Legal Innovation Spotlight

In this episode, Ted connects with Haley Altman for a dynamic conversation on Gen AI’s role in transforming legal operations, high valuation challenges, and opportunities for innovating within a corporate structure. Haley shares insights on balancing startup agility with corporate resources, detailing how her team developed Gen AI solutions that bridge real industry needs. Packed with practical anecdotes on managing client expectations, rapid tech cycles, and scalable solutions, this episode is a must-listen for anyone interested in the evolving landscape of legal tech.

In this episode, Haley shares insights on how to:

• Leverage Gen AI to enhance legal transaction processes
• Create a startup culture within a large corporate structure
• Balance aggressive growth goals with sustainable product-market fit in tech
• Manage investor expectations in rapidly evolving markets like AI
• Build strategic partnerships that bridge innovation and industry demands

Key takeaways: 

• Balancing entrepreneurial freedom within a corporate environment requires clear scope definitions and trust in partnerships to keep innovation-focused and aligned.
• Valuations in AI and legal tech are currently inflated by non-traditional investors who may not fully understand the industry’s slower sales cycles and compliance demands.
• Even within budgets or alternative fee arrangements, clients often still want to see detailed hours and breakdowns, reflecting a hesitancy to fully abandon traditional billing.
• In law firms, many are overwhelmed by the sheer number of new Gen AI solutions, creating significant delays in evaluating, piloting, and integrating new technologies.

About the guest, Haley Altman:

Haley Altman is a corporate attorney, founder, and advisor in the legal technology innovation space. She began her career in Big Law, first as an associate and then as a partner, before transitioning to entrepreneurship as the founder of Doxly, Inc., which was acquired by Litera. There, she rose to Global Head of Corporate Development and helped lead 10 acquisitions. Recently, Haley shifted to a strategic advisor role at Litera, supporting the leadership team in M&A and product strategy, including the development of two generative AI solutions, Dragon and Lattice. She leverages her extensive experience as an entrepreneur and former lawyer to understand the technology, processes, and workflows that help lawyers while maximizing client satisfaction.

“With Gen AI, there was so much going on all at once that you really need to think about: how can I build something new?” – Haley Altman

Connect with Haley Altman:

LinkedIn: https://www.linkedin.com/in/haley-altman/

Connect with Ted Theodoropoulos:

Website: https://getinfodash.com/

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

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

In this eye-opening episode, Ted sits down with Judge Scott Schlegel to discuss the urgent realities of AI and legal tech in today's courtrooms. Judge Schlegel, an advocate for practical tech in justice, shares his experiences with both the promise and peril of AI—from voice-cloning risks to affordable solutions for overburdened court systems. Join them as they explore how AI can revolutionize legal preparation and accessibility while highlighting the critical need for awareness, caution, and responsible use in an evolving digital landscape.

In this episode, Judge Scott shares insights on how to:

• Use low-cost technologies to streamline court operations
• Detect and address deepfakes in court evidence
• Leverage AI tools for trial preparation
• Mitigate the risks of AI-generated evidence in the justice system
• Implement practical technology solutions without extensive budgets

Key takeaways: 

• Deepfake audio poses critical risks in domestic cases, allowing cloned voices to manipulate protective orders, seize assets, and disrupt lives with minimal verification.
• Budget constraints in most courts limit access to advanced tech, pushing judges to rely on affordable tools to streamline operations and improve efficiency.
• AI tools like ChatGPT offer valuable support in trial prep, helping lawyers simulate juror perspectives and anticipate key questions before court.
• Rapid AI advancements bring significant challenges for courts unprepared for threats like deepfakes, with slow adoption rates and limited resources complicating responses.

About the guest, Judge Scott Schlegel:

Judge Scott U. Schlegel, a recent inductee into the Louisiana Justice Hall of Fame, was elected to the Fifth Circuit Court of Appeal in 2023. Known for pioneering one of the nation's most advanced online justice systems, he has also led as Chair of the Louisiana Supreme Court Technology Commission and served on the ABA & LSBA Task Forces on the Law and Artificial Intelligence. Judge Schlegel's work includes establishing the Reentry Court and Swift & Certain Probation programs to reduce recidivism. A Loyola University New Orleans College of Law graduate, he is married to Representative Laurie Schlegel and has one son in college.

