Claude Prompts for Leadership Decisions That Hold Up

[Paste strategy I'm considering]. Stress test it ruthlessly. Output: best case if right (and likelihood), worst case if wrong (and likelihood), what I'm assuming I shouldn't, what feedback I haven't sought, where I'm motivated-reasoning vs evidence-based, second-order effects I'm missing. Push back hard.

I'm considering [decision]. Run pre-mortem: assume 18 months from now this failed badly. What happened? Cause + contributing factors + warning signs ignored. Then: which warning signs are visible RIGHT NOW that I'm discounting? Honest read.

Help me articulate the tradeoff between [option A] and [option B]. Each option: what we gain, what we sacrifice, what assumes. Then: which option matches our actual values + constraints, which is "easier choice that we'll regret"? Force the choice; both being right = strategy without teeth.

[Paste current vision/mission]. Critique: too vague (could fit any company)? Too specific (boxes us in)? Inspirational without aspirational? Aspirational without believable? What changes would make stakeholders actually act differently?

I'm facing decision: [describe]. Help me classify: reversible (low cost to undo) or irreversible (one-way door). Then: if reversible, decide fast + iterate. If irreversible, gather more info + slow down. Most people invert this. Frame correctly = better decision speed.

For [decision], help me identify decision rights: who decides (single point), who's consulted (input expected), who's informed (kept in loop), who's impacted but not consulted (manage feelings). Force a single decider. Decision-by-committee = decision-by-nobody.

I'm delaying decision: [describe]. Help me quantify cost of delay: opportunity cost per week, optionality lost, team frustration accumulating, competitor advantage given. Compare to cost of premature decision. Often delay's cost > rush's cost; people miscalculate.

I have a difficult conversation pending: [describe]. Walk me through deciding whether to have it: cost of not having it (compounds), cost of having it (short-term pain), my actual fear (rejection? conflict? being wrong?), my obligation given my role. Decision: have it or not?

Write all-hands update on [topic]. Audience: full company. Tone: confident, honest, contextual. Cover: where we are (data), what changed (specific), what's next (clear), what we need from each team (asks). Avoid corporate hedging. Trust drops fast when execs hedge in front of full company.

I need to deliver hard news: [describe]. Help me draft message + plan delivery. Output: written message, audience-by-audience adaptation, in-person vs written tradeoff, sequence (who hears first), follow-up commitments, my own emotion management. Honesty + dignity, not corporate-speak.

Board update for [period]. Output: 1-page summary, 3 wins, 3 challenges + how we're responding, key metrics, asks of the board, what's ahead. Honest about what isn't working — boards smell BS + lose confidence faster than from honest hard news.

Internal memo announcing [strategic change]. Audience: full company. Output: what we're changing (specific), why now (data + context), what stays the same (calming), how this affects each function (preview), questions tomorrow's town hall will cover. Send write-up before town hall — give people time to digest.

I'm coaching [direct report leader]. Their situation: [describe]. Help me prep: what's probably going on under-the-surface, what they need from me (vs what they're asking for — often different), questions to draw out their thinking, where to push, where to support, how to leave them owning it.

[High potential employee]. Help me build their development plan. Output: strengths to leverage, gaps to close (specific), stretch assignments to design, exposure they need (visibility, networks), feedback cadence, when to promote vs when to keep stretching. Goal: ready when next role opens.

My direct-report leader is underperforming. Symptoms: [describe]. Help me diagnose: are they overwhelmed (capacity), in wrong role (fit), missing skill (gap), or wrong values (deeper)? Different intervention per cause. Be honest about which it likely is.