“I don’t have time for personal strategy planning. I’m so busy that I don’t have time to anything but work.”

Sound familiar?

In this month’s issue of my Personal Strategy Compass newsletter (paid subscription only), I’m tackling the #1 objection I hear about Personal Quarterly Offsites (PQOs). I’ve developed a stripped-down approach called the Minimum Viable PQO (“MVPQO) that takes just 30 minutes – less time than many lawyers I’ve known spend on average telling people how busy they are.

Want to know how to transform your life in half an hour? Our paid subscribers are learning three questions that cut through the noise and create immediate clarity and momentum. [Subscribe now to access the full issue]

I blend proven business concepts (like the MVP approach from “The Lean Startup”) with cutting-edge personal development insights from James Clear’s “Atomic Habits” and Nir Eyal’s work.

Paid subscribers are learning how to weave these powerful frameworks together into a 30-minute practice that creates real results. They’re also getting an exclusive AI prompt to hit the ground running.

Here’s the core insight: You don’t need a full day, or even half a day, to begin transforming your approach to personal strategy. You can start with just 30 minutes.


The biggest barrier to positive change isn’t technology – it’s getting started. We often let perfect be the enemy of good, waiting for the “right time” to begin something new.

Here’s the core insight: You don’t need a full day, or even half a day, to begin transforming your approach to personal strategy. You can start with just 30 minutes.

As someone who has long advocated for the intersection of technology, law, and personal productivity, I’ve found that the most successful innovations are often the ones that reduce friction and lower barriers to entry. The Minimum Viable PQO does exactly that – it takes the essence of the full PQO process and distills it into something anyone can do, regardless of how busy their schedule might be.

With its focus on quick wins and building momentum, the MVPQO provides a low-risk, high-reward entry point to personal strategy work.

In the latest issue of Personal Strategy Compass (available to paid subscribers), I break down the exact framework and give you:

In this issue, paid subscribers get:

  • The MVPQO framework
  • Three game-changing reflection questions
  • A practical AI prompt to get you off to a great start
  • Resources curated to help you move forward

If you’re interested in exploring this approach, you can subscribe to Personal Strategy Compass here. The MVPQO framework is just one example of how I’m working to make personal strategy accessible and actionable for busy professionals.

Remember: Sometimes the smallest steps lead to the biggest transformations. Start where you are, with what you have, even if it’s just 30 minutes. Subscribe here.

[Originally posted on DennisKennedy.Blog (https://www.denniskennedy.com/blog/)]

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As an avid reader, for many years I have set the goal of reading 52 books in 52 weeks. It’s ambitious, but reading is a hobby and this exercise helps me keep track of what I’ve read. In 2024, I read 72 books, exceeding my goal by quite a bit. Or, more accurately, I listed 72 books that I read. I don’t list books that might reveal certain things I might (or might not) be working on.

Picasso like image of people gathered and looking at book

In 2023, the total number was 92.

I again found that I was starting and abandoning quite a few books. And I’m reading way more audiobooks than ever before – largely a function of convenience and the trickiness of fonts and font sizes as I get older.

If you forced me to pick my top books for 2024 (in alphabetical order) that I’d recommend, I’d probably list:

  • 3 Shades of Blue, James Kaplan
  • After 1177 BC, Eric Cline
  • Brave New Words, Salman Khan
  • Co-intelligence, Ethan Mollick
  • How to Retire, Christine Benz
  • The 6 Types of Working Genius, Patrick Lencioni
  • The Great River, Boyce Upholt
  • Wild New World, Dan Flores

I’m doing the same thing in 2025. My approach is the same as in previous years – I’ll simply update this post from time to time from time to time throughout the year as I finish books.

I’ve enjoyed doing this challenge every year and hope you find the list useful. And I encourage you to take the challenge yourself.

I welcome your recommendations of good books I might read this year.

As Bill Taylor says, “Are you learning as fast as the world is changing?”

Challenging yourself to read 52 books is probably a good way to start to answer that question.

December

November

October

September

August

July

June

May

April

March

February

January

2. Power Metal, Vince Beiser
1. Tooth and Claw, Craig Johnson

[Originally posted on DennisKennedy.Blog (https://www.denniskennedy.com/blog/)]

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I spent the month of November doing what I called an “AI Sprint,” in which I experimented with a lot of new approaches and tried generating new types of outputs. I haven’t shared much of that yet, but I thought this exploration of what “AI in the Middle” might mean in law and law practice was interesting.

This is the topic in AI in law practice that fascinates me the most. I contend that we are overfocusing on what AI might do on commodity legal work and efficiency, and underfocusing on what it might do at the high end of law practice. My question, then, became, does that mean that the middle space might be especially interesting and underappreciated.

There are a number of ways to look at this issue. The area to watch in AI innovation, to me, is in the mid-sized law firm, law department, and legal organization space. See my predictions for legal AI in 2025 in this National Law Review article. I’ll also note that the LegalTechnology Hub has debuted a new Midsized Hub with a focus on midsized firms.

