Beyond The Fine Print: The Tech Law Podcast

Rory O'Keeffe
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Overworked, under-resourced, juggling complex legal challenges? If this sounds familiar, Beyond The Fine Print is the podcast for you. Managing high-stakes decisions on tight deadlines leads to stress and burnout, and keeping up with what’s coming next in law and the world of tech can feel like a full-time job in itself. Beyond The Fine Print cuts through the noise, delivering digestible insights on legal trends and developments in tech while breaking through the jargon. I’m your host, Rory O’Keeffe and each episode I’ll be bringing you a conversation with a thought leader in the space. This is the tech law podcast designed for in-house legal counsel in tech and commercial sectors, bringing you clarity on UK and European regulations, helping you feel more informed, effective and just a bit less stressed. This isn’t a legal seminar. If you want to gain real value without falling asleep, subscribe to Beyond The Fine Print on your favourite podcast platform now. Beyond The Fine Print ® 2024.

  1. JAN 29

    The Biggest Cyber Security Risk And How To Fix It With Robert Siciliano

    It’s easy to leave cyber security in the hands of the IT department. And to blame the hackers when a breach does happen. But there’s usually a human in the middle of it all. And that’s where the risk usually sits. I know I’ve clicked on things I shouldn’t have before… And that’s why, in this episode, we’re joined by Robert Siciliano - security analyst, author, media voice, and one of the most recognisable educators in personal and corporate cyber security protection. Robert has appeared on CNN, MSNBC, Fox News, CNBC, The Today Show, and is quoted in outlets like USA Today and Forbes. He also delivers security awareness training to organisations to help them to get their people to care about security. We explore why typical workplace security training often fails, how to build what Robert calls a “strategic human firewall” and how to move employees from reluctant compliance to personal investment. If you want to protect your own and build a culture that protects the people who you work with and your operations, this episode is essential. Covered in this episode: The biggest risk to cyber security.Why most cyber security training doesn’t stick.What needs to change to get employees to care about cyber security.The risks AI introduces to organisational security.Why companies resist investing in security training.The one security habit everyone needs.And more… If you got value from this episode of Beyond The Fine Print, subscribe on your favourite podcast platform so you don’t miss the next one. LEARN MORE RMOK Legal- https://www.rmoklegal.com/ CONNECT Robert Siciliano on LinkedIn - https://www.linkedin.com/in/robertsiciliano/ Rory O’Keeffe on LinkedIn - https://www.linkedin.com/in/roryokeeffe/ LISTEN Spotify - https://open.spotify.com/show/1gIj9v3yCsj5XNBbrS0byC?si=90ced509f70b4a35 Apple Podcasts - https://podcasts.apple.com/us/podcast/beyond-the-fine-print/id1826498926 YouTube - https://www.youtube.com/@BeyondTheFinePrint/

    49 min

  2. JAN 1

    Stop Wasting Money on Legal Tech! How to Get Rollouts Right with Merlin Beyts

    In-house legal teams are constantly under pressure to move fast and adopt AI, but rushing into new tech can be a fast track to wasted time and money. In this episode, we’re joined by Merlin Beyts, Content Director at LegalTechTalk, one of the biggest legal tech conferences around. Merlin sits at the intersection of legal and technology, asking the blunt questions lawyers often avoid.  We unpack the real reason why so many digital transformations fail, and how to ensure your tech implementations aren’t a wasted endeavour. Merlin uncovers the hidden signals that a team isn’t ready for more tech and the specific questions every legal leader should ask before rolling out AI. If you're about to pull the trigger on another tool, listen to this first - it might just save you a lot of time and money. Covered in this episode: How to avoid ‘shiny object syndrome’.When not to implement new tech.What sets successful tech rollouts apart from the flops.How to actually get ROI from a digital transformation.Why in-house teams experience buyers’ remorse after implementing tech solutions.The questions legal teams must answer before adopting AI.The truth about whether AI is coming for legal jobs.And more… If you got value from this episode of Beyond The Fine Print, subscribe on your favourite podcast platform so you don’t miss the next one. LEARN MORE LegalTechTalk - https://www.legaltech-talk.com/  RMOK Legal- https://www.rmoklegal.com/  CONNECT Merlin Beyts on LinkedIn - https://www.linkedin.com/in/merlin-beyts-652ab0168/  Rory O’Keeffe on LinkedIn - https://www.linkedin.com/in/roryokeeffe/  LISTEN Spotify - https://open.spotify.com/show/1gIj9v3yCsj5XNBbrS0byC?si=90ced509f70b4a35  Apple Podcasts - https://podcasts.apple.com/us/podcast/beyond-the-fine-print/id1826498926  YouTube - https://www.youtube.com/@BeyondTheFinePrint/

