Strategic Planning

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.

vpe-advisor is a VP of Engineering operating-advice skill for startup delivery throughput, hiring funnel health, team structure, and production discipline. Use its references and Python tools to analyze DORA metrics, hiring gaps, manager triggers, on-call practices, and strategic planning tradeoffs.

ma-playbook is an M&A strategy skill for acquiring companies or preparing to be acquired, with workflows for strategic rationale, due diligence, valuation, deal terms, negotiation, and post-close integration planning.

internal-narrative helps leaders build one coherent company story for employees, investors, customers, candidates, partners, and the board. Use it to plan all-hands updates, investor notes, board memos, recruiting narratives, and crisis communication while checking audience-specific risks and contradictions.

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.

coo-advisor is a Claude skill for internal operations leadership, helping scaling teams design operating cadence, improve processes, cascade OKRs, diagnose bottlenecks, and use included Python tools for OKR tracking and operational efficiency analysis.

cpo-advisor is a strategic Product Management skill for CPO-level decisions: product vision, PMF, portfolio strategy, org design, and board-ready product narratives. Includes references plus PMF scoring and portfolio analysis scripts for scaling companies.

company-os is a C-level advisory skill for designing company operating systems: framework selection, accountability charts, scorecards, meeting cadence, issue resolution, OKRs, and 90-day rollout planning for Internal Operations.

chro-advisor is a Claude skill for People Strategy in scaling companies, covering headcount planning, compensation frameworks, org design, retention, culture, and performance management. Includes references plus Python tools for hiring cost modeling and compensation benchmarking.

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.

chief-data-officer-advisor is a strategic CDO skill for startup data decisions: AI training data rights, warehouse vs lakehouse vs mesh strategy, customer-data asset valuation, M&A readiness, and data team hiring. Includes references and Python tools for decision support, not tactical data engineering.

chief-customer-officer-advisor is a Customer Success leadership skill for B2B SaaS retention, segmentation, CS coverage, and org design. Use its references and Python scripts to analyze GRR vs NRR, tier customers, size CSM headcount, and plan CS hires.

chief-ai-officer-advisor helps founders and CAIO-style leaders make strategic AI decisions: API vs fine-tune vs in-house build, EU/US AI risk classification, API-to-self-hosted cost economics, and AI hiring sequence. Includes reference guides and Python calculators for structured planning.

cfo-advisor helps founders and Finance Operations teams model runway, burn, unit economics, fundraising dilution, cash management, and board-ready finance narratives. Includes references plus standard-library Python scripts for burn rate, unit economics, and fundraising scenarios.

ceo-advisor is a Claude skill for executive Strategic Planning, board prep, investor communication, culture work, and CEO decision support. It includes reference guides plus Python tools for weighted strategy assessment and financial scenario analysis.

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.

arquiteto-de-empresa is a Company Architect skill that turns founder input into an OKF company knowledge base: linked Markdown files with YAML frontmatter, indexes, logs, and controlled types. Use it for Strategic Planning, company-as-code workflows, and phased interviews covering strategy, market, finance, product, operations, people, legal, and governance.

board-deck-builder helps create board and investor update decks with executive narrative, SaaS metrics, risks, and board asks. Use it for quarterly board meetings, investor updates, QBRs, and fundraising readiness with templates that preserve [TBD] for unknown numbers.

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.

board-prep is a Claude skill for adversarial board meeting and investor update prep. It helps leaders know key metrics cold, anticipate hard questions, and shape a candid narrative around misses, runway, growth, and decisions.

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.