Jack Shepherd, a former lawyer and legal tech expert at iManage, discusses the gaps between AI promises and legal practice realities. He highlights the challenges of AI implementation, stressing the need for clear understanding and caution when adopting new technologies. Jack reveals the pitfalls of over-hyped tools and emphasizes the importance of basic data hygiene and targeted applications. He also talks about how generative AI often fails in critical legal tasks, advocating for pragmatic approaches to improve workflows and encourage knowledge-sharing among lawyers.