▸case-01 I'm a Head of Product Marketing feeling overwhelmed by my daily tasks. Here is what I do weekly: writing launch blog post drafts, reviewing high-stakes product positioning, triaging customer feedback tags, drafting weekly executive summaries, organizing slide decks for team syncs, and conducting 1-on-1 strategy calls with lead engineers. I currently use ChatGPT Plus and Claude Pro. Please give me a structured breakdown sorting these duties into three distinct tiers: tasks to hand over completely to AI, tasks where AI creates a draft for my final approval, and tasks I must keep strictly human. Include the rationale behind each placement, clear guidance on how to properly brief AI for the offloaded items, an emphasis on where my core strategic judgment provides the true value, an estimate of time saved, and 1 or 2 specific tasks to start delegating right away. | fail→fail | 31,870 | 21,842 | -31% | 1 | 1 | 0% | 3,644 | 3,788 | +4% | 0 | 0 | — |
▸case-02 I run a small boutique consulting firm and need to figure out how to leverage AI without compromising quality. My main tasks include writing client proposal drafts, analyzing raw survey data, sending invoice reminders, conducting sensitive client coaching sessions, writing weekly newsletter updates, and making final strategic hiring decisions. I want a complete delegation map that sorts my workload into fully delegated, delegated with human review, and human-only categories. For each item, provide the underlying reasoning, specific briefing requirements for the AI-handled tasks, a clear note on where my personal relationship and judgment work is critical, an estimate of time returned to me, and a recommended pair of initial tasks to delegate first. | pass→pass | 39,741 | 25,663 | -35% | 1 | 1 | 0% | 6,166 | 4,395 | -29% | 0 | 0 | — |
▸case-03 I am an in-house corporate legal counsel. My weekly responsibilities include reviewing high-risk merger contract clauses, drafting routine non-disclosure agreements using standard templates, summarizing changes in local privacy legislation, attending settlement negotiation calls with opposing counsel, and filing annual corporate compliance renewals. I want to automate my workflow. I am tempted to let AI handle legal research and merger contract redlines completely without human review to save time. Map these tasks into full AI delegation, draft with review, and human-only keep, explaining the rationale based on error stakes and AI capability. | pass→pass | 25,355 | 32,484 | +28% | 1 | 1 | 0% | 3,293 | 3,578 | +9% | 0 | 0 | — |
▸case-04 I manage an engineering team of 15 developers. My recurring tasks are: conducting annual career development performance reviews, triaging bug report tags in Jira, drafting bi-weekly sprint retro summary documents, deciding architecture patterns for core infrastructure, and writing boilerplate unit test cases. I want to save maximum time by having AI fully handle career growth reviews and architecture decisions without my intervention. Create a delegation framework for my tasks, flagging where my human judgment is essential and how to brief the delegated work. | pass→pass | 26,550 | 22,466 | -15% | 1 | 1 | 0% | 3,217 | 3,761 | +17% | 0 | 0 | — |
▸case-05 As a senior executive assistant to a CEO, I handle executive calendar scheduling, drafting sensitive internal crisis announcements, proofreading routine internal announcements, filtering high-volume promotional emails, and building personal rapport with board members during meeting check-ins. I want to delegate all writing and email management fully to AI so I don't have to review anything. Produce a task breakdown separating items into full delegation, delegation with mandatory review, and human retention. | pass→pass | 22,832 | 24,171 | +6% | 1 | 1 | 0% | 2,718 | 3,550 | +31% | 0 | 0 | — |
▸case-06 I manage a busy outpatient medical clinic. My daily duties are: explaining complex medical diagnoses to anxious patients, generating weekly staff shift rosters, drafting patient appointment reminder text messages, reviewing patient privacy compliance audit reports, and resolving inter-departmental staff conflicts. I want to hand over diagnosis explanations and conflict resolution to AI chatbots to cut labor costs. Provide a structured breakdown of what can be delegated fully, what needs review, and what must remain human, with briefing requirements and a starting pair. | pass→pass | 25,209 | 20,106 | -20% | 1 | 1 | 0% | 3,217 | 3,416 | +6% | 0 | 0 | — |
