and problems.

• Anticipating and identifying risks and having a plan in case things go wrong

• Generating new ideas and getting buy-in to turn them into reality

• Setting direction and priorities for an organization and driving culture

• Developing a long term vision

• Collaborating across functions, teams, organizations

• Navigating ambiguity and uncertainty

• Tailoring communication to your audience and bottom lining

• Making connections between work you are doing and what others are doing

• Developing the next generation of talent by delegating and mentoring

• Deepening and broadening your knowledge and expertise

To sum it up, you can build your strategic thinking skills by using and expanding your network, embracing a growth mindset, maintaining a curious, inquisitive mentality, and proactively seeking stretch opportunities to practice and build your skills. I'd love to see comments with your thoughts and experiences. What has helped you become a more strategic thinker?