“We need to build a more modern justice system—needs to be more efficient, more effective, and more accessible. And I just think that we can use simple technologies to modernize the justice system to make everybody’s lives better.” – Judge Scott Schlegel

Connect with Judge Scott Schlegel:

Website: https://judgeschlegel.com/

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

Twitter: https://x.com/judgeschlegel

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 AI and data management expert Aron Ahmadia to explore the transformative impact of AI on the legal industry. They explore agentic AI and its autonomy, discussing its potential to reshape legal processes, cut costs, and improve decision-making. Aron shares insights into both the opportunities and challenges of integrating AI in legal workflows, highlighting the journey from innovation to practical application. 

In this episode, Aron shares insights on how to:

• Define and integrate agentic AI in legal workflows
• Assess AI's impact on efficiency and cost savings in legal services
• Overcome data quality challenges in law firm document management
• Navigate the development and deployment of AI for legal research and discovery
• Manage risk in AI applications within legal and compliance contexts

Key takeaways: 

• AI systems in legal discovery have greatly improved cost efficiency, with one case saving over a million dollars using a trial AI product.
• Agentic AI, known for its autonomy and planning, is expected to transform the legal sector by automating repetitive tasks and enhancing strategic roles.
• Advanced AI data organization tools also help law firms manage disorganized data by identifying, categorizing, and cleaning it—key steps toward fully leveraging AI.
• Current AI tools, like those for document review, enable rapid analysis of large datasets, setting the stage for broader use across knowledge management and other legal tasks.

About the guest, Aron Ahmadia:

Dr. Aron Ahmadia is the Senior Director for Applied Science at Relativity, leading AI development for RelativityOne, including the aiR suite and its Active Learning and Analytics. An expert in machine learning and AI, he specializes in AI for Law, Model Risk Management, and Responsible AI. Previously, he was an adjunct faculty at George Washington University and a founding Computer Science Professor at KAUST, teaching one of Saudi Arabia’s first coed classes. He has experience in Capital One’s Model Risk Office and U.S. government service. Dr. Ahmadia holds a Ph.D. in Applied Math from Columbia University and a B.S. in Computer Engineering from Illinois Institute of Technology.

“We're potentially going to see a level of data understanding and data management that we don’t currently consider because it's just too expensive. But that cost will go away, and the capability will come.” – Aron Ahmadia

Connect with Aron Ahmadia:

LinkedIn: https://www.linkedin.com/in/aron-ahmadia/

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 Theodoropoulos dives into the realities of legal tech with Matthew Dunne and Andrew Sprogis, focusing on innovation, AI, and operational efficiency. They examine the decision to build or buy technology, the responsible integration of generative AI, and how firm culture affects tech adoption. Tune in for valuable insights on optimizing legal workflows and making informed, risk-aware choices in a rapidly changing landscape.

In this episode, Matthew and Andrew share insights on how to:

• Evaluate build-versus-buy decisions for technology in legal practice
• Balance innovation with established knowledge management (KM) practices
• Introduce generative AI in a law firm environment
• Assess and define ROI in innovation projects
• Use technology to increase operational efficiency in law firms

Key takeaways: 

• Law firms should take a measured approach to AI, focusing first on lower-risk, business-related use cases before handling client-sensitive data.
• Generative AI doesn't necessarily require perfectly clean data, but basic data hygiene and correct document selection are essential.
• Innovation efforts in law firms are often guided by organizational culture, with a strong influence from senior management's risk tolerance.
• Building proprietary tools is typically discouraged for most firms unless it provides a unique competitive edge; support and maintenance are often overlooked in cost assessments.

About the guests, Matthew Dunne & Andrew Sprogis:

Matthew Dunne is the Sr. Innovation and Data Science Manager at Katten Muchin Rosenman LLP, where he integrates data science and legal tech. He leads Katten’s DataLAB, offering legal data science services and Gen AI applications. Matthew holds an MS in Applied Data Science from the University of Chicago and a JD from Indiana University, and he is a licensed attorney.

Andrew Sprogis is Katten's Chief Innovation Officer and former Executive Director. He converts innovative ideas into practical solutions, helping attorneys and clients navigate industry changes. His team improves the client experience through enhanced quality and communication, emphasizing collaboration and leveraging new data.

