AI is Changing Work and Thinking
- Act as a devil’s advocate with X industry expertise. I’m about to make this decision: [describe it]. Do three things: (1) List the 3 strongest objections a skeptical SVP would raise — steel-man them. (2) Identify the hidden assumption I’m most likely not seeing. (3) Suggest one alternative option I probably haven’t considered. Be blunt. No reassurance.
- You are an expert in organizational communication within large matrixed enterprises. Draft a short email (under 200 words) to [role/team] requesting their support on [initiative]. Frame it entirely around what’s in it for them — their KPIs, their pain points, their visibility. No jargon from my function. End with a specific, low-friction ask (not “let’s find time to chat”). Tone: peer-to-peer, not needy.
- What might be unclear/missing/controversial in this email to my team/boss at company X? Make this email sound kinder and more inclusive.
- You are a chief of staff to the CEO at X. I’m going to describe an initiative in plain language. Reframe it as a one-page executive brief with: (1) the business problem in revenue/margin/churn terms, (2) the proposed action in one sentence, (3) three quantified benefits tied to company-level KPIs, (4) investment required and payback period, (5) the one reason leadership might say no — and a pre-emptive counter. Write for a skip-level audience that scans, doesn’t read. My initiative: [describe initiative]
- Create five different but specific action plans for company/unit X to achieve Y/C-Suite Goals/company sales targets in time Z. Make versions/variations for the CEO, CFO, CIO etc.
- Identify what are the most important findings and insights in this report/link/article for me [position and place]. Specifically highlight anything that relates to topic X and note recommendations for what someone in my position should consider doing now/over the next year. Organize this into a 300-word report with bullet points and provide quotations and evidence from the report for each.
- Put this into simpler terms for new customers. Or create a relevant analogy that will explain how this works to a younger/older audience.
- Watch/read this ad/message/email and tell me what audience X is most likely to think it means.
- You are an innovative thinker with a very broad range of new ideas and experience. Provide 10 ways I might solve this problem. [Describe the problem in as much detail as possible]
- You are a senior partner at a top-3 strategy consulting firm. Produce a concise strategic assessment of [PRODUCT] in the style of a Bain or McKinsey executive briefing. Use this structure:
- Executive Summary — Lead with the “so what.” One paragraph, hypothesis-driven.
- Market Context — TAM/SAM/SOM, growth trajectory, key macro forces. Quantify.
- Competitive Positioning — Where the product sits vs. alternatives. Use a framework (e.g., value curve, positioning map, or jobs-to-be-done).
- Value Chain & Unit Economics — How the product creates and captures value. Flag margin pressure points.
- Strategic Risks — Top 3 threats, ranked by likelihood × impact.
- Recommendation — 2–3 prioritized, actionable moves with estimated impact and timeframe.
- Rules: Be MECE. Every claim needs a “so what.” Quantify wherever possible. Flag assumptions and confidence levels explicitly. No filler. Write for a C-suite audience with 10 minutes to read.
- Suggest ten ways to make this proposal/email/assignment/project more motivating, engaging/relevant to engineers/basketball fans/my project manager/my team.
- Create a quick game/icebreaker/activity for my team to introduce topic X.
- I am hoping to convince my boss/company to support this idea. Read these emails/strategic goals and advise me how to align this proposal/request with my company or boss’s values/language? Can you find a quote from my boss’s favorite author that aligns with this project?
Analyzing Patterns or Data Visualization
- Analyze this customer/employee feedback and identify the key concerns. Where are they most concerned/confused/angry.
- You are a new customer hoping to X. Go to our company Y web page and test it like a naive user hoping to find out about/make a purchase Z. Then go to three other competitor sites and do the same thing. Collect your findings in a brief report that highlights the difficulties and how we might make using our website better for new customers.
- Given current market conditions/competitor X/data Y what are reasonable and stretch goals for revenue in the next quarter for unit A?
- Watch my presentation/this video and analyze all of the factual mistakes/safety concerns/weak arguments/lapses in judgement/poor communication strategies and make a list of things that need correcting/monitoring.
- Review my email with employee X and identify common themes. Categorize the issues into groups.
- Create an image that ranks sales by store location, experience of staff and time of day.
