Welcome back and thank you for being part of the Legally Speaking podcast journey. We appreciate your listening, sharing, showing up, and for sticking with us as this podcast packed its bags and traveled the world. From Dubai to Ibiza, from the Festival of Entrepreneurs to Mercedes world, all the way through to ClioCon 2025 in Boston, Massachusetts. You joined us with every step of the way, and that means everything to us. A massive shout out as well to our incredible sponsor, Clio. backing the show, supporting the vision, and helping make these conversations possible. Coming up right now, as we come to a close with Season 9, we're going to be rolling straight into the snippets from the top 10 episodes of Season 9, bringing you the moment you loved, shared, and replayed the most. And here's the thing, this isn't goodbye, not even close. So don't go anywhere because season 10 is just around the corner. We're coming back bigger, bolder and better than ever. This has been an incredible season. Thanks for joining us on the adventure. Happy New Year and we'll see you very soon.
So why should you be listening in?
You can hear Rob and his guests discussing:
- What Comes Next for Legally Speaking Podcast
- Disruptive Legal Career Journeys
- Advocating for Clients in Medical Negligence
- Leadership and Diversity in Legal Practice
- Navigating Sanctions and White Collar Crime
- Exploring Private Wealth Law
- AI and Legal Technology Trends
- Legal Tech Research and Innovation
- Entrepreneurial Journeys
- Expert Guidance and Advice from Seasoned Veterans in Law
Stay Tuned here - https://legallyspeakingpodcast.com/
On today’s Legally Speaking Podcast, I'm delighted to be joined by Brett Colvin. Brett is the CEO and Co-Founder of Goodlawyer, branded Canada’s most trusted in-house counsel network, Goodlawyer provides cost-effective in-house legal solutions. Goodlawyer has helped over 5,000 businesses and they are just at the start of their venture.
So why should you be listening in?
You can hear Rob and Brett discussing:
- Flexible Legal Careers with Goodlawyer
- Embracing New Legal Technology
- Leadership & Company Culture
- Strategic Customer Focus
- Community and Brand Building
Connect with Brett Colvin here - https://ca.linkedin.com/in/brettrcolvin
On today’s Legally Speaking Podcast, I'm delighted to be joined by Damien Riehl. Damien is a lawyer with experience in litigation, counselling businesses, handling cybersecurity crises and managing intellectual property matters. He has represented Fortune 500 companies, startups and nonprofits. He is also the Solutions Champion at Clio. As a technologist, Damien has spent more than a decade designing and developing AI tools in the legal practice. His goal is to build technology connecting law to the people it serves.
So why should you be listening in?
You can hear Rob and Damien discussing:
- AI Transforming Legal Services
- Data Quality and Access
- Ethical and Practical Impacts of Legal Tech
- Intellectual Property in the Age of AI
- Alignment of Tech with Human and Legal Values
Connect with Damien Riehl here - https://www.linkedin.com/in/damienriehl
On today’s Legally Speaking Podcast, I'm delighted to be joined by Marco Imperiale. Marco is the Founder and Managing Director of Better Ipsum. He graduated with a Master’s from Harvard Law School in 2016. Marco was an entertainment and copyright lawyer, before becoming the Head of Innovation of a leading Italian law firm. Marco now sits as the President of the Wellbeing Committee.
So why should you be listening in?
You can hear Rob and Marco discussing:
- The Evolution of Legal Design: Embracing User-Centric Services
- Navigating the Intersection of AI and Legal Innovation
- The Importance of Flexibility in the Legal Profession
- Mental Health and Well-being: A Priority in Law Firms
- The Role of Legal Design in Enhancing Access to Justice
Connect with Marco Imperiale here - https://it.linkedin.com/in/marco-imperiale/en
Today’s Legally Speaking Podcast ™️ Live, sponsored by Clio, with Andrew Berger was a masterclass in where copyright law is heading and what’s now at stake for creators, technologists and the courts.
