The LOPSided Podcast

The LOPSided Podcast
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Mar 1, 2026 • 55h 18min

Episode 25: Driving value for LegalOps in a changing legal market.

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
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Jan 29, 2026 • 41min

Episode 24: How to get buy-in and successfully integrate LegalOps into a firms culture and workflows.

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.
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Dec 21, 2025 • 36min

Episode 23: How Litigation Analytics Shape Cases - The Legal, Commercial and Strategic Predictability Benefits.

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.
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Dec 18, 2025 • 26min

Episode 22: Scaling AI Adoption – Beyond Pilots and Demos

In this discussion, Alex Fortescue-Webb, Head of Legal Engineering at Legora, shares insights from his journey from lawyer to AI advocate. He reveals why many legal firms remain stuck in pilot mode due to cultural resistance and unrealistic expectations of AI. Alex highlights the differences between successful and stagnant AI deployments, emphasizing the importance of clear KPIs. He also predicts that AI adoption will drive significant changes in legal operations, enhancing efficiency and service quality in the legal sector.
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Dec 17, 2025 • 33min

Episode 21: LPM By Design - Engineering Legal Delivery at Scale

Aaran Scott, former Director of Legal Project Management at Clifford Chance and founder of Telescope, dives into the evolution of legal delivery. He critiques the outdated billable hour model and highlights how AI is transforming the landscape. Aaran emphasizes the importance of structured project management over personality-driven approaches, advocating for adaptability in legal services. He outlines a scalable delivery framework and urges legal firms to focus on client expectations and technology to enhance profitability and efficiency.
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Dec 15, 2025 • 50min

Episode 20: Elevating How Law Departments Procure Legal Services - The Rise of the ALSP.

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.
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Dec 15, 2025 • 56min

Episode 19: Beyond the Tech: The Human, Operational, and Governance Realities of Legal Transformation

Justin North, a leading legal transformation expert and founder of Janders Dean, shares his extensive insights into legal innovation. He discusses the crucial role of psychology and culture in successful transformations, urging firms to understand behavior rather than blame tech or stubborn lawyers. The conversation dives into the build vs. buy dilemma in legal tech, highlighting the risks of firms acting as software developers. North also emphasizes the importance of genuine leadership support and the potential of AI across the revenue cycle, all while promoting a modernized governance approach.
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Sep 14, 2025 • 20min

Episode 18: BD Terminator - Rise of the Machines

A groundbreaking interview with an AI named Leonard explores the future of business development in law firms. Leonard shares its role in automating operations and discusses the balance between machine efficiency and the human touch. The conversation dives into the evolution of LegalOps, changing job roles, and how AI can enhance productivity while preserving essential human skills like empathy and creativity. Leonard warns that firms not embracing AI risk losing competitiveness, and advocates for value-based pricing models that focus on client outcomes.
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Sep 7, 2025 • 1h 17min

Episode 17: The GC as a LegalOps Innovator - Trust, Transparency & Transformation

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.
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Jul 2, 2025 • 44min

Episode 16: Pricing with Pride - Smarter Strategies, Stronger Values

In this insightful conversation, Chris Hanley, Head of Commercial and Pricing at Ashurst, shares his journey from retail to legal pricing. He emphasizes the need for equitable pricing strategies and discusses how authenticity can reshape workplace cultures, especially during Pride Month. Chris sheds light on evolving client expectations, the limitations of traditional hourly rates, and the future of pricing in an AI-driven world. His perspective on integrating diversity, equity, and inclusion into pricing shows how values can enhance client relationships and drive business success.

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