- Turn this excel spreadsheet (or a page of data) of my department financials into a dashboard.
- Write code to test, graph or visualize this model.
- Use this feedback to generate a chart that shows the progress or failure of this strategy
- Perform a sensitivity analysis of key assumptions in this data/proposal. RUn a Monte Carlo simulation. Assuming a normal distribution, what are the chances of my success? (Try using “artifacts” in Claude 3.5)
- Read this performance review and suggest 3 concrete steps I could suggest for improvement and how we would measure them.
- Using this data, create an analysis/recommendation/strategy…
- Review our current list of products and this data about our customers. Come up with 20 ways/products/services/ideas for how we could both leverage our existing expertise/products/supply chain and customer trust to grow our business. Each item should be different with a description of only 40-60 words.
Class Simulation GPTs
- Seeing Culture: Same Words, Different Worlds exercise. Here it is as a GPT or in BoodleBox, or Poe as a custom bot. (You will need a free account to access this in any of them.)
- Why Pitch Feedback (You will need a free ChatGPT account to access this.)
- Delegation Lab (You will need a free ChatGPT account to access this.)
- Introduction Coach You can use the GPT here or copy an paste this prompt into any chatbot.
- You are an expert coach helping mid-career professionals craft brief, memorable self-introductions that communicate brand, values, and impact—not just job title. Start by asking: “Tell me how you might introduce yourself.” Then help the user improve it. If needed, ask a few short follow-up questions such as: what do you do, who do you help, what change do you create, what do you want to be known for, and what makes your value distinctive. Guide them away from title-only language and toward introductions that are direct, emotionally resonant, and interesting. Make sure they start with why their work matters, the value they bring, the problem they solve, the people they serve, or the purpose behind their work. Starting with an engaging or provocative statement can be good. For example: We want to move away from introductions like “I’m a home chef” toward the much better “Do you know how families often don’t eat together? I come to your home and make healthy meals that bring families together.” The latter is emotionally engaging and creates the opening for a follow-up. Make the options different in tone: for example, one clear and professional, one more evocative, and one or two that are really bold and striking. Give 3-4 stronger alternative introductions that are brief, memorable and natural but are increasingly creative, vivid, and innovative. Keep each introduction short—ideally 1–2 sentences (or 30 words at most). Use plain, direct language, not jargon or clichés. Ask users to refine and try again. After they respond, do these things: Briefly explain what is weak or generic in their current introduction. Your tone should be encouraging, sharp, and practical. Push the user to sound more distinctive, human, and memorable. You can then additional examples and suggestions so they can keep refining it.
- Leadership Interview Coach: Brand Promise: You can access this in either ChatGPT (as a GPT) or in Claude (as an artifact). You need a (free) account in either.
- Telecom KPI Simulation: (You will need a free ChatGPT account to access this.) This uses publicly available information about AT&T to help you prepare for the next role you want. You can play it here. You can also find it by searching for Telecom KPI under Explore GPTs.
- Persuasion Simulation: Based on influence research by Robert Cialdini, the Dinnar & SusskindNegotiation work and more, this simulation also adds some cross-cultural difficulties. It is here in BoodleBox or in Claude, but you need a free account for either.
SIMULATIONS & What if...run experiments, test ideas, make suggestions, forecast futures
- Create an interactive simulation to help me test and stress test an idea A or business goal B and help me prepare for a short presentation to senior management or investors. The goal is to fill in the gaps in my knowledge and help me think more deeply about other possibilities and problems that might occur. You should be a little skeptical of the proposed business models if that is appropriate but also be encouraging. Ask questions to expand my awareness of complexity like a reasonable but deeply-experienced investor and mentor with 40-plus years helping businesses succeed–someone with the manner and experience of Mark Cuban. The game should take about 15 minutes to play. Begin by explaining how the simulation will work and then ask me for the proposal or business plan I wish to test. Stop. Wait for a response before you continue. Ask me for my most important goal or objective with this proposal or this exercise. Stop. Wait for a response before you continue. Then ask a series of questions that a senior executive might have about the idea: for example, what sources of revenue do you anticipate or what is your most dangerous competition or why you etc. Then begin the simulation: create and lead me through a series of realistic scenarios about how the market, competition or economy might change and require me to make choices. Create a series of decision points. Ask only one question at a time and then STOP and wait for a response. Ask only one question at a time and wait for a response and then go to the next step. At the end of the game, provide a brief analysis of how senior executives at a Fortune 50 company might respond and what else I might need to consider before I present to them.
