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Live from ILTACON | Sponsored by Steno
What can lawyers learn from Broadway?
More than you might think.
Live from Nashville, David Cowen sits down with Laura Bell Bundy, the actress, singer, songwriter, and producer who originated Elle Woods in Legally Blonde on Broadway, for a conversation about curiosity, grit, reinvention, self-advocacy, and the relationships that shape a career.
Laura shares the unlikely path that took her from Kentucky to Broadway, how she learned to turn imitation into originality, why perceived failures can open unexpected doors, and the lesson from her father that has stayed with her throughout her career:
Ask.
Because if you don't ask, you'll never know what might have been.
In this episode:00:10 | Back in Nashville 01:06 | A World Changing Fast 02:02 | Growing Up Around Music 04:20 | From Imitation to Originality 06:31 | Making Elle Woods Her Own 08:12 | Finding the Grit 09:28 | What Elle Woods' Transformation Really Means 09:59 | The Broadway Experience That Changed Everything 13:48 | Laura's First Big Break 14:20 | Why Everyone Needs a Sponsor 15:29 | Holding a Vision for Someone Else 17:09 | Redefining Success Through Goals 18:36 | Curiosity + Grit = From Now to Next 19:30 | Breaking Her Arm During Legally Blonde 20:52 | The Show Must Go On 22:36 | Following Another Dream 25:23 | Giving Yourself Permission to Try 26:13 | What Perceived Failure Can Teach You 26:58 | Careers Are Really About Relationships 28:10 | When the Vision Became Reality 32:21 | Know Your Value 33:24 | The Most Powerful Three-Letter Word: Ask 42:07 | Why Community Keeps Us Standing 43:27 | From Now to Next
The Big IdeaAsk.
Ask for the opportunity.
Ask for the promotion.
Ask the question you're afraid might get a no.
Laura's career is filled with moments where curiosity opened one door, grit carried her through another, and someone was willing to see potential before the outcome was obvious.
But there's another lesson underneath all of it.
You have to advocate for yourself.
Knowing your value matters. Having people who believe in you matters. Being willing to fail matters.
And so does having the courage to ask.
Because a career isn't simply a collection of jobs.
It's a collection of relationships, lessons, risks, failures, reinventions and people who catch you when you fall.
Follow SOLID for more conversations with the leaders shaping what comes next in legal: https://solid.legal/ π§ Subscribe on Apple Podcasts, Spotify, or wherever you listen. Share this episode and take your career from now to next! Never eat alone!
Live from ILTACON | Sponsored by Steno
Legal organizations are investing heavily in AI. But buying the technology is the easy part.
Getting people to actually change how they work is harder.
Live from ILTACON, David Cowen sits down with Jeffrey Roach, Managing Director at Harbor, to explore why the next phase of Legal AI isn't simply about technology. It's about behavior, talent, champions and organizational change.
Jeffrey argues that resistance isn't necessarily the problem. It's a signal. And instead of spending disproportionate energy trying to move the most resistant people, leaders may create more momentum by investing in the achievers, strivers and seekers already leaning into change.
In this episode:00:10 | Why Enablement Matters More Than Ever 00:43 | Adoption Is a Behavioral Problem 01:05 | Welcome to Perpetual Change 01:35 | Everything, Everywhere, All at Once 01:46 | Why Lawyers Resist Change 02:19 | Stop Treating Resistance as the Problem 02:41 | Achievers, Strivers, Seekers and Laggards 03:09 | How Do You Keep Your Top 20%? 03:22 | Making Your Best People Feel Seen 05:05 | Stop Lifting the Bottom. Raise the Top. 05:29 | Why Champions Drive Adoption 06:28 | Creating Agency Inside Legal Organizations 06:48 | How Gatekeeping Holds Talent Back 07:40 | Set Talented People Free 08:41 | Why Progress Requires Bravery 09:18 | New Talent Is Entering the Business of Law 09:32 | Forward Deployed Engineers and Legal AI Architects 10:31 | Curiosity, Adaptability, Resourcefulness and Grit 12:45 | From Individual to Organizational Enablement 13:50 | Why You Can't Save Everybody 14:12 | Double Down on Your Winners
The Big Idea"Double down on your winners."
