Ted sits down with Professor Heidi K. Brown, Associate Dean for Upper Level Writing at New York Law School, to discuss the evolving role of AI in legal writing and education. From understanding AI hallucinations to mastering effective prompt engineering, Heidi shares her expertise in helping law students and lawyers navigate the ethical and practical challenges of integrating AI into their research and writing workflows. With AI reshaping the legal landscape, this conversation highlights the importance of critical thinking, maintaining a strong writer identity, and balancing AI assistance with traditional legal methodologies.

Ted sits down with Peter Duffy, founder and CEO of Titans, to discuss the current state of AI adoption in the legal industry. From the challenges of measuring ROI and navigating AI hype to practical strategies for implementation, Peter shares his expertise in legal technology and innovation. Highlighting the importance of starting small with AI use cases and fostering trust in emerging tools, this conversation provides valuable insights for law professionals navigating the rapidly changing landscape of legal tech.

Ted sits down with Julien Steel, Director of Product Management at LexisNexis, to discuss the future of AI in legal workflows. From optimizing contract drafting to enhancing search relevancy, Julien shares his expertise in developing AI-powered solutions that drive efficiency for legal professionals. With AI transforming knowledge management and streamlining document review, this conversation highlights how law firms can leverage technology to stay ahead.

Ted sits down with Richard Tromans, Founder of Artificial Lawyer, to discuss the transformative power of AI and technology in the legal industry. From the challenges of adopting innovative tools to the cultural shifts needed for progress, Richard shares his expertise in legal tech, process improvement, and business innovation. Highlighting the impact of generative AI and the need to rethink traditional models like the billable hour, this conversation offers valuable insights for law professionals navigating the future of legal services.

Ted sits down with Avaneesh Marwaha, CEO at Litera, to discuss the evolving role of AI and remote work in the legal industry. From navigating the challenges of hybrid work environments to integrating cutting-edge AI solutions, Avaneesh shares his expertise in driving innovation and growth within legal technology. Highlighting how AI can enhance workflows, improve job satisfaction, and expand access to justice, this conversation offers actionable insights for law professionals looking to stay competitive and future-proof their practices.

In this episode, Ted sits down with Jack Shepherd to dissect the practical realities of implementing AI and knowledge management tools in the legal industry. Together, they challenge conventional assumptions, explore the pitfalls of over-hyped technologies, and highlight the understated value of focusing on basic, everyday challenges. With candid insights into AI adoption, enterprise search challenges, and the importance of clean data, this conversation is a must-listen for anyone seeking actionable strategies to tackle inefficiencies in legal workflows and knowledge management.

In this episode, Jack shares insights on how to:

• Evaluate AI tools effectively in the legal industry
• Address data hygiene challenges in law firm document management systems
• Integrate generative AI into law firm workflows without over-promising results
• Balance risk and reward when adopting enterprise search solutions in legal contexts
• Encourage lawyer engagement with knowledge-sharing initiatives

Key takeaways: 

• Generative AI tools like LLMs are limited by hallucinations and a lack of comprehension, often failing in critical legal tasks like accurate citations or respecting legal hierarchies, underscoring the need for cautious adoption in high-risk contexts.
• Many law firms invest heavily in enterprise search projects only to see them fail due to unclear ROI and poor integration, highlighting the importance of focusing on smaller, targeted use cases with tangible benefits like better document organization or locating key client information.
• Effective use of AI in law requires clean, structured data, as experiments show poor data hygiene leads to irrelevant or misleading outputs, undermining both efficiency and trust.
• The legal industry's focus on flashy, complex AI use cases often overlooks basic workflow inefficiencies—like time tracking, document versioning, or knowledge-sharing—which would yield quicker, more impactful results for lawyers.

About the guest, Jack Shepherd:

Jack Shepherd is a former lawyer and legal technology expert, with a particular interest in cutting through hype and confusion in technology to deliver value to practising lawyers and clients. He works at iManage, where he leads consulting initiatives on knowledge management projects.

“[The] accuracy thing is such a big deal around LLMs because the lawyer using a tool—they'll ask it a question, and I can guarantee you the first question they'll ask will be to test it. Then, if it gets even slightly wrong: 'No, I don't trust this. Never using it again.' You've got to be really careful about that.” – Jack Shepherd

Connect with Jack Shepherd:

Website: https://imanage.com/

LinkedIn: https://www.linkedin.com/in/jackwshepherd/

Connect with Ted Theodoropoulos:

Website: https://getinfodash.com/

LinkedIn: https://www.linkedin.com/in/tedtheo

YouTube: https://www.youtube.com/@getinfodash/podcasts

In this episode, Ted sits down with Neill Pemberton, Associate Partner at IBM Consulting, for a thought-provoking exploration of how AI is reshaping the legal industry. From leveraging smaller, greener models to overcoming cultural resistance within law firms, Neill shares his expertise in navigating the dynamic landscape of legal technology. Whether you're curious about the shift from traditional AI to generative AI or looking for strategies to maximize ROI on AI adoption, this conversation offers valuable insights for law professionals at every level.

