Jack Shepherd – Medium

Jack Shepherd

Why I built my own personal productivity tool…

Early on in my legal career, I dropped the ball regularly. I didn’t do tasks I had promised to do. I asked questions that had already been…

7 min readMar 28, 2024

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Why I built my own personal productivity tool…

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Jack Shepherd

The importance of use cases for AI in legal and how to discover them

Comments such as “did you even speak to anyone about this”, “this just doesn’t work”, or “it’s just another IT project” are commonplace in…

12 min readJan 9, 2024

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The importance of use cases for AI in legal and how to discover them

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Jack Shepherd

Old Ways of Accessing Knowledge + Generative AI

In this article I make the argument that generative AI capabilities will complement but not replace existing methods of accessing…

5 min readDec 5, 2023

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Old Ways of Accessing Knowledge + Generative AI

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Jack Shepherd

Lawyers: how much should you rely on AI to make first drafts?

Note — this article is not really about contracts. This article is about the (in my view, rather limited) circumstances in which lawyers…

10 min readNov 1, 2023

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Lawyers: how much should you rely on AI to make first drafts?

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Jack Shepherd

What are the specific use cases for generative AI in contract drafting?

Instead of asking “what generative AI can do for contracts”, I ask “what needs to be done for contracts, and can generative AI fix it”

32 min readSep 23, 2023

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What are the specific use cases for generative AI in contract drafting?

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Jack Shepherd

Practical ways to incentivise lawyers to be more innovative

Lawyers are very busy people. When you are a practising lawyer, you often don’t have time to breathe between all the client work you are…

7 min readAug 22, 2023

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Practical ways to incentivise lawyers to be more innovative

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Jack Shepherd

Presenting unfinished legal work to clients: the minimum viable product

9 min readJul 13, 2023

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Presenting unfinished legal work to clients: the minimum viable product

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Jack Shepherd

Knowledge management and AI: a match made in heaven

7 min readJul 3, 2023

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Knowledge management and AI: a match made in heaven

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Jack Shepherd

Is it time for law to properly embrace project management?

In my years as a practising lawyer, I never once worked with a project manager. To those outside the legal industry, it might seem bizarre…

8 min readJun 1, 2023

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Is it time for law to properly embrace project management?

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Jack Shepherd

The AI Mirage in Law — Starting conversations

People working in software development are always on the lookout for ways they can optimise how they work. For example, linters are…

8 min readMay 2, 2023

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The AI Mirage in Law — Starting conversations

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Jack Shepherd

Jack Shepherd

Ex biglaw insolvency lawyer and innovation. Now legal practice lead at iManage. Interested in human side of legal tech and actually getting things used.

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