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

Mar 25, 2025

In this engaging conversation, Jack Shepherd, a former Freshfields lawyer now leading innovations at iManage, shares his unique insights on AI in the legal field. He emphasizes practical applications of technology that truly address lawyers' daily challenges, rather than succumbing to AI hype. Jack champions the importance of project management skills and strategic AI adoption to enhance efficiency without undermining critical thinking. He also discusses how junior lawyers can future-proof their careers in this rapidly evolving landscape.

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ANECDOTE

Jack’s Law to Legal Tech Journey

Jack Shepherd moved from law to legal tech due to his early tech interest and a lack of passion for distressed debt.
He joined Freshfields' innovation team, then transitioned to a tech role at iManage to impact law firms broadly.

INSIGHT

Legal AI Needs Real Value

Legal AI must be useful and solve lawyer pain points, not just be technology for its own sake.
Early AI excitement overlooked accuracy issues and proper fitting to legal workflows, leading to vanity projects.

INSIGHT

AI Should Assist, Not Replace

AI is better viewed as an assistant, not a junior lawyer replacement, especially for complex legal thinking tasks.
Automating thinking via AI risks degrading legal service quality where learning and engagement is vital.

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