How strategic judgement is actually learned
A lot of today’s senior leaders learned strategy without ever being formally taught it. They learned it by sitting close to decisions. By watching how problems were framed, which trade-offs were taken seriously, and how uncertainty was handled when there was no obvious right answer. Over time, they absorbed not just what decisions were made, but how those decisions were reached.
Nobody labelled this as training. It wasn’t a competency framework or a development plan. It happened because they were nearby, involved and trusted with increasing responsibility.
This often gets forgotten when organisations talk about strategic capability today. Strategy is treated as something people acquire through courses, frameworks or role progression. In practice, much of what we recognise as good judgement is built through repeated exposure to real decisions and the reasoning behind them.
There is a long-standing body of research that supports this. Work on social learning shows that people develop judgement by observing others, not just through instruction. In organisational settings, that means watching experienced leaders think in public, weigh options and live with the consequences of their calls.
Related research on situated learning describes a similar process. People become skilled by being close to real work before fully owning it, gradually moving from observation to participation. This is how apprentices learn a craft, but it is also how many strategists have historically learned theirs.
In everyday work, this used to look fairly ordinary. Junior and mid-level people sat in meetings, listened to how decisions were shaped, saw which arguments held and which were pushed aside, and slowly built an internal sense of what good judgement looked like. Learning happened without being named.
That mechanism is far less reliable now.
Remote work, higher pace and constant delivery have reduced many of the informal moments where this kind of learning used to take place. People still attend meetings, but those meetings are often narrower and more transactional. Decisions are frequently made elsewhere and shared later as conclusions, rather than being observed as they are formed.
Research shows informal, everyday interactions between colleagues are a key vehicle for learning at work. Those unplanned moments of discussion and feedback are disrupted when work is remote, which can weaken how judgement and practice get shared.
This helps explain why feedback like “be more strategic” lands so badly. It names a gap, but offers no access to the behaviour that fills it. Research into feedback effectiveness shows that vague prompts are difficult to act on because they don’t expose the underlying decisions or trade-offs someone needs to learn from.
The consequences are often misread, confidence dips and progression stalls. Good people start to assume the problem is personal. In reality, the conditions that once developed judgement have quietly weakened.
There is a wider organisational cost to this. Research consistently links development opportunity to retention, which means that when learning pathways feel unclear or inaccessible, people leave. What shows up as a talent issue is often a structural learning problem.
The everyday strategist understands that strategic capability is not transferred through documents or training alone. It is built through exposure to reasoning, access to judgement and opportunities to practise decision-making with support.
If organisations want more strategic thinkers, they need to make strategic reasoning visible again. That means narrating decisions, not just announcing them. It means creating space for people to see trade-offs being worked through, not just the outcomes.
Strategy is not learned in abstraction. It is learned by watching someone think, and then being trusted to think alongside them.
Further reading
Bandura, A. (1977). Social Learning Theory.
Lave, J. & Wenger, E. (1991). Situated Learning: Legitimate Peripheral Participation.