“It's the interaction of the technology plus the people and process part that leads to the ultimate outcome.” – Matthew Dunne

“One of the challenges with the innovation space in general, and I think it's going to be this way for Gen AI, is that different people at different arcs of their careers are going to have different motivations to do things.” – Andrew Sprogis

Connect with Matthew and Andrew:

Website: https://katten.com/

Matthew’s LinkedIn: https://www.linkedin.com/in/matthew-dunne-02842221/

Andrew’s LinkedIn: https://www.linkedin.com/in/andrew-sprogis-88997b20/

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 Darryl Cross, US Executive Sales Coach at Norton Rose Fulbright, to explore how law firms can innovate in business development while maintaining a client-focused approach. Darryl shares his unique perspective on coaching lawyers in sales, breaking down the barriers of skepticism and autonomy that often hinder business growth. This conversation is packed with valuable insights on transforming law firms into thriving, revenue-driven enterprises without sacrificing the professional integrity that defines the legal industry. 

In this episode, Darryl shares insights on how to:

• Adopt a client-centric sales mindset
• Overcome lawyers' skepticism toward business development
• Foster collaboration across offices and practices within a global law firm
• Integrate sales methodologies into the daily work of lawyers
• Balance risk management with innovation

Key takeaways: 

• Focusing on a small group of key clients, prospects, and referral sources, and dedicating most of your effort to them, is a highly effective approach to business development.
• Lawyers may resist traditional sales tactics, but reframing sales processes using familiar legal skills like discovery and due diligence can make business development more natural and effective.
• Having an internal sales coach with access to firm data and financials can significantly improve cross-practice collaboration, client service, and overall business growth.
• Running a law firm with a business mindset—focusing on revenue and profitability—provides the resources needed for investments in DEI programs, professional development, and broader community contributions.

About the guest, Darryl Cross:

Darryl Cross, US Executive Sales Coach at Norton Rose Fulbright, brings over 25 years of legal industry experience. A pioneer in in-house coaching for law firms, he blends sales methodologies with professional services to drive growth. Previously, he was part of the Sales and Leadership Academy at Amazon Web Services and held senior roles as a law firm CMO and VP of Performance Development at LexisNexis. Known for shifting mindsets to a client-centric business approach, he focuses on enhancing lawyers' sales skills and building scalable programs. He is the author of Cultivating Excellence: The Art, Science, and Grit of High Performance in Business and also volunteers as a girls' high school rugby coach.

“When you are better at generating revenue and have a sales methodology, it allows you to pick and choose the work you want and the work that's most beneficial to the client.” – Darryl Cross

Connect with Darryl Cross:

Website: https://www.nortonrosefulbright.com/en

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

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 Stephen Embry, publisher of TechLaw Crossroads, to explore the transformative potential of generative AI in the legal field. Stephen shares insights on AI adoption in law firms, the surprising gap between perceptions and reality, and the critical role AI could play in shaping associate training. Tune in for an engaging discussion on how AI might redefine legal practice, offering both challenges and opportunities for the profession.

In this episode, Stephen shares insights on how to:

• Integrate generative AI tools in legal practice
• Identify AI use cases for law firms of various sizes
• Address AI challenges in junior associate training
• Use AI to bridge the technology gap between large and small firms
• Measure AI effectiveness and mitigate risks in law firms

Key takeaways: 

• Despite surveys suggesting widespread AI adoption, many lawyers are not actively using AI tools in practice, revealing a significant gap between perception and reality.
• Larger law firms are adopting AI tools more rapidly than smaller firms due to cost and resource availability, which is widening the gap between them.
• Generative AI tools can aid younger lawyers in preparing for tasks like depositions by generating comprehensive lists of questions, saving time, and improving confidence.
• Ethical concerns around AI, particularly related to data privacy and the potential for bias in AI decision-making, are raised as important factors that legal professionals must navigate.

About the guest, Stephen Embry :

Stephen Embry is a lawyer, speaker, blogger, and writer. He publishes TechLaw Crossroads, a blog focused on exploring the tension between technology, the law, and the practice of law. He is a past Chair of the ABA’s Law Practice Division and the Chair of the Kentucky Bar Association’s Law Practice Committee. Additionally, Stephen is the past Chair of the Data Breach, Privacy, and Cyber Insurance Section of the FDCC, a member of the FDCC Evolve Program, and a faculty member of FedTechU. He also serves as Webinar Chair and Steering Committee member of the Defense Research Institute’s Law Practice Management section. As a national litigator and advisor, Stephen specializes in mass tort, business and consumer class action, and privacy and data breach cases.