I’ve just pulled a section of the output from a series of prompts I did on this topic last month. I’ve managed the prompts to shape the output in the direction of my ideas and questions, but I have not edited it. There is a goldmine of ideas, insights, action steps, and new strategic approaches in this output. See if you agree? Also, the US Copyright Office has apparently decided that my work in creating this output is not protectable. Would you agree after reading it?


Your clarification reframes the discussion of AI’s potential in legal practice, particularly in redefining the boundaries of bespoke and commodity legal work. By “high-end,” you refer to AI’s ability to act as a stand-in for the most highly customized legal advice—strategic, complex, and nuanced work traditionally reserved for elite, highly compensated legal professionals. The “middle ground,” in this context, represents the domain between commodity legal tasks and bespoke strategic work, encompassing semi-complex, moderately tailored tasks.

This approach frames AI as a disruptive partner in both middle-ground and high-end legal work, with the potential to redefine the delivery of strategic legal services.


Here are refined insights based on this perspective:

  1. High-End AI as a Strategic Partner
    • AI has the potential to function as a preliminary strategist in areas such as trial preparation, negotiation planning, and overarching legal strategy.
    • By analyzing massive datasets, precedents, and historical outcomes, AI could provide first-pass recommendations on highly tailored issues, such as:

    o Optimal litigation strategies for specific jurisdictions.
    o Suggested negotiation tactics based on the opposing counsel’s history.
    o Risk assessments for complex, bespoke transactions.

    Why It Matters:

    This challenges the notion that bespoke legal advice is solely the domain of human partners. AI can offer actionable insights and frameworks that elite professionals can refine, significantly accelerating the process without compromising quality.
  2. The Middle Ground: More Bespoke Than People Expect

    • The middle ground includes tasks like contract negotiation, compliance strategies, regulatory guidance, and other semi-bespoke services that require more customization than standard templates but less nuance than high-end legal strategy.
    • Current tools, like contract review platforms, often stay within the “commodity” level of automation. However, AI can:

    o Draft customized legal documents tailored to specific business models or industry needs.
    o Provide detailed “first-pass” negotiation frameworks or playbooks that mimic bespoke advice.
    o Perform comparative analysis for regulatory compliance, flagging gaps with contextual explanations.

    Why It Matters:

    AI has the potential to blur the lines between commodity and bespoke services, delivering scalable solutions that were once thought possible only at the highest levels of human expertise.
  3. The Middle Ground as the Most Disruptive Zone

    • The middle ground represents the most economically transformative zone for AI because:

    o It includes work typically handled by mid-level associates or lower-cost partners.
    o It bridges the gap between efficiency (commodity tasks) and deep insight (bespoke strategy).
    • Examples:
    o AI-driven mediation tools that suggest compromise points based on precedent and party preferences.
    o Strategic portfolio analysis for legal risks across multiple contracts, providing tailored recommendations for each scenario.

    Why It Matters:

    This is where client expectations are evolving—they want bespoke quality at a lower cost, and AI can meet that demand.
  4. AI in High-End Work: The First-Pass Revolution

    • In high-end work, AI can excel as a thought partner during the ideation stage, particularly for:

    o Modeling trial strategies by simulating different judge and jury profiles.
    o Drafting negotiation roadmaps, including fallback positions and alternative strategies.
    o Suggesting legal arguments by analyzing similar cases and predicting outcomes.

    Why It Matters:

    Partners can spend less time on preliminary work and more time on refining and personalizing insights, allowing them to scale their expertise across more clients.
  5. Redefining Value in Bespoke Services

    • Traditional bespoke services emphasize depth of human wisdom and customization. AI, however, can:

    o Perform data-driven customization, identifying nuances often missed by humans.
    o Generate bespoke solutions faster by analyzing vast amounts of precedent and contextual data.

    Why It Matters:

    AI enables a new dimension of “bespoke” services that are faster, data-rich, and cost-effective, providing clients with value at scale.
  6. The Middle Ground as a Testing Ground

    • The middle ground is ideal for developing and refining AI tools that could eventually migrate into high-end strategy work.

    • For instance:
    o Tools for mid-level contract negotiation could evolve into complex deal negotiation assistants.
    o AI handling semi-complex regulatory guidance could inform bespoke compliance strategies for multinational corporations.

    Why It Matters:

    The middle ground allows AI to gain credibility, refine its capabilities, and build trust for eventual deployment in high-end legal strategy.
  7. Key Challenges to Overcome

    • Context Sensitivity: High-end and middle-ground AI must incorporate nuanced understanding of:

    o Client-specific goals and risk tolerances.
    o Non-verbal cues and emotional intelligence in negotiations.
    • Trust Issues: Convincing high-value clients and top-tier partners that AI can deliver a useful first-pass without diluting bespoke quality.

    Why It Matters:

    Addressing these challenges will determine how quickly AI moves from middle-ground applications to true high-end bespoke work.
  8. The Role of Human-AI Collaboration

    • AI is unlikely to replace bespoke legal work entirely but will elevate human capacity, particularly in high-end cases.
    • Example: AI could identify 50 potential arguments for a trial strategy, while a seasoned partner refines the list to three that align with the client’s values and goals.

