A high-challenge, high-energy workshop designed exclusively for senior and executive leaders
Senior leaders are not short of strategic frameworks. Most have been exposed to SWOT, PESTLE and competitive analysis many times over. What they are often short of is the time, the space, and the structured peer challenge to apply that thinking with rigour to the real strategic questions facing their organisation right now.
Research consistently shows that even experienced leaders default to operational thinking under pressure — prioritising the immediate over the important, planning for the most likely future rather than the most consequential one, and avoiding the explicit trade-offs that give strategy its teeth. The higher the seniority, often the more pronounced the effect: more meetings, more urgency, less altitude.
This workshop is designed for that reality. It assumes strategic knowledge and builds on it — creating the conditions for honest, high-quality strategic conversation, sharpening the instincts that separate good strategy from well-intentioned aspiration, and leaving senior teams with greater alignment, sharper choices, and renewed confidence in how they think and lead at the top.
- Explain clearly what strategic thinking is — and how it differs from operational thinking
- Apply four core strategic analysis tools with confidence: SWOT, TOWS, PESTLE, and the Impact vs. Effort prioritisation grid
- Use scenario planning to stress-test strategy against multiple possible futures — not just the most likely one
- Apply the day’s tools and frameworks to a real strategic challenge — generating, evaluating and presenting strategic options with confidence
- Recognise and resist the common traps that pull leaders away from strategic thinking
- Leave with a specific personal commitment and peer accountability structure to sustain the learning back at work
Our Introduction to Strategic Thinking programme builds the foundations: frameworks, language, and habits for those new to thinking strategically. This workshop starts where that one ends. The tools are assumed. The challenge is sharper. The conversations are harder. And the focus shifts from “what is strategic thinking?” to “how well are we actually doing it – and what needs to change?”
Workshop outline
1. Opening provocation: how strategic is your leadership, really?
- A short, sharp diagnostic: participants rate their organisation against six hallmarks of genuinely strategic leadership — individually and anonymously, before comparing results
- Surfaces the gaps between where the group believes the organisation is operating strategically and where it actually is — creating honest energy for the rest of the day
- Replaces the typical away-day opening of “we’re all doing brilliantly” with a more useful question: “where are the honest gaps?”
2. Strategic thinking under pressure: The Balloon Factory
- Participants run competing companies across five simulated business years, making strategic decisions as conditions change: new competitors, regulatory shocks, supply disruption, shifting consumer behaviour
- At senior level, the simulation is run with minimal instruction — participants are expected to self-organise, set their own strategy, and adapt. The dynamics that emerge (who leads, who defers, how the group makes decisions under pressure) are as revealing as the outcomes
- The debrief is an extended peer reflection: where do these patterns show up in your real leadership? What does your Round 1 behaviour reveal about how you approach strategy at the top?
3. Assumption audit: what is your strategy actually betting on?
- Every strategy rests on assumptions about the future. This session makes those assumptions explicit — surfacing what the organisation is betting on, how confident it is in each assumption, and how robustly those assumptions are being monitored
- Participants identify their “danger zone”: the assumptions that are both critical to the strategy succeeding and low-confidence. These become the focus of the scenario session that follows
- One of the most uncomfortable — and most valuable — conversations a senior team can have. Often the first time these assumptions have been named explicitly in the same room
4. Scenario planning: thinking about the future
- Built around the danger-zone assumptions from Session 3, the group develops four plausible futures using a 2x2 scenario matrix — then tests the current strategy against each one
- The question is not “which future will happen?” but “which elements of our strategy are robust across all four — and which are fragile bets we should be actively managing?”
- Produces a clear map of strategic resilience — what to invest in regardless of how the future unfolds, and where contingency thinking is needed
5. Making the hard choices
- Strategy fails most often not in the analysis phase but in the moment of choice — when leaders avoid naming the trade-off, hedge their bets across too many options, or let good intentions substitute for clear decisions
- Working in small groups, participants apply Roger Martin’s Choice Cascade to a real live challenge from their own organisation — producing a strategic recommendation that includes an explicit statement of what the organisation will not do
- Each group presents to the room. Peer challenge is direct and structured. The facilitator holds the standard: if the trade-off is absent or vague, the strategy is sent back
- The most demanding session of the day — and consistently the one participants find most valuable
6. Strategic leadership commitments
- Each participant articulates one specific change to how they will lead strategically — not a vague aspiration, but a named behaviour with a named deadline
- The group agrees a small number of shared strategic commitments — the two or three things they will do differently together as a leadership team from this point forward
- Optional: a 60-minute follow-up session 6–8 weeks later to review progress, surface what has and hasn’t shifted, and sustain momentum
