The LOPSided Podcast

In episode twenty five, the LOPSided Podcast host John O'Donoghue interviews Jack Tuttle, Director of the Center of Excellence for Continuous Improvement at Proskauer Rose. John and Jack discuss driving value for LegalOps in a changing legal market. They explore how value is created through legal project management from a business stakeholder perspective, the approaches that have proven most effective in Jack's experience, what law firms are prioritising right now, the challenges they’re facing, and how to secure meaningful senior leadership buy‑in. IMPORTANT NOTE: The views and furthermore all views shared by the presenters and guests of this podcast in no way reflect the views of current nor previous companies that employ them. All views and expressions reflect personal views and not those of any affiliated businesses. Listeners should consider these discussions as personal perspectives and not official stances endorsed by any organisation. Always seek professional advice and verify information independently. Explore the podcast

In episode twenty four, the LOPSided Podcast host John O'Donoghue interviews Hayleigh Lippiatt-Durnell, Head of Legal Project Management and Legal Process Improvement at Charles Russell Speechlys. They discuss the role of Legal Operations in law firms and how to get buy-in and integrate LegalOps best practices into a firms culture and workflows. They touch on key topics including: Which cultural or structural differences influence the effective implementation of Legal Operations. The biggest cultural barriers you've encountered when introducing new services or ways of working. The role of partners and senior leadership in shaping a firm culture that embraces Legal Operations. Ensuring your LegalOps teams are being asked to deliver the right type of work. Balancing consistency in delivering LegalOps products and services with the need for bespoke solutions to particular problems. Displaying a tangible ROI for the investment the firm is making. The impact of GenAI on LPM delivery, and the legal industry more generally. IMPORTANT NOTE: The views and furthermore all views shared by the presenters and guests of this podcast in no way reflect the views of current nor previous companies that employ them. All views and expressions reflect personal views and not those of any affiliated businesses. Listeners should consider these discussions as personal perspectives and not official stances endorsed by any organisation. Always seek professional advice and verify information independently.

Episode twenty three is the final episode in our #TransformingLegal mini-series. The LOPSided Podcast host John O'Donoghue interviews Edward Bird, the CEO of Solomonic, the worlds leading litigation analytics and intelligence platform. John and Edward navigate three key topics: What Is Solomonic? And why Litigation Analytics matter before action even begins, and why early strategic insight is increasingly decisive. Real-World Scenarios: How better information drives better decisions, exploring concrete examples where deeper analytics reshape strategy, risk, and outcomes. The Future: When data becomes the default lens for Litigation Strategy, the next frontier - how analytics, forecasting, and behavioural insights will reshape the competitive landscape. IMPORTANT NOTE: The views and furthermore all views shared by the presenters and guests of this podcast in no way reflect the views of current nor previous companies that employ them. All views and expressions reflect personal views and not those of any affiliated businesses. Listeners should consider these discussions as personal perspectives and not official stances endorsed by any organisation. Always seek professional advice and verify information independently.

Episode twenty two is the penultimate in our #TransformingLegal mini-series. The LOPSided Podcast host John O'Donoghue interviews Alex Fortescue-Webb, Head of UKI and legal engineering at Legora. John and Alex navigate three key topics:. Why Legal AI Gets Stuck in Pilot Mode? What misconceptions do firms often have when they start experimenting with legal AI? From Legora’s vantage point, what are the most common operational blockers - tech, culture, workflow, or something else? What Successful AI Rollouts Actually Look Like? What separates firms that scale AI successfully from those that don’t? Which KPIs or metrics are firms actually using to measure success-and which ones don’t matter as much as people think? How Scaling AI Will Shape the Future of LegalOps? Will AI adoption force law to modernise its operational foundations? What is it that firms must get right today to be ready for the next wave of AI-powered practice? IMPORTANT NOTE: The views and furthermore all views shared by the presenters and guests of this podcast in no way reflect the views of current nor previous companies that employ them. All views and expressions reflect personal views and not those of any affiliated businesses. Listeners should consider these discussions as personal perspectives and not official stances endorsed by any organisation. Always seek professional advice and verify information independently.