In this episode, Neill shares insights on how to:

• Integrate AI into legal workflows effectively
• Balance innovation with cost efficiency in law firms
• Navigate the shift from traditional AI to generative AI in legal practice
• Use small AI models to address privacy and energy concerns
• Overcome resistance to change within law firms

Key takeaways: 

• IBM’s Granite AI models use only 8 billion parameters, proving that smaller, efficiently trained models can achieve high performance while reducing costs and energy consumption, making them ideal for enterprise applications.
• Law firms can maximize the value of generative AI by integrating it with their existing labeled data, enabling more accurate and cost-effective workflows for tasks like clause identification and document review.
• Incrementally introducing AI through low-risk, back-office functions like internal policy management or HR tasks allows firms to build confidence in the technology while avoiding the risks associated with client-facing errors.
• Overcoming lawyers’ deeply ingrained "lone wolf" mindset requires strategic leadership and innovation teams to create a culture that prioritizes collaboration and long-term investment in transformative technology.

About the guest, Neill Pemberton:

Neill Pemberton is a former solicitor in England and an expert in the use of Generative AI in professional services. After 10 years at the global law firm Dentons, Neill joined Orbital Witness, where he became Head of Legal Innovation and grew the Legal Engineering team from one qualified lawyer to seven in just two years. Neill is now an Associate Partner with IBM Consulting.

“We use our own models, but we use others too. We use Llama and all sorts in our day-to-day work, and we find we can get good results using small models. So I think it's about how you use it, rather than what it is that you use.” – Neill Pemberton

Connect with Neill Pemberton:

Website: https://www.ibm.com/us-en

YouTube: https://www.youtube.com/ibm

LinkedIn: https://www.linkedin.com/in/neillpemberton/

Connect with Ted Theodoropoulos:

Website: https://getinfodash.com/

LinkedIn: https://www.linkedin.com/in/tedtheo

YouTube: https://www.youtube.com/@getinfodash/podcasts

In this episode, Eric DeChant joins Ted to explore the transformative potential of AI in the legal industry. From the rise of AI-driven C-suite roles to the nuanced challenges of trust in value-based billing, this conversation delves into the critical dynamics shaping legal tech today. Eric offers practical insights on leveraging purpose-built AI tools, tackling innovation theater, and aligning AI strategies with organizational realities.

In this episode, Eric shares insights on how to:

• Navigate the emergence of AI-focused C-suite roles in organizations
• Identify and implement impactful generative AI use cases in law firms
• Evaluate the readiness of AI tools for operational use in the legal industry
• Balance innovation aspirations with practical constraints in legal tech
• Use small language models locally to ensure privacy and efficiency

Key takeaways: 

• The legal industry's adoption of AI often prioritizes appearance over substance, with many roles and tools being created as part of "innovation theater" rather than to address real needs.
• Effective AI implementation in legal contexts requires deep collaboration with existing vendors and a strategic focus on low-risk, high-reward business use cases like HR and marketing.
• Trust remains a significant barrier to value-based billing in law; even advanced analytics often fail to persuade clients to move away from billable hours.
• Small, purpose-built AI solutions, such as tools for patent drafting or local language models, demonstrate significant efficiency gains without compromising privacy.

About the guest, Eric DeChant:

Eric DeChant is the founder of Gammawave AI, a consultancy offering AI and innovation advisory services to law firms, corporations, governments, and nonprofits, with a focus on building intelligent systems, addressing technology threats, and protecting intellectual property. Formerly the Product Director at xMentium, an AI-driven SaaS platform for Fortune 500 legal departments, Eric combines practical expertise with technical knowledge. He holds an M.S. in Law from Northwestern University and a B.A. in Business & Project Management from DePaul University. Eric also founded The American Society of Legal Engineers (ASLE) and publishes on legal tech innovation. A registered patent agent, PMP, and AIGP, he enjoys captaining charter yachts on Lake Michigan.

“One of the worst tricks ChatGPT pulled on the world was convincing everyone AI was good at everything.” – Eric DeChant

Connect with Eric DeChant:

Website: https://www.gammawave.ai/

LinkedIn: https://www.linkedin.com/in/ericdechant/

Connect with Ted Theodoropoulos:

Website: https://getinfodash.com/

LinkedIn: https://www.linkedin.com/in/tedtheo

YouTube: https://www.youtube.com/@getinfodash/podcasts

Join Ted as he sits down with Alex Su to explore the evolving role of AI and technology in transforming law firm operations and client service delivery. Together, they discuss the challenges law firms face in adopting new technology, balancing tradition with innovation, and driving efficiency without compromising trust or quality. Discover actionable strategies to navigate AI adoption, enhance client value, and stay competitive in the evolving legal landscape—tune in now!

