Strategic Two Pager

Make sure to use this skill whenever a decision is being avoided despite clear urgency, the stated reason for delay is 'we need more data' but more data wouldn't change the decision, a leader recognizes they're afraid of a decision, distinguishing valid risk from psychological discomfort, or coaching someone through decision paralysis — even if the request is about 'decision-making' or 'risk assessment' rather than explicitly about fear.

Make sure to use this skill whenever bad news must be delivered, structuring a layoff announcement, preparing for a difficult performance conversation, communicating a project cancellation, or drafting any message that will negatively affect people — even if the request is about 'communication' or 'difficult conversations' rather than explicitly about message preparation.

Make sure to use this skill whenever debriefing a high-pressure decision, running a retrospective on crisis response, evaluating whether a decision was good independent of its outcome, identifying common failure modes in leadership decisions, or learning from a decision that went wrong — even if the request is about 'retrospectives' or 'decision quality' rather than explicitly about wartime audits.