executive-mentor

Board meeting preparation for the adversarial scenario, not the friendly one. Forces numbers-cold mastery, anticipates hard questions, builds a narrative that acknowledges weakness without losing the room. Use when preparing for a board meeting, an investor update, fundraising presentation, or any high-stakes adversarial review where every number must live in your head not just on a slide.

Pre-mortem plan analysis. Imagine the plan failed 12 months from now and work backwards to find the weaknesses. Surfaces assumptions, dependencies, and execution risks before committing resources. Use when before significant resource commitment, before presenting to a board or investors, when feedback has been one-sidedly positive, or when there is pressure to move fast and figure it out later.

Adversarial thinking partner for founders and executives. Stress-tests plans, prepares for brutal board meetings, dissects decisions with no good options, and forces honest post-mortems. Use when you need someone to find the holes before the board does, make a decision you've been avoiding, or understand what actually went wrong.

/em:hard-call — Framework for decisions with no good options. Use when every option is painful and a structured 10/10/10 + regret-minimization pass is needed — e.g. choosing between a layoff and a down round, or killing a beloved product line.

/em:postmortem — Honest analysis of what went wrong. Use after a failed launch, missed quarter, or bad hire to run a blameless 5-Whys retrospective with a change register — e.g. dissecting why the Q3 release slipped six weeks.

/em:stress-test — Business assumption stress testing. Use before betting on a plan whose core assumptions are unvalidated — e.g. stress-testing 'enterprise buyers will tolerate a 6-month pilot' or a hockey-stick revenue model.