The AI adoption challenge may not be about getting every person in an organization to move at the same speed.
Some people are already curious. They're experimenting. They're resourceful. They're asking questions and pushing beyond their comfort zones.
Those people can become your champions.
Invest in them. Give them visibility. Give them authority. Give them room to make mistakes and learn.
Because trying to pull the bottom 20% forward can consume enormous energy, while the people most capable of creating momentum may leave if they don't feel seen, challenged and supported.
AI transformation isn't only about deploying better technology.
It's about identifying the people ready to lead the change and helping them soar.
Follow SOLID for more conversations with the leaders shaping what comes next in legal: https://solid.legal/ π§ Subscribe on Apple Podcasts, Spotify, or wherever you listen. Share this episode and take your career from now to next! Never eat alone!
Live from ILTACON | Sponsored by Steno
What if the real value of AI isn't how much more work you can do, but what you can do with the time it gives back?
Live from ILTACON, David Cowen sits down with Rachel Shields-Williams, Director of AI and Knowledge Management at Bass, Berry & Sims, to explore how AI is changing not only the work of lawyers, but the way they learn, lead and develop.
For Rachel, AI should help people show up at the highest and best use of themselves. That means more capacity for judgment, creativity, curiosity and the human moments that matter.
But as AI takes on more of the work, the skills lawyers need are changing too.
In this episode:00:10 | Using AI Without Letting AI Use You 01:03 | AI Should Help Us Live Better, Not Just Work More 01:46 | The Humanity Behind the Technology 02:03 | Why Curiosity Matters More Than Ever 02:35 | How AI Can Give You Time and Reduce Anxiety 04:45 | Stepping Into a New AI and Knowledge Leadership Role 05:06 | Putting the Client at the Center of Innovation 05:49 | Inside the Nine-Week Summer AI Lab 06:57 | Reverse Mentorship With AI in the Middle 07:25 | Teaching Workflow, Not Just How to Use the Tool 08:14 | How Future Lawyers Are Already Thinking in Agents 08:41 | Keeping the Human in the Loop 09:39 | The New Roles Emerging Around Legal AI 10:07 | Why the Lawyer Training Model Needs to Change 11:14 | From Managing Junior Lawyers to Coaching AI-Enabled Teams 12:35 | How to Prepare for Difficult Conversations 13:54 | Build Your Own Panel of Trusted Advisors 14:48 | Leading Change Through Relationships and Culture 16:28 | What the ILTACON Floor Says About What's Coming Next 17:04 | Why Legal AI Investment Means Demand for New Talent
The Big IdeaAI isn't just giving lawyers more capacity to work. It can give them more capacity to be human.
As technology takes on more tasks, the differentiators shift toward curiosity, judgment, creativity, communication and leadership.
That changes how the next generation of lawyers needs to be trained.
Junior lawyers will increasingly learn the law while working with AI. More experienced lawyers will need to become better coaches, giving feedback, guiding judgment and helping people understand when human intervention matters.
The technology may be accelerating.
But the skills required to lead through that acceleration are deeply human.
Follow SOLID for more conversations with the leaders shaping what comes next in legal: https://solid.legal/ π§ Subscribe on Apple Podcasts, Spotify, or wherever you listen. Share this episode and take your career from now to next! Never eat alone!
Live from ILTACON | Sponsored by Steno
Legal is changing fast, and everyone wants answers.
But what if the real advantage isn't having the answer? What if it's knowing how to ask the next question?
Live from ILTACON, David Cowen sits down with Priti Saraswat, Director of Knowledge and Innovation at Levenfeld Pearlstein, whose career has taken her across the legal technology ecosystem, from technology provider and solutions engineering to consulting, legal process engineering and law firm innovation.
That 360-degree perspective has given her a different view of the AI transformation. Instead of trying to solve everything at once, Priti argues for agility, small adjustments and learning from industries that have already navigated their own disruption.
