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Hilary Gridley's 30 days of GPT
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Week 1: Foundations of LLM Interaction
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Get Better Outputs by Providing ContextLearn how providing detailed context to ChatGPT can significantly improve the relevance and specificity of its answers, helping you get better recommendations and insights.1. Begin by prompting, “Help me plan an upcoming vacation. What information can I give you that would be the most helpful?” ChatGPT will respond with a variety of follow-up questions. Answer as many as you like and see what sorts of answers you get.
2. Prompt, “Let me tell you about some of the best vacations I’ve ever had.” Add specific context, like the names of hotels or restaurants you’ve enjoyed.
3. Prompt, “Your suggestions are too _____, make them more ____.” Use a variety of adjectives: too generic, expensive, touristy, predictable, etc. Notice how this changes the output.
4. Prompt, “Let’s go with [destination]. Ask me three questions that will allow you to build the perfect itinerary for me” ChatGPT will ask you three questions and then suggest an itinerary for you.
5. Prompt, “Make this 100x more specific.” Notice how this changes the output.
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Get Ideas for Use Cases Relevant to Your RoleBrainstorm use cases for AI that are specific to your role.1. Prompt, "I"m a [job] at [company] focusing on [domain] and I am trying to identify use cases for using ChatGPT. Can you suggest some non-obvious ideas? Be extremely specific."
2. If you have any doubts about the ideas it provides, explain those doubts. For example, if it generates ideas about using AI to write copy, you could say, "I feel like AI writes generic and uncanny sounding copy," "focus on something other than writing" or simply "I don't like these ideas."
3. Prompt, "Give me an extremely specific step by step guide to implementing the best use case here, including any prompts I should use."
4. Prompt, "What changes would you make if I told you I have an extremely high bar for quality and will accept nothing but the best? Explain your reasoning."
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Summarize and Simplify Complex Documents Quickly understand dense or complex documents by having ChatGPT summarize key sections and clarify technical or difficult parts1. Upload a document (e.g., PDF or Google Doc) and type, “Please summarize the key points, in a way that will be helpful for me, a [title] at [company].
2. Prompt, "Make this even more helpful and actionable for me."
3. Prompt, "What are the three most important and non obvious insights I should take away from this, and what action should I take as a result?"
4. Prompt, "Make those even more specific and personalized for me, a [job title] who focuses on [domain]."
5. Review the summary and continue asking any other questions you have to shape and clarify the output, for example, "Make those recommendations more creative," or "highlight less obvious insights."
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Break Down a Project into StepsFigure out a structured approach to solving a problem or making a plan.1. Share your project goal and deadline with ChatGPT, asking, “Can you suggest different ways to break down this project into manageable parts?”
2. Once you have some options, ask ChatGPT, “Which of these breakdowns would be most efficient given a [timeline/limited team]?”
3. Review ChatGPT’s feedback, select a breakdown approach, and then ask ChatGPT to recommend milestones or checkpoints to track progress.
4. Use this structured approach to manage the project and adjust as you go.
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Create a Pros/Cons List for a DecisionDescribe an upcoming decision and ask ChatGPT to help you create a structured pros and cons list, with weighted factors for each point.1. Describe the decision you’re facing and any key factors. Ask ChatGPT, “Can you suggest some frameworks to evaluate this decision?”
2. Choose a framework you like and then say, “Help me list the pros and cons of each option, factoring in [specific criteria like time, resources, potential impact].”
3. Review ChatGPT’s list, and if needed, ask for weighted factors to better understand the trade-offs.
4. Use the refined list to guide your final decision-making process.
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Identify AI Use Cases Based on your CalendarIdentify relevant AI tools and strategies for your upcoming meetings by sharing your calendar with ChatGPT, ensuring you have tailored support for each task.1. Take a screenshot of your calendar for the week. Paste it into ChatGPT and prompt, “I have a busy schedule this week, and I’d like to use AI to help me prepare effectively for each of my meetings. I am attaching a screenshot of my calendar. Can you suggest specific AI strategies or approaches that I can use to maximize the value of each meeting? For example, preparing talking points, generating questions, brainstorming creative ideas, or summarizing key takeaways. I’d like actionable and non-obvious suggestions for each meeting to make sure I contribute effectively and stay organized.
2. Choose one idea you’d like to try. Prompt, “I’d like to try [idea]. Recommend a step-by-step approach to implementing this. Write out any AI prompts I should use and clarify any additional context I would need to provide the AI to get a good output.”