    Why It Matters:

    This collaboration allows humans to focus on the most creative and judgment-based aspects of their work while delegating preliminary tasks to AI.
  9. The Economic Case for the Middle Ground
    • Clients are already questioning the cost of bespoke services, especially for moderately complex work. AI’s ability to provide:

    o Faster first-pass results.
    o Semi-bespoke solutions at a fraction of the cost.

    Why It Matters:

    The middle ground is where AI can reduce cost barriers, allowing smaller firms and underserved clients to access tailored legal solutions.
  10. Building Momentum for High-End Adoption

    • Success in the middle ground will pave the way for AI adoption in high-end work by demonstrating its:

    o Reliability.
    o Practicality in complex scenarios.

    Why It Matters:

    This phased approach to adoption will help firms build trust and integrate AI into even their most sensitive and high-value workstreams.

Action Steps for Exploring This Space

  1. Develop Use Cases: Identify specific middle-ground and high-end scenarios (e.g., negotiation playbooks, trial simulation tools).
  2. Prototype Middle-Ground Solutions: Use the AI Lab to experiment with tools that blend commodity and bespoke work.
  3. Educate Stakeholders: Present case studies and ROI analyses to demonstrate AI’s potential in this middle zone.
  4. Refine Bespoke Applications: Collaborate with elite professionals to test AI-driven first-pass tools for high-end tasks.
  5. Create Adoption Frameworks: Build a step-by-step model for integrating AI into higher-value legal workstreams.

This approach frames AI as a disruptive partner in both middle-ground and high-end legal work, with the potential to redefine the delivery of strategic legal services.

And, yes, I did go on through several more rounds to refine these ideas. I’m not willing to share that output until it becomes protectable.

[Originally posted on DennisKennedy.Blog (https://www.denniskennedy.com/blog/)]

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I’m excited to announce the launch of Personal Strategy Compass, my new premium newsletter focused on helping professionals implement Personal Quarterly Offsites (PQOs) in their lives and careers. Subscribe here.

Does this seem all too familiar?

Late on Sunday night, sleep eludes you. Your law practice is successful by any objective measure, but something isn’t right. Maybe you’re a partner wondering if there’s life beyond billable hours or an in-house counsel dreaming of teaching or consulting. The weekend is ending, and once again, you’ve made no real progress on planning your first step, let alone a potential escape route.

Your thoughts circle between staying in a role that no longer fits, the uncertainty of making a change, and the gnawing feeling that you’re letting opportunities pass by. You are haunted by anxiety about Monday morning and the growing certainty that you need to make a change or one will be made for you.

Sound familiar?

I’ve been there. More importantly, I found a way through it.

That’s why I’m excited to announce Personal Strategy Compass, a premium newsletter that helps successful professionals who feel stuck in career transitions create clarity and forward momentum through a proven quarterly planning framework that transforms career uncertainty into intentional action.

In my decades of working with legal professionals and high achievers, I’ve noticed a common challenge: despite their success, many struggle to find clarity and direction when facing major career transitions or life changes. The daily demands of work and life often prevent them from stepping back to think strategically about their future.

Navigating your success your way, one quarter at a time

For many years, I’ve used PQOs to navigate major transitions, make strategic decisions, and maintain focus on what truly matters. From retiring from corporate law to building a teaching and writing career, PQOs have been my secret weapon for maintaining clarity and purpose. This proven framework combines the precision you bring to your legal work with the deeper insights needed to align your future with your true potential.

Think of it as a monthly masterclass from a trusted advisor who understands both the complexities of legal leadership and the challenges of career transitions.

From the first issue, I explain why PQOs matter:

“What makes PQOs so transformative? They’re a blend of strategy and mindfulness, offering clarity and a concrete plan to move forward. In this fast-paced world, it’s easy to get stuck in the churn of daily demands. PQOs pull you out of the whirlwind and give you the space to think deeply about what matters most.”

On their practical nature:

“PQOs aren’t about perfection. They’re about building momentum and staying adaptable. They work because they’re simple, repeatable, and flexible enough to fit into any lifestyle – while maintaining the rigor legal professionals expect.”

A Framework Built for Legal Leaders

This newsletter is designed for accomplished legal professionals who:

  • Have mastered their current role but sense it’s time for a strategic pivot
  • Are approaching retirement but know their leadership journey isn’t over and are looking for an encore career
  • See potential in moving from traditional practice to thought leadership
  • Want to apply their strategic excellence to personal transition planning
  • Want to be ready to move on to their next chapter

Strategic Guidance Delivered Monthly

Instead of another sleepless Sunday night, you’ll receive proven methodologies and actionable tools. Here’s what’s in the first issue:

Contents from Issue #1:

  • Welcome to the First Step in Your PQO Journey
  • What Is a Personal Quarterly Offsite and Why Does It Matter?
  • Finding the Time for Your First PQO
  • A Starter Exercise: Immediate Implementation for Quick Wins
  • AI Prompt of the Month
  • Your Next Step Your Next Step Toward a More Intentional Life
  • Helpful Resources and My PQO Templates

Yes, you get my own templates to help you get started. Subscribe here.

