Agent skills, free to install

Make sure to use this skill whenever deploying an AI agent or model into production and the team expects it to work perfectly on day one, evaluating an AI vendor that claims 'one-click deployment,' or designing the data-feedback loop that makes an AI system improve post-deployment — even if the request is about 'AI deployment' or 'agent design' rather than explicitly about flywheels.

Make sure to use this skill whenever a growth team is stuck locally optimizing without finding new opportunities, the team is scattershot trying random ideas without a through line, a growth review needs to assess whether effort is balanced between finding new mountains and climbing the current one, or experimentation feels productive but metrics aren't moving — even if the request is about 'growth strategy' or 'experimentation' rather than explicitly about explore vs exploit.

Make sure to use this skill whenever a freemium product needs to increase conversion by showing free users the value of paid features, the free tier experience doesn't communicate what paid offers, or users perceive the product as simpler than it actually is — even if the request is about 'monetization' or 'conversion rate optimization' rather than explicitly about feature sampling.

Make sure to use this skill whenever a product doesn't fit neatly into known categories, analysts and customers struggle to classify the product, debating whether to create a new category or position in an existing one, evaluating the cost of market education for a new category, or deciding between subcategory and full category creation — even if the request is about 'positioning' or 'go-to-market' rather than explicitly about category creation.

Make sure to use this skill whenever positioning is vague or the team gives different answers to 'what do we do', a product is being repositioned for a new market, competitive pressure requires clarifying differentiation, designing the 'only we...' statement, or preparing messaging for a website or pitch deck — even if the request is about 'messaging' or 'competitive positioning' rather than explicitly about positioning.

Make sure to use this skill whenever preparing for a sales presentation or demo, the current pitch leads with features instead of customer problems, win rates are low and pitch structure is suspected, training a sales team on consultative selling, or rebuilding a pitch after a competitive loss — even if the request is about 'sales' or 'presentations' rather than explicitly about pitch structure.

Make sure to use this skill whenever choosing between a CDP-centralized stack vs a warehouse-first reverse-ETL approach, evaluating martech architecture for a growing company, or deciding whether to consolidate on one SDK or invest in a data warehouse pipeline — even if the request is about 'marketing tools' or 'data architecture' rather than explicitly about martech stacks.

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 bad news must be delivered, structuring a layoff announcement, preparing for a difficult performance conversation, communicating a project cancellation, or drafting any message that will negatively affect people — even if the request is about 'communication' or 'difficult conversations' rather than explicitly about message preparation.

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 team tracks output metrics they can't influence, building a metric dashboard, understanding which levers drive revenue or retention, mapping the causal chain from actions to outcomes, or diagnosing why metrics are stagnant despite effort — even if the request is about 'metrics' or 'dashboards' rather than explicitly about input vs output metrics.

Make sure to use this skill whenever a proposal needs to convince a skeptical audience, a bullet-point deck failed to persuade, documenting a strategic decision that needs to survive without the presenter, writing a 6-pager for an exec review, or structuring a persuasive argument with evidence — even if the request is about 'writing' or 'proposals' rather than explicitly about narrative memos.

Make sure to use this skill whenever starting a new product or feature initiative, the value proposition is vague and needs forcing clarity, writing a PRD and needing a customer-centric anchor, testing whether a product idea is compelling before building, or aligning the team on what customers will actually care about — even if the request is about 'product definition' or 'PRD writing' rather than explicitly about press releases.

Make sure to use this skill whenever a working relationship seems strained, decisions are being second-guessed without clear rationale, collaboration between two parties is degrading, a new partnership needs a baseline trust assessment, or delegation levels need calibration — even if the request is about 'collaboration' or 'working relationships' rather than explicitly about trust.

Make sure to use this skill whenever a product opportunity exists at the intersection of multiple existing categories, the team is building something that doesn't fit neatly into one product category, or a competitive analysis requires understanding whether the product redefines the category rather than competing within it — even if the request is about 'product strategy' or 'competitive positioning' rather than explicitly about category redefinition.

Make sure to use this skill whenever a new technology wave is emerging and growth strategy needs updating, existing channels are showing diminishing returns industry-wide, annual growth planning requires forward-looking channel assessment, competitors are investing in new platforms, or the team needs to identify the next big distribution opportunity — even if the request is about 'growth planning' or 'new channels' rather than explicitly about disruption scanning.

