June 30, 2025 Welcome to the
21 Days of AI, Grit, and Growth Mindset Challenge
Week One
Why Should (A)I ?
This challenge was designed with four primary objectives:
- Grit and growth mindset research shows the importance of purpose. Determining your intentions for this challenge will be a cornerstone of your journey. What is your purpose in doing this challenge? Why should (A)I?
- Acknowledge the many reasons people don’t engage, whether that be time, overwhelm, safety, liability, concerns of accuracy, and/or losing critical thinking skills.
- Address the gender gap in technology and its impacts. What happens when women are not involved in shaping the conversation and policies surrounding generative AI?
- Provide 21 days of thought-provoking content and action items, grounded in grit and growth mindset principles, to sustain your learning. We want to help build your AI muscle, however you decide to use it!
Thought Leaders: Each day, we will introduce you to pioneers in innovation and emerging technology. Following the work of experienced leaders is far less intimidating than jumping into the wide ocean of artificial intelligence, machine learning, and emerging technology. Our thought leaders to get you started are Miriam Kim, Colleen Chien, and Shilpa Bhandarkar, whose work uses data to highlight emerging AI gaps, including gender gaps, which inspired us, in part, to create this challenge. Read “No Woman Left Behind: Closing the AI Gender Gap in Law,” by Bhandarkar and collaborators, and Kim and Chien’s paper on “Gender AI and Legal Aid: Results from a Field Study and 100 Use Cases to Bridge the Access to Justice Gap." For more thought-provoking discussion from these thought leaders.
To Do - Determine your reasons for starting this Challenge. Ask yourself the following question: Do you want to broaden your understanding of how others use AI or are you hoping to discover ways to utilize these tools to benefit your own productivity? Embrace potential shifts in your goals; this challenge is about growth. Whatever your personal goals may be, consider how you will maintain momentum, such as daily calendar reminders or finding an accountability buddy. We encourage you to create a space for reflection, allowing you to build on your ideas and reflect on your progress holistically as you decide on the next steps in your AI journey.
User Note - Like anything worth discussing, there are polarities. A healthy dose of skepticism is required when using GenAI. It is designed to “please” you; stay alert! [Pro tip: Ask your GenAI tool to adopt a persona that raises your skepticism.] For more on things to balance - from leadership opportunities to climate impacts, bias mitigation versus creation, critical thinking versus cognitive decline - feel free to jump to day 14 where we talk about holding multiple truths at once, and some of the polarities around GenAI.
Reflection - Explore your own thoughts and experience about today’s GenAI journey with the following self-prompts: “I like…,” “I wish…,” and “I wonder…”
― Day 1 ―
Ready, Set Up, Go. Suiting up for the 21 Day Challenge.
Intro: There are many tools at our disposal and more continue to evolve every day. Today is about selecting your tools and understanding how they differ including safety, responsible use, and terms and conditions.
Thought Leader: Miriam Vogel is a leader in responsible AI, AI governance, and AI literacy. As the CEO of EqualAI, she led the White House AI Advisory Council and is a special advisor for the ABA Taskforce on Law and Artificial Intelligence. Her goal is to bridge the gap between passive AI use to deliberate and responsible engagement. Now more than ever, this framework is critical in building agency while molding the future of AI. Check out past webinars from the ABA’s AI Task Force.
To Do: Pick a tool or tools. Today's leading GenAI assistants (ChatGPT, Claude, Gemini, Grok, Co-Pilot, others). All offer robust free versions perfect for learning and experimenting. Paid versions have additional capabilities. Like most technologies, it is essential to identify potential risks, such as security and privacy issues, and that includes understanding the terms of use agreements.
GenAction: Ask your new GenAI tool to explain its terms and conditions on privacy and security, and how it compares to others.
Sample Prompt: “I’m a lawyer exploring GenAI tools and want to understand how different GenAI tools impact my privacy, security, and other relevant protections/exposure based on their terms and conditions. Please summarize key terms and conditions of [ChatGPT, Claude, Perplexity, Gemini, Copilot, etc.]”
Grit and Growth Guide: A grit and growth mindset reminds us to persist with our queries and continuously follow up and evaluate the challenge. Do not give up when your first answer doesn’t yield perfect results.
Reflection: What surprised you? What do you want to keep exploring? What may be valuable for you? What isn’t?