3. Prompt, “I don’t like any of these ideas” and notice how ChatGPT responds.
4. Choose one idea and commit to trying it out this week.
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Develop a Checklist for Reviewing WorkDescribe a type of work you frequently review (like code, writing, or designs) and ask ChatGPT to help you create a checklist for quality and consistency.1. Describe the type of work you typically review (e.g., reports, code). Ask ChatGPT, “Can you suggest an initial checklist for quality and consistency in this area?”
2. Review the checklist and say, “What additional criteria should I add to capture common issues I see, like [specific issues]?”
3. Ask ChatGPT for examples of how to evaluate each checklist item, ensuring clarity.
4. Save the refined checklist and update it over time as you identify new review needs.
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Week 2: Improving your Communication with AI
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Increase the clarity of your written communicationMake your writing easier to understand. Use ChatGPT to identify and revise any ambiguous language or confusing sentence structures.1. Copy and paste a message you are preparing to send over email or Slack into ChatGPT.
2. Prompt, “I am [a product manager] sending this message to [a marketing manager]. Can you edit it for clarity, and explain any changes you made?”
3. Review the response. If it sounds too formal or AI-generated, provide that feedback: “This sounds like a machine wrote it. Can you make it sound more like me?”
4. Once you have a version you like, ask “On a scale from 1-5, how clear is this message?”
5. Finalize the message and send it with confidence.
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Structure a PresentationGet help identifying the best structure for an upcoming presentation.1. Describe the main points and purpose of your presentation. Ask ChatGPT, “Can you suggest multiple ways to structure this presentation to best engage my audience?”
2. Pick a structure you like, and ask, “What types of visuals or examples would help strengthen each section?”
3. Use the suggestions to draft your presentation, then ask for feedback on specific sections you want to improve.
4. Refine your presentation based on ChatGPT’s ideas for a more engaging delivery.
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Generate a First Draft from an OutlineSpeed up the drafting process by expanding a rough outline into a more complete draft. ChatGPT can help with organization, filling gaps, and adding depth to your ideas.1. Without using AI, write a basic outline with bullet points for each section of your document.
2. Share the outline with ChatGPT and say, “I’m working on [topic] to achieve [goal]. Here’s my draft outline. What improvements can you suggest, like structure changes or filling gaps?”
3. Review ChatGPT’s additions, and integrate relevant suggestions.
4. If the result feels too general, prompt it with, “Can you make the introduction more engaging?” or “Add concrete examples to each section.”
5. Refine the draft further by adding your own insights or expertise, making it better aligned with your style and goals.
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Generate Key Points for an Executive SummaryAfter drafting a document, distill the key points into a clear and concise executive summary.1. Provide ChatGPT with a draft or outline of your report. Ask, “Can you identify the most critical points for an executive summary?”
2. Once you have key points, say, “Help me refine these points into concise sentences that are impactful and clear.”
3. Review the summary and ask ChatGPT "From the point of view of [audience], what questions or objections might you have?" Then ask, "How can I update my summary to address these?"
4. Finalize the summary for a polished, executive-ready version of your report.
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Iterate on Drafts to Improve QualityLearn how iterative, back-and-forth feedback can improve your writing quality.1. Write a rough draft of your document or message and paste it into ChatGPT.
2. Ask, “Can you review this draft for tone, structure, and clarity, and suggest specific improvements to make it more engaging and clear?”
3. Review ChatGPT’s feedback, focusing on actionable suggestions (e.g., reordering sections, simplifying language, or enhancing key points).
4. Revise your draft based on the feedback and paste the updated version back into ChatGPT. Ask, “Here’s the revised version. Can you now check for flow and ensure it’s concise and impactful?”
5. Continue refining through several iterations, with each round focusing on different improvements, like strengthening the introduction or adding concrete examples, until you’re satisfied with the final draft.
6. Zoom out with a more vague and general question like, "What am I missing?" See if you get any interesting feedback.
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Get Feedback on Visual DesignUse ChatGPT to evaluate your slides, designs, reports, or other visual content, helping you refine design elements, improve layout, and enhance clarity.1. Take a screenshot of your visual content or download it as a PDF and upload it into ChatGPT. This could be a slide deck, a single slide, a Figma design, a diagram, etc.
2. Ask, “What feedback can you give me on the layout, clarity, and audience engagement of this visual?”
3. Review ChatGPT’s feedback, noting any specific improvement suggestions.
4. If the feedback is vague, prompt ChatGPT with, “Be 100x more specific. Which elements, like color, font size, or spacing, could improve readability?”