    53 min

  3. 12/18/2025

    How To Stop Being The “Department of NO” And Earn Trust At The Leadership Table with Dr. Heidi Gardner

    If you want to move beyond being seen as the department of “no,” this conversation is for you. Most legal teams are fighting a similar battle. They want influence, they want trust, and they want a seat at the strategy table. But siloed cultures and broken communication keep pulling them back. In this episode, we’re joined by Dr. Heidi Gardner, a force in the world of collaboration and leadership. Heidi is a Distinguished Fellow at Harvard Law School and CEO of research/advisory firm, Gardner & Co. Heidi also has had two Washington Post best sellers, just to name a few things that make this conversation not to be missed… When it comes to understanding how professionals can stop tripping over silos and start working smarter, together, Heidi is the real deal. So if you want to step into the role of strategic collaborator, who shapes the direction of the business, don’t miss this episode. Covered in this episode: How in-house lawyers can flip the narrative and become growth enablers.The causes behind mistrust between legal departments and the rest of the business.Turning “no” into a tool for alignment rather than friction.Communicating legal advice in a way that influences decisions.Translating legal risks into strategic value.Building trust across departments.Future-proofing legal teams.The surprising way AI can strengthen collaboration inside legal teams.And more… If you got value from this episode of Beyond The Fine Print, subscribe on your favourite podcast platform so you don’t miss the next one. LEARN MORE RMOK Legal- https://www.rmoklegal.com/  CONNECT Dr. Heidi Gardner on LinkedIn - https://www.linkedin.com/in/heidi-k-gardner-ab5b825  Rory O’Keeffe on LinkedIn - https://www.linkedin.com/in/roryokeeffe/  LISTEN Spotify - https://open.spotify.com/show/1gIj9v3yCsj5XNBbrS0byC?si=90ced509f70b4a35  Apple Podcasts - https://podcasts.apple.com/us/podcast/beyond-the-fine-print/id1826498926  YouTube - https://www.youtube.com/@BeyondTheFinePrint/

    51 min

  4. 12/04/2025

    Every Lawyer Needs To Do THIS. We Cut Contract Cycle Time By 40%! with Sarah Derbyshire

    Legal departments need to evolve fast, and it’s not just AI that’s applying the pressure. In this episode, we’re joined by Sarah Derbyshire, General Counsel at Baringa. Sarah is a calm and collected, yet fiercely driven legal leader who’s built legal functions from scratch, helped pilot AI effectively, and co-founded a career-shaping network for in-house lawyers. Sarah’s career looks more squiggly than a game of snakes and ladders, and that’s part of what makes her so effective. We dig deep into how Sarah was able to cut contract cycle time by 40% in her first year at Baringa, the approach she uses to turn resistance into applause, and the key to implementing change without causing chaos. This is for anyone working within a legal department who wants to have more of an impact and keep up, without burning out. Covered in this episode: How Sarah reduced contract cycle time at Baringa by 40%.How to implement change in a way that creates minimum chaos.The one thing every lawyer needs to do with regards to AI.Understanding needs vs wants with AI.The benefits of a squiggly career.How Sarah went from hating networking to co-founding a thriving network.What makes a leader in modern legal teams?Why compliance isn’t only legal’s responsibility.And more… If you got value from this episode of Beyond The Fine Print, subscribe on your favourite podcast platform so you don’t miss the next one. LEARN MORE RMOK Legal- https://www.rmoklegal.com/  CONNECT Sarah Derbyshire on LinkedIn - https://www.linkedin.com/in/sarah-derbyshire-aa4a5684/  Rory O’Keeffe on LinkedIn - https://www.linkedin.com/in/roryokeeffe/  LISTEN Spotify - https://open.spotify.com/show/1gIj9v3yCsj5XNBbrS0byC?si=90ced509f70b4a35  Apple Podcasts - https://podcasts.apple.com/us/podcast/beyond-the-fine-print/id1826498926  YouTube - https://www.youtube.com/@BeyondTheFinePrint/