Explore your own thoughts and experience about today’s GenAI journey with the following self-prompts: “I like…,” “I wish…,” and “I wonder…”
― Day 2 ―
AI Possibilities and Grit and Growth Mindset
Intro: Today, we are exploring AI's possibilities and how we can leverage grit and a growth mindset to achieve them.
Thought Leader: Orly Lobel is a Professor of Law at the University of San Diego School of Law and author of The Equality Machine. In her new book, Lobel laid out the potential of AI to create opportunities, encouraging us to experiment and regulate rather than shy away or prohibit.
GenAction: Introduce yourself to your GenAI tool and ask how it can help you.
Sample Prompt:
- “I am a [brand new/moderate/etc] user of GenAI tools. I am aware of many risks, but I am willing to approach the possibilities that GenAI presents with an open and growth mindset. Where should I start?”
- Follow Up: “What would be helpful for me to add about myself or otherwise to get more specific/helpful uses?
- Keep asking for 10 minutes!
Grit and Growth Guide: Recognize that learning any new tool or skill involves initial discomfort. Allow yourself to make mistakes as part of the learning process.
Self/Group-Reflection: Reflect on the uses you came up with, and the use cases proposed by your GAI partner. Did anything stand out (good or bad)? Did your approach or feelings about using the tool change from the first prompt to the last?
Explore your own thoughts and experience about today’s GenAI journey with the following self-prompts: “I like…,” “I wish…,” and “I wonder…”
― Day 3 ―
Playing with Prompting
Intro: Prompting is crucial in maximizing the potential of GenAI. The key to effective prompting is context, specificity of tasks and goals, and clarity of format. This is where the grit and growth mindset come in; keep trying to find effective prompting formulas!
Thought Leader: Ethan Mollick. is an Associate Professor and Co-Director of the Generative AI Lab at Wharton, working hands-on with students, businesses, and beyond. Ethan’s newsletter seeks to understand the implications of AI for work, education, and real life as well as observations on advancing research, developing tools, and prompting. Ethan also urges us to be gritty and growth-minded for at least 10 hours while working with GenAI. If you spend 30 minutes over the next 21 days, you’ll reach this checkpoint.
Cecilia Ziniti is the founder and CEO of GC AI, a leading AI tool for in-house counsel. As a founding member of Amazon’s Alexa team and a former big firm lawyer, Cecilia is at the intersection of technology and the legal profession. She is deeply involved in the tech and venture communities as an investor and frequent speaker on leadership, startups, and women in tech.
GenAction: Pick something you’re working on—a memo, a client letter, an email, a meeting presentation—and start asking your colleague GenAI (Claude, ChatGPT, Pi, Gemini, etc.) for help.
Sample Prompt:
- Instead of asking "Help me draft an email," provide context, clarity, and formatting instructions:
- “I am writing an email to send to prospective [clients/collaborators/partners] to ask them for [X].”
- If you feel like going into a substantive topic, create a prompt on a topic related to your subject matter expertise. Then ask for more versions.
- You can keep tweaking and modifying, combining answers to see what is most useful. Your GenAI partners are gritty, but you bring the growth mindset, finesse, and expertise!
Grit and Growth Guide: Embrace the feeling of confusion or failure as you start. Acknowledge that frustration is a regular part of learning, not a reason to give up.
Reflection: What surprised you? What do you want to keep exploring? What may be valuable for you? What isn’t?
Explore your own thoughts and experience about today’s GenAI journey with the following self-prompts: “I like…,” “I wish…,” and “I wonder…”
― Day 4 ―
Text Generation
Intro: Most GenAI tools are built on Large Language Models, which are complex statistical model that processes high-volume, text-based datasets to predict every word to mimic human languages. Therefore, utilizing an LLM GenAI tool for text generation is a great starting point, leveraging its inherent strengths.
Thought Leader: Janelle Shane is a self-proclaimed AI Humorist. One way to remain gritty when things are hard is to find points of joy and hilarity. In her work, Janelle Shane sheds light on GenAI and provides delightful levity around where it can go awry in her books and blog, AI Weirdness. She is an excellent inspiration for your own prompts.
GenAction: Use AI to generate something you write regularly like product descriptions or professional emails. Focus on clarity, tone, and style. Review and refine several times to improve its quality. Ask your GenAI for suggestions on making this more persuasive, clear, authoritative, empathetic, etc.
Pro Tips
- Be specific about your role and the intended audience as well as your desired outcome and avoid vague statements like “make this better”
- Be specific about your role, the intended audience, and your desired outcome, and avoid vague statements like “make this better.”
