21 Days of AI: A Grit and Growth Mindset Challenge

― Week 3 ―

Use Cases for AI Elevation

Intro: All too often, we hear lawyers described as great at law, terrible at leadership. But there is always an opportunity to practice your skills and lead wherever we are, whether that be as the most junior member of a team, leading a department of 50 people, or even in our unofficial, unpaid roles at home. AI can help build those muscles and better prepare you to grow into leadership, leveling up, or helping colleagues improve. We hope you find this week’s uses of AI, particularly in key leadership skills such as communication, presenting, collaborating, and creating valuable cohesion, useful in whatever arena you find yourself. 

― Day 15 ―

AI for Communicating Effectively

Intro: Whether or not you are familiar with the term “attention economy,” you have likely experienced the constant flow of information and messaging from all angles. In this fast-paced world, it is more essential than ever to communicate effectively. AI can be a valuable tool to assist with certain forms of communication, such as making your writing more concise and impactful, testing message clarity, and exploring different styles that resonate with your audience. Knowing what you are trying to convey and communicating it in a way that connects with your audience is something where AI may be helpful. At the same time, more transparent communication helps you get the most out of your AI partner. As Stanford Professor Russ Altman shared in an interview, "If you're worried that a ChatGPT-type tool can replace you, I think you need to think about why I'm communicating, what I'm trying to say, am I being authentic, do I have a message? Because if those things are true, it shouldn't be a problem. It should just help you amplify and improve your message."

Thought Leader: Being focused on communication as a skill and willing to speak up bravely and strategically is more critical than ever in the emerging AI era. Kim Scott, author of Radical Candor, is a leader in this space, and is experimenting with an AI “portrait” of herself to share her experience and research-based insights.

GenAction: Write a description of your current project. Ask your AI tool to shorten your writing sample and improve the word choice to have the most impact.  As a follow-up, ask it to explain why it made those changes.

Tips: Your desired impact will change depending on the context and audience for your content. If your program description, for example, appears in promotional materials, your prompt for the AI tool should specify a persuasive tone for a specific audience. Remember to follow up and ask what makes it more persuasive than your original version so you can understand and replicate that process when your AI tool is not available.

Grit and Growth Guide: Even if you spend a substantial amount of time at your computer, it is essential to leverage these tools to build your skills, not replace them. Artificial Intelligence replicates our capability to adapt to learning new information. It may be cliché, but practice is essential to mastery.

• 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…”

Resources:  Think Fast, Talk Smart Podcast on AI in Communication

― Day 16 ―

AI for Vision and Mission Statements

Intro: According to BCG research that surveyed 2,000 marketers globally, organizations that have integrated AI tools deeply into their marketing workflows report measurable growth. Examples of these strategies include analyzing data, identifying customer trends, and fostering cross-functional partnerships. These strategies highlight opportunities for early AI adopters who are beginning to see success. Tomorrow we will explore how AI can be used to elevate pitches and presentations; first, let’s look at distilling your mission and vision as cornerstones for your brand identity.

Thought Leader: Jessica Apotheker is the global chief marketing officer at Boston Consulting Group and BCG X (BCG’s tech build and design unit). Throughout her career, she has helped many companies implement data-driven marketing agendas, build advanced digital and data marketing capabilities, and deploy advanced marketing AI platforms. Jessica is an expert in helping marketers strategically position themselves in the AI landscape based on their preference for data and/or creativity. 

GenAction: Developing a vision and mission statement is essential to communicating with your audience. It outlines what you do, why you do it, and why you do it. Understanding these pillars, it provides you with the specificity needed to use your AI tool to the best of its capability.

Draft your own vision and mission statement, touching on these three components. Then ask your AI tool to revise your statements with specific considerations for audience, tone, and clarity. Example: “Edit my vision and mission statements below to attract X audience, in Y style.

Pro Tips

• Remember, AI works best with specifics. Use as many strong action verbs as possible and consider how you would want your clients to describe you and your organization.
• Experiment with different styles and tones to align the text with your brand, voice and personality.