- How might we fully automate this process?
- Generate scenarios from this data for how we might reach this sales target.
- Using only CDC/government data, predict how might more X reduce the usage of Y?
- Reimagine my pitch/this product for an Asian American audience and summarize what might need to be changed.
- Help me stress test the attached business plan by simulating how our business might evolve over the next 2 years. I will play the CEO. You will simulate and describe economic, market and political challenges that might interfere with our plan. Every quarter you will update me and ask me to respond to new events and circumstances. You will then assess my actions and describe how the plan must change as a result.
- (Variation 2) Predict what make happen over the next 3 years as we execute this business plan.
- (Variation 3) Using the attached business plan, simulate how our business X might evolve over the next 20 years. I will play the CEO. You will simulate and describe economic, market and political challenges and changes. Every year you will update me and ask me to respond to new events and circumstances. You will then assess my actions, the describe how the corporation and business change as a result.
- —There are also lots of ready-made APIs that allow you to talk with historical or public figures and many that go even further and you to create your own character or talk to fantasy characters etc: HelloHistory, Character.AI, Replika, and Talkie (among many others). There are also speciality AI like Elliq which is billed as an “AI sidekick for healthier aging.”
- Here is an article from Ethan and Lilach Mollick about How to Use AI to Create Role-Play Scenarios for Your Students with another (long) sample prompt on negotiation.
Design Thinking
- ROLE PLAYING & EMPATHY INTERVIEWS: I am trying to gain a richer understanding of problem X. You will help by responding as a trusting and honest potential customer/a Y person/expert in Z/average A to help deepen my knowledge. Question my assumptions when necessary and tell me stories to build my empathy for the real causes of this problem.
- ANALYZE PATTERNS: Analyze and identify the key themes or problems from this product feedback/online reviews/interviews/oral histories/narratives/stories…
- SEEING THE FUTURE: Twenty years from now, how will the assumptions about problem Z have changed? What new approaches or technologies will be available?
- REFRAME THE PROBLEM: Reframe my formulation of the problem into ten radically different “how might we…” problem statements that center how we might frame what needs to be designed or built to create a new solution for humans.
- BRAINSTORMING: Imagine 50 new and different ways we might solve problem X. Use data Y or template Z. OR Using examples from X, create 500 new products and write descriptions. OR List 20 potential problems with our thinking/assumptions about this idea/product/service. OR Give me 10 different ideas for a new/improved product/business/service/process that combines these ideas/concepts/problems and costs less than $/will be attractive to this market/is not currently available etc. (MORE BELOW in CREATIVITY)
- TESTING: How might audience X react to this idea/product Y? Provide thorough and constructive feedback. What will they like most? What will they hate most? What would they change? How could I improve this idea/product?
Finding Materials & Examples
- Find me # relevant videos appropriate for audience A on subject B that are #-# minutes in length and give me a summary for each that includes its content, reliability and source.
- Assemble real documents/ innovative examples/data concept X from the news/TikTok/YouTube/company website to make point X.
- Create a scenario…
- Find me 5 examples from company history where we altered course/reevaluated our strategy/expanded our market/grew profits…
AI for Nudging
- SPECIFIC EXAMPLE: You are an expert in nudging and behavior modification. Inspired by the ideas around libertarian paternalism and research in the book Nudge: Improving Decisions about Health, Wealth, and Happiness by Richard H. Thaler and Cass R. Sunstein (published in 2008 and revised in 2021), you use psychology and behavioral economics research to engineer choice architecture to nudge American citizens to alter their behavior in a predictable way that will encourage more voting without restricting options or significantly changing their economic incentives. You understand that the best nudges require minimal intervention and are cheap. Help me come up with new nudges to encourage American citizens to vote in elections beyond the Presidential elections. Start by creating 20 new ideas to change processes or choice architecture.
- I note that Claude pushes back and needs to be further encouraged with: “Why are there ethical concerns about encouraging citizens to vote in a democratic society? That seems an essential component of equity.”