In this episode:00:10 | A 360-Degree Career Across the LegalTech Ecosystem 01:00 | Seeing the Compounding Effect of AI 01:49 | Why AI Value Depends on Where You Sit 02:20 | We Don't Know What We Don't Know Yet 02:49 | Stop Waiting for All the Answers 03:43 | What Previous Legal Transformations Can Teach Us 04:19 | Small Adjustments Beat Trying to Change Everything 04:55 | Why Agility Is Becoming a Career Essential 05:57 | Why Legal Needs More Outside Perspectives 06:32 | What Legal Can Learn From Other Industries 07:38 | What Agriculture Can Teach Us About AI 09:11 | Visioning What Comes Next 11:44 | Start With the Problem You Actually Want to Solve 12:28 | Turning a Vision Board Into Action 13:52 | Why You Need Professional and Personal Visions 14:44 | What Do You Want to Accomplish Next?
The Big Idea"All we've figured out is to ask the next question."
We are still early.
The roles are changing. The technology is changing. The way lawyers practice is changing. And the answers we have today may not be the answers we need tomorrow.
Priti's approach is simpler: stay agile, look beyond the boundaries of legal, make small adjustments and keep moving.
Because when there is no established map, progress doesn't require knowing the entire route.
It requires knowing your next question and taking action on what you learn.
Follow SOLID for more conversations with the leaders shaping what comes next in legal: https://solid.legal/ π§ Subscribe on Apple Podcasts, Spotify, or wherever you listen. Share this episode and take your career from now to next! Never eat alone!
Live from ILTACON | Sponsored by Steno
What if the next path for a lawyer isn't the traditional path to partnership?
Live from ILTACON, David Cowen sits down with Megan McMillin, Legal Innovation Partner at Harvey, to explore one of the most important shifts happening in legal: the emergence of an entirely new career ladder around Legal AI.
From Forward Deployed Legal Engineers to Legal Innovation Partners, firms and technology companies are building roles that combine legal expertise, workflow knowledge, technology and client value.
The challenge? There is no established playbook yet.
In this episode:00:10 | From Cleary to Legal Innovation Partner at Harvey 01:23 | The Rise of the Forward Deployed Legal Engineer 02:10 | Why Firms Need Their Own Embedded AI Expertise 03:18 | Pairing Vendor Engineers With Firm Experts 03:46 | Understanding the Tool, the Workflow and the Why 04:17 | Moving From AI Use Cases to Client Value 05:15 | Why Legal AI Isn't "Choose Your Own Journey" 06:04 | What Embedded AI Talent Really Means 07:09 | Building With the Customer, Not Just for Them 08:21 | The Five-Year Career Path for Forward Deployed Engineers 09:20 | Could Legal AI Become a Second Path to Partnership? 10:16 | Why New Legal AI Roles Command New Compensation 10:46 | There Is No Clear Career Path Yet 11:51 | Stop Trying to Fit New Roles Into Old Structures 12:37 | What Law Schools Need to Rethink 13:41 | The Lawyer's Superpower in the AI Era 14:36 | Why Intellectual Curiosity Matters More Than Ever
The Career SignalThere is no clear path. It's white space. It's a green field.
That's exactly what makes this moment so important.
The Legal AI career ladder is being built in real time.
You can enter as a builder. Then manage. Then lead. Then set strategy and vision.
For lawyers who don't see themselves following the traditional route to partnership, these roles may represent something much bigger than an alternative career.
They may be the beginning of an entirely new path.
And as Megan puts it, when lawyers and engineers bring their respective expertise together:
"The best is yet to come. And we're building it together."
Follow SOLID for more conversations with the leaders shaping what comes next in legal: https://solid.legal/ π§ Subscribe on Apple Podcasts, Spotify, or wherever you listen. Share this episode and take your career from now to next! Never eat alone!
Live from ILTACON | Sponsored by Steno
AI promises to make lawyers faster and more productive. But what happens when we use every hour it saves to simply do more?
Live from ILTACON, David Cowen sits down with Sarah Hirebet, Director of Knowledge and Innovation at Stradley Ronon, for a conversation about the human side of AI adoption.
Sarah explores why this technology shift is different from the ones legal has navigated before. AI can sound like us, write like us and engage with the same language lawyers use every day. But it does not bring lived experience or human judgment to the conversation.
That creates a bigger challenge for legal leaders: how do we embrace the productivity AI creates without losing judgment, creativity, voice and the space to actually think?