Episode twenty one is the third in our #TransformingLegal mini-series. The LOPSided Podcast host John O'Donoghue interviews former Director of LPM at Clifford Chance, and founder of Telescope, Aaran Scott. The topic is LPM by Design - Engineering Legal Delivery at scale. We focus on three key areas: Then and Now: How legal work has historically been delivered and why it’s no longer enough, and why the complexity of modern legal work has outgrown informal, personality-driven project handling. Platformisation: Designing legal delivery at scale, and why scaling legal delivery demands structure, platforms, playbooks, and cross-functional orchestration - not just good project managers. The Future of Legal Delivery: Designing for adaptability, not just efficiency, and why the future of legal service is engineered - designed for consistency, scalability, and continuous improvement. IMPORTANT NOTE: The views and furthermore all views shared by the presenters and guests of this podcast in no way reflect the views of current nor previous companies that employ them. All views and expressions reflect personal views and not those of any affiliated businesses. Listeners should consider these discussions as personal perspectives and not official stances endorsed by any organisation. Always seek professional advice and verify information independently.

Episode twenty is the second in our #TransformingLegal mini-series. The LOPSided Podcast host John O'Donoghue interviews co-founder of Elevate Legal John Croft. John and John discuss the shifting landscape in legal service procurement, the fast evolving legal ecosystem, and how ALSPs are helping to reshape effective and efficient delivery models. IMPORTANT NOTE: The views and furthermore all views shared by the presenters and guests of this podcast in no way reflect the views of current nor previous companies that employ them. All views and expressions reflect personal views and not those of any affiliated businesses. Listeners should consider these discussions as personal perspectives and not official stances endorsed by any organisation. Always seek professional advice and verify information independently.

Episode nineteen is the first in our enabling #TransformingLegal mini-series. The LOPSided Podcast host John O'Donoghue interviews leading consultant and renowned Legal Transformation expert Justin North. The conversation focuses on three critical components: The Human Side of Transformation: Psychology, Behaviour and Culture in Legal Ops. Grounding transformation in behaviour, culture, and leadership. AI & Legal Tech: Adoption vs. Reinvention: Exploring the build-vs-buy debate, the future of AI adoption, and how firms can integrate tech effectively. Governing Technology & Change: Pragmatism, Risk and Sustainable Transformation. We discuss governance, risk appetite, approvals, and how to ensure transformation sticks. IMPORTANT NOTE: The views and furthermore all views shared by the presenters and guests of this podcast in no way reflect the views of current nor previous companies that employ them. All views and expressions reflect personal views and not those of any affiliated businesses. Listeners should consider these discussions as personal perspectives and not official stances endorsed by any organisation. Always seek professional advice and verify information independently.

Episode eighteen is a first on the podcast, LOPSided host John O'Donoghue interviews his first non-human guest as we navigate a critical question: what happens when AI takes on business development in law firms? To find out, John interviewed Leonard, an agentic AI developed by Legal Engine, a UK-based legal tech company building AI tools designed to help firms automate operations, scale efficiently, and win more work. We tackle the big questions: Is this the future of BD, or the end of the human touch? Is Leonard driving real innovation - or just delivering a slick, overhyped sales pitch in an AI wrapper? Either way, the machines have entered the chat - and they’re not just taking notes... IMPORTANT NOTE: The views and furthermore all views shared by the presenters and guests of this podcast in no way reflect the views of current nor previous companies that employ them. All views and expressions reflect personal views and not those of any affiliated businesses. Listeners should consider these discussions as personal perspectives and not official stances endorsed by any organisation. Always seek professional advice and verify information independently.

In episode seventeen, LOPSided Podcast host John O'Donoghue is joined by Dan Winterfeldt (Regional GC at Jefferies). In a continued celebration of PRIDE, we're joined by trailblazers transforming the world of legal operations. On this episode, we explore the evolution of the GC role into an operational thought leader - aligning legal with business strategy through dashboards, KPIs, and cross-functional partnerships. Topics include: Dan's personal journey. Law Firm Collaboration: Lightening the Load and Adding Real Value. Trust and Transparency in Modern Legal Leadership. Transformation through Ops and Innovation Inclusive Leadership and LGBTQ+ Representation Mythbusters IMPORTANT NOTE: The views and furthermore all views shared by the presenters and guests of this podcast in no way reflect the views of current nor previous companies that employ them. All views and expressions reflect personal views and not those of any affiliated businesses. Listeners should consider these discussions as personal perspectives and not official stances endorsed by any organisation. Always seek professional advice and verify information independently.