Make sure to use this skill whenever ROI on a growth channel is declining but stopping feels riskier than continuing, increasing spend on a channel just to maintain position, all competitors are investing more for less return, evaluating whether to exit a commoditized channel, or diagnosing why growth spend keeps rising without proportional returns — even if the request is about 'growth efficiency' or 'channel ROI' rather than explicitly about the prisoner's dilemma.

Make sure to use this skill whenever evaluating a new distribution channel for investment, diagnosing why an existing channel's ROI is declining, assessing whether to invest in ChatGPT/AI search as a growth channel, planning growth strategy around emerging platforms, or deciding whether to double down on or exit a maturing channel — even if the request is about 'growth strategy' or 'channel planning' rather than explicitly about platform cycles.

Make sure to use this skill whenever evaluating what creates defensibility for a new distribution platform, assessing whether an AI product's moat is context and memory, or determining which platform in a competitive market will win — even if the request is about 'competitive strategy' or 'AI moats' rather than explicitly about platform moats.

Make sure to use this skill whenever a business needs to forecast growth quantitatively, strategic decisions require understanding which lever has the most impact, building a financial model for fundraising or planning, creating a unit economics model, or figuring out whether to invest in acquisition vs retention vs monetization — even if the request is about 'financial modeling' or 'forecasting' rather than explicitly about growth models.

Make sure to use this skill whenever marketplace GMV growth is stalling, the team debates investing in supply vs demand, supply quality or quantity is the suspected bottleneck, liquidity metrics are declining, or a marketplace needs to diagnose its chicken-and-egg problem — even if the request is about 'marketplace growth' or 'supply acquisition' rather than explicitly about supply diagnosis.

Make sure to use this skill whenever cohort retention data needs interpretation, evaluating product-market fit from quantitative data, building the retention component of a growth model, comparing retention across product versions or segments, or diagnosing why users leave after a specific time period — even if the request is about 'retention' or 'churn' rather than explicitly about curve analysis.

Make sure to use this skill whenever multiple growth levers compete for investment, resource allocation needs data-driven prioritization, a growth model exists and the team needs to decide where to focus, comparing the impact of improving acquisition vs retention vs monetization, or preparing for a strategic planning discussion with quantitative backing — even if the request is about 'prioritization' or 'resource allocation' rather than explicitly about sensitivity analysis.

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.

Make sure to use this skill whenever interviewing or evaluating PM candidates, designing a structured PM interview loop, assessing an internal PM for promotion, comparing candidates across a standardized rubric, or debriefing an interview panel — even if the request is about 'hiring' or 'interviews' rather than explicitly about candidate assessment.

Make sure to use this skill whenever a product is approaching launch and the team debates readiness, quality standards are inconsistent across releases, defining launch gates for a new product, deciding what's 'good enough' to ship, or preventing a launch from being rolled back due to quality — even if the request is about 'launch readiness' or 'quality' rather than explicitly about quality bars.

Make sure to use this skill whenever a product debate has lasted more than 2 meetings, participants argue from different mental models with no shared reference, a design or architecture decision needs convergence, the team is going in circles with abstract arguments, or a decision requires comparing approaches side by side — even if the request is about 'decision-making' or 'alignment' rather than explicitly about artifacts.

Make sure to use this skill whenever a product decision is justified by gut feeling, a senior leader has a strong opinion but the reasoning is implicit, a debate is stuck because both sides argue from intuition, a feature is being championed without data, or the team needs to convert a hunch into something testable — even if the request is about 'decision-making' or 'product strategy' rather than explicitly about testing intuitions.

Make sure to use this skill whenever designing a test for a subjective or 'soft' feature, building a business case for UX improvements, measuring the impact of design polish, validating whether a feature that 'feels good' actually moves metrics, or justifying investment in non-functional improvements — even if the request is about 'A/B testing' or 'experiment design' rather than explicitly about delight.

Make sure to use this skill whenever a product decision trades customer delight against business margin, pricing changes are being evaluated for customer perception impact, or the team debates investing in a 'nice to have' feature vs improving unit economics — even if the request is about 'pricing' or 'product strategy' rather than explicitly about delight vs margin.