Here are a few highlights:
🔴 Why courts can’t agree on copyright’s purpose in the AI era
🔴 How the four-factor fair use test is under unprecedented pressure
🔴 The real significance of the $1.5B Anthropic settlement
🔴 Why the next frontier may be “market dilution” as AI content floods the field
🔴 Why legislative reform is unlikely, leaving judges to define the boundaries
🔴 How history’s big tech shifts compare, and why AI is fundamentally different
Two standout messages from Andrew:
1️⃣ When AI eats its creative source, that source will stop producing the works copyright is intended to encourage.
2️⃣ No other industry gets its raw material from a competitor for nothing.
If you missed it, this one is worth watching.
AI has exploded across the legal industry but for many lawyers, it still feels overwhelming, risky, or simply “not for them.” Today’s guest has made it his mission to change that. Joining us is Robert Eder an intellectual property lawyer, legaltech educator, and one of Europe’s leading voices on AI prompting for lawyers. Robert designs legal automation solutions, and teaches lawyers around the world how to use AI safely, effectively, and creatively. Robert has trained hundreds of lawyers across Europe and is one of the clearest voices on how to use AI responsibly, safely and with real legal precision.
Here are a few standout takeaways:
Lawyers aren’t bad at prompting they’re undersold. Their analytical mindset actually gives them an advantage.
Most people still treat AI like Google. Adding structure through XML tags, roles and answer-levelling changes everything.
The first AI skill every lawyer should learn isn’t drafting it’s controlling output. Structure before substance.
Hallucinations aren’t a deal-breaker. Responsible AI frameworks give you quality control, not guesswork.
You don’t need 70% of AI tools on the market. With the right prompting, one model + the right workflow beats shiny software every time.
Legal prompting is not the same as general prompting. Law has edge cases, nuance, and risk your prompts must reflect that.
Two general points to reflect on:
AI isn’t replacing lawyers. Lawyers who understand AI are replacing the ones who don’t.
On today’s Legally Speaking Podcast, I'm delighted to be joined by Grace Williams. Grace is a Certified Health and Nutrition Coach. A former Whit & Case Associate, she has experienced the high-pressure environments of working at a US law firm. Grace’s mission is to support high-performing individuals, personalised nutrition and lifestyle strategies, all whilst developing their energy, resilience and wellbeing.
So why should you be listening in?
You can hear Rob and Grace discussing:
- Elevating Legal Performance Through Well-Being and Resilience
- Going From Burnout to Breakthrough with a Path to Sustainable Success
- Tailored Strategies for Health: The Next Level of Lawyer Well-Being
- Techniques for Staying Resilient in Law
- Power Habits and Honest Conversations and Wellness Essentials
Connect with Grace Williams here - https://uk.linkedin.com/in/grace-williams-coach
On today’s Legally Speaking Podcast, I'm delighted to be joined by Darryl Cooke. Darryl is the Co-Founder and Executive Chairman of Gunnercooke LLP, an award-winning international law firm. Darryl’s firm is known for redefining what it means to lead and innovate in professional services. A successful corporate lawyer, Darryl has built one of the UK’s most disruptive legal firms - and is on a mission to change the legal model, putting people and purpose at the core of business.
So why should you be listening in?
You can hear Rob and Darryl discussing:
- Creating a Revolutionary Fee-Share Model
- How to Live Through Values, Not Just Words
- Methods of Empowering Leadership
- Making the Most of Community-Driven Impact
- Designing Your Life, Your Way
Connect with Darryl Cooke here - https://uk.linkedin.com/in/darryljcooke
Welcome to Clio Con Clips 2025, recorded live from Boston and proudly sponsored by Clio, the world’s leading legal technology company transforming the legal experience for all.
On the final episode of our miniseries, we round off the conversations at Clio Con with Alexander Almazan. He is the founder and managing partner of Almazan Law, a 30-person firm based in Florida with offices in Miami, Tampa and Palm Beach. He specialises in civil defence, insurance defence, real estate, and commercial litigation. Alex is a consistent attendee of Clio Con, emphasising the importance of staying ahead in legal technology field. He is an advocate for AI adoption in law, highlighting his firm’s successful implementation of AI timekeeping, which greatly improved efficiency and ROI. He encourages legal professionals to embrace innovation, overcome unfounded fears about AI, and connect with him on LinkedIn for industry insights and collaboration.