5. If the feedback isn’t aligned with your needs, clarify the context by explaining your goal, audience, guidelines, or any past discussions on this topic (e.g. "XYZ team specifically asked for ABC")
6. Apply the revised feedback to make your visual clearer and more effective for your audience.
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Provide colleagues with the best answer to their questions.Get help breaking down complex questions when you’re not sure how to proceed.1. Prompt, “I am a product manager who just received this question from an engineer and I want to ensure I come up with the best possible answer in the next 3 minutes. Provide a step by step guide for how I should determine the answer: “What’s the acceptable latency threshold for [feature], and what’s our plan if latency increases during peak usage times?”
2. Prompt, “Can you suggest an initial target based on similar features or benchmarks? Show your work so I can validate it.”
3. Prompt, “Give me a better answer, and explain why it's better”
4. Ask, “Imagine you are [the person who sent you the question.] What pushback might you have to this response?”
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Bonus: Help Craft “No” Responses That Maintain RelationshipsWhen you need to decline a request, share the context with ChatGPT and ask, “Can you help me say no in a way that keeps the relationship positive?”1. Start by sharing the request and providing context, e.g., who the request is coming from, whether you feel like you have the authority to say no, why it doesn’t fit your current priorities. Ask, “What are some alternative ways I could support this person’s needs without taking on the full ask?” and "What are some questions I can ask this person to better understand how urgent/important this ask is?"
2. Explore the suggestions ChatGPT provides. Then ask, “Can you help me write a response that both suggests these alternatives and keeps the relationship positive?”
3. After receiving the response, ask ChatGPT how the other person might respond to your message, and what you can do to improve the interaction.
4. Finalize the response and keep note of any useful phrasing for future “no” responses.
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Bonus: Complete Documents in Your StyleDraft a framework and initial content, then use ChatGPT to complete the remaining sections in a style that matches your own, ensuring consistency and polish.

1. Set up your document by writing an outline, creating sections and bullet points to guide the structure.
2. Draft the first 20% by writing a solid introduction and some initial content to set the tone, style, and voice.
3. Paste your outline and initial draft into ChatGPT, and say, "Please complete the remaining sections, using 4. my style and structure as a basis."
5. Review the AI’s additions to ensure they match your tone. If adjustments are needed, ask, "Can you make this more [concise, formal, detailed, etc.] to better align with my writing?"
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Bonus: Summarize Meeting Takeaways to Keep Everyone InformedCreate a concise, actionable summary of meeting takeaways and decisions with ChatGPT, then share this broadly to increase transparency and ensure everyone (both people who were in the room and people who weren't) are on the same page.1. Copy detailed meeting notes (with speaker attributions if possible) and paste them into ChatGPT.
2. Say, “Distill these notes into a clear, structured summary, including key decisions, rationale, highlights, and specific action items with ownership and deadlines.”
3. Review and edit ChatGPT’s summary to ensure accuracy and alignment with meeting outcomes.
4. Share the summary with the group, requesting a “thumbs up” for alignment on takeaways and next steps.
5. Share the summary with anyone who was not in the meeting who could benefit from the context
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Week 3: Improving Creativity and Strategy
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Prepare Talking Points for MeetingsImprove your contributions in meetings by using ChatGPT to generate relevant insights, potential questions, or key points that align with the meeting’s goals.1. Provide ChatGPT with the meeting agenda and your role, saying, “I have a meeting about [topic]. Here’s the agenda and my role: [details].”
2. Ask, “What are some specific points or questions I could bring up to add value to this discussion?”
3. Review ChatGPT’s suggestions and highlight any that resonate with you or fit your expertise.
4. If suggestions feel off-track, add context by explaining your point of view, notes from prior meetings, other attendees, or specific concerns you have about the meeting.
5. Ask ChatGPT for help preparing a few selected talking points or questions to contribute meaningfully to the meeting.
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Prioritize Tasks Based on Impact Use ChatGPT to prioritize tasks or ideas effectively by applying a scoring framework, ensuring you focus on the highest-impact efforts.1. List your tasks or ideas and paste them into ChatGPT.
2. Ask, “Can you prioritize these tasks based on urgency and impact, focusing on the most high-impact items first?”
3. If needed, ask, “What additional information would you need from me to prioritize more confidently?” and provide the requested context.