Make sure to use this skill whenever converting a feature commitment into a testable experiment, designing validation for a product bet, creating kill criteria for a planned initiative, structuring a roadmap item as a hypothesis, or preparing for a build/kill decision — even if the request is about 'roadmap planning' or 'product strategy' rather than explicitly about hypotheses.

Make sure to use this skill whenever evaluating whether to build a requested feature, triaging feature requests from a vocal minority, auditing the product for low-adoption features, deciding what to cut during scope reduction, or assessing whether a feature adds complexity disproportionate to its usage — even if the request is about 'feature prioritization' or 'simplification' rather than explicitly about killing niche features.

Make sure to use this skill whenever determining the right team size and first PM hire timing, designing the product development process for a growing company, figuring out when a startup needs its first dedicated PM, or structuring the atomic product team — even if the request is about 'team structure' or 'hiring' rather than explicitly about atomic teams.

Make sure to use this skill whenever a quarterly review reveals the same priorities as last quarter, the team describes work as 'steady' or 'maintaining', an individual feels stuck but can't identify why, checking for comfortable patterns that prevent growth, or diagnosing organizational inertia — even if the request is about 'team health' or 'growth' rather than explicitly about autopilot.

Make sure to use this skill whenever burnout signals are present, a person works long hours but feels unproductive, a role change or restructuring needs data on what to keep vs delegate, diagnosing the mismatch between effort and satisfaction, or rebalancing work toward high-energy high-impact activities — even if the request is about 'burnout' or 'work-life balance' rather than explicitly about energy audits.

Make sure to use this skill whenever a decision is presented as 'data-driven' but the data quality hasn't been assessed, distinguishing between opinions and evidence in a debate, grounding a decision in the actual quality of supporting evidence, rating the strength of claims in a proposal, or identifying what additional evidence would increase confidence — even if the request is about 'decision quality' or 'evidence' rather than explicitly about confidence ratings.

Make sure to use this skill whenever a new product idea needs validation before full investment, de-risking an idea incrementally instead of build-and-pray, comparing multiple ideas by evidence strength, designing the cheapest test for a hypothesis, or preventing premature commitment to an unvalidated idea — even if the request is about 'validation' or 'product discovery' rather than explicitly about validation ladders.

Make sure to use this skill whenever a product discussion has strong opinions on both sides with no resolution, a document makes claims without citing evidence, a decision is about to be made and the team needs to separate known from assumed, checking whether a debate is opinion-driven or evidence-driven, or preparing for a critical review — even if the request is about 'critical thinking' or 'decision-making' rather than explicitly about opinion detection.

Make sure to use this skill whenever competitive pressure is rising and the team's advantage feels thin, the product pitch relies on 'better' instead of 'different', assessing long-term competitive position, evaluating whether advantages are structural or incremental, or diagnosing why competitors are catching up despite the team shipping more — even if the request is about 'competitive strategy' or 'differentiation' rather than explicitly about differentiation audits.

Make sure to use this skill whenever burnout signals are visible, everything feels urgent all the time, the team is consistently overwhelmed, assessing operational health during a planning cycle, or diagnosing why high effort isn't producing proportional results — even if the request is about 'team health' or 'burnout' rather than explicitly about operational intensity.

Make sure to use this skill whenever meeting load exceeds 15 hours/week per person, meetings regularly end without decisions, a productivity audit identifies meetings as the top time sink, the team feels over-meetinged, or designing async replacements for synchronous rituals — even if the request is about 'productivity' or 'time management' rather than explicitly about meeting elimination.

Make sure to use this skill whenever a project is too large for its timeline, feature scope has expanded during planning, the team needs to ship something valuable in a fixed timeframe, reducing scope without losing core value, or deciding what to cut from a roadmap — even if the request is about 'project scoping' or 'deadline pressure' rather than explicitly about scope reduction.

Make sure to use this skill whenever a project depends on deliverables from other teams, a project timeline slipped because a dependency wasn't tracked, planning requires understanding external dependencies on the critical path, managing risk across team boundaries, or designing a project plan with multiple team inputs — even if the request is about 'project management' or 'planning' rather than explicitly about dependency mapping.