A Premium Investment in Leadership Excellence

This newsletter is premium-only ($176/year or $20/month) because it’s designed for leaders who value strategic excellence. This newsletter is premium-only ($176/year or $20/month) because I want to build a committed community of practitioners.

Each month, subscribers receive:

  • Strategic planning tools refined through years of legal leadership
  • Proven methodologies for uncovering your next chapter
  • Ready-to-use templates and exercises designed for high-achieving professionals
  • AI-enhanced planning strategies for modern leaders with helpful AI prompts
  • Monthly guidance to maintain momentum and clarity
  • Practical, actionable advice on implementing PQOs with personal insights from my own PQO discipline
  • Monthly guidance for your own PQO practice

Think of it as a monthly masterclass from a trusted advisor who understands both the complexities of legal leadership and the challenges of career transitions. Subscribe here.

Leading Your Next Chapter

You’ve led your legal career with precision and purpose. Now it’s time to apply that same strategic excellence to your future. If you’re ready to transform those sleepless nights into productive planning and purposeful action, subscribe now at https://dennis538.substack.com/about.

Don’t let another weekend slip away in uncertainty. Join other legal leaders who are using the PQO framework to uncover their path forward and lead their next chapter with confidence. Subscribe now.

And, yes, the idea for this newsletter was the result of one of my PQOs.

[Originally posted on DennisKennedy.Blog (https://www.denniskennedy.com/blog/)]

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I see the future of legal education transforming before our eyes, and I’m excited to share that I’m contributing in my own small way to that transformation. My Fall 2024 syllabus for “Artificial Intelligence and the Law” at Michigan State University College of Law is now available on the Syllabi Commons, thanks to John Mayer at CALI. Think of the Syllabi Commons as open-sourcing legal education – we’re not just teaching about innovation, we’re modeling it.

You might wonder, why share a syllabus publicly? Just as early investors in transformative technologies often reap the greatest rewards, early adopters in legal education who share their resources help shape the future of our profession. When we pool our knowledge, we accelerate everyone’s learning curve.

The course design reflects what I believe tomorrow’s lawyers need today. Students aren’t just studying AI – they’re living it. They’re creating personal AI learning assistants, tackling real-world practice simulations, and developing practical skills that will serve them throughout their careers. It’s like giving them a GPS app to navigate the rapidly evolving legal landscape.

Here’s what makes this course different: it’s built around actionable outcomes. Students don’t just learn about AI – they use it. They don’t just study ethics – they wrestle with real ethical dilemmas. They don’t just read about technology competence – they develop it. By the end of the semester, they’ll have:

  • Mastered the fundamentals of AI and its legal implications
  • Created their own AI learning assistant
  • Completed a practice simulation with an AI-focused client
  • Delivered a three-minute presentation on their research
  • Written a substantial paper on an AI legal topic of their choice

I see this syllabus as a living document – one that will evolve as rapidly as the technology it covers. It certainly feels like a living document in real life as I make adjustments to it, the reading materials, and what we cover based on fast-breaking developments and the vital feedback of my students.

Special thanks to the amazing John Mayer for maintaining the Syllabi Commons and encouraging professors teaching tech and law classes to contribute their materials. It’s this kind of collaborative approach that will help our profession adapt and thrive in the AI era.

If you’re teaching or planning to teach a course AI and the Law, or a course on any other topic in law and technology or innovation, I encourage you to explore my syllabus and others that catch your attention on the Syllabi Commons. And if you’re teaching a similar course, consider sharing your syllabus too.

What innovative approaches are you taking to teach law students about AI? I’d love to hear your thoughts.

[Originally posted on DennisKennedy.Blog (https://www.denniskennedy.com/blog/)]

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photo of Dennis speaking with a brick wall background

If innovation is on your law department’s agenda for 2024, this message is for you. As 2024 draws to a close, I’ve found myself reflecting on how far the world of law department innovation has come—and how much work remains. There’s one small problem: I have only one or two open slots left for 2024 keynote presentations in December.

My keynote, “Successful Innovation Outcomes in Your Law Department,” isn’t just another talk about the importance of innovation. It’s a roadmap designed to help law departments deliver measurable, transformative results—especially in this new age of AI. It’s built on the foundations of my book and new research I’ve conducted specifically to address law department innovation challenges. Whether you’re struggling to hit your innovation objectives or looking for ways to integrate AI into your strategies, this talk is packed with actionable insights you won’t want to miss.

Now, here’s where it gets even more interesting. AmLaw 50 law firms are reportedly raising their rates significantly, if not shockingly, in 2025—no surprise there. In the spirit of friendly competition, I’ll be raising my speaking fees by a modest 2% more than the average AmLaw 50 rate increase. But if you book before December 31, 2024, you can lock in my 2024 prices for a keynote engagement in 2025.

A bit of irony, perhaps? Law firms are passing even more of their costs along to clients like you, while I’m actually giving you the chance to beat the market.

But, like all good things, this offer won’t last forever. One or two remaining slots. 2024 pricing. Don’t wait too long—your innovation journey depends on it. And trust me, with what I’ve learned about AI this year, you’re going to want to hear these insights.

