The LOPSided Podcast

The LOPSided Podcast

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The LOPSided Podcast episodes

  • 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.
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    55 hr 18 min
  • 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:

    1. Which cultural or structural differences influence the effective implementation of Legal Operations.
    2. The biggest cultural barriers you've encountered when introducing new services or ways of working.
    3. The role of partners and senior leadership in shaping a firm culture that embraces Legal Operations.
    4. Ensuring your LegalOps teams are being asked to deliver the right type of work.
    5. Balancing consistency in delivering LegalOps products and services with the need for bespoke solutions to particular problems.
    6. Displaying a tangible ROI for the investment the firm is making.
    7. The impact of GenAI on LPM delivery, and the legal industry more generally.

      8. 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.

      42 min
    8. 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:

      1. What Is Solomonic? And why Litigation Analytics matter before action even begins, and why early strategic insight is increasingly decisive.
      2. Real-World Scenarios: How better information drives better decisions, exploring concrete examples where deeper analytics reshape strategy, risk, and outcomes.
      3. 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.

        4. 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.

        36 min
      4. Episode 22: Scaling AI Adoption – Beyond Pilots and Demos

        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:.

        1. 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?
        2. 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?
        3. 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?

          4. 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.

          27 min
        4. Episode 21: LPM By Design - Engineering Legal Delivery at Scale

          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:

          1. 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.
          2. Platformisation: Designing legal delivery at scale, and why scaling legal delivery demands structure, platforms, playbooks, and cross-functional orchestration - not just good project managers.
          3. 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.

            4. 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.

            34 min
          4. 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.

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

            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:

            1. The Human Side of Transformation: Psychology, Behaviour and Culture in Legal Ops. Grounding transformation in behaviour, culture, and leadership.
            2. AI & Legal Tech: Adoption vs. Reinvention: Exploring the build-vs-buy debate, the future of AI adoption, and how firms can integrate tech effectively.
            3. Governing Technology & Change: Pragmatism, Risk and Sustainable Transformation. We discuss governance, risk appetite, approvals, and how to ensure transformation sticks.

              4.  

              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.

              57 min
            4. Episode 18: BD Terminator - Rise of the Machines

              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.

               

              21 min
            5. 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.

                1 hr 18 min
              • Episode 16: Pricing with Pride - Smarter Strategies, Stronger Values

                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.

                45 min

              About The LOPSided Podcast

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              Welcome to the LOPSided Podcast!