Podcast
Legally Speaking Podcast
Hosted by Legally Speaking Podcast™ · EN
Inspiring Legal Minds. Transforming Legal Futures.
The Legally Speaking Podcast, sponsored by Clio, inspires, educates and entertains. Think of it as a law library—with better snacks and standout guests.
Hosted by Rob Hanna, legal careers expert, LinkedIn Top Voice and Founder, we interview lawyers, law firm leaders, legal tech pioneers, DEI champions, and even Netflix stars.
Guests explore legal innovation, career growth, AI, wellbeing and redefining success. New episodes every Monday for the main show, with minisodes as well for quick enjoyment.
Tune in now to supercharge your legal career.
43episodes
Episodes
Newest firstAll episodes
Legally On The Move: The Lawyers Retreat is Back in Ibiza 2026 - Gretchen Lennon - E04
2w ago00:08:06Tap to summarizeWelcome to Legally on the Move, the Lawyers Retreat Ibiza 2026, a special legally speaking podcast mini series sponsored by Clio. We're back here in Ibiza as the official media partner for the Lawyers Retreat. And if last year taught me anything, it's this, when you get the right people in the right environment, good conversations quickly turn into real opportunities. Across this series, we'll be bringing you voices, ideas and honest reflections from a retreat built around leadership, wellbeing, AI, growth, business development and the future of law. So whether we're poolside, post panel or catching up in between sessions, expect practical insights, fresh thinking and conversations that go beyond the surface. Gretchen Lennon is the founder of Lennon Legal, a firm that provides legal consultancy services. With experience working both in-house and on a consultancy basis, Gretchen has gained a deep understanding of business operations and team dynamics. Her consultancy work has allowed her to collaborate with a diverse range of founders, enhancing her expertise in the legal field. You can follow Lennon Legal on Instagram at @lennon_legal and on LinkedIn. So why should you be listening in? You can hear Rob and Gretchen discussing:- Precision Over Volume Driving Legal Value- Small Incremental Changes Generating Big Momentum- The Value of Early, Honest Conversations in Employment Issues- Cost-Effective Legal Support- Why You Should Build Legal Foundations.Connect with Gretchen Lennon here - https://www.linkedin.com/in/gretchen-lennon-55455664/
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Legally On The Move: The Lawyers Retreat is Back in Ibiza 2026 - Trevor Sterling - E03
2w ago00:07:14Tap to summarizeWelcome to Legally on the Move, the Lawyers Retreat Ibiza 2026, a special legally speaking podcast mini series sponsored by Clio. We're back here in Ibiza as the official media partner for the Lawyers Retreat. And if last year taught me anything, it's this, when you get the right people in the right environment, good conversations quickly turn into real opportunities. Across this series, we'll be bringing you voices, ideas and honest reflections from a retreat built around leadership, wellbeing, AI, growth, business development and the future of law. So whether we're poolside, post panel or catching up in between sessions, expect practical insights, fresh thinking and conversations that go beyond the surface. Trevor Sterling is a senior partner and founder of "Be The Ladder." He is recognized for his exceptional ability to connect with people and has led major trauma initiatives for decades. Trevor is committed to developing others and emphasizes the importance of having an open mind. He is also active on LinkedIn and TikTok, where he shares insights as "Trevor D Sterling" and "Diary of the Senior Partner," respectively. So why should you be listening in? You can hear Rob and Trevor discussing:- Simultaneously Being a Senior Partner and Founder- The Lawyers Retreat’s Values for Growth- Ignoring Noise and Distraction- Helping and Developing Others in Leadership- Showcasing Young Talents' Potential.Connect with Trevor Sterling here - https://uk.linkedin.com/in/dr-trevor-d-sterling-hon-causa-33841320