Grit and Growth Guide: Content enhancement is a key benefit of AI.  You can polish your narratives, value propositions, and key messages by having AI rewrite them in a manner that resonates with your target audience. While GenAI may be weaker at nuanced reasoning, it excels as a non-judgmental brainstorming partner that doesn't care if you have “stupid” ideas.  When you're stuck on how to present particular concepts or data, consider using GenAI for creativity, fresh ideas, and new angles.

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…”

What surprised you when using AI during your drafting and brainstorming journey? Any "aha!" moments or unexpected twists? Where did AI shine and where did it stumble? Take a moment to explore new possibilities—what other areas of your work and life could AI add value by challenging your thinking or offering constructive insights?

― Day 17 ―

AI for Presentations

Intro: After crafting your vision and mission statements, you can begin to conquer how that message reaches your target audience, like pitch decks and presentations. The right tools can match the best design styles to your content and audience. You can tap into AI’s capabilities by creating visuals that are eye-catching and emphasize your messaging.

Thought Leader: Don Allen is a creative technologist and artist who bridges the worlds of cutting-edge technology and artistic innovation. As a visionary in the tech and creative space, he has collaborated with major tech companies including Meta, Adobe, and OpenAI. His extensive experience includes working as a specialist trainer at DreamWorks Animation, where he taught creative software and was recruited after studio executives noticed his educational 3D software livestreams.

GenAction: Effective data visualization is a powerful way to enhance your presentations.  Access those daunting and complex data sets and spreadsheets (i.e., annual financial reports, industry analytics, or sales and marketing data). Process the data through your AI tool to track patterns, identify outliers, and create visual representations that are more digestible than a list of numbers.

Sample Prompt:

•  “Using this financial report, create a slide for a presentation that highlights revenue growth over the last three months.”
• “Transform this statistical dataset into a compelling visual story that makes the patterns and trends immediately apparent to my non-technical audience.”

Grit and Growth Guide: Overloading slides with too much information can leave your audience overwhelmed with data. Yet stripping away crucial context could leave your audience wondering what story you're trying to tell. Finding the correct wording for a presentation can certainly be challenging, which is why working with a dataset, iteration, and prompt refinement will be key.

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…”

Were you surprised at AI’s data analytic capabilities? Did the visuals help to communicate your thesis, conclusions, or arguments more effectively? How can you use GAI visuals to enliven your future presentations and make your points more compelling?

― Day 18 ―

AI for Honing Leadership Skills

Intro: Communication skills form the cornerstone of effective leadership, though let’s be honest—who hasn’t panicked before a big presentation? Team leaders often juggle communicating complex or tricky ideas to different stakeholders while having little time to prep. Whether you are rallying your team on Monday morning, pitching to stone-faced executives, or gently breaking the news about timeline “adjustments” to clients, AI can help ensure your message hits just the right note.

Thought Leader:  Dr. Louise Kelly is a Professor of Management and Leadership at the University of La Verne, California.  With expertise in entrepreneurial team dynamics and women’s leadership, she has expanded strategic management discourse to embrace its often-neglected “soft side.” Having published seven books and over twenty articles, Dr. Louise Kelly has also contributed research that explores the relationship between artificial intelligence and authentic leadership.

GenAction: Before your next leadership presentation, feed your AI the relevant internal analysis along with specific notes about your audience’s sensitivities and priorities. You should pay special attention to confidentiality and sensitive information. Since we are dealing with proprietary information, review your Day 1 outputs for privacy and terms of usage guidelines. Indicate where you need to soften language or reframe challenges into opportunities. The AI will recalibrate your message to address unspoken concerns, highlight the wins that matter most to your audience, and manage expectations —all while preserving your professional voice and credibility.