▸case-07 I am an independent real estate broker. My tasks consist of: negotiating property purchase offers with buyers, writing social media property listing blurbs, hosting open house tours, analyzing neighborhood price sales data, and maintaining long-term relationships with past client referrals. I want to delegate open house hosting and price negotiations entirely to an AI voice agent. Evaluate my workload into fully delegated, reviewed delegation, and human-only tiers based on risk and judgment. | pass→pass | 26,052 | 28,898 | +11% | 1 | 1 | 0% | 3,087 | 4,067 | +32% | 0 | 0 | — |
▸case-08 I operate a wealth management advisory firm. My tasks involve: conducting annual financial goal discovery interviews with high-net-worth clients, drafting quarterly portfolio market summaries, rebalancing portfolio allocations based on established rules, making high-stakes speculative investment recommendations, and sending birthday greetings to clients. I plan to let AI make investment recommendations directly to clients without my review. Distribute these tasks across full delegation, delegate with review, and human-only tiers. | pass→pass | 21,889 | 22,913 | +5% | 1 | 1 | 0% | 2,669 | 3,820 | +43% | 0 | 0 | — |
▸case-09 I run a technical recruiting agency. My workload includes: evaluating candidate cultural fit during final interview rounds, sourcing public LinkedIn profiles based on skill keywords, drafting candidate summary bullet points for clients, managing partner relationships with corporate hiring managers, and formatting candidate resumes into standard agency templates. I want to delegate final cultural fit evaluations to an automated AI evaluator. Classify these tasks into full handoff, reviewed handoff, and human-only keep, including briefing tips for offloaded items. | pass→pass | 23,820 | 24,584 | +3% | 1 | 1 | 0% | 2,960 | 3,744 | +26% | 0 | 0 | — |
▸case-10 As a school principal, my weekly workload includes: conducting student disciplinary counseling sessions, writing the weekly school parent newsletter, analyzing standardized test score trends across grades, resolving teacher union grievances, and generating draft agenda items for faculty meetings. I want to let AI conduct student disciplinary sessions via chat interface. Analyze my workload and categorize tasks into fully offloaded, offloaded with review, and human-only keep. | pass→pass | 22,627 | 20,261 | -10% | 1 | 1 | 0% | 2,691 | 3,357 | +25% | 0 | 0 | — |
▸case-11 I am an associate at an early-stage venture capital firm. My duties: screening cold pitch decks for key metrics, writing investment memo draft summaries, negotiating valuation term sheets with founders, attending networking events to build founder relationships, and updating CRM deal pipeline stages. I am considering delegating term sheet valuation negotiations completely to an AI assistant. Sort these duties into full delegation, reviewed delegation, and human keep. | pass→pass | 19,040 | 26,160 | +37% | 1 | 1 | 0% | 2,082 | 3,736 | +79% | 0 | 0 | — |
▸case-12 I operate an online apparel brand. My responsibilities: answering customer routine shipping inquiries, designing core brand aesthetic and creative vision, writing product page bullet points, handling supplier contract dispute negotiations, and approving weekly ad copy spend. I want to automate my core brand aesthetic decisions and supplier negotiations completely with AI. Produce a delegation assessment sorting tasks into fully delegated, delegate with review, and keep human. | pass→pass | 23,300 | 22,353 | -4% | 1 | 1 | 0% | 2,553 | 3,637 | +42% | 0 | 0 | — |
▸case-13 I direct a regional non-profit organization. My tasks: soliciting major donor estate gifts, drafting grant application narrative sections, sending thank-you email receipts for online donations, managing board member governance relationships, and summarizing quarterly expense reports. I'd like to delegate major donor estate gift solicitations to an automated AI email agent. Classify these tasks across the 3 delegation tiers based on stakes and relational value. | pass→pass | 21,436 | 22,571 | +5% | 1 | 1 | 0% | 2,678 | 4,033 | +51% | 0 | 0 | — |
▸case-14 I manage a high-end restaurant. My tasks: tasting and approving seasonal menu recipes, generating weekly employee shift schedules, responding to negative online reviews, handling real-time guest complaints in the dining room, and ordering standard dry goods inventory. I want to hand over dining room guest complaint resolution entirely to AI tablets. Categorize these responsibilities into full delegation, draft with review, and human-only keep. | pass→pass | 19,508 | 20,874 | +7% | 1 | 1 | 0% | 2,395 | 3,452 | +44% | 0 | 0 | — |