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From Selling Out Tours with Tom Jones to Thriving at One Essex Court: Sam Grimley’s Journey - S10E19
2w ago00:40:00Tap to summarizeOn today’s Legally Speaking Podcast, I’m delighted to be joined by Sam Grimley. Sam is a Barrister at One Essex Court. He specialises in commercial, competition and intellectual property litigation and has appeared in disputes before the High Court, IPEC and UKIPO. Before pursuing a career at the Bar, Sam worked with artists including Sir Tom Jones, Ed Sheeran and Jessie J. So why should you be listening in? You can hear Rob and Sam discussing:- Career Transition from Music to Law- Transferable Skills and How to Use Them Well- Resilience Through Hardship and Academic Challenges- The Importance of Seeking Feedback and Mentorship- Current Practice and Specialist Legal Work at One Essex CourtConnect with Sam Grimley here - https://uk.linkedin.com/in/sam-grimley-47105224
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Legally On The Move: The Lawyers Retreat is Back in Ibiza 2026 - Ryan Hopkins - E02
3w ago00:15:10Tap to summarizeWelcome to Legally on the Move, the Lawyers Retreat Ibiza 2026, a special legally speaking podcast mini series sponsored by Clio. We're back here in Ibiza as the official media partner for the Lawyers Retreat. And if last year taught me anything, it's this, when you get the right people in the right environment, good conversations quickly turn into real opportunities. Across this series, we'll be bringing you voices, ideas and honest reflections from a retreat built around leadership, wellbeing, AI, growth, business development and the future of law. So whether we're poolside, post panel or catching up in between sessions, expect practical insights, fresh thinking and conversations that go beyond the surface. Ryan Hopkins is an author, speaker and CEO of Healthy. He has a background in leading wellbeing initiatives at Deloitte and Bupa, focusing on making wellbeing accessible and practical. Ryan emphasizes the importance of understanding oneself and creating quality time. He advocates for simplifying wellbeing practices and encourages embracing one's authentic self. His book, "52 Weeks of Wellbeing," offers practical tips for personal growth. So why should you be listening in? You can hear Rob and Ryan discussing:- Focusing On Wellbeing and Personal Growth- The Importance of Simplifying Wellbeing Practices- Ryan's Book, "52 Weeks of Wellbeing," - Embracing One's Authentic Self and Making Small, Intentional Changes- The Need for Digital Sanity.Connect with Ryan Hopkins here - https://uk.linkedin.com/in/theryanhopkins
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Legally On The Move: The Lawyers Retreat is Back in Ibiza 2026 - Special Poolside Panel - E01
3w ago00:31:30Tap to summarizeWelcome to Legally on the Move, the Lawyers Retreat Ibiza 2026, a special legally speaking podcast mini series sponsored by Clio. We're back here in Ibiza as the official media partner for the Lawyers Retreat. And if last year taught me anything, it's this, when you get the right people in the right environment, good conversations quickly turn into real opportunities. Across this series, we'll be bringing you voices, ideas and honest reflections from a retreat built around leadership, wellbeing, AI, growth, business development and the future of law. So whether we're poolside, post panel or catching up in between sessions, expect practical insights, fresh thinking and conversations that go beyond the surface. Our poolside panel is happening right now as we dive into this miniseries, so stay tuned for a thrilling discussion!So why should you be listening in? You can hear Rob and the panel discussing:- The Inspiring Voices from the Lawyers Retreat.- Importance of Time Management.- How the AI Adoption Journey Begins.- Deciding Your Professional Path.- Avoiding Potential Mistakes Now.