So why should you be listening in?
You can hear Rob and Alexander discussing:
- Staying Ahead & Embracing Legal Technology at Clio Con
- How AI Timekeeping Transforms Law Firms
- Building a Tech-Forward Firm Culture
- Leading with Vision: Earning Team Trust Through Innovation
- Fostering Collaboration & Building Connections in the Legal Industry
Connect with Alexander Almazan here - https://www.linkedin.com/in/alexander-almazan-8b681115
Welcome to Clio Con Clips 2025, recorded live from Boston and proudly sponsored by Clio, the world’s leading legal technology company transforming the legal experience for all.
On today’s minisode, we get the chance to speak with Niamh Pollak. She is the Vice President of Legal at Clio, bringing extensive international legal experience and a strong focus on plain language, transparency, and customer-centric practices. Known for her multilingual background and global perspective, she leads Clio’s legal team through innovation in legal tech and compliance, notably overseeing product launches and contributing to major company initiatives like the Vlex deal. Niamh champions the use of AI for efficiency, fosters collaboration across departments, and is recognized for her impactful leadership in the rapidly evolving legal industry.
So why should you be listening in?
You can hear Rob and Niamh discussing:
- Clio's Global Impact: Revolutionizing Legal Tech from Boston to the World
- Balancing Innovation and Risk: Navigating AI's Role in Legal Practice
- Transparency in Legal Products: Ditching Jargon for Client Trust
- AI-Powered Legal Teams: Elevating In-House Counsel Beyond Routine
- Uniting Brilliance: Collaboration, M&A Innovation, and ClioCon 2025 Highlights
Connect with Niamh Pollak here - https://ca.linkedin.com/in/niamh-pollak-69867b3
On today’s Legally Speaking Podcast, I'm delighted to be joined by Emily Monastiriotis.
Emily is the Global Managing Partner at Simmons & Simmons. She specialises in international construction disputes and is a market-leading expert on fire safety cases. Her work has been recognised in the Lawyer Top Cases of 2024. Emily firmly believes in her three guiding principles - clients, people and technology. Earlier this year, she was named on of Financial News’ Top 50 Most Influential Lawyers 2025.
So why should you be listening in?
You can hear Rob and Emily discussing:
- Emily's Inspiring Path to Leadership
- How to Lead with Integrity
- Pioneering Innovation at Simmons & Simmons
- A Balancing Act: Emily Monastiriotis' Secrets to Resilience
- Building a Creative Legal Culture
Connect with Emily Monastiriotis here - https://uk.linkedin.com/in/emily-monastiriotis
Welcome to Clio Con Clips 2025, recorded live from Boston and proudly sponsored by Clio, the world’s leading legal technology company transforming the legal experience for all.
On today’s minisode, we get to to Harsha Chandra Shekar. He is the Vice President of Business Development at Clio. Formerly a corporate attorney at a large law firm, he transitioned from practicing law to the business and technology side of the legal industry. Drawing on influential experiences at companies like Uber, Harsha brings a strategic and adaptable approach to building partnerships and driving innovation at Clio, especially in areas involving AI, data and legal technology ecosystems.
So why should you be listening in?
You can hear Rob and Harsha discussing:
- Clio’s Strategic Partnerships
- AI and Data-Driven Innovation
- Lessons from Big Tech
- Trust and Data Protection
- Uniting Brilliance: The Collaboration and Execution
Connect with Harsha Chandra Shekar here - https://www.linkedin.com/in/harshacs1
Welcome to Clio Con Clips 2025, recorded live from Boston and proudly sponsored by Clio, the world’s leading legal technology company transforming the legal experience for all.
On today’s minisode, we get to speak with Denise Farmer. She is Clio's General Manager for the APAC region. Denise is recognised for leading Clio’s growth and innovation efforts across Asia-Pacific, expanding the team, and helping drive legal tech adoption in a diverse and rapidly evolving market. Denise emphasises the importance of collaboration, change management, and partnerships with law societies and universities. She is passionate about using technology to improve efficiency for law firms, democratise access to justice, and support pro bono work. Denise is personally excited by the rapid pace of innovation, her growing APAC team and the transformative opportunities technology brings to legal professionals in the region.