See you in December?

[Originally posted on DennisKennedy.Blog (https://www.denniskennedy.com/blog/)]

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Dennis with award in front of checkered background

This past Sunday, I was deeply honored to receive the Lifetime Achievement award at the American Legal Technology Awards.

As I stood there, absorbing the magnitude of the moment, I couldn’t help but think about the vast network of innovators, mentors, and colleagues who have shaped not just my career, but the entire field of legal technology. There are too many to mention, but I often trace my approach to legal technology to an exchange of emails with Marc Lauritsen many years ago that was extraordinary in both its helpfulness and generosity to someone starting in document assembly who Marc didn’t even know.

As I accepted the award after a generous introduction from my friend Cat Moon, I found myself reflecting on the path that lies ahead for the next generation of legal tech innovators. This recognition serves as an opportunity to share insights with those just beginning their careers in this exciting field.

The legal tech community has always been more than just a professional network; it’s been a source of inspiration, support, and relentless innovation. From the early days of document assembly software to the pioneering days of websites, blogs, and podcasts to today’s AI-driven opportunities, we’ve witnessed a transformation that has redefined the practice of law and the delivery of legal services. Yet, amidst all this change, one thing has remained constant: the spirit of generosity and collaboration that defines our community.

In my acceptance speech, I tried to capture this sentiment:

“People often say it takes a village to support a lifetime achievement award, but when I think about my journey in legal tech, it feels more like I’ve been uplifted by a vast global network of pioneers, visionaries, and generous peers who have shaped the paths we all now walk on. The legal tech community has been a source of strength and a home for me, and it’s an honor to stand here today because of the generosity of this community.

I’ve been fortunate to contribute and give back in ways modeled after the group of legaltech pioneers I first met. One of the ways I’ve chosen to honor this community is by creating the ‘Fresh Voices on Legal Tech’ interview series on my podcast with Tom Mighell. It reflects the spirit of giving back—helping emerging voices, just as the pioneers before me once did for me.

I want to leave you with a question that I often challenge my law students with: as business writer Bill Taylor puts it, ‘Are you learning as fast as the world is changing?’ It’s a question that guides me daily and one that I hope will inspire all of us to keep pushing forward. Thank you for honoring me today, and let’s continue learning together.“

Are you learning as fast as the world is changing?

For those looking to build a career in legal technology, here are some key lessons I’ve learned:

  1. Embrace the Community: The legal tech field is unique in its collaborative spirit. Don’t hesitate to reach out to others, attend conferences, join online forums, and participate in discussions. The connections you make can lead to mentorship opportunities, collaborations, and even job prospects.
  2. Cultivate a Growth Mindset: As highlighted in my speech, continuous learning is crucial. Technology evolves rapidly, and so must we. Stay curious, be open to new ideas, and never stop asking questions.
  3. Bridge the Gap: One of the most valuable skills in legal tech is the ability to bridge the gap between law and technology. Develop a strong understanding of both fields to position yourself as a valuable translator and innovator.
  4. Give Back: As you progress in your career, look for opportunities to mentor others and contribute to the community. This not only helps others but also reinforces your own learning and network.
  5. Be Adaptable: The legal tech landscape is constantly changing. Be prepared to pivot, learn new skills, and adapt to new technologies and methodologies throughout your career.
  6. Think Globally: Legal tech is a global field. Be aware of international trends, regulations, and innovations. A global perspective can open up new opportunities and insights.
  7. Balance Innovation with Practicality: While it’s exciting to work with cutting-edge technologies, remember that the ultimate goal is to create practical solutions that add real value to legal practice for both legal professionals and their clients. Innovation, especially with tech, arises directly from understanding a pain or a problem and then alleviating it or solving it.
  8. Understand the Business of Law: Technology doesn’t exist in a vacuum. Understanding the business aspects of law firms and legal departments will help you develop more relevant and impactful solutions.

Remember, the field of legal technology is not just about building tools or implementing systems. It’s about reimagining how legal services are delivered, improving access to justice, and shaping the future of the legal profession. Your contributions, no matter how small they may seem at first, have the potential to make a significant impact. In my case, doing a little bit at a time over a long time led to a significant body of work and network.

For me, this award is not just a recognition of past achievements but a call to action for the future. Now, more than ever in this era of AI, legaltech needs fresh voices, diverse perspectives, and innovative ideas. In a field as dynamic as legal technology, complacency is not an option. We must remain curious, adaptable, and forward-thinking.

Now is not the time to stand back and let it all be.

As we look to the future of legal technology, I’m cautiously optimistic. The challenges we face might be greater than ever. But I’ve seen firsthand the brilliance and dedication of the people in our community, and I know we’re up to the task, if we work together. The future requires our active engagement and thoughtful stewardship. Now is not the time to stand back and let it all be.

To everyone in the legal tech community, whether you’re a seasoned veteran or just starting your journey: thank you. Your ideas, your passion, and your willingness to collaborate and share knowledge are what make this field so exciting and impactful. Let’s continue to learn, innovate, and push the boundaries of what’s possible in legal technology.