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Brilliant Thinking: Why Lawyers Must See AI as an Opportunity, Not a Threat - Felix Riley - S10E18
3w ago00:49:12Tap to summarizeOn today’s Legally Speaking Podcast, I’m delighted to be joined by Felix Riley. Felix is a Business/Moonshot Strategist, passionate about helping organisations take a creative approach to problem-solving and growth. He has a wealth of experience as a comedy writer, Global Executive at an NYSE-listed brokerage, and is the author of two best-selling Penguin novels,‘The Set Up’ and ‘The Inside Job’. Felix is committed to equipping teams with practical frameworks for thinking differently and driving meaningful change in their organisations So why should you be listening in? You can hear Rob and Felix discussing:- Helping Law Firms Stop Playing Small- A Positive AI Revolution- AI enabling Quicker and Further Progress- The Importance of Brainstorming and Reimagining Work- Functional Tasks Being Done Quckly and Effectively by Machines.Connect with Felix Riley here - https://uk.linkedin.com/in/felix-riley-brilliant-thinking
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Big Law to Career Builder: Bridging the Gap with Imani Maatuka’s Ultimate Career Playbook - S10E17
4w ago00:50:15Tap to summarizeOn today’s Legally Speaking Podcast, I’m delighted to be joined by Imani Maatuka. Imani is a Managing Partnerof the Dallas Office at Maatuka Al-Heeti Emkes LLC.She is also the Co-Founder of the Bridging the Gap Scholarship, supporting minority students pursuing a career in corporate law. Recognised among Top 40 Under 40 attorneys, Imani has built a demanding legal career while leading purpose-driven initiatives.So why should you be listening in? You can hear Rob and Imani discussing:- Outsourcing as A Strategic Advantage, Not a Shortcut- Preparation Building Credibility and Confidence- Early Ownership Accelerating Career Growth- How to Advance with the Most Meaningful Experiences- Leadership Meaning Something Bigger Than YourselfConnect with Imani Maatuka here - https://www.linkedin.com/in/imanimaatuka
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The Law VS AI Slop: How Spellbook Helps Lawyers Win With Co-Founder & CRO Daniel DiMaria - S10E16
Apr 2700:46:00Tap to summarizeOn today’s Legally Speaking Podcast, I’m delighted to be joined by Daniel DiMaria. Daniel is the Co-Founder and CRO at Spellbook. As a lawyer, he helped build the legal AI tool now used by 4,000 corporate lawyers and law firms. Daniel, having worked in the legal industry firsthand, is passionate about driving the goal of making lawyers’ working lives easier and more enjoyable through technology.So why should you be listening in? You can hear Rob and Daniel discussing:- Focusing on a Core Problem to Drive Success.- How AI Must Be Grounded and Verifiable.- LLMs Transforming Legal Workflows.- Why AI Augments Lawyers Without Replacing Them.- Data-Driven Insights Being the Next Frontier.Connect with Daniel DiMaria here - https://www.linkedin.com/in/daniel-di-maria-340b80ab
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Flexing the Future: How AI, Access & Alternative Paths Change Legal Careers - Kate Gaskell - S10E15
Apr 2000:52:16Tap to summarizeOn today’s Legally Speaking Podcast, I’m delighted to be joined by Kate Gaskell. Kate is the CEO of Flex Legal. She was previously an Associate at Allen & Overy, and has more than 20 years of experience in the legal profession. Kate was the Director of Transformation at LexisNexis UK and is now an Advisory Board Member for qLegal. So why should you be listening in? You can hear Rob and Kate discussing:- Flex Legal as an Alternative Legal Services Provider.- How AI is Considered a Challenging and Creative Area.- Flex Launching a Qualifying Work Experience Training Scheme for Aspiring Solicitors.- The Scheme Includes a Dedicated Social Mobility Initiative.- The Advice Given For Individuals From Non-Traditional Legal Backgrounds.Connect with Kate Gaskell here - https://www.linkedin.com/in/kategaskell1111
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From Hollywood to Big Law: 8-Figure Founder Nick Abrahams on AI and the Future of Law - S10E14
Apr 1301:09:18Tap to summarizeOn today’s Legally Speaking Podcast, I’m delighted to be joined by Nick Abrahams. Nick is an AI Pioneer and Business Futurist, creating the world’s first AI-enabled privacy chatbot. He is a successful entrepreneur who co-founded Lawpath, an AI-powered legal services platform. Nick spent 25 years in partnership at Norton Rose Fulbright and is now dedicated to working with law firms and in-house teams on their AI strategies. He is also a comedian, with his show ‘The Accidental Lawyer’ scheduled for this year’s Sydney and Melbourne Comedy Festivals.So why should you be listening in? You can hear Rob and Nick discussing:- AI Not Replacing Lawyers But Reshaping Their Work- The Real Value Of Legal Services: Peace Of Mind- AI Increasing Legal Disputes, Not Reducing Them- Problem-Led Innovation Overcoming Product-Led Hype- Relationships And Trust Being Key To Driving Change In Law FirmsConnect with Nick Abrahams here - https://www.linkedin.com/in/nickabrahams/
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