The skill that separates leaders from managers

One of the questions that often comes up when I coach leaders, especially those who are a few years into the role, is: "How do I get better at thinking strategically?"

Most leaders are reasonably quick to master the day-to-day management of projects, people, processes etc., especially when they have the right training, coaching and guidance.

But strategic thinking is what separates leaders who manage from those who anticipate, prepare for and shape what comes next. For many leaders, this does not come naturally. So, it is easy to allow management to crowd out the deeper work.

In previous newsletters, we have looked at how to create more time for strategic work — through delegation, coaching, and structuring your time more intentionally.

This week, we go a step further and look at how you can actually develop and strengthen your capacity for strategic thinking.

As usual, experience and research give us some valuable answers.

Before we get to how to develop it, it is worth being clear about what we mean.

Strategic thinking is not just planning. It involves:

These abilities are not innate. They are skills. And, while they may come more naturally to some people, like any skill, they grow with deliberate practice (Casey & Goldman, 2010).

The single most powerful way to develop strategic thinking is through experience, such as stretch assignments, that force you into it. Ideally these would be roles or projects that require you to think in a longer time horizon, coordinate across functions, or navigate genuine uncertainty and complexity (Kazmi & Naaranoja, 2015).

For example, early on it my leadership career, I led a project to develop the advocacy capability of some 60 lawyers in the enforcement division of the financial regulator I worked for. This was a huge stretch for me. It required me to co-ordinate internal departments and external providers, bring senior management along with plans, and gain agreement for the significant expenditure involved.

It was a very different challenge from my day-job of managing legal cases, but it broadened my horizons and helped me practice most of the skills outlined above. What is more, it hugely boosted my confidence and upped my credibility as a leader.

So, ask yourself: is there a project, initiative, or cross-functional challenge you could get involved in that would push you to think differently? Even a modest stretch in scope can significantly accelerate your development.

Strategic thinkers look outward. They track industry and regulatory trends, competitor behaviour, technology shifts, and broader societal changes, and they connect what they observe to the long-term implications for their team and organisation (Chiș-Manolache, 2024).

If you work in a large organisation with constant change, you should practice looking out from your team and across the organisation. Track the structural changes, the changes in stakeholders you need to engage with.

For example, set aside some time each week to read something outside your usual field or talk to somebody outside your usual sphere of influence. Make it a habit to ask: "What is changing, and what might it mean for us in one, two or three years?"

Over time, this kind of regular, disciplined outward attention sharpens your ability to spot patterns and recognise the implications, risks and opportunities of change.

Experience alone does not build strategic thinking. Reflection does (Casey & Goldman, 2010). Reflection is the way that you can turn experience into intentional learning.

Here is a simple reflection framework. After any significant decision or project, pause and ask yourself these questions:

This kind of deliberate debriefing turns experience into insight and helps you build better strategic judgement.

In last week’s post, we discussed systems in the context of complex problem solving. We established how the complexity of relationships, people, processes, variables and norms make it difficult to know how current decisions and actions will play out across the system.

Nevertheless, one of the defining characteristics of strong strategic thinkers is their ability to see the systems themselves and thereby understand the context in which of people act and decisions are made. They do not treat problems in isolation.

So, while complex systems are inherently unpredictable, there are ways to prepare to meet this complexity. Tools that help here include scenario planning (imagining how things might play out under different assumptions), 'what if' analyses (challenging the assumptions behind a decision or plan), and red-team reviews (deliberately arguing against your own position to test its robustness) (Casey & Goldman, 2010; Chiș-Manolache, 2024).

These might sound like high powered exercises. But you can adapt them to your world. Asking yourself: "what are the second-order consequences of this decision?" before you act is a meaningful step in the right direction.

This means considering not just the immediate effects of a choice, but also what might happen because of those effects. Second-order consequences refer to the ripple effects that follow the initial outcome of a decision, essentially, what happens next because of what you've done.

For example, introducing a new policy may solve one problem, but could create new issues or unexpected behaviours down the line. By actively thinking about these knock-on impacts, you become more aware of the complexity of systems and can make better-informed decisions that take account of both short-term and long-term implications.

Research on expert strategic thinkers consistently highlights two common factors: mentors who challenged their thinking, and a breadth of experience that gave them multiple models and frameworks to draw on (Goldman, Scott & Follman, 2015).

If you have access to a mentor or a coach, inside or outside your organisation, use them. Ask them not just for advice, but for challenge and keep looking for opportunities to work across functions, industries, or cultures. Each new context adds to the mental toolkit you bring to strategic questions. 

It is worth noting that individual effort alone is not always enough. Research is clear that strategic thinking flourishes in environments that reward long-term focus, encourage external awareness, and invest in learning (Goldman & Casey, 2010).

If you are in an environment where short-term focus dominates it can be harder to develop strategically. That means you may need to be more intentional about creating your own pockets of space for this kind of thinking.

Strategic thinking is not a gift. It is a practice.

It grows through demanding experiences, reflection, and the habit of looking outward. None of these require a business school programme. They require intention — and a regular investment of time.

Start small. Read something different. Debrief a recent decision. Put your hand up for a piece of work that feels slightly harder than you feel ready for.

Do that consistently, and over time your strategic thinking capacity will develop.

Casey, A., & Goldman, E. (2010). Enhancing the ability to think strategically: A learning model. Management Learning, 41, 167–185.

Chiș-Manolache, D. (2024). Strategic leadership in an era of competition. Scientific Research and Education in the Air Force.

Goldman, E., & Casey, A. (2010). Building a culture that encourages strategic thinking. Journal of Leadership & Organizational Studies, 17, 119–128.

Goldman, E., Scott, A., & Follman, J. (2015). Organizational practices to develop strategic thinking. Journal of Strategy and Management, 8, 155–175.

Kazmi, S., & Naaranoja, M. (2015). Cultivating strategic thinking in organizational leaders by designing supportive work environments. Procedia — Social and Behavioral Sciences, 181, 43–52.

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