Sample Prompts:

• “I’m preparing for a board presentation on our [project/initiative]. Our internal assessment identifies [specific challenges], but I need to present these constructively. The board is especially focused on [key concerns] and [strategic priorities]. Please revise these talking points to address their concerns while maintaining transparency about the situation.”
• “I need to present this update to [client name] tomorrow. They are particularly concerned about [specific pain points] and focused on [priority metrics]. Can you help reframe this internal analysis to acknowledge the [challenging aspects] while emphasizing the [positive developments] and long-term value? Keep the tone confident yet empathetic.”

Grit and Growth Guide: Communications at the executive level often require striking a balance between factual accuracy and stakeholder management—a delicate equilibrium that can be challenging to achieve. When crafting client or board updates, you may encounter frustration as you search for phrasing that neither sugarcoats reality nor creates unnecessary alarm. This struggle is a natural part of developing leadership communication skills. Remember, every awkward first draft and tonal misstep is just part of the process of grit and growth. The goal isn’t perfection, but progress in crafting messages that honor both the facts and the humans receiving them.

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…”

After experimenting with AI assistance, consider which suggested phrasings resonated most deeply with your authentic voice. Did specific reframing approaches feel like “you at your best” rather than someone else entirely? Which versions maintained your distinctive perspective while addressing stakeholder concerns? Pay attention to adjustments that made you think, “That’s exactly what I wanted to say, just clearer.” The value isn’t just a polished update but also a better understanding of your unique communication strengths.

Resources:

• Leveraging Grit and Growth Mindset to Drive Team Success, ABA Commission on Women in the Profession
• “Using AI to Make You a More Compassionate Leader,” Jacqueline Carter, Rasmus Hougaard, Marissa Afton.

― Day 19 ―

AI for Adaptive Leadership and Tough Conversations

Intro: One of the most complex and most important parts of leadership is having tough conversations and providing helpful feedback. AI can be a valuable partner in preparing for these conversations and situations.

Thought Leaders:

• Jacqueline Carter: Is a leadership development and organizational culture expert who helps global companies create a more human world of work. Her work at Potential Project focuses on providing resources for leaders to utilize AI effectively.
• Scott Westfahl is the Director of Harvard School of Law Executive Education and teaches courses on leadership, design thinking, and innovation. He oversees and teaches in Executive Education’s core, global leadership programs for law firm managing and senior partners, emerging law firm leaders, law firm associates, senior in-house lawyers, and general counsel.

GenAction: Ready for hard conversations? Identify a meaningful conversation you have on the horizon that might be challenging, like feedback, budget discussions, growth plans, or strategic decisions. Ask your AI tool for advice on how to approach the situation, and follow up with additional nuances for more specific context. Role-play with your tool to prepare for different scenarios and potential pushback you may receive. This kind of preparation can help create clarity and space for you to be less reactive and more compassionate and strategic during the actual conversation.

Sample Prompts: I need to speak with several team members who were not promoted and have growth opportunities to complete before they are ready for promotion. They are valued, and I want to keep them, but I need to be honest with them. How might I approach this conversation? What kind of pushback should I anticipate? Help me practice a conversation with them by roleplaying a disgruntled team member.

Tips: Interested in learning more leadership skills from AI? Marshall Goldstein, author of several books on leadership and self-growth, has built a free GPT based on his books that can act as a coach. Check it out if interested here:  https://marshallgoldsmith.ai.

Grit and Growth Guide: Having hard conversations and creating an environment where they are effective requires a mindset of grit and growth. Grit helps us persevere through discomfort and potential conflict, while a growth mindset enables us to view these challenges as opportunities for learning, improvement, and stronger relationships.

Furthermore, Adaptive leadership is a framework that emphasizes flexibility, learning, and collaboration to address complex challenges. When it comes to adopting Generative AI (GenAI), adaptive leadership principles can be instrumental in navigating the uncertainties and complexities associated with GenAI. This combination enables us and our teams to engage in difficult dialogues productively rather than avoiding them.