- Break complex requests into smaller steps to avoid overloading requirements
- Use formatting in your prompt (bullet points, numbering) to get organized responses
- Remember to specify tone (formal, conversational, etc.) for any output
Grit and Growth Guide: Humor can be an incredibly effective tool for fostering and enhancing both grit and a growth mindset by reducing stress, encouraging a positive outlook, enhancing social connections, promoting creative problem-solving, fostering a learning attitude, and boosting confidence. Look for the humor in GenAI missteps as you navigate new uses. Even better, consider whimsical uses to help you through frustration. For example, ask your GenAI to use emojis, or give its answer in the tone of a historical figure. Nothing like a laugh to move us to a more open mindset.
Reflection: What surprised you? What do you want to keep exploring? What may be valuable for you? What isn’t? Could you reframe any setbacks with humor?
Explore your own thoughts and experience about today’s GenAI journey with the following self-prompts: “I like…,” “I wish…,” and “I wonder…”
― Day 5 ―
Image Generation
Intro: Image generation is a new facet in AI. From finding images for a presentation to marketing and headshots, it might save you time from scouring picture databases or serve as a creative spark. AI Image generation differs from text generation, which sometimes amplifies internal bias; therefore, image generation prompting can be challenging compared to text prompting and often needs additional refinement. Therefore, the best practice is not to add to an existing prompt, but to create new, detailed ones. Lastly, research indicates that image generation requires more computational power, which may lead to environmental impacts.
Thought Leaders:
Dr. Fei-Fei Li is a professor in the Computer Science Department at Stanford University and a Founding Co-Director of Stanford’s Human-Centered AI Institute. Creator of ImageNet, a critical large-scale dataset, and author of The Worlds I See: Curiosity, Exploration and Discovery at the Dawn of AI, Dr. Li is a pioneer of understanding the importance of diverse perspectives in building, using and shaping AI.
Manuel Sainsily is a futurist, artist, speaker, and advocate at Unity where he pioneers advancements in AI and Mixed Realities. Manual is regarded for his multidisciplinary approach to technology and art, and his advocacy for ethics, diversity, and inclusion.
GenAction:
See if your GenAI tool has image creation capabilities. If not, check out one of the others that do (if they meet your privacy and security thresholds!). Begin asking for an image for reports, presentations, or other areas where images can communicate more than words.
Example: “Create an image of a group of people collaborating in a workplace.” As a follow-up, use a similar prompt but suggest different ages, genders, or other characteristics/demographics be represented given the image, a theme, or artistic or photographic style. Such as “Create an image of people collaborating in the workplace, include six people, four women, one man, and a dog looking at a chart and having a lively group discussion, “then compare these images to each other.. Consider including words in the image - note whether this is successful.
Now, let’s try some other fun ways to test the imagination of image generation. Try a wild request—“create an image of a lawyer juggling balls of spaghetti on the tip of a spoon hovering over a sea of sauce.” Or doodle something yourself and then describe it in the GenAI tool to see how your imagination may differ from the output.
Grit and Growth Guide: Imagination and visualization are powerful cognitive tools that help develop grit and a growth mindset. They enable us to envision future possibilities, set goals, and mentally rehearse steps to achieve them. Integrating imagination and visualization into daily routines can transform resilience and foster a more adaptive mindset.
Reflection: What surprised you? What do you want to keep exploring? What may be valuable for you? What isn’t?
Explore your own thoughts and experience about today’s GenAI journey with the following self-prompts: “I like…,” “I wish…,” and “I wonder…”
― Day 6―
Research & Data Analysis
Intro: We spend much time researching everything from local eateries to regulations and global political and financial trends. Between work and home, there is endless information to find, sift, and analyze, especially when we want the benefit of broad data and perspectives. Today, we look at ways GenAI may help.
Thought Leaders:
Dr. Joy Buolamwini is an AI researcher, artist, advocate, and author of Unmasking AI. In her book, she exposes the role of bias in data training and pushes us to confront our blind trust of supposedly trustworthy AI systems.
Karen Silverman is a data-focused researcher and practitioner. As the Founder and CEO of Cantellus Group, Karen is a leading global expert in practical governance strategies for AI and other frontier technologies.