By fostering a culture of continuous learning, embracing diverse perspectives, and maintaining our commitment to justice and ethical practice, we can ensure that legal technology continues to evolve in ways that benefit not just the legal profession, but society as a whole.

To everyone in legal tech: your ideas, passion, and willingness to collaborate are what make this field so exciting and impactful. Let’s continue to learn, innovate, and push the boundaries of what’s possible. May the best be yet to come.

[Originally posted on DennisKennedy.Blog (https://www.denniskennedy.com/blog/)]

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About a year-and-a-half ago, Tom Mighell and I decided to start an interview series on our podcast, The Kennedy-Mighell Report. We called it “Fresh Voices on Legal Tech” because we wanted to highlight both a new generation of legal tech and new perspectives and approaches on legal tech. We thought “fresh voices” covered what we wanted to accomplish and it also let us include some of our favorite people who fall into the “everfresh” category.

We had a good idea about what the “usual voices” were saying about legal tech and we wanted some, well, “fresh” perspectives that would challenge our assumptions and help us see legal tech from different perspectives, including from outside the US.

We could not be happier with how the series has turned out and invite you to sample some (or all) of the nineteen interviews (so far). We especially like the stories all the interviewees tell about their career paths.

Here’s a list of the interviews we did in 2024 so far (and we have more great guests on the way in the rest of the year):

Kennedy-Mighell Report podcast logo

Start with someone you know or, perhaps even better, someone you don’t know. They’re all great and will shake up your thinking about legal tech. You’ll want to listen to them all.

New episodes of the show arrive every other Friday. We encourage you to subscribe to the podcast in your favorite podcast app.

[Originally posted on DennisKennedy.Blog (https://www.denniskennedy.com/blog/)]

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Is the legal profession shifting away from litigation, perhaps dramatically? Do we need to rethink legal education in light of changing practice patterns? Are only 25% of US lawyers now litigators? Is that percentage decreasing and at what rate? How can we find out?

I heard a while back that only a relatively small percentage of US lawyers are now lawyers. Since I rarely run into anyone who is a litigator anymore, I was inclined to believe that because that is what we do these days. “I don’t know anyone who likes X, therefore no one likes X” seems to be the argument I hear most commonly lately.

It seems like a simple question: “What percentage of US lawyers are litigators?”

Three recent experiences got me thinking further about this topic. I spoke to a group of about 150 Michigan lawyers and almost everyone in the room was a litigator and, yes, someone did assert that trial lawyers are the highest form of lawyers, as always happens in such a group. The second was a statistic Bridget McCormack, CEO of the American Arbitration Association, used in her keynote at the recent SubTech conference that only 4% of cases that are filed now go to trial. The third was that I simply could not find again anything that confirmed my memory of seeing something that referred to a “relatively small percentage.”

For better or worse, that made me want to find out what the actual composition of the US legal profession might be. It seems like a simple question: “What percentage of US lawyers are litigators?”

This question, however, led me down a rabbit hole of research, highlighting both the scarcity of reliable data in our field and the potential of new technologies to fill these information gaps.

I have returned to share my findings with you.

My quest for answers began with a quick survey of various sources, including AI language models and traditional search results, all using the basic question I had. Here’s what I found at the time I tried this (your results are likely to vary, of course):

  • ChatGPT 4.0: 34%
  • Top Google result: 27%
  • Claude 3.5: 25-30% (citing “ABA stats”)
  • My own calculation from other survey results: 19%
  • Bing CoPilot: 0.52% (stated with surprising confidence)

I did a little more math. Lawyers who are afraid of math, bear with me a second. This should be painless.

Using the Olympic judging approach, I discarded the high and low numbers and averaged the remaining numbers.

I arrived at, drum roll please, an average in the 24-25% range. I’ve decided to keep it simple and round to 25%.

There you have it, the percentage of US lawyers who are litigators can be set at 25%. While I’ll admit my confidence in this figure is limited, it provides a starting point for discussion. #confirmationbias, anyone? For the curious, transactional lawyers seem to outnumber litigators significantly.

This exercise raised several important questions, chief among them: Does this percentage suggest we need to revisit our approach to legal education, bar exam priorities, and our overall understanding of law practice?

The potential implications are significant. If only a quarter of lawyers are engaged in litigation, are we adequately preparing law students for the diverse realities of modern legal practice? Are we over-emphasizing courtroom and litigation skills at the expense of other crucial areas like negotiation, contract drafting, regulatory and policy work, or alternative dispute resolution?

Do we need to reevaluate our focus in legal education, ethics training, bar exams, and our general conception of the legal system?

Yes, what about that damn bar exam?

What’s particularly striking – and somewhat ironic – is the difficulty in finding accurate, comprehensive data on the legal profession. For a field that prides itself on evidence-based decision-making, we seem to be operating with a surprising lack of solid numbers. This data scarcity extends beyond litigation percentages to various aspects of legal practice areas.

