Today, we speak with Jack Shepherd.

Jack started out as a restructuring lawyer at Freshfields before moving into legal tech via the firm’s in-house innovation team. He now works at iManage - the US-based legal tech company behind the document management system used by most major law firms.

Jack is a well-known voice in the legal tech space and a regular speaker at industry conferences. He often takes a refreshingly contrarian view on AI - not for the sake of it, but because, having been a practising lawyer, he actually understands how lawyers work day-to-day.

In this conversation, Jack shares insights on the evolving landscape of legal AI and technology. He discusses his transition from practising law to working in legal tech, emphasising the importance of understanding the pain points of lawyers and how technology can address these issues.

Jack critiques the current hype around AI, advocating for a more practical approach that focuses on enhancing the legal profession rather than replacing it. He also highlights the significance of project management skills in law, the ROI of legal AI tools and offers advice for lawyers looking to transition into legal tech. The discussion ends with thoughts on future-proofing legal careers and the traits of successful junior lawyers.

Chapters

00:50 From Lawyer to Legal Tech

03:33 Understanding Legal AI: Current Landscape

06:20 The Role of AI in Legal Work

09:25 AI's Impact on Junior Lawyers

12:19 Identifying Pain Points in Legal Practice

15:25 The Future of Law Firms and SaaS

18:40 iManage: Revolutionising Document Management

27:46 Cultural Challenges in Legal Tech Adoption

28:27 Understanding ROI in Legal AI Tools

31:18 Strategic Technology Procurement in Law Firms

34:41 The Role of AI in Law Firm Marketing

36:38 Innovative Legal AI Tools to Watch

40:19 Future-Proofing Legal Careers

40:43 Advice for Lawyers Transitioning to Legal Tech

44:08 Traits of Successful Lawyers

49:25 Recommended Reads for Legal Professionals

About Non-Billable

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What lawyers really want from AI: ex-Freshfields lawyer turned legal tech leader on what we’re getting wrong

The Non-Billable Podcast

What lawyers really want from AI: ex-Freshfields lawyer turned legal tech leader on what we’re getting wrong