4. Say, “Can you suggest prioritization criteria and score each item based on those criteria?”
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10x Ideas after a BrainstormGet more out of brainstorming sessions by asking ChatGPT to generate additional ideas or explore variations, providing new angles to consider.1. Share a list of core ideas from your brainstorming session with ChatGPT, saying, “Here are our main ideas: [list ideas].”
2. Ask, “Can you generate 30 additional ideas or suggest variations worth exploring? Ensure these ideas are [excellent/unique/thoughtful/creative].” Try different words and see what happens. You can even give the GPT a persona, like, "You are a Creative Director at a prestigous Ad Agency. Come up with your 50 most creative ideas" and see how this impacts the quality of the ideas you get.
3. Ask, "Can you set scoring criteria for the quality of these ideas, score each one, and prioritize the top ten?"
4. If ideas are repetitive, prompt ChatGPT with, “Make these ideas 100x more unique,” or “Focus on adding innovative twists to each one.”
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Kickstart Research on New TopicsBegin researching a new topic by asking ChatGPT to generate essential questions, guiding you to explore foundational concepts and issues deeply.1. Enter a broad topic you want to explore (e.g., "healthcare economics" or "behavioral change") into ChatGPT. Ask, "What are the essential questions I should research to gain a deep understanding of this topic?"
2.. Use the list of questions as a guide, selecting 2-3 to start with and diving into those first. Ask ChatGPT to answer those questions and also recommend the best and most credible resources to learn more.
3. As you research, return to ChatGPT for help refining answers or to explore follow-up questions.
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Build a Personalized Learning PathDesign a structured learning path for a new topic by asking ChatGPT to outline key concepts, modules, and resources, tailored to your development goals.1. Prompt, “What are the key concepts I should understand to build a basic foundation in [domain]?” If the response seems irrelevant to your role, follow up with, “Can you make this more specific to my role as [job] at [company]?” Provide any additional context that would be helpful, like how you will use this information in your role.
2. Prompt, “Can you create a step-by-step learning path covering these concepts, with modules and milestones for each stage?”
3. Prompt, “Break down the first module into smaller, manageable lessons or exercises. Include specific resources I can use and explain how to use them. Define any words I am unlikely to understand as a beginner."
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Create a Targeted Professional Growth Plan for YourselfDevelop a targeted growth plan with ChatGPT to build specific skills. Get actionable deliverables and feedback questions to track your progress effectively.1. Prompt, “I am a [product manager] focused on [domain]. I would like to improve my [strategic thinking] over the next three months. What specific skills or behaviors help me do this while making a tangible impact in my role?”
2. Prompt, “Suggest 3 specific deliverables I could work on over the next month to practice these skills in a way that adds value to [my company].” If the output is too generic, say “Make this 100x more specific.”
3. Choose one deliverable and ask, “Is there a more lightweight way to approach [idea] so it doesn’t become a big project that distracts me from short-term execution?”
4. Prompt, “Can you suggest questions I could ask my manager to get feedback on my progress along the way?”
Use these ideas and questions to gui
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Brainstorm Multiple Approaches to Solve a ProblemOutline a problem you’re facing and ask ChatGPT, “Can you suggest several distinct approaches to tackle this?” to encourage creative thinking.1. Outline the problem and any constraints. Ask, “What are a few different approaches I could take to solve this problem?”
2. Review the suggestions, then ask, “What are the potential benefits and downsides of each approach?”
3. If you find an approach interesting but incomplete, ask, “Can you expand on this approach with specific steps or examples?”
4. Choose an approach to implement and revisit it if adjustments are needed.
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Week 4: Advanced Prompting & Using Voice
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Ask an LLM to Write its own PromptLearning to lean on the LLM to craft specialized prompts. This exercise helps you become more precise and effective in guiding AI responses.1. Prompt, "I want to generate new ideas for [something you are working on]. Can you help me write a prompt that will effectively achieve this goal?"
2. Follow up with, "Ask me three questions that would give you helpful information to improve the prompt."
3. Answer each of ChatGPT’s questions, or simply say, "What would you recommend as answers to each question if I were unsure?"
4. Prompt, "Now that we have these details, can you update the prompt and explain what you changed so I can understand how to write better prompts?"
5. Read the updated prompt and notice the structure and content of it.
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Refine Ideas with Voice-to-Text ExplorationUse Voice AI to talk through early-stage ideas, turning rough thoughts into structured concepts. This approach helps improve clarity and expression for brainstorming.1.Open Voice mode on the ChatGPT mobile app and say, “I have an idea I’d like to refine with your help.”