Make sure to use this skill whenever the team debates 'ship now vs polish more', a deadline is approaching and quality isn't at desired level, different team members have different quality standards, calibrating the quality bar based on reversibility and audience exposure, or deciding whether to ship behind a feature flag vs full release — even if the request is about 'quality' or 'release management' rather than explicitly about speed-quality tradeoffs.

Make sure to use this skill whenever a decision is blocked by incomplete information, the team says 'we don't have enough data', multiple unknowns exist and the team is paralyzed, a time-sensitive decision is being delayed for perfect information, or separating knowable from unknowable questions — even if the request is about 'decision-making' or 'risk management' rather than explicitly about uncertainty.

Make sure to use this skill whenever scoping a v1 product that needs to win hearts not just function, the product works but users don't love it, a redesign needs to identify delight features, determining the 'signature' feature that defines the product's personality, or deciding which features create emotional connection vs just avoid complaints — even if the request is about 'product scoping' or 'MVP' rather than explicitly about MLP.

Make sure to use this skill whenever the product pitch gets blank stares, different team members describe the product differently, testing whether a product explanation passes the 30-second dinner party test, checking for jargon that blocks understanding, or rewriting a tagline or elevator pitch — even if the request is about 'messaging' or 'copywriting' rather than explicitly about story testing.

Make sure to use this skill whenever activation rates are low, users sign up but don't reach the product's core value, the onboarding flow has grown complex, measuring time-to-value, or identifying the specific step where most users give up — even if the request is about 'activation' or 'onboarding' rather than explicitly about onboarding audits.

Make sure to use this skill whenever competing against a dominant incumbent, the team feels overwhelmed by a larger competitor, designing competitive strategy based on structural advantages, identifying what the giant can't do because of its size, or planning growth in a market dominated by big tech — even if the request is about 'competitive strategy' or 'market positioning' rather than explicitly about competing with giants.

Make sure to use this skill whenever a product has too many settings or configuration options, users struggle to get started because of choice overload, the team debates adding a preference vs picking a default, reducing configuration to strong defaults, or defining the product's identity through opinionated choices — even if the request is about 'simplification' or 'UX design' rather than explicitly about opinionated design.

Make sure to use this skill whenever a product release needs a craft quality check, the product works but feels unfinished, reviewing edge case handling and loading states, evaluating design system adherence, or preparing a quality score before launch — even if the request is about 'quality review' or 'QA' rather than explicitly about craft review.

Make sure to use this skill whenever negotiation outcomes are below expectations, the team accepts initial offers without pushing back, reviewing recent decisions for missed opportunities to ask, diagnosing patterns of underasking, or coaching assertiveness in professional contexts — even if the request is about 'negotiation' or 'assertiveness' rather than explicitly about ask audits.

Make sure to use this skill whenever onboarding a new hire and wanting to set up the working relationship intentionally, two collaborators need to align on how they work together, or a working relationship is strained and needs a reset — even if the request is about 'onboarding' or '1:1s' rather than explicitly about relationship design.

Make sure to use this skill whenever evaluating whether adding a new service to a platform will actually cross-sell, someone claims 'we have the eyeballs so the new service will grow for free,' or a super-app or multi-product strategy is being designed — even if the request is about 'product expansion' or 'platform strategy' rather than explicitly about super-app synergies.

Make sure to use this skill whenever entering a B2B price negotiation, the customer is focused on discounting and you need to shift to value, or a renewal negotiation needs to demonstrate ROI — even if the request is about 'negotiation' or 'pricing' rather than explicitly about value audits.

Make sure to use this skill whenever pricing a new product, identifying which features drive willingness to pay, simplifying a pricing structure that creates sales friction, evaluating whether pricing communicates value or just cost, or checking if your pricing can be explained back to you by a prospect — even if the request is about 'pricing' or 'monetization' rather than explicitly about willingness to pay.

Make sure to use this skill whenever a product leader needs to decide which problems to give to empowered teams, evaluating whether teams are solving problems or just shipping features, designing the portfolio of team assignments for a quarter, or checking if the team topology matches the strategic bets — even if the request is about 'resource allocation' or 'team planning' rather than explicitly about bet allocation.