GenAction:
While rule #1 of using GenAI always raises questions about accuracy, GenAI can be useful in conducting research and data analysis. Identify a metric you want to track - whether it’s something at home, like spending habits, or at work, like client satisfaction or hours worked. If you’re a lawyer or consultant, it may be billable hours. Then, ask your GenAI to help you better understand the chosen metric and give you ideas on identifying key data points to track, analyze trends, and present the data best. You can then ask the tool to create a visual effect to display the data (a chart with labels, etc).
Spend 10+ minutes following up with questions, trying different outputs and metrics, and coming up with other ideas for leveraging GenAI for data-based analysis, as well as how others may be using it to persuade you.
Sample Prompt: “Help me come up with a prompt to help me create a metric related to [XXX], better understand it, ideas on how to identify key data points to track, how to analyze trends, how to present as a framework, and how to create an effect visual to display the data (chart with labels, etc).”
Resources: Check out VAILL Day 4 on Research and Data for more in-depth prompt suggestions and uses, as well as links to further resources.
Grit and Growth Guide: Metrics and data can play a crucial role in fostering grit and a growth mindset by providing tangible evidence of progress, identifying areas for improvement, and motivating individuals to persist through challenges. They can also be frustrating to create and therefore the perfect place to leverage your grit and growth mindset. Remember that you can develop greater resilience and a more adaptive mindset by setting clear goals, tracking progress, providing feedback, identifying strengths and weaknesses, encouraging persistence, and celebrating achievements.
Reflection: What surprised you? What do you want to keep exploring? What may be valuable for you? What isn’t?
Explore your own thoughts and experience about today’s GenAI journey with the following self-prompts: “I like…,” “I wish…,” and “I wonder…”
― Day 7―
Teaching AI to Work for You
Intro: After exploring the possibilities of GenAI, you might have noticed a pattern of its capability to assist with foundational tasks that might have historically been assigned to an intern or entry-level employee. While AI cannot replace real interns who benefit from having hands-on experiences and shadowing industry leaders, this comparison offers insight into how to train your AI tool like an intern to maximize its efficacy.
Having an intern is a privilege, and requires remembering what it was like not to have experience and context. Understanding that AI, like humans, lacks context but is eager to do a great job, can be a helpful frame for using AI effectively. Today is about learning how to prompt and guide your AI to produce beneficial, accurate, and helpful work product while controlling its overeager tendencies to please you (sometimes by making things up).
Thought Leader: Judy Spitz is a former CTO and founder and CEO of Break Through Tech. Judy is passionate about redesigning pathways and access to technical fields by empowering anyone with the skills and experience necessary to participate in the ever-evolving technological landscape. Judy acknowledges that utilizing AI for “intern tasks” can be beneficial, but having a human intern actively engage, if not lead, your AI efforts is even more effective.
GenAction: Choose a real task from work that you would usually give to an intern (e.g., summarizing a legal article, drafting a case alert, reviewing a legal issue). Then, prompt your AI to complete it. Because your AI is an “intern”, you should not expect the first draft to be camera-ready.
Tips:
- Give your AI clear, written instructions on what to do as if you were explaining the assignment to a new intern. What institutional knowledge does your AI tool need to complete the assignment to your expectations?
- Tell your AI what not to do (e.g., Don’t fabricate legal citations). Broad parameters might be obvious to you, but not to someone or something new to your team.
- If you are prompting the tool to review or analyze a case, contract, or other document, make sure you provide a copy of it to the AI for reading. What other resources would an intern need to fully understand the task?
- Provide any sample outputs of the AI to assist in modeling tone, specificity, format, and other relevant aspects.
- When the output isn’t accurate or sufficient, ask your AI tool to explain its reasoning and decision-making. Understanding its process will help you tailor your prompt and provide more specificity for better results.
- After receiving the first draft, provide the AI with specific, actionable feedback to help improve the next draft.
Grit and Growth Guide: Recognize that training any new intern takes time, but the investment is worthwhile. If your intern is not meeting your expectations, ask again. It is widely accepted that one can learn a great deal while teaching. Knowing where your team members (either human or AI) made missteps provides the opportunity to identify subjects or tasks that require more detail and clarity, familiarize yourself with the needs of your team to meet your expectations, and potentially uncover new perspectives while understanding their thought processes.
Reflection: What surprised you? What do you want to keep exploring? What may be valuable for you? What isn’t?
Explore your own thoughts and experience about today’s GenAI journey with the following self-prompts: “I like…,” “I wish…,” and “I wonder…”