In this episode:00:10 | Meeting the Moment of Change in Legal 01:42 | Why This Technology Shift Is Different 03:07 | AI Sounds Like Us, But It Doesn't Have Judgment 03:43 | When AI Superpowers Become Exhausting 05:12 | What AI Means for Talent, Culture and Work 05:44 | The AI Dividend: What Do You Do With the Time? 06:06 | From Doing the Work to Redesigning the System 06:48 | Humanity in the Loop 07:18 | How Lawyers Preserve Their Voice in an AI World 08:24 | Rest, Sabbaticals and Making Space for Creativity 10:29 | Why Knowledge Workers Need to Build Tangible Things 11:00 | Inside the Stradley Labs AI Training Program 12:25 | The New Titles Emerging Around AI 13:26 | Should AI Actually Be in Your Job Title? 14:51 | When Communication Should Stay Human 15:56 | What AI Still Can't Replicate
The Big IdeaThe AI dividend isn't automatically more work.
If AI gives us time back, leaders have a choice about where that time goes.
It can become more output, more emails and more tasks.
Or it can create space to redesign systems, develop new ideas, learn, reflect, build relationships and preserve the distinctly human capabilities that technology cannot replicate.
Sarah calls this "humanity in the loop."
The more fluent AI becomes, the more important it may be for lawyers to protect their own voice, judgment and lived experience.
Follow SOLID for more conversations with the leaders shaping what comes next in legal: https://solid.legal/ π§ Subscribe on Apple Podcasts, Spotify, or wherever you listen. Share this episode and take your career from now to next! Never eat alone!
Live from ILTACON | Sponsored by Steno
Legal technology used to move on annual planning cycles. Now, even 90 days can feel too slow.
Live from ILTACON, David Cowen sits down with Damien Riehl, Solutions Champion at Clio, to unpack what happens when the pace of AI development becomes exponential and the traditional boundaries between law, LegalTech and frontier AI begin to disappear.
Their conversation moves from the influx of capital and outside talent into legal to the arrival of foundation model companies as new competitors. But the bigger question is what all of this means for lawyers.
Could AI reduce the cost of legal work so dramatically that instead of shrinking the market, it unlocks entirely new demand?
In this episode:00:10 | Why LegalTech Is on an Exponential Curve 01:18 | From 12-Month Planning to 90-Day Change Cycles 01:42 | Where to Look to Understand What AI Will Do Next 02:39 | The New Talent Entering the Legal Industry 03:21 | Why Capital Is Flooding Into LegalTech 04:27 | When Frontier AI Companies Enter Legal 05:46 | Disruption Disrupting Disruption 06:28 | What Blockbuster, Nokia and Kodak Can Teach Legal 07:16 | The New Build vs. Buy Question 08:10 | You Don't Have to Keep Up With Everything 09:07 | Curiosity, Adaptability, Resourcefulness and Grit 10:19 | What Was Impossible Three Months Ago Is Possible Today 10:35 | The Shift From AI Answers to AI Agents 11:50 | What Happens to Human Capital in an AI Economy? 12:59 | Could AI Actually Increase Demand for Lawyers? 13:38 | The Opportunity to Serve Unmet Legal Needs
The Big IdeaWhat if AI doesn't make the legal market smaller? What if it makes the pie dramatically bigger?
If AI lowers the cost of legal services, work that was previously too expensive to justify may suddenly become accessible.
That creates a very different future for the profession.
Instead of lawyers becoming less necessary because of AI, Damien sees the possibility that lawyers become busier than ever because of AI, while serving legal needs that historically went unmet.
The challenge isn't knowing everything that's changing.
It's staying curious enough to see what just became possible.
Follow SOLID for more conversations with the leaders shaping what comes next in legal: https://solid.legal/ π§ Subscribe on Apple Podcasts, Spotify, or wherever you listen. Share this episode and take your career from now to next! Never eat alone!
Live from ILTACON | Sponsored by Steno
Legal AI isn't just creating new technology. It's creating new roles, new responsibilities and entirely new career paths.
Live from ILTACON, David Cowen sits down with Leigh Zeiser, Director of AI and Automation at Troutman, to trace her journey from becoming one of the first Legal Process Engineers in the U.S. in 2018 to leading AI and automation today.