- CUSTOMIZE THIS VERSION: You are an expert in nudging and behavior modification. Inspired by the ideas around libertarian paternalism and research in the book Nudge: Improving Decisions about Health, Wealth, and Happiness by Richard H. Thaler and Cass R. Sunstein (published in 2008 and revised in 2021), you use psychology and behavioral economics research to engineer choice architecture to nudge customers/employees/citizens to alter their behavior in a predictable way that will encourage X without restricting options or significantly changing their economic incentives. You understand that the best nudges require minimal intervention and are cheap. Help me come up with new nudges to encourage X to do Y. Start by creating 20 new ideas to change processes or choice architecture.
Job Search
- Describe the culture/reputation of company X have as reported by the people who work there.
- What questions should I be sure to ask other employees/management about company X when I interview with them?
- Read this job description and compare it to available information about [the company] strategy and culture, what are the priorities/personality traits/job experience/values/skills that are really important here? How should I focus my application?
- Pretend you are VP X at company Y. Read this position description, my cover letter, resume and these emails/company strategy from VP X. How might X react to my materials? List missing elements and suggest ways for me to improve my application.
- Read this position description, my cover letter, resume and these emails/company strategy from X. What are some interview questions that I should expect for this job/company/location/date?
- Interview me for job A as if you were X.
- You are typical hiring manager at company X for a leadership position. Read my cover letter/resume and help me improve my answers to standard interview questions, like with what is your greatest weakness and what did you learn from a failure.
Communication & Predicting Responses
- Create a kind and caring but firm no response to this email.
- You are an experienced marketing specialist. Generate a professional but enthusiastic description of this product/service/project or service that is targeted to an X audience. Use this description as a starting point. Develop innovative new ideas to reach new customers in market Y.
- Pretend you are X with an open position. Read the uploaded position description, my cover letter and resume. How might X react to my materials? List missing elements and suggest ways for me to improve my application.
- What might an average reader/customer/IRS auditor/Latino audience find confusing/objectionable/interesting?
- Analyze these successful advertisements/initiatives and identify common elements, ideas, methods, structures, or language that might have contributed to their success. Recommend how I might adapt my current proposal to be more successful.
- Give me feedback from a range of different types of customer from different political/academic/social backgrounds. How might they misunderstand my intentions?
- Act as an experienced writing editor that is focused on writing that is easy to read and understand. Transform this email into one that will be easier to read but still have a professional tone for a team/manager/client. (OPTIONAL Use these examples of my other writing to mimic my voice and tone.) Shorten it by at least half. Start with a brief explanation of why the issue in the email matters. Provide clear navigation with bullets or numbers as necessary. Put the most important information at the top. Make it easy to respond by providing a clear call to action. Limit the response needed to one or maybe two things. Make sure there are no grammatical or spelling errors.
Tutor and Coach
- How would you explain this to a beginner/non-expert?
- Explain this to me using a soccer/legal/tech analogy
- Explain this passage/concept by creating scenarios and personalized examples
- Why did my boss object to this solution? I would like you to act as my personal tutor and teach me about subject X. Start by asking me a question that helps you gauge my level of understanding
- Create feedback that will challenge me. Include feedback with inaccurate information and feedback that looks like a compliment but really is not.
- Act like a friendly but experienced project manager. Read my plan and lead me through a dialogue that will challenge my perspectives. Ask me one question at a time to help me anticipate problems and refine my plan.
Role-Playing, Empathy and Dialogues
- Respond as if you were my boss during my performance review…
- Pretend you are VP X at company Y. Read this position description, my cover letter, resume and these emails/company strategy from VP X. How might X react to my materials? List missing elements and suggest ways for me to improve my application.
- Now interview me for the job as if you were X.
- I am trying to gain a richer understanding of why students might be struggling with problem X. You will help by responding as a honest first-year/first gen/minority/non-major student to help deepen my knowledge. Question my assumptions when necessary and tell me stories to build my empathy for the real causes of this problem.
- I am trying to gain a richer understanding of why latino business owners are less likely to grow their business. You will help respond as a trusting and honest latino business owner to help deepen my knowledge. Question my assumptions when necessary and tell me stories to build my empathy for the real causes of this problem.
- Respond as my boss A as I ask for a raise. Here are her website and emails.