    39 min

  5. 11/20/2025

    Inside the Legal Strategy Powering the World’s Boldest Ads

    You can’t scroll past it, mute it, or ad-block it. Out-of-home advertising is evolving quickly, with head-turning billboards, bus stops and spectacular stunts taking over headlines, as organisations seek to stand out in a crowded marketplace. But the legal questions behind those dazzling digital displays are just as complex as the technology powering them. In this episode, I’m joined by Yvonne Fern, General Counsel at Talon, who’s steering legal strategy in one of the most dynamic corners of advertising. With experience at BBC and Deutsche Telekom, Yvonne brings a sharp legal and commercial lens to everything from AI liability to ESG compliance. For in-house lawyers, this conversation is packed with insight on balancing priorities, building boundaries and keeping pace with a rapidly changing industry. Covered in this episode: The legal and ethical challenges in ad tech and out-of-home advertising.Navigating AI liability.The rise of ESG compliance and how critical it will become.Setting boundaries as an in-house lawyer.The secret to smoother negotiations.Is AI a legal lifeline or a liability?And more… If you got value from this episode of Beyond The Fine Print, subscribe on your favourite podcast platform so you don’t miss the next one. LEARN MORE RMOK Legal- https://www.rmoklegal.com/  CONNECT Yvonne Fern - https://www.linkedin.com/in/yfern/  Rory O’Keeffe on LinkedIn - https://www.linkedin.com/in/roryokeeffe/  LISTEN Spotify - https://open.spotify.com/show/1gIj9v3yCsj5XNBbrS0byC?si=90ced509f70b4a35  Apple Podcasts - https://podcasts.apple.com/us/podcast/beyond-the-fine-print/id1826498926  YouTube - https://www.youtube.com/@BeyondTheFinePrint/

    41 min

  6. 11/06/2025

    Are We Training The Lawyers of the Future or Programming Compliance Bots?

    Are we preparing the next generation of lawyers for the world that’s coming, or the one that’s already been and gone? In this episode, we’re joined by Professor Richard Ashcroft, Executive Dean at City Law School, City St George's, University of London, a bioethicist, and former Alan Turing Fellow. Richard has spent his career navigating the crossroads of law, ethics, and technology, and now he’s helping shape how tomorrow’s lawyers are trained to lead and judge. With AI tools taking root within universities, opportunities and risks both come with it. Richard has a unique perspective as an academic leader, which he shares with us. We dive deep into what ethical leadership looks like in the age of AI and whether legal education is evolving fast enough to keep pace with disruption. This conversation might just make you rethink how we train and trust legal minds… Covered in this episode: Is legal education keeping pace with AI disruption?Is AI doing more harm or good for the legal profession?The mindset lawyers need to thrive in an AI-powered world.How law students are actually using AI tools today.Why the law’s fluid nature clashes with the rigidity of LLMs.Why human creativity in law can’t be automated.Building the future legal workforce.And more… If you got value from this episode of Beyond The Fine Print, subscribe on your favourite podcast platform so you don’t miss the next one. LEARN MORE RMOK Legal- https://www.rmoklegal.com  CONNECT Richard Ashcroft on LinkedIn - https://www.linkedin.com/in/richard-ashcroft-1834736/  Rory O’Keeffe on LinkedIn - https://www.linkedin.com/in/roryokeeffe/  LISTEN Spotify - https://open.spotify.com/show/1gIj9v3yCsj5XNBbrS0byC?si=90ced509f70b4a35  Apple Podcasts - https://podcasts.apple.com/us/podcast/beyond-the-fine-print/id1826498926  YouTube - https://www.youtube.com/@BeyondTheFinePrint/