So why should you be listening in?
You can hear Rob and Denise discussing:
- APAC Diversity & Opportunity
- The Promise of AI & Cloud
- Overcoming Change Management
- Partnerships for Progress
- Access to Justice & Team Growth
Connect with Denise Farmer here - https://au.linkedin.com/in/denisefarmer
What if the best way to understand a Supreme Court is to play it, explore it, and step inside its stories?
🎥 Our next Legally Speaking Podcast™ LinkedIn Live, sponsored by Clio, features Nicolas Monet; lawyer, journalist, and the creative force behind Supreme Court Experience.Nicolas and his team at the University of Ottawa have built one of the most innovative legal education platforms in years, blending documentary storytelling, interactive learning, and even a video game to bring the Supreme Court of Canada to life.Here’s what we’re covered:
🔴 How immersive storytelling can demystify the justice system
🔴 Why collaboration between lawyers and creators is essential for public legal education
🔴 What citizens who’ve lived Supreme Court cases really want the profession to understand
🔴 The role technology plays in rebuilding public trust in democratic institutions
🔴 How interactive media can help young people engage with law in meaningful ways
Two standout takeaways from Nicolas:
- When people see themselves in the justice system, trust grows and learning becomes real.- Law isn’t just doctrine. It’s stories, lives, and decisions that shape communities for generations.If you’re passionate about legal education, access to justice, or the future of how we teach law you’ll want to catch this one.
🔗 Go explore Supreme Court Experience for yourself at supremecourtexperience.ca.
It’s a brilliant resource for lawyers, educators, students, and anyone curious about how justice works behind the doors of a Supreme Court.What if the best way to understand a Supreme Court is to play it, explore it, and step inside its stories?
Welcome to Clio Con Clips 2025, recorded live from Boston and proudly sponsored by Clio, the world’s leading legal technology company transforming the legal experience for all.
On today’s minisode, Sarah Murphy is our guest! She is Clio’s Manager for International Business, playing a pivotal role in driving the company’s global expansion and regional strategies. She is recognised for her leadership in scaling Clio’s presence across diverse legal markets, intentional team-building, and commitment to fostering a mission-driven, customer-centric culture. Sarah has experienced remarkable career progression at Clio, and she is soon to celebrate the opening of Clio’s new EMEA HQ in Dublin - a milestone reflecting her and her team’s significant achievements within the organisation.
So why should you be listening in?
You can hear Rob and Sarah discussing:
- Clio’s Global Reach, Local Focus
- Mission-Driven, Passionate Culture
- Client Experience & AI Lead Legal Tech
- Awards Highlight International Impact
- Leadership Development Fuels Hyper-Growth
Connect with Sarah Murphy here - https://ie.linkedin.com/in/sarah-murphy-96503b22
On today’s Legally Speaking Podcast, I'm delighted to be joined by Jacqueline Watts. Jacqueline is an Emerging Technologies Lawyer at boutique law firm, Allin1 Advisory. She is also the Head of Corporate Commercial Law. Jacqueline is passionate about discussing law in the virtual world - publishing her book on ‘Law in the Metaverse’. Earlier this year, she was on the panel as part of the City of London’s Access to Finance for Early-Stage SMEs, and at the end of last year, she spoke about legal issues concerning the metaverse & Web3 at the Tech Summit.
So why should you be listening in?
You can hear Rob and Jacqueline discussing:
- The Evolving Role of Lawyers in Emerging Technologies and AI
- Why the Metaverse Matters and How Immersive Virtual Worlds Reshape Legal Practice
- Regulatory Challenges and the Future Governance of Virtual Rnvironments
- The Importance of Contractual Foundations for Innovators and Tech Founders
- Ethical, Safety and Human-Behaviour Considerations in Virtual and Immersive Spaces
Connect with Jacqueline Watts here - https://uk.linkedin.com/in/wattsjacqueline
Welcome to Clio Con Clips 2025, recorded live from Boston and proudly sponsored by Clio, the world’s leading legal technology company transforming the legal experience for all.