Make sure to use this skill whenever reviewing a team's shipped work against impact metrics, diagnosing why features ship but metrics don't move, auditing whether success is measured by delivery or behavior change, shifting a team from feature counting to outcome tracking, or preparing for a quarterly review — even if the request is about 'metrics' or 'team performance' rather than explicitly about output vs outcome.

Make sure to use this skill whenever an idea exists only in someone's head, a decision needs to be documented before discussion, the team is debating something that hasn't been externalized as text, or someone believes they understand something but hasn't written it down — even if the request is about 'documentation' or 'decision-making' rather than explicitly about writing to think.

Make sure to use this skill whenever a company lacks a written strategy, the CEO or product leader has a vision but hasn't articulated it on paper, the team is executing without a shared strategic document, or a portfolio of strategic intents needs to be prioritized — even if the request is about 'strategy' or 'vision' rather than explicitly about writing a two-pager.

Make sure to use this skill whenever an AI feature is partially working but not reliable enough for full autonomy, deciding how much human oversight to maintain alongside AI automation, calibrating the automation level for a human-in-the-loop workflow, shipping an AI feature that works most of the time but fails unpredictably, or defining graduation criteria for increasing AI autonomy — even if the request is about 'AI deployment' or 'automation' rather than explicitly about the messy middle.

Make sure to use this skill whenever measuring the ROI of AI coding tools, justifying continued investment in Copilot or Cursor, comparing developer output before and after AI adoption, calculating cost savings from AI-assisted development, or evaluating whether to expand AI tool adoption across teams — even if the request is about 'AI tools' or 'developer efficiency' rather than explicitly about productivity measurement.

Make sure to use this skill whenever evaluating code quality from AI tools or new contributors, investigating high code churn, assessing whether generated code sticks past review, monitoring the quality of AI-generated PRs, or benchmarking code quality across team members — even if the request is about 'code quality' or 'AI code review' rather than explicitly about survivability.

Make sure to use this skill whenever developer satisfaction is declining, a platform or DevEx team needs to prioritize investments, engineering productivity seems low but the cause is unclear, build times or CI pipelines are slow, or developer tooling improvements need ROI justification — even if the request is about 'developer productivity' or 'tooling' rather than explicitly about friction audits.

Make sure to use this skill whenever assessing engineering team delivery performance, benchmarking deployment speed against industry standards, diagnosing whether a team is moving fast enough, evaluating the impact of process changes on delivery, or comparing speed vs stability across teams — even if the request is about 'engineering productivity' or 'team health' rather than explicitly about DORA metrics.

Make sure to use this skill whenever a large product org needs metrics that cascade from R&D level to team level, metrics feel disconnected from strategy, or teams are optimizing local metrics that don't roll up to org-level goals — even if the request is about 'metrics' or 'OKRs' rather than explicitly about nested metrics.

Make sure to use this skill whenever the feature backlog is large and driven by diverse user voices, feature decisions are influenced by the loudest complainers, the team needs to reduce the backlog to high-signal requests, ensuring only core-audience requests drive the roadmap, or diagnosing why shipped features don't improve satisfaction — even if the request is about 'backlog management' or 'feature prioritization' rather than explicitly about request filtering.

Make sure to use this skill whenever the team debates whether product-market fit has been achieved, needing a quantitative PMF measurement for investors, understanding why users stay or leave, segmenting users by satisfaction level, or benchmarking PMF progress over time — even if the request is about 'product-market fit' or 'user satisfaction' rather than explicitly about the Sean Ellis survey.

Make sure to use this skill whenever product decisions try to serve all users equally, PMF survey data shows different satisfaction across segments, the team needs to decide which users to prioritize, building a segment-specific product strategy, or identifying which user segment to focus the next product cycle on — even if the request is about 'segmentation' or 'user prioritization' rather than explicitly about segmentation matrices.

Make sure to use this skill whenever comparing two independent assessments, identifying perception gaps between evaluators, analyzing rating discrepancies in any domain (performance, quality, risk), building a gap analysis from paired scores, or diagnosing why two parties disagree on the same set of items — even if the request is about 'feedback' or 'assessment' rather than explicitly about competency ratings.

