Most leadership teams have sat through at least one strategy session that produced a lot of energy in the room and very little change in the months that followed. The problem is rarely the quality of the thinking. It is usually the design of the session itself: what was prepared in advance, how the agenda was structured, and whether the real disagreements in the room were named or avoided.
Preparation is most of the work ¶
We spend more time preparing for a strategy session than we spend running it. That preparation includes reading the organisation's recent strategic documents, interviewing four to six participants in advance, and identifying the two or three questions that the session genuinely needs to resolve. Those questions become the spine of the agenda. Everything else is structured to produce the information needed to answer them.
Agenda design around real disagreements ¶
The most common mistake in strategy session design is building an agenda around the questions the leadership team is comfortable discussing rather than the ones they are not. Comfortable questions produce comfortable answers. The sessions that produce real decisions are the ones where the agenda is structured around the genuine disagreements in the room: the strategic bets that some people believe in and others do not, the trade-offs that have been deferred because they are difficult to name.
The role of the facilitator ¶
A facilitator's job is not to be neutral. It is to make sure the real questions get asked and that the conversation does not resolve prematurely into false consensus. That sometimes means naming the disagreement that is present in the room but not being said. It sometimes means slowing down a conversation that is moving toward a decision before the relevant information has been surfaced. It is not a comfortable role, and it requires the facilitator to have enough credibility with the group to hold the tension.
What the written output needs to contain ¶
A strategy brief produced after a facilitation session should contain three things: the decisions that were made, the decisions that were explicitly deferred and why, and the questions that remain open with an owner and a timeline for resolution. It should not contain a summary of everything that was discussed. The value of the document is in its precision, not its comprehensiveness.
If your leadership team is planning a strategy session and wants to think through the design, we are glad to have that conversation before any engagement is agreed. The design questions are worth working through carefully.