    1 hr

  7. 10/23/2025

    A Lawyer’s Guide To Finding Your Identity & Reinventing Yourself

    What happens when the job title you’ve built your identity around suddenly disappears? For many lawyers, redundancy (or other kinds of career shifts) can feel like losing a part of yourself. But leadership coach, Daryl Seager, who joins me on this episode tells a different story. Daryl has helped over 2500 leaders across 20 countries reclaim their confidence, clarity and voice. And he brings us a reminder that what we do isn’t who we are. If you’re facing a redundancy, or career panic of any sort, this episode will help you to start taking the right steps towards discovering what really matters to you, and how to many is a part of your life. Covered in this episode: How to rebuild your identity after losing a role.The ‘three lists’ strategy for figuring out who you are beyond your job.The impact of AI and tech advancements on finding a new path.The ‘small steps’ approach to start moving forward today.How to hold yourself accountable when starting over.Why your title doesn’t define your worth.And more… If you got value from this episode of Beyond The Fine Print, subscribe on your favourite podcast platform so you don’t miss the next one. LEARN MORE Daryl Seager - https://darylseager.com/  RMOK Legal - https://www.rmoklegal.com/  CONNECT Daryl Seager on LinkedIn - https://linkedin.com/in/darylseager-leadershipcoach  Rory O’Keeffe on LinkedIn - https://www.linkedin.com/in/roryokeeffe/  LISTEN Spotify - https://open.spotify.com/show/1gIj9v3yCsj5XNBbrS0byC?si=90ced509f70b4a35  Apple Podcasts - https://podcasts.apple.com/us/podcast/beyond-the-fine-print/id1826498926  YouTube - https://www.youtube.com/@BeyondTheFinePrint/

    45 min

  8. 10/09/2025

    How To Build The Right Legal Tech Stack On A Budget with Jon Bartman

    With thousands of legal tech options on the market (and more popping up every day), deciding what’s right for your in-house legal team can be overwhelming. In-house teams are facing a compliance crunch with AML reforms, AI regulations, ESG mandates and more, and piling on a plethora of platforms to peruse (and finding one that’s within budget), is a mighty task in itself. That’s why, in this episode, we’re joined by Jon Bartman, Co-Founder of The Law Tech Consultancy. Jon has made a career of cutting through the noise by helping legal teams avoid pitfalls, stretch their budgets, and choose tech that actually works and scales. If you’re drowning in tech options to implement into your in-house team, this conversation will help you separate hype from what actually works, and how to keep your head while doing so. Covered in this episode: How to evaluate legal tech without falling for marketing hype.The blind spots most in-house teams miss when implementing new systems.What makes a legal tech stack scalable?How to stretch your budget and punch above your weight.Where AI should and shouldn’t fit into your legal tech stack.The qualities lawyers need today to thrive.And more… If you got value from this episode of Beyond The Fine Print, subscribe on your favourite podcast platform so you don’t miss the next one. LEARN MORE RMOK Legal - https://www.rmoklegal.com/  CONNECT Jon Bartman on LinkedIn - https://www.linkedin.com/in/jon-bartman-4578777/  Rory O’Keeffe on LinkedIn - https://www.linkedin.com/in/roryokeeffe/  LISTEN Spotify - https://open.spotify.com/show/1gIj9v3yCsj5XNBbrS0byC?si=90ced509f70b4a35  Apple Podcasts - https://podcasts.apple.com/us/podcast/beyond-the-fine-print/id1826498926  YouTube - https://www.youtube.com/@BeyondTheFinePrint/

    50 min
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Overworked, under-resourced, juggling complex legal challenges? If this sounds familiar, Beyond The Fine Print is the podcast for you. Managing high-stakes decisions on tight deadlines leads to stress and burnout, and keeping up with what’s coming next in law and the world of tech can feel like a full-time job in itself. Beyond The Fine Print cuts through the noise, delivering digestible insights on legal trends and developments in tech while breaking through the jargon. I’m your host, Rory O’Keeffe and each episode I’ll be bringing you a conversation with a thought leader in the space. This is the tech law podcast designed for in-house legal counsel in tech and commercial sectors, bringing you clarity on UK and European regulations, helping you feel more informed, effective and just a bit less stressed. This isn’t a legal seminar. If you want to gain real value without falling asleep, subscribe to Beyond The Fine Print on your favourite podcast platform now. Beyond The Fine Print ® 2024.

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