“These tools aren’t going to go away, and we can’t just say, ‘Well, we’re going to keep doing what we’ve always done and not adopt these programs,’ because lawyers, especially younger ones, are frankly going to use them no matter what we do.” – Stephen Embry

Connect with Stephen Embry:

Website: https://www.techlawcrossroads.com/

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

Twitter: https://x.com/stephenembryjd

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 Dan Hauck, Chief Product Officer at NetDocuments, to explore the cutting-edge advancements in legal tech, particularly around AI-driven document management systems (DMS). Dan shares insights on how AI is transforming the way law firms handle document profiling, classification, and workflow automation, while also discussing the exciting integration of Microsoft Copilot. Tune in for a deep dive into how AI is reshaping legal workflows, providing powerful tools to increase efficiency and knowledge management in the legal sector.

In this episode, Dan shares insights on how to:

• Leverage AI for document management in law firms
• Enhance document search capabilities
• Streamline workflows with AI-driven document profiling
• Integrate generative AI tools with existing legal DMS platforms
• Automate document classification and metadata extraction at scale

Key takeaways: 

• Generative AI can now classify and extract metadata from various legal documents, improving document organization and making search processes more efficient.
• AI-powered tools enable law firms to automate routine tasks, such as contract reviews and summarizing depositions, creating more consistent and predictable outcomes.
• AI-driven document management systems can embed knowledge management directly within workflows, reducing the need to transfer documents to external systems for enrichment.
• The integration of AI tools into legal workflows allows for real-time collaboration and retrieval of documents with advanced search and automation capabilities, all while maintaining security and efficiency.

About the guest, Dan Hauck:

Dan is the Chief Product Officer at NetDocuments. As an experienced lawyer, entrepreneur, and award-winning product visionary, he oversees the planning and development of software solutions across various areas, including document management, collaboration, automation, artificial intelligence, and governance.

“A legal-specific [document management system (DMS)] is crucial for law firms because it's the lifeblood of the firm.” – Dan Hauck

Connect with Dan Hauck:

Website: https://www.netdocuments.com/

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

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 chats with Senne Mennes, Co-Founder of ClauseBase, about the game-changing impact of AI and document automation in legal work. Senne shares his journey from lawyer to legal tech innovator, discussing how tools like ClauseBase are transforming legal drafting. They explore the balance between AI and manual curation, the challenges of outdated document systems, and how to best leverage AI while addressing its limitations. This conversation offers valuable insights for anyone looking to enhance legal processes with technology.

In this episode, Senne shares insights on how to:

• Implement document automation in legal workflows
• Balance manual curation with AI for legal drafting
• Manage legal document management systems in large law firms
• Integrate generative AI effectively in legal technology solutions
• Mitigate limitations of AI-powered enterprise search tools

Key takeaways: 

• Generative AI is revolutionizing legal tech, but its potential should be harnessed carefully as a supportive tool rather than being relied on as the sole solution for legal challenges.
• Advanced document automation platforms like ClauseBase can significantly streamline legal drafting, but successful implementation requires integration with existing legal workflows and careful consideration of firm-specific needs.
• Legal teams must proactively curate and clean up outdated document management systems to fully leverage AI-driven solutions, as unstructured or conflicting data can severely limit AI's effectiveness.
• Despite significant advancements, AI technologies still face major challenges, including hallucinations, context window limitations, and reliance on legal data quality, all of which must be addressed before AI can fully meet the demands of legal professionals.

About the guest, Senne Mennes:

Senne Mennes is the Co-Founder and COO of ClauseBase, where he leverages his legal background and expertise in document automation to transform contract drafting. With prior experience as an attorney at DLA Piper, he combines practical legal knowledge with cutting-edge technology to streamline workflows for law firms and legal departments. Senne is passionate about creating user-friendly tools that enhance efficiency and empower lawyers to focus on higher-value work.

“A supercar can only go as fast as the road allows it to, and legal data is really that road.” – Senne Mennes

Connect with Senne Mennes:

Website: https://www.clausebase.com/

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

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 welcomes back Richard Robbins and is joined by Brian Blaho from Reed Smith to discuss the challenges of integrating AI into legal research. You'll gain insights from the recent Stanford study, which highlights the limitations of current AI tools, and learn why these models often struggle with legal reasoning. If you’re exploring AI for your firm, this conversation highlights how transparency, collaboration, and smart implementation drive innovation.