In episode sixteen, The LOPSided Podcast host John O'Donoghue is joined by Chris Hanley (Head of Pricing and Commercial at Ashurst). In celebration of PRIDE Month, we're joined by trailblazers transforming the world of legal operations - Chris is not only pioneering smarter, more equitable pricing models, but also leading with authenticity and courage. Today, we explore how innovation and identity intersect in the legal industry, and what it means to price with pride. Topics include: - Chris' personal journey. - Innovation in Legal Pricing. - What clients want, and what value looks like. - Are AFAs even a thing anymore? - Advice and forward-thinking. - PRIDE, Inclusion & Cultural Change IMPORTANT NOTE: The views and furthermore all views shared by the presenters and guests of this podcast in no way reflect the views of current nor previous companies that employ them. All views and expressions reflect personal views and not those of any affiliated businesses. Listeners should consider these discussions as personal perspectives and not official stances endorsed by any organisation. Always seek professional advice and verify information independently.

In episode fifteen, The LOPSided Podcast host John O'Donoghue is joined by Karen Rayment (Founder and CEO of Marble Grange Recruitment). In celebration of PRIDE Month, we're joined by a trailblazers transforming the world of legal operations. For Karen, that's not only by pioneering smarter, more equitable recruitment, but also by leading with authenticity and courage. Today, we explore how talent acquisition and identity intersect in the legal industry, and what it means to recruit with pride. Topics include: Karen's personal journey. Spotting & Hiring Legal Ops Talent. The Talent Equation: Skills, Strategy & Self-Identity. Retention & Development. The future of talent in Legal Ops. PRIDE, Inclusion & Cultural Change IMPORTANT NOTE: The views and furthermore all views shared by the presenters and guests of this podcast in no way reflect the views of current nor previous companies that employ them. All views and expressions reflect personal views and not those of any affiliated businesses. Listeners should consider these discussions as personal perspectives and not official stances endorsed by any organisation. Always seek professional advice and verify information independently.

In episode fourteen, The LOPSided Podcast host John O'Donoghue is joined by Kevin Wheeler (Founder and CEO of Wheeler Associates). Kevin and John touch on growing key clients and the low-hanging fruit of BD, the role of Legal Operations on pitches and delivering work, and why Law Firms need to stop pitching for everything! Topics include: Growing key client relationships. The low hanging fruit in BD. Why law firms should stop pitching for everything. The demand for LegalOps services on pitches. MythBusters - Separating fact from fiction. IMPORTANT NOTE: The views and furthermore all views shared by the presenters and guests of this podcast in no way reflect the views of current nor previous companies that employ them. All views and expressions reflect personal views and not those of any affiliated businesses. Listeners should consider these discussions as personal perspectives and not official stances endorsed by any organisation. Always seek professional advice and verify information independently.

In episode thirteen, The LOPSided Podcast host John O'Donoghue is joined by Kevin O'Sullivan (Global Director of Legal Project Management at Baker McKenzie). Kevin and John cover how to set LPM functions up for success, how to win hearts and minds with internal stakeholders and external clients, creating FOMO between lawyers, staying ahead of an ever-evolving LPM and broader Legal Operations market, and what its like managing the largest Legal Project Management function in the Legal industry. Topics covered include: Winning Hearts: Building relationships and culture. Winning Minds: Mindset and knowledge-sharing. Winning Mandates: Gaining organisational buy-in. Tools, techniques, and practical insights. Overcoming challenges. The future of LPM. MythBusters: Separating fact from fiction. IMPORTANT NOTE: The views and furthermore all views shared by the presenters and guests of this podcast in no way reflect the views of current nor previous companies that employ them. All views and expressions reflect personal views and not those of any affiliated businesses. Listeners should consider these discussions as personal perspectives and not official stances endorsed by any organisation. Always seek professional advice and verify information independently.