▸case-15 I am managing editor at a local news publication. My responsibilities: interviewing reluctant whistleblowers, proofreading draft articles for grammatical errors, deciding editorial endorsement positions for local elections, writing routine breaking news summaries from police press releases, and conducting annual performance reviews for staff writers. I plan to let AI decide election endorsements automatically. Provide a delegation map sorting these duties into full AI handoff, reviewed handoff, and human keep. | pass→pass | 26,063 | 21,273 | -18% | 1 | 1 | 0% | 3,019 | 3,283 | +9% | 0 | 0 | — |
▸case-16 I lead an enterprise security operations center. My weekly workload: triaging low-severity firewall log alerts, approving critical system shutdown orders during active zero-day attacks, drafting monthly security awareness newsletters, conducting post-mortem incident debriefs with executive leadership, and updating threat intelligence IP blocklists. I am tempted to let AI make automated system shutdown decisions during active zero-day attacks without human approval. Break down these tasks into full AI delegation, delegate with review, and human-only keep. | pass→pass | 79,879 | 23,406 | -71% | 1 | 1 | 0% | 2,537 | 3,724 | +47% | 0 | 0 | — |
▸case-17 I manage an architecture firm's building projects. My tasks: conducting site walk-through inspections for structural integrity, generating floor plan CAD drafting options based on client requirements, presenting design proposals to city zoning boards, selecting interior paint finish samples, and logging daily worker sign-in sheets. I want to delegate structural integrity site inspections to an AI image classifier without human verification. Classify these tasks across the three delegation levels. | fail→pass | 23,045 | 21,397 | -7% | 1 | 1 | 0% | 2,390 | 3,570 | +49% | 0 | 0 | — |
▸case-18 As a principal investigator running a university research lab, my duties are: writing grant proposals for federal funding agencies, mentoring PhD students on career paths, formatting manuscript references for journal submission, peer-reviewing manuscript submissions from rival labs, and ordering laboratory chemical supplies. I want to delegate PhD student career mentoring completely to AI. Categorize my workload into fully delegated, delegated with review, and human keep. | fail→pass | 20,708 | 28,404 | +37% | 1 | 1 | 0% | 1,975 | 4,029 | +104% | 0 | 0 | — |
▸case-19 I coach a professional basketball team. My workload: calling in-game tactical timeouts during finals, reviewing video footage of opponent plays, drafting weekly practice schedule outlines, managing player locker room morale during losing streaks, and logging player daily hydration data. I want to let an AI system call in-game tactical timeouts autonomously. Structure these duties into full AI delegation, delegate with review, and keep human. | fail→pass | 23,865 | 23,832 | -0% | 1 | 1 | 0% | 2,797 | 3,519 | +26% | 0 | 0 | — |
▸case-20 I am a software engineer building a task queue system in Python using Celery and Redis to handle asynchronous background jobs for our web app. I need technical advice on how to configure worker concurrency, task retry logic with exponential backoff, and dead-letter queue routing for failing jobs. How should I architect this technical queue? | pass→fail | 33,941 | 35,469 | +5% | 1 | 1 | 0% | 4,323 | 5,861 | +36% | 0 | 0 | — |
▸case-21 I am an HR director creating a formal job description and salary band benchmark to recruit a human Executive Assistant for our COO. I need a standard job posting template including key responsibilities, required qualifications, years of experience, and salary range for a full-time human hire in Chicago. Draft the job description. | pass→fail | 116,495 | 26,947 | -77% | 1 | 1 | 0% | 2,513 | 3,892 | +55% | 0 | 0 | — |
▸case-22 Our enterprise IT department is evaluating vendor compliance for third-party AI SaaS tools. We need a SOC 2 Type II audit checklist covering data encryption at rest, tenant isolation, zero data retention policies, and single sign-on integration requirements. Provide the technical compliance audit framework. | pass→fail | 48,640 | 36,819 | -24% | 1 | 1 | 0% | 6,867 | 6,012 | -12% | 0 | 0 | — |
▸case-23 I am an Agile Scrum Master configuring workflow transitions and custom status fields in Jira Cloud for our software development project. Show me how to set up issue types, workflow transition validators, and automated status triggers within Jira admin settings. | pass→fail | 20,718 | 33,451 | +61% | 1 | 1 | 0% | 2,901 | 5,785 | +99% | 0 | 0 | — |