Strengthening Your Strategic Thinking Skills

We have a familiar way of talking about strategy. Some people are described as strategic. Others are described as operational. One person is said to be a “big-picture thinker,” while another is seen as someone who simply gets things done.

Over time, these descriptions become the way that we hard-code identities. So you’ll find that the strategic people are invited into the “important” conversations. The operational people are asked to implement what has already been decided. Eventually, some people begin to tell themselves: “I am simply not a strategic person.” BUT dear reader, the more I spend time as a strategist myself, the more I am not convinced that in reality, strategy is not a personality trait. It is simply a way of thinking. And, like most ways of thinking, it gets stronger with practice. You know, like any muscle.  

What might look like instinct could actually just be exposure. We know that some people are naturally curious. While some are more comfortable with ambiguity. Other people find it easier to step back and see the wider picture. Those qualities can certainly help. But those are not the same as strategic capability. Many people who seem to be “naturally strategic” have spent many years close to the center of decision-making. They simply had the opportunities and access to information that others did not have. As a result of this, they have watched experienced leaders weigh competing priorities, and within that space, they have also been allowed to ask difficult questions, test their judgement and learn from what happened next.

So today it might look like instinct, but it has been built through repeated exposure. 

What radio taught me about developing a strategic muscle

I learned some of my earliest lessons about strategy while working in radio.

At first glance, radio programming can look like a largely creative or operational exercise. You develop programmes, schedule them, interview guests, manage presenters and respond to the news of the day. But I was curious about much more than the programme immediately in front of me.

I wanted to understand why certain programmes were scheduled at particular times. Why did one conversation generate calls while another produced silence? Who did we imagine was listening, and who was actually listening? How did audience needs, commercial interests, public responsibility, political sensitivities and the station’s wider identity influence what went on air?

That curiosity opened doors for me. I had opportunities to speak with station leadership and was invited into discussions that were, quite frankly, well above my pay grade at the time. I listened as senior leaders considered questions that were much wider than any individual programme (audience growth, revenue, reputation, political risk, staff capacity, competition), and the role the station wanted to play in public life.

Those conversations gave me access to context I would not have gained from simply completing my assigned tasks. They helped me understand that what may look like a straightforward programming decision is often connected to a much larger set of choices. In that experience, I began to see that good decisions required more than creativity or technical competence. They required an ability to hold several realities at once, recognise the trade-offs between them and understand how one decision might affect the wider system.

Over time, I was no longer only listening to those conversations. I was learning how to contribute to them. That repeated exposure allowed me to test my own judgement and learn from what happened next. This was the beginning of how my strategic muscle developed.

What many who know me today call “Yop’s natural instinct”,  is in reality, the cumulative result of curiosity, access, trust and years of practice.

Perhaps you are under-practised, not incapable

When someone says, “I am not strategic,” I sometimes wonder what the foundation of that conclusion might be. I wonder if perhaps they have spent most of their career being rewarded for responding quickly rather than pausing to interpret what is happening. Perhaps they have been expected to implement decisions without being given enough context to understand how those decisions were made. Or they have noticed important patterns but have never been invited into the room where those observations could shape direction. And nobody has taught them how to turn what they are seeing into a clear question, hypothesis or decision.

In short, they have simply not had enough opportunities to practise strategy and strategic thinking. 

The difference between being incapable and being under-practised is that the former suggests a fixed limitation, while the latter points to something that can be strengthened.

So what is actually involved in practicing strategic thinking? 

The most important thing to know is that it does not always begin with a grand vision or a sophisticated framework. It often begins with ……… pause. Just pause….

For a strategic thinker, before diving into the question, “What should we do?”, the first questions may ask:

  • What is actually happening here?
  • What has changed (financially, environmentally, etc.)?
  • What keeps showing up?
  • Whose perspective are we missing?
  • What matters most now?
  • What are our real constraints?
  • What choice are we avoiding?
  • How does this action connect to the outcome we say we want?

These questions don’t have to show up formally, and can be practiced in very simple ways. You practice strategy when you look beyond a single incident and ask whether it is part of a wider pattern or system. You can also practice it when your are trying to; 

  • distinguish between an attractive ambition and what your available resources can realistically support.
  • decide what not to do.
  • test an assumption before treating it as fact.
  • See if your activities today will deliver the intended results tomorrow. And then return later to ask whether that connection was true.

Strategic muscle gets stronger the more often it is used.

Organisations can prevent people from becoming strategic

You may not like to be reading this, but it is true. Many organisations say they want their staff to “be more strategic” while at the same time, they are also creating conditions that make strategic thinking almost impossible.

Think of a situation where a person is given a task with no context, then the person’s performance is rewarded for volume and speed. In this scenario, pausing for reflection is treated as a luxury, which means that information is concentrated at the top. So then if/when this person questions an established approach, it will be interpreted as resistance. Then leadership wonders why people are waiting to be told what to do…. sigh!

An organisation cannot demand strategic thinking while withholding the information, time, permission and decision-making space that allow it to develop. If only a few senior people are permitted to interpret what is happening, the organisation has not built strategic capacity. It has built strategic dependency. What this organization has then failed to do is provide both the environment and the opportunities for people to: 

  • understand the wider system around their work;
  • see how decisions are made;
  • test their judgement on real problems;
  • receive feedback on their reasoning;
  • make choices with meaningful consequences; and
  • reflect on what those choices produced.

This is how a way of thinking becomes an organisational capability.

Strategy is a muscle

In conclusion, I do not believe strategy belongs only to a small group of exceptionally brilliant people. Especially not in a world consumed with artificial intelligence and emergent tech. It is the ability to pause, understand what is happening, recognise what matters most and make choices that connect present action to future possibility.

Some people have exercised that ability for longer than others. Some have had better access, stronger mentors or more permission to practise. 

And if you have ever concluded that you are simply “not a strategic person,” perhaps there is another possibility worth considering.

Perhaps you are not incapable.

Perhaps you are just under-practised.

Think for a minute now and ask … what might become possible if we stopped treating strategy as something a few people are—and began building it as something more people can learn to do well?

Ready to strengthen your strategic muscle?

The Blue Sky to Reality Walk is a guided 120-minute strategy experience designed to help you move from an idea or ambition to a clearer, more practical pathway. You will examine what matters, what you can leverage, what needs to become tangible and what your next 30, 60 and 90 days could look like.


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PxP is led by Yop Rwang Pam, a systems strategist and philanthropic advisor known for helping bold institutions navigate complexity and unlock transformative clarity.

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