In episode twelve, The LOPSided Podcast host John O'Donoghue is joined by Amanda Chaboryk (Head of Legal Data and Systems at PwC). Amanda and John discuss how law firms are navigating the GenAi evolution and discuss practical deployment in legal service delivery. Topics include: How lawyers can work more effectively alongside Generative AI, and how it changes the role of legal professionals. The emerging trends in Generative AI that could have a major impact on the legal sector over the next five years, if not sooner! The main challenges or limitations in implementing Generative AI in legal services today (accuracy, transparency, trust). Key ethical considerations when implementing Generative AI in legal services. The safeguards are necessary to prevent misuse of AI-generated content in legal documents, especially in terms of accuracy and responsibility. IMPORTANT NOTE: The views and furthermore all views shared by the presenters and guests of this podcast in no way reflect the views of current nor previous companies that employ them. All views and expressions reflect personal views and not those of any affiliated businesses. Listeners should consider these discussions as personal perspectives and not official stances endorsed by any organisation. Always seek professional advice and verify information independently.

In episode eleven, The LOPSided Podcast host John O'Donoghue is joined by Chantelle Jalland (Associate Director of Digital Services and e-discovery at Ashurst Advance). Chantelle and John discuss how law firms are using e-discovery systems, not just as a tool for litigation, but as a strategic offering for clients. This includes how firms are leveraging e-discovery tools to manage risk, ensure compliance, or even assist with regulatory investigations. We also deep dive into the increasing market impact and disruption GenAI. Topics include: Introduction to E-Discovery. The evolution of Legal Tech. Procuring and integrating new technology. LegalOps in e-Discovery: pricing and cost management. The future of e-discovery. MythBusters: Separating fact from fiction. IMPORTANT NOTE: The views and furthermore all views shared by the presenters and guests of this podcast in no way reflect the views of current nor previous companies that employ them. All views and expressions reflect personal views and not those of any affiliated businesses. Listeners should consider these discussions as personal perspectives and not official stances endorsed by any organisation. Always seek professional advice and verify information independently.

In episode ten, The LOPSided Podcast host John O'Donoghue is joined by Luc Baldwin (Leading expert in Legal Operations recruitment) to discuss how to recruit, retain, and develop talent in a competitive Legal Operations landscape. The podcast covers key topics including: Recruiting LegalOps Talent: How would you describe the current landscape for recruiting LegalOps talent? Are there enough skilled candidates to meet the demand? In which areas of LegalOps expertise are you seeing an increasing demand for experienced candidates? What key skills and attributes are businesses looking for when recruiting for a LegalOps role? Are there particular qualifications or experiences that make a candidate stand out for LegalOps roles? What are the most common misconceptions or misunderstandings candidates have about LegalOps roles? How do you ensure a candidate is the right fit for both the technical and cultural aspects of a particular law firm or team? Retaining LegalOps talent: The opposite side of the coin – What do you think are the key factors that cause top LegalOps talent to leave an organisation? Once a LegalOps professional is hired, what strategies should employers use to ensure long-term retention? How important is career progression and professional development for LegalOps employees? Or are most moves motivated by salaries and bonuses? What role do workplace culture and team dynamics play in retaining LegalOps professionals? Also, remote work and flexible working arrangements Developing LegalOps talent What kind of training and development programmes are most effective for LegalOps professionals? How do you see the future evolution of the LegalOps profession, and how can professionals stay ahead of the curve? In terms of continuous learning, which areas do LegalOps professionals need to focus on to stay competitive? Are there any emerging trends in LegalOps that professionals should be aware of, especially in terms hiring habits of businesses? What advice would you give to someone starting their career in LegalOps to ensure they stay relevant and grow within the field? IMPORTANT NOTE: The views and furthermore all views shared by the presenters and guests of this podcast in no way reflect the views of current nor previous companies that employ them. All views and expressions reflect personal views and not those of any affiliated businesses. Listeners should consider these discussions as personal perspectives and not official stances endorsed by any organisation. Always seek professional advice and verify information independently.

In episode nine, LOPSided Podcast host John O'Donoghue is joined by Richard Burcher (Leading expert in law firm pricing) to discuss developing trends and challenges in the ever evolving world of law firm pricing. The podcast covers key topics including: What are the biggest pricing related challenges in law firms right now? Are pricing experts reporting back on clients changing needs and behaviours? How can law firms ensure they are setting their pricing functions up for success? What does a good law firm pricing strategy look like? Navigating the challenges in how law firms pricing legal tech and AI. The tension between the billable hour and technological efficiency. Are we at a point where the industry has outgrown the billable hour model? Can law firms price AI & Tech in the same way as conventional legal services? Are law firms doing enough to think about how to price tech focussed services? Are law firms without pricing functions at risk of missing out on new opportunities? IMPORTANT NOTE: The views and furthermore all views shared by the presenters and guests of this podcast in no way reflect the views of current nor previous companies that employ them. All views and expressions reflect personal views and not those of any affiliated businesses. Listeners should consider these discussions as personal perspectives and not official stances endorsed by any organisation. Always seek professional advice and verify information independently.