Make sure to use this skill whenever auditing a roadmap for strategic coherence, checking if planned features connect to a clear end-state, evaluating whether metrics are driving the roadmap instead of a destination, translating a vision statement into execution priorities, or diagnosing why a team is building features that don't compound — even if the request is about 'roadmap planning' or 'OKRs' rather than explicitly about destinations.

Make sure to use this skill whenever reviewing a plan for iteration speed, evaluating whether experiments validate fast enough, auditing cycle times in a roadmap, diagnosing why a startup feels slow despite shipping a lot, or assessing whether a team is trying to outproduce rather than out-iterate competitors — even if the request is about 'execution speed' or 'productivity' rather than explicitly about latency vs velocity.

Make sure to use this skill whenever translating a strategy into screen layouts, defining information architecture, resolving conflicting interpretations of a product vision, scoping navigation for a new platform, or deciding what goes on the home screen — even if the request is about 'product strategy' rather than explicitly about wireframes or IA.

Make sure to use this skill whenever analyzing revenue concentration, investigating why a small segment generates disproportionate revenue, validating assumptions about high-value user motivation, designing pricing for power users, or diagnosing monetization anomalies — even if the request is about 'user segmentation' or 'pricing' rather than explicitly about whales.

Make sure to use this skill whenever deciding what work to delegate to an AI agent, scoping tasks for an autonomous AI engineer like Devin, evaluating whether a task matches an AI's jagged capability profile, or designing the human-AI handoff for a coding workflow — even if the request is about 'AI delegation' or 'task management' rather than explicitly about jagged intelligence.

Make sure to use this skill whenever prioritizing a task list, deciding where to invest effort across competing responsibilities, auditing how time is allocated across work types, coaching someone on focus and prioritization, or diagnosing why high effort isn't producing high-impact results — even if the request is about 'time management' or 'task prioritization' rather than explicitly about the LNO framework.

Make sure to use this skill whenever reviewing a plan that contains only safe projects, diagnosing why the roadmap lacks transformative bets, evaluating whether the team is avoiding ambiguous but high-potential initiatives, rebalancing a portfolio toward higher risk/reward, or asking 'what are we NOT doing?' — even if the request is about 'strategic planning' or 'portfolio review' rather than explicitly about opportunity cost.

Make sure to use this skill whenever starting an important project, preparing for a product launch, kicking off a multi-week initiative, or any time the team is about to commit significant resources — even if the request is about 'risk assessment' or 'project planning' rather than explicitly about pre-mortems.

Make sure to use this skill whenever a team is about to invest engineering effort into a feature whose impact will be invisible to users, a guaranteed-loser micro-optimization is proposed, or the cost of measuring exceeds the cost of the feature itself — even if the request is about 'experimentation' or 'feature planning' rather than explicitly about over-measurement.

Make sure to use this skill whenever de-risking a solution before building, breaking an idea into small testable pieces, running parallel assumption tests across multiple solution candidates, diagnosing why an experiment is too big or too slow, or shifting from project-based research to continuous assumption testing — even if the request is about 'validation' or 'experimentation' rather than explicitly about assumptions.

Make sure to use this skill whenever structuring a large problem space, deciding what to build when many options exist, mapping from an outcome goal to concrete solutions, organizing user research findings into actionable structure, or preparing for a strategy review that needs to show the path from goal to execution — even if the request is about 'product planning' or 'roadmap' rather than explicitly about opportunity solution trees.

Make sure to use this skill whenever defining the problem space for a product initiative, mapping user journeys to find opportunity areas, identifying where the biggest experience gaps are, ensuring the team explores needs before jumping to solutions, or structuring a user research plan around temporal moments — even if the request is about 'user research' or 'opportunity identification' rather than explicitly about scope mapping.

Make sure to use this skill whenever a new feature is being added to an already complex product, product bloat is accumulating, onboarding time or support tickets are increasing, enforcing a net-zero complexity rule for new additions, or auditing total product complexity — even if the request is about 'simplification' or 'product complexity' rather than explicitly about complexity budgets.

Make sure to use this skill whenever a decision is being made by convention without examining why, a proposed solution feels unnecessarily complex, the team is adopting an industry standard without verifying fit, challenging 'that's how it's always done' assumptions, or stripping inherited constraints from a problem — even if the request is about 'decision-making' or 'problem-solving' rather than explicitly about first principles.