Their conversation goes beyond titles. What happens when responsibility grows faster than authority and resources? How do you earn the trust to lead? And what separates the people waiting for the next opportunity from those creating it?
Lee also shares what Troutman is learning as Generative AI adoption grows, why deterministic layers matter in legal, and how the firm's agentic AI platform, Athena, is evolving.
In this episode:00:10 | From Legal Process Engineer to Director of AI and Automation 01:33 | Eight Years of Emerging Legal AI Roles 02:20 | The Arrival of the Applied AI Manager 03:09 | Role, Responsibility, Authority and Resources 03:28 | Why AI Adoption Is Actually Increasing Demand 04:35 | How to Advocate for Authority and Resources 05:15 | Lead From Any Role 07:00 | Why Speaking Up Creates Career Opportunity 08:12 | Resourcefulness and Learning to Trust Your Talent 09:10 | Everything Is White Space: Don't Wait for the Assignment 10:29 | Why Everybody Owns AI 10:38 | Why Legal AI Needs Deterministic Layers 11:43 | What's Next for Legal AI in 2027? 12:08 | How Troutman's Athena Became Agentic 13:00 | AI Economics, Token Costs and Responsible Adoption 14:24 | Looking Ahead to SOLID Atlanta
The Career Signal"You can't wait for anybody to assign it to you."
Legal AI is creating white space across the industry. The roles, responsibilities and career paths are still being defined.
The people who see an opportunity, step into it, earn trust and advocate for the authority and resources to execute may be the ones who define what these roles become.
Follow SOLID for more conversations with the leaders shaping what comes next in legal: https://solid.legal/ π§ Subscribe on Apple Podcasts, Spotify, or wherever you listen. Share this episode and take your career from now to next! Never eat alone!
Live from ILTACON | Sponsored by Steno
AI is everywhere in legal. But the biggest change over the last year isn't simply better answers from AI. It's the ability to begin automating the work itself.
Live from ILTACON, David Cowen sits down with Chris Emerson, Chief Legal Operations & Innovation Officer, to explore what AI is actually changing inside legal teams, what still hasn't changed, and where the biggest opportunities are emerging.
From the growing war for Legal AI talent to turning knowledge trapped inside lawyers' heads into AI-ready workflows, Chris offers a practical look at where legal is heading next, including how his team built an AI-assisted pre-bill review capability in just 33 days.
In this episode:00:10 | AI Everywhere: What Changed in the Last 12 Months? 01:40 | Why Legal's Adoption Problem Hasn't Changed 02:59 | What Leaders Should Look for in Legal AI Talent 04:05 | Curiosity, Resourcefulness, Adaptability & Grit 05:28 | Why Leaders Need to Invest in Their Top 20% 08:30 | Grit, Failure & Why Lawyers Need Rapid Prototypes 10:36 | What Legal AI Still Needs in 2027 12:07 | Where AI Will Create the Next Career Opportunities 13:13 | Turning Legal Knowledge Into AI Playbooks 14:00 | Building AI-Assisted Pre-Bill Review in 33 Days 14:56 | Building an Internal AI Platform Around Firm Data 15:37 | What Should Humans Keep as AI Automates the Work?
The Closing Thought"AI is not aware of where we are culturally on the journey."
As AI gets better at doing the work, the responsibility for strategy, direction, guardrails and judgment remains human.
Follow SOLID for more conversations with the leaders shaping what comes next in legal. https://solid.legal/
π§ Subscribe on Apple Podcasts, Spotify, or wherever you listen. Share this episode and take your career from now to next! Never eat alone!
The legal industry has moved beyond asking which AI tool to buy. The real competitive edge now comes from building AI infrastructure that keeps firm knowledge private, connected, and ready for innovation. David Cowen sits down with Maged Helmy, Founder & CEO of Newcode AI, to explore why the future belongs to firms that own their AI architecture, not just their software, and how legal leaders can move from AI users to AI innovators.
Key Topics Covered:
π§ Subscribe on Apple Podcasts, Spotify, or wherever you listen. Share this episode and take your career from now to next!
π‘To learn more about the future of legal innovation, visit https://solid.legal/podcasts/ Never eat alone!
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