Decision Making

reflect is a mid-conversation reassessment skill for pausing execution, rereading from the original goal, checking bias and drift, and deciding whether to continue, pivot, or pause. Use it for Decision Support, planning, debugging loops, and strategy work when you need a frank sanity check instead of another summary.

andreessen is a market-first Strategic Planning skill for pressure-testing ventures, product ideas, features, PMF signals, career bets, and daily priorities. It uses an anti-sycophancy operating prompt, verdict labels, reference guides, examples, and stdlib Python scripts for market scoring, PMF checks, and 3x5 Anti-Todo execution.

grill-me is a Decision Support skill that stress-tests plans and designs through one-question-at-a-time interrogation, recommended answers, codebase exploration, and helper scripts for extracting decision branches and tracking sessions.

decision-logger is a Decision Support skill for approved board decisions. It separates raw transcripts from a Layer 2 decision index, tracks owners, deadlines, rejected options, and follow-ups, and includes a Python tracker for summaries, overdue items, conflicts, owner filters, and search.

cto-advisor is a CTO leadership skill for architecture decisions, technical debt, engineering metrics, technology evaluation, team scaling, and strategic planning. Includes ADR, DORA, evaluation frameworks, plus Python tools for debt analysis and team scaling.

chief-of-staff is a C-suite orchestration skill for founder decision support. It routes questions to the right executive advisor roles, convenes board-style reviews for complex calls, synthesizes tradeoffs, and supports decision logging using routing and synthesis references.

board-meeting is a Claude skill for structured strategic decisions using /cs:boardroom, isolated C-suite roles, critic review, founder approval, and decision records. Includes agenda and minutes templates for repeatable board-meeting usage.

stress-test is a Claude executive mentor skill for pressure-testing business assumptions before strategic planning, fundraising, GTM, hiring, or revenue bets. Use /em:stress-test <assumption> to isolate a measurable claim, challenge counter-evidence, and expose where a plan may break.

hard-call is an executive decision-support skill for painful choices with no clean option. Use /em:hard-call <decision> to assess reversibility, 10/10/10 impact, regret minimization, and the cost of delay for layoffs, pivots, shutdowns, co-founder exits, or down rounds.

post-mortem is a Strategic Planning skill for reviewing executed decisions against pre-committed success metrics, kill criteria, execution plans, and preserved dissent. Use `/cs:post-mortem <decision-path>` at 90-day checkpoints, kill triggers, reversals, or quarterly reviews.

office-hours runs /cs:office-hours <topic> as a YC-style six-question founder interrogation before advice. Use it to clarify problem, customer, distribution, defensibility, capital, and founder fit before Strategic Planning, pivots, fundraising, or major product bets.

freeze is a Claude chief-of-staff skill for locking high-cost strategic decisions during a cooldown period. Use /cs:freeze <decision-path> <days> to prevent re-litigation unless clear kill criteria trigger.

execute turns an approved decision record into a 90-day operating plan with weekly milestones, named DRIs, success metrics, definitions of done, and check-in cadence. Best for Project Management and leadership workflows that need accountable execution after /cs:decide.

cto-review is a Strategic Planning skill for pressure-testing architecture, scaling cliffs, tech debt, team ramp risk, and build-vs-buy decisions with /cs:cto-review <plan>. It is prompt-first; verify optional referenced analyzer scripts after install.

decide logs founder-approved board memos as durable company memory via decision-logger, separating approved decisions from raw transcripts for Knowledge Capture workflows.

cdo-review is a Chief Data Officer review skill for pressure-testing data strategy plans, AI training data rights, architecture choices, data productization, M&A diligence, and data-team hiring before commitments.

boardroom is a C-suite strategic deliberation skill that turns a decision brief into a 6-phase board memo with independent executive positions, cross-examination, critic pre-screen, and synthesis. Use it for high-stakes cross-functional decisions like pricing, runway, product bets, risk, or Strategic Planning.

documentation-and-adrs helps agents write decision-focused technical documentation and ADRs. Use it to capture context, constraints, tradeoffs, rejected options, and consequences for architecture, APIs, infrastructure, auth, and feature changes. It is ideal when you need durable rationale for future engineers and agents, not just a polished summary.

swot-analysis skill for structured SWOT assessments with actionable recommendations. Use it for strategic assessment, competitive analysis, and product or business positioning when you need a clear internal-vs-external view.

The product-strategy skill helps you create a structured Product Strategy Canvas for new products, repositioning, launches, or strategic planning. It guides vision, segments, costs, value propositions, trade-offs, metrics, growth, capabilities, and defensibility so you can build a decision-ready product strategy.

The porters-five-forces skill helps you assess competitive rivalry, supplier power, buyer power, substitutes, and new entrants. Use it for porters-five-forces for Competitive Analysis when you need a structured view of market attractiveness, pricing pressure, and barriers to profit.

pestle-analysis skill for assessing Political, Economic, Social, Technological, Legal, and Environmental factors around a market, product, or business decision. Use it for strategic planning, market entry checks, and external risk review when you need a structured, decision-ready analysis.

prioritize-features skill for Product Management helps rank a feature backlog into a defensible top 5 using impact, effort, risk, and strategic fit. Use it when you need to compare feature ideas, make scope decisions, and explain why one item should come first.

Prioritize-assumptions helps teams rank assumptions with an Impact × Risk matrix and recommend experiments for each item. Use prioritize-assumptions for Strategic Planning to turn uncertain ideas into a clear test plan, especially when you need a practical prioritize-assumptions guide, usage flow, and next-step validation.