- Act as a devil’s advocate/booster and present counter arguments/connections to company goals to the ideas in our meeting.
- You are a hiring manager. Interview me for a job at X.
- You are a busy venture capitalist (act like Mark Cuban on Shark Tank), and I am an entrepreneur looking for funding from you. Ask me to make my pitch and then ask me questions about my idea.
- Respond as if you were my employee X and we have had this email exchange. Help me practice talking to you about Y.
A.I. as Mentor
- Respond like an experienced and supportive [gender, race, discipline, background] executive and mentor. Read my resume, LinkedIn, performance reviews, 360 and X. Look at [local, region, company, national, international] job openings, leadership opportunities, and my goals, and consider these personal circumstances Y. Lead me through a dialogue that will help me decide what to do in this situation Z. Ask me one question at a time and respond to help me learn what I should do.
A.I. as Team Leader or Project Manager
- Act as our team coach and prompt us with questions to discuss how could learn about our collective strengths and work together as an effective team.
- Provide guidance that will help us ensure that all team members contribute equally to this project.
- Act like a friendly but experienced project manager. Read my plan and lead me through a dialogue that will challenge my perspectives. Ask me one question at a time to help me anticipate problems and refine my plan.
- Different members of our team want to proceed in different directions on this project. Read the individual proposals and provide a summary of where they overlap and where they do not. Read the assignment instructions, and provide a neutral compromise for how we can move forward.
Get Feedback from Different Customers, Readers and Perspectives
- You are a kind but sensitive average reader/customer from culture/group/background Y. You often get confused. Read X and help me simplify things to make everything in this writing clear.
- You are a scrupulous and experienced manager with no tolerance for lack of evidence. Focus on making this writing more persuasive and powerful.
- You are a disagreeable skeptic/customer/reader from group Z. List all of the counterarguments and flaws in my position and respond as if you were a critic on social media.
- You are an innovative writer. Offer critical feedback to help me improve this writing. Look for new connections, arguments and observations I may have missed. Your tone is warm and you are also wildly speculative, creative and fun.
- You are a typical reader of X type of reports/writing. Offer me helpful and direct suggestions to make this work more agreeable to you.
- You are a deeply conservative/liberal X from Y. Create a detailed and clear list of all of this things you find objectionable in this project/writing/work.
- You are a technical specialist with expertise in X. Offer suggestions to improve the accuracy and clarity of terminology and concepts in this work. You are warm but a stickler for details.
- You are [demographic profile X] and easily bored. Help me make this pitch more engaging.
Creative Quantity, Innovation and Problem Solving
- Using examples from X, create 500 new products and write descriptions
- How could I broaden the appeal/market for this service/product?
- How could I reimagine this product/service for a new audience/circumstance/climate?
- List 20 potential problems with our thinking/assumptions about this idea/product/service.
- Give me 10 different ideas for a new/improved product/business/service/process that combines these ideas/concepts/problems and costs less than $/will be attractive to this market/is not currently available etc.
- Create 50 new ideas for what we might do about this problem or in this situation?
- This next more complicated prompt is adapted from Meincke, Lennart and Mollick, Ethan R. and Terwiesch, Christian, Prompting Diverse Ideas: Increasing AI Idea Variance (January 27, 2024). https://ssrn.com/abstract=4708466 or http://dx.doi.org/10.2139/ssrn.4708466 Generate new product ideas with the following requirements: The product must be a physical good/service/software that could be sold at a retail price of less than X USD 50. The ideas are just ideas. The product need not yet exist, nor may it necessarily be clearly feasible. Follow these steps. Do each step, even if you think you do not need to. First generate a list of 100 ideas (short title only) Second, go through the list and determine whether the ideas are different and bold, modify the ideas as needed to make them bolder and more different. No two ideas should be the same. This is important! Next, give the ideas a name and combine it with a product description. The name and idea are separated by a colon and followed by a description. The idea should be expressed as a paragraph of 40-80 words. Do this step by step!
Six Hats Prompt from TAAFT (Long but useful)
- AI is changing Work and Thinking (Every job has a task that is going to change.)
- AI is changing Average
- AI is changing Creativity
- AI is a new form of LABOR
- AI is changing Strategy