Why Strategy Succeeds in the Field
Strategy often looks strongest in the boardroom. The data is clean, the story is coherent, and the outcomes feel controllable. But more often than not, they fail. Now, the reasons they fail vary, but one of them is because our world changes faster than the assumptions behind them. On top of this, markets don’t behave logically. Customers don’t follow frameworks. What looks like a sharp plan on paper can collapse the moment it meets reality.
That’s why some of the most “strategic” decisions leaders make are shaped outside the room – through exposure to live markets, operators, and ecosystems where decisions are being made under pressure, and where value is shifting in real time. McKinsey research reinforces the scale of the problem: executives spend almost 40% of their time making decisions, yet believe much of that time is poorly used. Harvard Business Review has also argued that the best leaders don’t choose between data and instinct – they build “informed intuition”, where judgment is strengthened through lived experience and pattern recognition, not guesswork.
In that context, field exposure isn’t “inspiration” – it’s a faster way to sharpen judgment, validate assumptions, and reduce decision drag.
At Learning Expedition, our design philosophy behind every programme we curate is that leaders make better decisions when they experience the environment they’re trying to win in – and then convert what they learn into execution within a defined window.
Let’s get into it.
The Closed-Loop Trap: Why Boardroom Strategy Doesn’t Translate into Lasting Change
In many organisations, strategy is developed inside a closed system: analysts translate market change into a deck, leadership stress-tests it internally, teams align around a narrative, and execution begins after, sometimes months after.
The issue isn’t competence. It’s distance.
When leadership teams interpret the market mostly through secondhand information, they tend to over-index on what is measurable, underestimate behavioural change, assume customers will behave as expected, and treat competitors as stable reference points. Over time, strategy becomes less about understanding the market – and more about maintaining internal coherence and keeping people happy.
This is also why many leadership and strategy programmes create short-term motivation, but fail to create lasting change. Harvard Business Review captured the problem bluntly: “For the most part, the learning doesn’t lead to better organizational performance, because people soon revert to their old ways of doing things.”
That reversion is predictable. Leaders return to the same environment, the same incentives, and the same operating patterns that created the old decisions – and the insight fades under day-to-day pressure.
Field exposure helps solve both problems at once. It reduces distance by forcing leaders to confront what data can’t fully capture:
cultural shifts
customer emotion
operational constraints
speed of iteration
where value is actually being created.
In that sense, market immersion isn’t a “nice-to-have”. It’s a correction mechanism – one that recalibrates assumptions early, sharpens judgment in context, and makes change more likely to stick.
The Field Forces Leaders to See What Dashboards Can’t
In the boardroom, leaders debate secondhand signals. In the field, they confront first-order reality:
what customers do, not what they claim
how operators make trade-offs under pressure
what “speed” actually looks like in high-adaptation environments
A field-based learning environment creates a different kind of leadership input. When leaders meet founders, operators, and innovators firsthand, they encounter decisions made with fewer resources and more urgency, consumer behaviour in its raw form, new models of service design and adoption, and organisational structures built for speed.
This experience is informational – and it produces something more valuable than inspiration: compression of learning time. It becomes harder to defend old assumptions when the market evidence is directly in front of you. That is why the field often produces better strategy than the boardroom: leaders stop theorising about change and start interpreting it in real time.
McKinsey’s transformation research also points to why this matters: even when organisations pursue transformation, success remains elusive without a holistic approach.
“ … our latest McKinsey Global Survey confirm an enduring truth: the more transformation actions a company takes, the greater its chances for success.2 Yet success remains the exception, not the rule. While we’ve known for years that a comprehensive approach to organizational transformation is more conducive to lasting change, the average success rate has remained persistently low. Less than one-third of respondents—all of whom had been part of a transformation in the past five years—say their companies’ transformations have been successful at both improving organizational performance and sustaining those improvements over time.”
The Real Strategy Gap Isn’t Vision — It’s Translation into Work
However, exposure alone isn’t strategy. Leaders can visit the most innovative ecosystem in the world and still return home unchanged if there is no structure to convert insight into action. This is where many programmes fall short: they end at observation.
Even when leaders see what needs to change, the harder question is what that change looks like inside the organisation:
what does this mean for priorities next quarter?
what gets stopped?
what gets piloted?
who owns what?
That is why real strategic value requires three stages:
exposure (what we saw)
synthesis (what it means)
activation (what we will do next)
In other words, data, insights, then action.
This is where Learning Expedition is designed to be different. We don’t treat market immersion as the outcome. We treat it as the input – the starting point for sharper priorities, faster decisions, and execution that can actually hold under pressure.
And that conversion challenge isn’t just operational – it’s human. Deloitte points to how organisations are wrestling with fast-changing conditions and evolving leadership models. This isn’t simply an HR issue. It’s a strategy issue, because strategy only works when the organisation can absorb change through people: decision-making, habits, incentives, and operating rhythm.
What Learning Expedition Changes
Our programs are structured learning environments built to improve decision quality – by getting leaders closer to the market forces they’re responding to, and then converting what they learn into action.
1) Curated exposure
We don’t choose companies because they’re famous. We choose them because they reveal what’s changing: category shifts, consumer signals, new operating models, and innovation patterns worth decoding. The goal isn’t inspiration – it’s clarity.
2) Facilitated synthesis
Seeing more isn’t the same as learning faster. Without synthesis, immersion becomes noise. That’s why each day is designed around structured reflection: what surprised us, what assumptions broke, what behaviours are emerging, and what this implies for the next 12 months. The output is shared interpretation – not individual opinions.
3) 90-day activation
This is where Learning Expedition is deliberately different. We design for what happens after the experience. The 90-day window isn’t a motivational deadline – it’s one business quarter: the smallest timeframe where implementation can be tested, measured, and adjusted.
It forces the right questions immediately: What changes next? What stops? What gets piloted? Who owns it?
Because a strategy that can’t produce movement within a quarter is often not strategy – it’s ambition without mechanics. That’s why our expeditions aren’t built around what leaders will see. They’re built around what leaders will do afterwards.
At its core, Learning Expedition makes exposure useful. Not by turning it into inspiration, but by turning it into execution – before leaders return to routine and the insight disappears.