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Strategic Thinking Skills

think independently Feb 24, 2024

Every board of directors is looking for strategic thinkers. And if you’re working on your Board Value Proposition, you’ll probably want to highlight your own skills in that area.

So, what exactly are we talking about when we refer to strategic thinking skills?

I searched in vain for a standard definition of the term “strategic thinking,” but I found there really isn’t one. Still, there’s been a lot written about how important these skills are for decision-makers.

So, let’s explore the value that strategic thinkers bring to your board. And, for those who wouldn’t describe themselves as a strategic thinker just yet, let’s take a look at a few tips for how to develop your own skills.


Strategic Thinking and the Board

Why is strategic thinking so important to a board of directors? Because, when it’s done well, it ultimately leads to a clear set of goals, plans, and new ideas required for organizations to survive and thrive in a complex, changing environment – a VUCA world.

When we talk about strategic thinking, we’re referring to the intentional and rational thought process that focuses on analyzing the critical factors that will influence the long-term success of an organization. But it’s more than just a rational process - it goes beyond that to enable a powerful way of looking at and understanding the fundamental drivers of a business, challenging conventional wisdom to discover unexpected opportunities.

The board’s role in strategic thinking is to bring their accumulated wisdom to the table, to provide an outside perspective, and to test the consistency of management’s thinking. As individual board directors, thinking strategically allows us to make a greater contribution to board deliberations. And, for the board as a whole, group strategic thinking creates value by supporting a creative dialogue where different perspectives on critical and complex issues are shared.


The Characteristics of a Strategic Thinker

Strategic thinking may be hard to define, but strategic thinkers share certain identifiable traits.

Seeing the Big Picture. Strategic thinkers stand out because of their sweeping view of the world. They don’t confine their interests and observations to narrow silos. Instead, they take into account the entire system, integrating and synthesizing information and insights from many different – sometimes unexpected - sources.

Spotting Patterns. Strategic thinkers are adept at connecting dots that are, at first glance, separate and unrelated. They see relationships between key elements and recognize patterns in the data that may remain hidden to others. They somehow create clarity out of complex and seemingly disconnected details.

Challenging Assumptions. Strategic thinkers aren’t reluctant to question current beliefs and prevailing mindsets – not just others’ but their own as well. They reframe problems to uncover hidden biases and assumptions.

Fostering Dialogue. Strategic thinkers engage key stakeholders to build trust and encourage diverse views. They understand what drives other people's agendas and they’re not afraid to bring tough issues to the surface.

Focusing on the Future. Strategic thinkers seem to be able to feel the winds of change and sense what has not yet taken shape. They have the foresight to be aware of risks, but also to recognize opportunities.

Making Decisions. Strategic thinkers don’t seek perfection. When making decisions, they balance speed and agility with rigorous data collection and in-depth analysis. If they have to, they can take a stand even with imperfect information.


Developing Your Strategic Thinking Skills

Although we might all like to think of ourselves as strategic thinkers, the truth is that not everybody naturally leans that way. Fortunately, we can all cultivate habits that will help us, as directors, to develop the strategic thinking skills that will add value to our boards.

Find time for reflection

Business leaders are encouraged to actively disengage from their mundane daily tasks – to pause and step back – so they can focus their creativity, energy, and attention on matters of longer-term significance. They have to break free from the activity trap to free up their minds to think more broadly.

For board directors, it’s important to do the same. During your PREP work, you’ll no doubt immerse yourself in the reading material that management has provided for the upcoming meeting. Remember that these reports, no matter how well executed, do not represent the entire world of information and options available to you. Try taking some time to pause and shift into a strategic frame of mind before you start your PREP. And after you’ve reviewed the material, remember to find time for reflection - to “Let It Soak” for a while.


Stay informed

Information – and lots of it – is vital to strategic thinkers. As a board director, it’s important not to rely solely on the management team to keep you informed. Locate and monitor key sources of information – not just about your own organization and your own industry, but about the larger business environment as well.

Strategic thinkers spot and interpret cues from this kind of continuous stream of intelligence. Search beyond the current boundaries of your business. You may find game-changing information at the periphery of your industry, or outside your industry, or even totally outside the business world.

Read widely and keep your mind open. With practice, you’ll be surprised to find that new ideas and perspectives come from the strangest places – a podcast, a spy novel, or a science fiction movie might be the inspiration that helps you connect the dots or reframe a thorny problem.

Work on your self awareness

The Savvy Director blog frequently returns to the theme of self-awareness. That’s because it’s a vital competency for effective directors. Learn to monitor and question your own thoughts, to acknowledge that your ideas might be flawed, and admit that you are as prone to cognitive biases and subconscious assumptions as the next person. Doing so doesn’t reflect poorly on your own credibility – it does just the opposite. It leaves you open to thinking outside the box, asking yourself, “Is my perspective valid?” and “What other points did I not consider that I should have?”

Ask great questions

I read somewhere that “Questions are the language of strategy.” Strategic thinking requires you to question everything, not cynically but in a constructive way that allows you to see ideas objectively. Great questions can be the catalyst for strategic inspiration because they provoke deep insight, forcing us to step back and see things from a different perspective and explore new possibilities.

Here are some questions - gathered from the resources listed below - that might help us, as directors, consider issues and make decisions more strategically:

  • Why do we need to care about this issue?
  • What happens if we don’t decide on this issue?
  • What outcomes are we trying to achieve?
  • What are our interests or values?
  • Whom will this decision affect?
  • Who cares about the outcomes and why?
  • What are the potential consequences – positive and negative - of this decision?
  • What is the worst result this decision can bring? Can we live with that?
  • What are forces for or against this decision?
  • What is our fallback position? Is it viable? How do we know?

Improve your listening skills

Broaden your view of the world by listening to others intently so you can learn from their perspectives. The opinions of board members, the management team, and stakeholders are valuable inputs to your decision-making, and they deserve to be heard. When you demonstrate good listening skills, it encourages others to voice their opinions and fosters a boardroom culture where everyone feels safe to contribute strategically.

Communicate clearly

Think ahead of time about how you want to structure your communication so that it helps your fellow directors focus on your core message – one that will have them challenging the status quo and talking about underlying assumptions. Work on prioritizing and sequencing your arguments in a clear and concise way, to walk people through the process of identifying issues, shaping common understanding, and framing strategic choices.

Think through the consequences of your choices

Every choice has consequences. When making key decisions, it’s important to deliberately and consciously think through the repercussions of each option. Clearly identifying different scenarios and their possible effects – intentional and non-intentional – is a vital step in evaluating choices. You can help your board with this step by asking these questions to gauge what outcome will align best with the organization’s vision.

  • What are the pros and cons of each option?
  • Which option will help meet our goals best?
  • Is there an option that will open long-term opportunities?


Your takeaways:

  • Strategic thinking ultimately leads to a clear set of goals, plans, and new ideas required for organizations to survive and thrive in a complex, changing environment.
  • At the board, strategic thinking creates value by enabling a creative dialogue where individuals gain other people's perspectives on critical and complex issues.
  • Strategic thinkers share certain traits - they see the big picture, spot patterns, challenge assumptions, and focus on the future.
  • To develop your own strategic thinking skills, work on taking the time for reflection, staying well-informed, becoming more self-aware, asking great questions, and listening intently.




Thank you.


Scott Baldwin is a certified corporate director (ICD.D) and co-founder of – an online membership with practical tools for board directors who choose a growth mindset.

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