2. Describe your idea out loud, as if explaining it to a colleague or mentor.
3. Ask ChatGPT for clarifying questions that could help refine or sharpen the concept.
4. If ChatGPT’s responses are too verbose, remind it to stay concise and focused, saying, “Keep your questions brief and specific.”
5. After 5 minutes of back-and-forth, ask ChatGPT to outline a one-pager to present the idea to your manager, specifying their role and what would appeal to them.
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Get Hyper-Personalized Recommendations Based on your TasteUse examples to articulate what "good" looks like in your eyes.1. Gather a set of examples that reflect your preferences (e.g., outfits, books, designs) and upload or describe them to ChatGPT.
2. Ask, "Based on these examples, can you analyze my taste and describe it in very specific terms?"
3. Once ChatGPT provides a description of your taste, say, "Using these specific characteristics, write a prompt that will help me get personalized recommendations that match my style."
4. Use the generated prompt to ask ChatGPT for personalized recommendations that align with your unique taste.
5. Review the recommendations and refine the prompt if needed, asking ChatGPT to make adjustments like “focus more on [specific elements you like].”
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Reflect on Your Core Values Engage in a guided voice conversation with ChatGPT to uncover and clarify your core values through easy-to-answer, reflective questions.1. Start by enabling Voice AI and telling ChatGPT, "I want to clarify my core values. Can you ask me specific, easy-to-answer questions, one at a time, to keep this conversational?" (It's helpful to tell the AI when you are speaking to it vs typing to it, because it generally defaults to "written-style" answers like a long list of questions)
2. Begin the conversation, responding to one question at a time. Skip any questions you don't want to answer or don't know the answer to.
3. After several rounds, ask ChatGPT to summarize the recurring themes and values it identified, using specific words and phrases from your responses to ensure it captures your language and perspective.
4. Provide feedback on whether the summary feels true to you or not, and why
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Talk Through Problems for ClarityUse Voice AI to work through a problem where you feel stuck. ChatGPT will guide you with reflective questions, helping you gain clarity and possible next steps.1. Think of any challenge you are facing in your professional or personal life. If you’re not sure, make one up.
2. Open ChatGPT Voice mode on the mobile app. Say, "I’m feeling stuck on a problem, and I’d like to talk it through with you. Can you act as my coach and help me work through the problem?”
3. Tell ChatGPT, “I am talking to you on voice mode, so let’s keep this conversational.
4. Describe the problem and how you are feeling about it. If you don’t have a problem to talk through, you can use this one as a hypothetical: “I want to improve my work-life balance, but I find it hard to set boundaries without feeling like I’m falling behind at work.”
5. As you explain, ChatGPT will listen and offer prompts to help you dig deeper. If the conversation is not going in a helpful direction, say that.
6. After a couple minutes, ask ChatGPT to summarize any key insights or new perspectives that emerged during the discussion.
7. Say, “Can you suggest a few next steps based on our conversation?” to help you move forward with a clearer plan.
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Prepare for Difficult ConversaiontsPrepare for challenging conversations by using ChatGPT to simulate potential scenarios, helping you approach interpersonal dynamics with empathy and grace.1. Describe the situation in ChatGPT. For example, you might say, “I need to talk to my colleague about missed deadlines without making them feel defensive.”
2. Ask for suggestions on how to bring up the topic with your colleague.
3. Choose one suggestion to “play out” and ask, “Help me anticipate their possible reactions and suggest graceful responses for each.”
4. Continue playing out the scenario, asking ChatGPT for options and alternate approaches as needed.
5. Request specific phrases by asking, “What wording can I use to stay calm and respectful?”
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Reverse-Engineer Prompts to Make LLMs that Think Like YouImprove your prompting skills by reverse-engineering the transformation from a rough draft to a final draft. This exercise helps you craft prompts for specific outcomes.1. Start with Two Drafts: Choose a piece of your writing with both a rough first draft and a refined final version (e.g., an initial idea and a polished proposal). Upload both into ChatGPT.
2. Ask the LLM to describe the major differences between the first and final draft.
3. Say, "Write a prompt that would take the first draft as an input and transform it into something like the final draft." This will help ChatGPT understand how to replicate the changes.
4. Test the Prompt: Use the prompt ChatGPT creates on a new rough draft to see if it achieves a similar transformation. Refine the prompt if needed by asking ChatGPT for ways to make it more effective.
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