Make sure to use this skill whenever a strategy optimizes for quarterly results at potential long-term cost, debating between a safe short-term play and a risky long-term bet, a competitor's move triggers a reactive response, evaluating whether a decision sacrifices customer trust for revenue, or checking if a strategy is sustainable long-term — even if the request is about 'strategy' or 'long-term planning' rather than explicitly about infinite games.

Make sure to use this skill whenever a marketplace or platform has AI doing matching in the background but the match quality isn't measured, the AI strategy is disconnected from the core value exchange, or AI is treated as a separate technical initiative rather than the matchmaking engine — even if the request is about 'marketplace optimization' or 'AI strategy' rather than explicitly about matchmaking.

Make sure to use this skill whenever a team is stuck debating who is right instead of deciding what to do next, alignment is blocked by people attached to their positions, a strategy review is going in circles, or a decision needs to move forward despite incomplete information — even if the request is about 'decision-making' or 'alignment' rather than explicitly about clarity vs correctness.

Make sure to use this skill whenever designing an AI-powered product experience where the instinct is to dictate every interaction detail, transitioning a product team from controlling UX to providing AI with guidelines and constraints, or evaluating whether a product spec is over-prescribing the experience vs defining the ingredients — even if the request is about 'AI product design' or 'UX strategy' rather than explicitly about the ingredients metaphor.

Make sure to use this skill whenever runway is below 9 months, a fundraising round failed or was delayed, monthly burn is increasing without proportional revenue growth, identifying specific cost cuts to extend survival, or computing the impact of expense reductions on runway — even if the request is about 'financial planning' or 'cost reduction' rather than explicitly about runway extension.

Make sure to use this skill whenever an unexpected negative event has occurred, the team needs to decide between panic mode and measured response, multiple problems hit simultaneously and need prioritization, classifying the severity of a business threat, or designing the appropriate response intensity for a crisis — even if the request is about 'crisis management' or 'incident response' rather than explicitly about severity triage.

Make sure to use this skill whenever bad news needs to go out to multiple stakeholder groups, crisis communication to investors vs employees vs customers, structuring what to tell whom and when, acknowledging unknowns honestly, or preventing stakeholders from learning bad news through the wrong channel — even if the request is about 'crisis communication' or 'stakeholder management' rather than explicitly about crisis comms.

Make sure to use this skill whenever a long document needs a summary for senior readers, a Slack thread needs to be summarized for a decision-maker, meeting outcomes need concise communication, structuring any communication using BLUF (Bottom Line Up Front), or writing a summary under 150 words — even if the request is about 'writing' or 'summarization' rather than explicitly about executive summaries.

Make sure to use this skill whenever sending a status update or request to someone senior, previous updates got 'what do you need from me?' responses, drafting a Slack message or email to an executive, restructuring a message to lead with the ask, or coaching someone on executive communication — even if the request is about 'communication' or 'writing' rather than explicitly about managing up.

Make sure to use this skill whenever a good idea keeps getting rejected because it's framed wrong, presenting the same proposal to different audiences, a technically correct pitch isn't persuading the decision-maker, adapting messaging to match the audience's priorities, or resubmitting a rejected proposal — even if the request is about 'persuasion' or 'presentations' rather than explicitly about framing.

Make sure to use this skill whenever Slack threads frequently produce 'what do you mean?' follow-ups, async decisions take too long due to ambiguous messages, a team going remote needs to improve written communication, auditing message clarity across a team, or designing guidelines for effective async collaboration — even if the request is about 'communication' or 'remote work' rather than explicitly about async audits.

Make sure to use this skill whenever establishing authority on a new topic, writing a bio or introduction, entering a domain where the audience doesn't know you, building trust before making a recommendation, or assessing the strength of your credibility claims — even if the request is about 'personal branding' or 'introductions' rather than explicitly about credibility.

Make sure to use this skill whenever written content gets low engagement because it's generic, a pitch or position doesn't stand out from competitors, a presentation needs a memorable central argument, sharpening bland takes into differentiated positions, or testing whether a statement passes the substitution test — even if the request is about 'content creation' or 'thought leadership' rather than explicitly about spiky POVs.