In this episode, Alex shares insights on how to:

• Navigate AI adoption challenges in traditional law firm models
• Leverage technology for more efficient legal service delivery
• Address client expectations with innovative legal tech solutions
• Build and use proprietary AI systems within law firms
• Balance reputation management with technological disruption in the legal industry

Key takeaways: 

• High hourly rates in law firms are justified by the trust, reputation, and additional value clients perceive, rather than the hourly service itself.
• Legal tech adoption is hindered by firms' reliance on trusted, longstanding reputations and a focus on reliable over experimental solutions.
• Firms integrating innovation with AI and automation can lower operational costs and increase profitability without sacrificing service quality.
• Outsourcing high-caliber contract attorneys for specialized projects, such as AI training, helps firms overcome staffing challenges and opportunity costs.

About the guest, Alex Su:

Alex Su is the Chief Revenue Officer at Latitude Legal, where he leads the company’s sales and marketing initiatives. With a career spanning nearly 14 years at the intersection of law and innovation, Alex has held key roles in legal tech startups, including as Head of Community Development at Ironclad. A Northwestern Law graduate and former attorney at Sullivan & Cromwell, Alex clerked for Hon. Edmond E. Chang in the Northern District of Illinois. Beyond his professional achievements, Alex engages over 250,000 followers across social media platforms and writes Off The Record, a newsletter exploring alternative legal careers and business development. 

“Legal is not in the business of something like sales or marketing, where if you roughly get it right, it's okay. If you get it wrong just a little bit in legal, it has huge consequences.” – Alex Su

Connect with Alex Su:

Website: https://latitudelegal.com/

Newsletter: https://www.alexofftherecord.com/

LinkedIn: https://www.linkedin.com/in/alexander-su/

Twitter: https://x.com/heyitsalexsu

TikTok: https://www.tiktok.com/@legaltechbro

Instagram: https://www.instagram.com/heyitsalexsu/

Connect with Ted Theodoropoulos:

Website: https://getinfodash.com/

LinkedIn: https://www.linkedin.com/in/tedtheo

YouTube: https://www.youtube.com/@getinfodash/podcasts

Join Ted as he engages with Damien Riehl to explore the transformative intersection of AI and the legal profession. This conversation unpacks the evolving role of large language models in legal reasoning, how they reshape traditional tasks, and the philosophical implications of trusting AI outputs. Whether you're curious about the limits of AI's "reasoning" or its practical benefits for attorneys, this episode offers fresh perspectives and insights you won't want to miss.

In this episode, Damien shares insights on how to:

• Assess the reasoning capabilities of large language models in legal contexts
• Leverage generative AI to enhance legal document drafting and research
• Interpret the limitations of AI outputs in subjective fields like law
• Test the reliability and objectivity of AI systems in complex decision-making
• Navigate ethical considerations in adopting AI-driven tools in legal practice

Key takeaways: 

• AI’s reasoning in law aligns with its backward-looking nature, as legal tasks often rely on precedent and existing data, making large language models effective for linking facts to statutes and regulations.
• The “anesthesia test” emphasizes evaluating AI by its practical outputs, as effectiveness matters more than understanding its internal workings.
• While large language models excel at connecting legal concepts, they struggle with objective tasks like math, reflecting their contextual strengths.
• Studies like Stanford’s highlight AI’s limitations, but the legal industry should focus on practical applications for everyday workflows rather than edge cases.

About the guest, Damien Riehl:

Damien Riehl is a lawyer and technologist with experience in complex litigation, digital forensics, and software development. A lawyer since 2002 and coder since 1985, Damien clerked for the chief judges of state and federal courts, practiced in complex litigation for over a decade, has led teams of cybersecurity and world-spanning digital forensics investigations, and has built AI-backed legal software.

At vLex Group — which includes Fastcase, NextChapter, and Docket Alarm — Damien helps lead the design, development, and expansion of various products, integrating AI-backed technologies (e.g., GPT) into a billion-document dataset from 100+ countries, all to improve legal workflows.

“How much of the law is looking backward—that is, looking to precedent? You're always looking to statutes; you're always looking to something that is in the data set. So, if it is in the data set, really, all of our reasoning that is legal is backward-looking, not forward-looking.” – Damien Riehl

Connect with Damien Riehl:

Website: https://vlex.com/

LinkedIn: https://www.linkedin.com/in/damienriehl/

Connect with Ted Theodoropoulos:

Website: https://getinfodash.com/

LinkedIn: https://www.linkedin.com/in/tedtheo

YouTube: https://www.youtube.com/@getinfodash/podcasts