Hard Conversation Prep

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 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.

Make sure to use this skill whenever a PM's decision authority is unclear, multiple PMs overlap on the same product area, onboarding a new PM who needs explicit ownership boundaries, resolving territorial conflicts between product owners, or defining who decides what in a matrixed organization — even if the request is about 'role clarity' or 'PM management' rather than explicitly about scope definition.