On the Craft of the Strategy Day: Nine Considerations

29/10/2024

Most of us have been to one. The offsite that hums with energy, fills flipcharts with ambitious arrows, and sends everyone home feeling that something significant has occurred, only for Monday morning to arrive and nothing, in fact, to have shifted. I call this “strategy theatre.” It’s a day when the rituals of strategy are performed. It looks rather like a strategy. But it is not, in any meaningful sense, the thing itself. What follows are nine considerations for those who would prefer their strategy days to be something more than theatre. I offer these to governance professionals as they prepare for an annual strategy day.

1. The day is not the strategy

The first discipline is to resist the belief that strategy can be built between morning tea and an early finish. Strategy is better understood as a continuing conversation, a way of thinking and planning that unfolds over time, rather than as an event or a deliverable. The strategy day can contribute meaningfully to that conversation, but only if one is clear-eyed about what can and cannot be achieved within its bounds, and about the work that must happen before and after.

2. The disciplines of design

A strategy day is a particular species of meeting, but it is a meeting nonetheless. The ordinary disciplines apply: clear objectives, a well-considered agenda, pre-reading distributed with sufficient time for genuine engagement, and careful thought about who needs to be present. There is often a perceived status attached to attendance at strategy off-sites, but the question worth asking is simpler: who will actually add value?

The choice of venue matters more than it might first appear. The aim is to minimise distraction and to create conditions in which a different kind of thinking becomes possible. It is difficult to be expansive in a windowless room that smells faintly of yesterday’s sandwiches. For most organisations, leaving the office altogether is wise. There is also much to be said for engaging an external facilitator: someone who can manage process and time, freeing everyone else to participate fully.

3. Bringing people into the room

Many participants will arrive in firefighting mode, their attention fragmented, their thinking oriented toward the immediate and tactical. The opening of the day must help them shift register. This might be achieved through an address that is forward-looking and expansive, or through what facilitators call an “inclusive question”—something everyone can answer, with no right or wrong responses, designed to signal that a different kind of conversation is about to begin. A useful example: What is the one thing that makes you most proud to be associated with this organisation?

If there is an elephant in the room: a poor set of results, an unresolved tension, it is generally better to name it openly and set it aside than to pretend it does not exist.

4. Divergence and convergence

Strategic thinking requires both divergent processes, generating ideas, casting the net wide, asking “what if?”, and convergent processes, which involve analysis, prioritisation, and choice. Both are essential, but they should never be mixed. If both must occur on the same day, aim for divergence before lunch and convergence after. Be clear, in your design, about which mode the day is intended to serve.

5. Holding the strategic register

The strategy day is an occasion for considering the larger shape of things: which markets or populations the organisation should serve, how it should position itself, what it ought to look like in a decade’s time. It is not an occasion for operational detail, for team-building, or for addressing other matters “while we have everyone in the room.” Each departure from the strategic focus draws people back into tactical mode. The discipline required is to hold the larger picture in view, and to protect the space for that kind of thinking.

6. The role of evidence

Strategy ought to be an evidence-based undertaking, yet the workshop format does not always lend itself to careful engagement with data. Consider what evidence participants need before the day, whether it should be distributed in advance or presented in the room, and what further information will need to be gathered afterwards. A useful closing exercise: What do you most wish you knew now that you did not know this morning?

7. Making the work visible and actionable

As the conversation unfolds, notes should be captured visibly: on flipcharts, on a screen, or through other means. This reassures people that their contributions have been heard and creates a shared record for what follows. A word of caution: the note-taker wields considerable power. How ideas are captured, whose language is used, and what is quietly set aside; these choices shape the narrative.

More importantly, a strategy day that produces no clear actions is little more than an extended conversation. Actions need not be decisions; they might involve gathering data, consulting others, or ceasing to do something that no longer serves. The important thing is that participants leave with a shared understanding of what happens next.

8. Movement and energy

Strategy days are taxing. The session after lunch, sometimes called the graveyard shift, is particularly challenging. A little movement can restore attention: even asking people to change seats can shift perspective. Build this into your design.

9. Communicating beyond the room

When senior people disappear for a day, others notice. In the absence of information, speculation flourishes. Plan a brief communication within a few days of the event. One need not disclose everything, but there is almost always an opportunity to say something constructive and to signal that the conversation is continuing.