On today’s minisode, we speak with Joshua Lenon, the Lawyer in Residence at Clio. He is a New York-licensed attorney and is passionate about legal technology. Joshua plays a key role in thought leadership at Clio, often participating in industry-leading research and discussions on AI, legal practice transformation, access to justice, client satisfaction, and ethics. He is recognised for his innovative mindset and direct involvement in advancing legal technology's role in law firms and client services.
So why should you be listening in?
You can hear Rob and Joshua discussing:
- Legal Technology's Impact at Clio Con 2025
- Neuroscience Studies Reveal AI Benefits for Lawyers
- The Importance of Client Satisfaction in Law Firm Growth
- Ethical and Transparency Considerations in Legal AI
- Data-Driven Insights Advancing Access to Justice
Connect with Joshua Lenon here - https://www.linkedin.com/in/joshualenon
Welcome to Clio Con Clips 2025, recorded live from Boston and proudly sponsored by Clio, the world’s leading legal technology company transforming the legal experience for all.
On today’s minisode, we talk to A.J. Axelrod. He is the VP of Payments and Financial Services at Clio, responsible for leading the company’s payment and financial product innovations. A.J. is focused on making legal services more accessible through new solutions like Pay Later and Clio Capital, aiming to remove financial barriers for both clients and law firms. A.J. is dedicated to compliance and security, works closely with reputable partners, and values customer feedback to drive adoption and usability. His approach emphasizes clear, context-specific solutions for legal professionals, and he is enthusiastic about Clio’s mission and advancements showcased at his first Clio Con.
So why should you be listening in?
You can hear Rob and A.J. discussing:
- Innovation and Updates in Clio’s Legal Payments
- Addressing Legal Affordability through Flexible Payment Solutions
- Ensuring Compliance and Building Trust in Financial Technology
- User Feedback and Rapid Adoption of Clio Payment Features
- The Evolving Intersection of Legal Tech and FinTech
Connect with A.J. Axelrod here - https://www.linkedin.com/in/ajaxelrod
Welcome to Clio Con Clips 2025, recorded live from Boston and proudly sponsored by Clio, the world’s leading legal technology company transforming the legal experience for all.
On today’s minisode, Michelle Dunlea is our guest. She is the Vice President of Product Management at Clio. Known for her strong customer-centric mindset, Michelle leads Clio’s product strategy, focusing on unifying and innovating legal technology solutions. At Clio Con 2025, she shared insights on the company’s approach to AI integration, team collaboration, and building products that truly address lawyers’ real-world needs. Michelle’s leadership emphasises listening to customers, thoughtful design, and empowering teams to create lasting impact in legal tech.
So why should you be listening in?
You can hear Rob and Michelle discussing:
- One Platform Ruling Legal Work: Clio’s Vision in Action
- How to Design with Lawyers, for Lawyers
- AI That Works While You Work
- Triads of Innovation: Teams Uniting to Transform Legal Tech
- Invisible AI, Lasting Impact - The Future of Law Starts Now
Connect with Michelle Dunlea here - https://ca.linkedin.com/in/michelledunlea
On today’s Legally Speaking Podcast, I'm delighted to be joined by Emerald De Leeuw-Goggin. Emerald is the Global Head of AI Governance and Privacy at Logitech. She is also the Co-Founder of Women in AI Governance, a professional network advancing women’s leadership in AI regulation, policy and governance. Emerald has been recognised as one of the top 100 European Female Founders to follow. She has been awarded European Young Innovator of the Year, Privacy Executive of the Year 2023 and Women in AI Ambassador in 2024.
So why should you be listening in?
You can hear Rob and Emerald discussing:
- Values-Driven AI and Privacy Governance
- Cross-Functional, Collaborative AI Governance
- Global Compliance Through Unified Standards
- Women in AI Governance and Inclusive Leadership
- Balancing Innovation and Ethics Through Stable Principles
Connect with Emerald De Leeuw-Goggin here - https://ie.linkedin.com/in/emeralddeleeuw