My experiment in using AI language models to gather this information was partly born out of necessity and partly out of curiosity. The hypothesis was that current LLMs might provide a useful averaging effect, potentially smoothing out definitional issues that lawyers often grapple with. That’s why I used the very simple question, “What percentage of US lawyers are litigators?” While not a replacement for rigorous statistical analysis, this approach could offer a “good enough” starting point for discussions and further research. Thinking about this experiment will also give you some great insights into both how AI and humans work these days.

As we move forward, it’s clear that we need more robust data collection and analysis within the legal profession. Even more important, despite the suggestions of some, that analysis should not be done by me.

Without accurate information, how can we make informed decisions about the future of legal education, professional development, and the allocation of resources within the justice system?
Moreover, the potential disconnect between legal education and actual practice raises ethical considerations. Are we adequately preparing new lawyers for the realities they’ll face? Are we fostering the right skills and mindsets for success in today’s legal landscape?

While my “25% litigator” rule of thumb might be far from definitive, it serves as a catalyst for important conversations. What are your thoughts? Do you have access to more accurate figures on practice areas? How do you think we can improve data collection and analysis in the legal field? Let’s continue this crucial conversation and work towards a more informed, adaptable legal profession and start to question our assumptions and consider how we might evolve legal education and professional standards to better serve both lawyers and their clients in the 21st century.

My final verdict: the rule of thumb number that you will keep hearing me use until someone makes me stop because they have something more accurate than 25%, even though I suspect that the true percentage might be lower and diminishing over time. I’ll let others track that answer down.

[Originally posted on DennisKennedy.Blog (https://www.denniskennedy.com/blog/)]

Want to schedule a Zoom call to talk with me about Legal Innovation as a Service, Speaking, or other services? Schedule a Zoom with Dennis via Calendly.

DennisKennedy.com is the home of the Kennedy Idea Propulsion Laboratory

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DennisKennedy.Blog is now part of the LexBlog network.

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How Can Law Professors Effectively Teach AI Literacy to Law Students?

Image of poster for AI Studio - green with spartan image and description of sessions and other info

Last spring at the Michigan State University College of Law and the MSU Center for Law, Technology & Innovation we introduced the “LegalRnD AI Studio,” a groundbreaking mini-course series designed to elevate law students’ AI literacy, focusing on practical skills in generative AI. I want to share how you can replicate this successful model and provide your students with the essential AI literacy they need at your school and beyond.

The LegalRnD AI Studio was born out of a simple observation: our students need practical AI skills, and they need them now. The legal industry is rapidly evolving because of technology, and generative AI is at the forefront of this change. Yet, many law schools are still grappling with how to incorporate AI training into their curricula.

The LegalRnD AI Studio is more than just a series of lectures; it’s a hands-on, practical approach to learning AI with the goal of helping law students (and others) level up their AI literacy. By focusing on effective prompting techniques and aligning with current industry expectations, this mini-course prepares law students for the future of legal practice. The course’s blend of lectures and hands-on exercises ensures that students not only understand the theoretical aspects of AI but also gain the practical skills needed to excel in their careers.

Session 1: Prompting 101 for Law Students: Start with the Basics.
The first session laid the foundation for understanding generative AI. As anyone who’s worked with AI tools knows, the quality of your output is directly related to the quality of your input. Teaching law students how to craft effective prompts is a valuable skill that will serve them well in the future. Law students were introduced to AI capabilities and tools, learning the art of crafting effective prompts. This session was all about getting the basics right, ensuring students could generate useful responses from AI applications.

Key components included:

  • Ethical and Responsible AI Use within University Policies and Guidelines: We started each session with a reminder about following university rules, policies, and guidelines, and keeping AI use ethical and responsible. We stressed the importance of data privacy and made it clear that students are responsible for what they input into third-party AI applications.
  • Introduction to Generative AI: We explained the basics, including the role of large language models (LLMs), temperatures, comparing results from the same prompts, and the significance of tokens versus words.
  • Crafting Effective Prompts: Students learned to create clear, specific prompts to guide AI outputs.

Session 2: Advanced Prompting for Law Students: Build on Foundation Skills.
Building on the basics, the second session took students deeper into the realm of AI prompting. Advanced techniques like iterative refinement, chain of thought, RAG, personas, and prompt chaining were explored. This session aimed to equip students with the ability to handle more complex tasks using generative AI. The hands-on practice component was particularly valuable, allowing students to apply sophisticated structured prompting strategies and receive constructive feedback.

Highlights included:

  • Advanced Prompt Examples: We provided students with structured prompts and hands-on practice to enhance their AI interaction skills and to achieve desired outputs.
  • Enhancing Conversational AI Interactions: We demonstrated techniques for refining AI responses through iteration, personas, memory refreshing, and conversational styles.
  • PCRO Approach: We used my PCRO model (Persona, Context, Request, Outcome) for crafting detailed and structured AI prompts and getting desired output.

Session 3: What Legal Employers Expect and Want from Law Students and Graduates in 2024: Make it Relevant.
The final session bridged the gap between academic learning and professional expectations. Students gained insights into what legal employers are looking for in new hires, with a special emphasis on AI literacy. Practical exercises based on real-world scenarios ensured that students could align their learning path with industry needs. This session was a critical component, preparing students to meet employer expectations and stay competitive in the job market.