In episode eight, LOPSided Podcast host John O'Donoghue is joined by Alex Liddle (Director of sales at PwC) to discuss what not to do when engaging clients, and how to build deep and long term relationships by avoiding common pitfalls. The podcast covers key topics including: What is it about law firms that clients complain about the most? Which aspects of legal services they find most frustrating? Which fee structures tend to cause the most frustration for clients? Are clients generally receptive to leveraging LegalOps capabilities? The particular sectors or markets, where clients feel their needs are hardly ever addressed. Any trends directly linking client dissatisfaction to particular practices. How clients are responding to law firms looking to leverage technology on their matters. Three key pieces of pitching advice for law firms. IMPORTANT NOTE: The views and furthermore all views shared by the presenters and guests of this podcast in no way reflect the views of current nor previous companies that employ them. All views and expressions reflect personal views and not those of any affiliated businesses. Listeners should consider these discussions as personal perspectives and not official stances endorsed by any organisation. Always seek professional advice and verify information independently.

In episode seven, LOPSided Podcast host John O'Donoghue is joined by Shakeel Sameja (Legal Operations Manager at UBS) to discuss how Law Firms are using their Legal Operations capabilities to enhance the client value proposition. The podcast covers key topics including: How large financial institutions measure value from law firms. Whether clients are increasingly partnering with their panel firms LegalOps functions. The process within large banks for procuring LegalOps support from law firms. The emergence and adoption of GenAi through an in-house lens. Leveraging e-billing data to obtain critical insights on law firm performance. How to encourage law firms to have better time recording disciplines. The one thing that all law firms could be doing better. How clients encourage honest pricing as opposed to a "race to the bottom" approach. Three pieces of advice for in-house teams looking to build a LegalOps function. Whether you need to be a multi-disciplinarian expert to work in-house in LegalOps. Whether procuring legal services is no longer just about who provides the best legal advice. Whether RFP responses are way too long and don't actually tell clients the things they want to know! IMPORTANT NOTE: The views and furthermore all views shared by the presenters and guests of this podcast in no way reflect the views of current nor previous companies that employ them. All views and expressions reflect personal views and not those of any affiliated businesses. Listeners should consider these discussions as personal perspectives and not official stances endorsed by any organisation. Always seek professional advice and verify information independently.

In episode six, LOPSided Podcast host John O'Donoghue is joined by Steve Jones (Managing Director of M&A, Litigation and Tax at AJ Gallagher) to discuss which insurance backed solutions are available in the market, how they are helping law firms and clients to consider risk in a different way, and the vital role that Legal Operations professionals play in getting these solutions from theory to application. The podcast covers key topics including: 1. What are the main insurance backed products in the market and what do they do? 2. Satisfying the lawyers professional obligation to offer ATE insurance to their clients. 3. How these risk transfer solutions can also be used on defendant/respondent cases. 4. What are Law Firms or clients actually buying? 5. The insurance backed solutions that are experiencing the most growth. 6. Law firms missing the opportunity to get ahead? 7. How many firms are joining the dots on pricing, AFAs and commercial risk transfer options? 8. Understanding more about Judgment Preservation Insurance (JPI) a product we're hearing lots about. 9. Understanding how litigation funder "multiples" work. 10. Leveraging LegalOps professional to identify the commercial drives and manager client expectations. 11. How the early adopters are reaping the benefits of this as a USP. 12. Is legal expense insurance a disruptor or facilitator for Litigation Funding? 13. The benefits of having an LPM acting as the conduit to all parties involved. 14. The process for pricing professional bolting insurance backed solutions onto risk based AFAs. IMPORTANT NOTE: The views and furthermore all views shared by the presenters and guests of this podcast in no way reflect the views of current nor previous companies that employ them. All views and expressions reflect personal views and not those of any affiliated businesses. Listeners should consider these discussions as personal perspectives and not official stances endorsed by any organisation. Always seek professional advice and verify information independently.