Explore your own thoughts and experience about today’s GenAI journey with the following self-prompts: “I like…,” “I wish…,” and “I wonder…”

Resources:

Crucial Conversations: Tools for Talking When Stakes Are High. Grenny, J., Patterson, K., McMillan, R., Switzler, A. and Gregory, E., 3rd ed. 2021.

― Day 20 ―

AI Collaboration + Agentic AI

Intro: So far, we’ve focused on Generative AI, with you in the driver's seat directing AI to help you. Generative AI focuses on producing content, such as text, images, or code, based on patterns learned from existing data when given a prompt. Agentic AI, on the other hand, goes beyond content creation to autonomously make decisions and take actions within an environment to achieve specific, predefined goals. Using agentic AI involves a different set of risk calibrations as you decide how much access or entitlement to give an agent to your identity, finances, passwords, and more. It also holds the possibility of receiving even greater support from digital tools.

Thought Leaders: Anna Gressel + Katherine Forrest, two world-renowned AI legal experts, break down all kinds of AI

GenAction: Explore different agentic AI that are already available and read reviews of those tools. Many of our thought leaders from earlier days, like Allie K. Miller and Ethan Mollick, regularly evaluate AI tools, including agents, and offer insight into how they currently perform. Consider exploring not just text agents, but also voice agents, which utilize AI to understand, interpret, and respond to human speech, thereby performing various tasks.  Consider revisiting Day Zero and reassessing the terms and conditions surrounding privacy and security, as well as other ethical considerations related to using these tools, particularly in comparison to non-agentic Generative AI tools.

Grit and Growth Guide: Embracing Change requires resilience and persistence (grit) as well as a belief that abilities can be developed through effort (growth mindset). While agentic artificial intelligence feels like a whole new beast entering the arena, the adaptive leadership skills, grit, and growth mindset essentials will follow you as you attack innovations and challenges.

Reflection: What surprised you? What do you want to keep exploring? What may be valuable for you? What isn’t?

Prompt yourself! Explore your own thoughts and experience about today’s GenAI journey with the following self prompts: “I like…,” “I wish…,” and “I wonder…”

 Resources:

• Waking Up with AI podcast
• Agents Today Substack by Mike Clark

― Day 21 ―

Reflections: Staying Gritty, Growth Minded, and Committed to Building GenAI Muscle and Responsible Use Beyond Day 21

During the past 21 days, while you’ve been on this journey, the technology has changed again. Most likely, with the introduction of entirely new models with more seamless and integrated modalities, with more apparent reasoning capability and emerging capacity for automation. And in the next 21 days, this will happen again and again. The grit and resilience we are developing – and the habits and muscle memory – are how we will function with skill and (mostly) equanimity in the face of relentless change. We won’t always succeed, and not every change requires our attention or adaptation; however, being part of the discussion and contributing to the human solution is critical, ongoing work. Your ability to do this now, after 21 days, and to continue doing it 21 days and months from now, is precisely how we will manage and develop the technologies that work for us and enable our communities, both at home and at work. No one else can do this work for us, and we are grateful to be on this journey together!

ACTION FOR THE NEXT 21 DAYS - AND BEYOND

Build your own AI plan - follow thought leaders, send us yours, create generative groups, and invite us to discuss.  Planning for future study:

• Bookmark those thought leaders and others you’ve found along the way - and the ABA Commission on Women in the Profession and the Center for Innovation.
• Set a quarterly calendar reminder to revisit the challenge, try things you want to dig in more in the following rounds
• Please share your learnings with us so we can continue to work on ways to share community assets and knowledge.
• Want to do a group session? The Challenge was assembled by Gabrielle Kohlmeier, Anna Gressel, Madeline Amonick, and Joey Gartner, with an advisory council comprising world-renowned AI and legal leaders, as well as leadership experts. We are happy to discuss conducting kick-off presentations, facilitating discussions for groups before, during, and after the 21-day challenge.

Reflect on your 21-day journey. What surprises you now? What do you want to keep exploring? What may be valuable for you? What isn’t?

Links

Week One | Week Two | Week Three

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