  • Industry Insights: We discussed research findings on employer expectations regarding AI proficiency.
  • Practical Exercises: We experimented with scenario-based activities that simulated real-world legal tasks.
  • Future Steps: We shared strategies for continuing AI learning and staying competitive.

Comprehensive Handout:.
We provided a detailed handout that served as both a course guide and a future reference. This included everything from basic concepts to advanced prompting techniques and useful resources. You can download a free PDF of the handout here. Consider creating something similar for your students. I’m happy with you adapting a version of my handout so long as you include attribution to the Center and me.

Key Takeaways for Law Professors

  1. Ethical Considerations: Emphasize the importance of ethical and responsible AI use, data privacy, and compliance with university policies.
  2. Start Small: A mini-course or workshop series can be a great way to test the waters without overhauling your entire curriculum.
  3. Interactive Learning: A blend of lectures and hands-on practice is essential. Students must see the practical application of theoretical concepts. This approach helps students understand theoretical concepts and see their practical applications.
  4. Progressive Skill Building: We started with basic prompting techniques and gradually introduced more advanced concepts. This allowed students of all skill levels to engage and improve.
  5. Focus on Prompting: Effective prompting is the cornerstone of generative AI success. Help students master basic and advanced prompting techniques.
  6. Real-World Relevance: Align your course content with industry expectations and employer expectations. This prepares students for the demands of the job market and makes the learning experience more relevant. Engage students in practical exercises simulating legal tasks they might encounter in their careers.
  7. Stay Flexible: Be prepared to adapt your course as AI technology and industry needs evolve and you learn your students’ interests and needs. I started all the sessions with a short segment I called “What did I try in AI” so students could share what they had experimented with and what they had found.
  8. Continued Learning: Offer strategies for ongoing AI education and staying competitive in the job market.
  9. Feedback and Practice: Regular feedback is vital. It helps students refine their skills and understand the nuances of effective AI use. Short “homework” assignments are also useful.
  10. Collaborate: Reach out to legal tech companies, law firms, and other schools. Their insights can be invaluable in shaping your course.

Challenges to Consider

  • Ethical Considerations: We had to carefully navigate the ethical implications of AI in legal practice, which added another layer of complexity to the course, especially for students who have not already had a professional responsibility class.
  • Balancing Depth and Breadth: While it’s tempting to try to cover everything, we found it more effective to focus on core skills that students can build upon. We wanted to provide valuable skills without overwhelming students who might be new to AI. Our solution was to start with the basics and progressively introduce more complex concepts, always tying them back to legal practice.
  • Time Constraint: Covering such a broad topic in just three sessions was challenging. We had to be very selective about what to include.
  • Keeping up with Rapid AI Advancements: What’s cutting-edge today might be obsolete tomorrow. We needed to be prepared to continually update our course materials.

Why This Course Matters
By following this “AI Studio” approach, you can create a successful AI literacy course that equips your students with the skills they need to thrive in the modern legal landscape. I intentionally chose the word “studio” to reflect that using generative AI is both an art and a science and is learned best by working hands-on. Consider implementing a similar course at your institution to help your students stay ahead in a rapidly evolving field.

Of course, a three-session mini-course isn’t a complete solution to the tech skills gap in legal education and it won’t turn anyone into an AI expert overnight. But it’s an important step in the right direction. What it can do is provide a solid starting point and, perhaps more importantly, spark an interest in further learning. My hope is that more law schools will follow MSU’s lead and start integrating practical AI training into their curricula.

The response from students has been overwhelmingly positive. They appreciate the practical skills they’re gaining and feel more confident in navigating the world of AI. I also created a certificate of completion graphic for them to put on their LinkedIn profiles.

I can’t wait to teach more offerings of the LegalRnD AI Studio this academic year. I’ve also done versions for our law librarians and as a CLE for Michigan lawyers. I’m also considering training my research assistants to teach it.

For law students reading this: if you have the opportunity to take a course like this, jump on it. If your law school does not offer something like it, advocate for your law school to create something similar.

For law schools, it’s a model worth considering. Short, focused courses like this can be an effective and helpful way to introduce generative AI right now without overhauling the entire curriculum.

Download a free PDF of the handout here.

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[Originally posted on DennisKennedy.Blog (https://www.denniskennedy.com/blog/)]

Want to schedule a Zoom call to talk with me about Legal Innovation as a Service, Speaking, or other services? Schedule a Zoom with Dennis via Calendly.

DennisKennedy.com is the home of the Kennedy Idea Propulsion Laboratory

Like this post? Buy me a coffee

DennisKennedy.Blog is now part of the LexBlog network.

Need a little help with your legal innovation efforts? Check out my Legal Innovation as a Service offerings.

As an Amazon Associate I earn from qualifying purchases.

Kennedy-Mighell Report Podcast
Noted legal technologists Dennis Kennedy and Tom Mighell bring listeners an in-depth analysis of the latest advancements in legal technology, in addition to best practices for utilizing existing tools.