The LOPSided Podcast
Welcome to the LOPSided Podcast! We’re thrilled to introduce our new podcast series. This isn’t just another podcast; it’s a gateway to the minds of global leaders in the world of Legal Operations. Everything but the Law - Each episode brings you in-depth interviews with trailblazers and thought leaders from the industry. Our guests have all made significant contributions to the industry and are shaping its future. They come from diverse backgrounds and bring a wealth of experience, insights, and stories. Join us as we delve into discussions on industry developments, best practices, innovations, and the challenges that legal operations professionals face. Whether you’re a seasoned legal operations professional or just starting your journey in this field, The LOPSided Podcast is your resource for all things related to legal operations.
Episodes

Monday Apr 21, 2025
Monday Apr 21, 2025
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.

Monday Apr 21, 2025
Episode 13: Legal Project Management - Winning hearts, minds, and mandates.
Monday Apr 21, 2025
Monday Apr 21, 2025
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.

Sunday Mar 02, 2025
Episode 12: GenAI - Practical application in legal service delivery.
Sunday Mar 02, 2025
Sunday Mar 02, 2025
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.

Sunday Mar 02, 2025
Sunday Mar 02, 2025
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.

Sunday Feb 09, 2025
Episode 10: Recruiting, retaining, and developing the best LegalOps talent.
Sunday Feb 09, 2025
Sunday Feb 09, 2025
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.

Tuesday Dec 10, 2024
Episode 9: Law firm pricing - a 360 view
Tuesday Dec 10, 2024
Tuesday Dec 10, 2024
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.

Tuesday Dec 10, 2024
Episode 8: Clients don't like that - The business of relationships.
Tuesday Dec 10, 2024
Tuesday Dec 10, 2024
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.

Sunday Sep 29, 2024
Sunday Sep 29, 2024
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.

Monday Aug 26, 2024
Monday Aug 26, 2024
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.

Wednesday Aug 07, 2024
Episode 5: Navigating AI & Digital and successfully implementing strategy in law firms
Wednesday Aug 07, 2024
Wednesday Aug 07, 2024
In episode five, LOPSided Podcast host John O'Donoghue is joined by Alex Smith (Senior Director at iManage) to discuss navigating AI & Digital and successfully implementing digital strategy.
The podcast covers key topics including:
The differences between working in a law firm and in a world leading legal tech firm.
What is the main thing law firms get wrong when deciding whether to buy or build tech.
Are businesses bolting AI onto anything and everything?
Is misinformation being shared around AI in Legal, by people over-estimating their knowledge in this space?
Are law firms doing enough around responsible usage of AI
There are current trends on law firms focussing on their data, does this align with buyer habits that you're seeing in the market?
Advice for professionals tasked with procuring AI or digital tools for their firms
Getting the tech implementation team right from the outset.
Will lawyers be obsolete by 2035?
Do law firms generally have large skill and knowledge gaps when it comes to AI?
If law firms truly understood the potential of their data, would they be investing more into harnessing it to understand their business better?
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.