In this episode, Richard and Brian share insights on how to:

• Approach and evaluate AI systems for legal research
• Assess the limitations of retrieval-augmented generation (RAG) systems in legal AI
• Navigate the potential biases in academic studies about legal AI tools
• Effectively benchmark legal technology and AI performance
• Integrate generative AI tools into law firm workflows

Key takeaways: 

• The Stanford study criticized current legal research AI tools from major vendors, highlighting their limitations in accuracy and understanding legal nuances.
• Legal research is more complex than initially anticipated for AI models, particularly regarding how models handle the nuances of legal precedent and authority.
• Despite the shortcomings of current AI tools, vendors are actively working to improve their systems, but transparency and collaboration on benchmarks are essential for progress.
• A broader, community-led approach, rather than vendor-driven initiatives, is critical for establishing accurate benchmarking standards for AI in the legal industry.

About the guests, Richard Robbins and Brian Blaho:

Richard Robbins is the Director of Applied AI at Reed Smith, leading AI and data science initiatives. A former law firm partner and general counsel, he specializes in legal tech and generative AI. Richard also supports UC Berkeley’s graduate class on generative AI and frequently writes and speaks on the subject.

Brian Blaho is the Global Director of Library Services at Reed Smith, managing library operations, budget, and innovations. With over 20 years in legal research, Brian focuses on legal tech and analytics. He leads global research and training and is active in professional associations.

“It’ll be up to the vendors who build on top of the [legal AI] models to add the other workflows, the agentic systems, and other elements to get us there.” – Richard Robbins

“Generative AI can potentially help us get much better results so that we have to either spend far less time reading through and curating which ones we're going to pass on or no time at all.” – Brian Blaho

Connect with Richard Robbins and Brian Blaho:

Website: https://www.reedsmith.com

Richard’s LinkedIn: https://www.linkedin.com/in/richard-robbins-a88014117/

Brian’s LinkedIn: https://www.linkedin.com/in/brian-b-37684524/

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, our guest Carolyn Humpherys discusses how AI tools like Microsoft Copilot are transforming law firms by automating routine tasks and optimizing workflows. She highlights Copilot's potential in platforms like Excel and PowerPoint, the challenges of adopting tools like Teams and OneDrive, and the balance between innovation and security for law firms embracing AI.

In this episode, Carolyn shares insights on how to:

• Use Microsoft Copilot in law firms
• Find the best AI use cases in legal work
• Boost productivity with AI in Office apps
• Optimize Copilot with Teams and OneDrive
• Ensure confidentiality with AI tools

Key takeaways: 

• Microsoft Copilot is transforming legal workflows by automating repetitive tasks like creating narratives from Excel data, drastically reducing time spent on administrative work and increasing overall productivity across teams.
• The effective use of Microsoft Copilot in law firms depends heavily on integrating platforms like OneDrive, SharePoint, and Teams, as these tools enable Copilot to access and organize data in real-time, which is crucial for its functionality.
• Many large law firms remain hesitant to fully adopt Microsoft tools like Teams and SharePoint, which limits their ability to capitalize on the full potential of Copilot, particularly in terms of collaboration.
• Security concerns, such as maintaining client confidentiality and adhering to ABA rules, make Microsoft Copilot a preferred AI solution for law firms compared to other AI tools like ChatGPT, as it offers enhanced privacy protections and data grounding through the Microsoft Graph.

About the guest, Carolyn Humpherys:

Carolyn Humpherys is a Learning and Change Management Consultant at Traveling Coaches, a leading provider of legal technology adoption services. With over 30 years in the legal industry, she has helped many firms transition to modern working practices. She develops strategies for initiatives ranging from cloud technologies to compliance and cultural transformation. Carolyn has successfully led change consulting projects, helping firms adopt new technologies. As leader of the Copilot and AI initiative at Traveling Coaches, she helps firms leverage generative AI to enhance legal professionals' performance. She is passionate about AI's potential to transform the legal industry.

“If we can use tools to free us up for higher-value-add work, more creative work, more thought leadership, connecting with clients—whatever that looks like based on your role—then I think that dictates what tool you should choose and what tool would most benefit you.” – Carolyn Humpherys

Connect with Carolyn Humpherys:

Website: https://www.travelingcoaches.com/

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

Connect with Ted Theodoropoulos:

Website: https://getinfodash.com/

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

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