What Actually Happened When I Used AI As A Junior Associate

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Happy Sunday Reader:

It's been a few months since you've heard from me, and I owe you an explanation.

Since September, I've been completely immersed in a commercial arbitration that pulled me away from everything else - including this newsletter.

The case concluded two weeks ago, and what I learned changes everything I thought I knew about practicing law in 2025.

In this newsletter I want to share how what I learned previews the battles every business and legal practice will face over the next few years.

The Case - and the Irony

I represented a minority shareholder founder whose co-founders wanted her out - while wanting to keep using the intellectual property she'd disclosed to the company without compensating her.

IP she'd developed over decades.

While the founder never assigned her IP to the company, her co-founders believed that AI changed everything; that once information exists "out there," artificial intelligence makes it non-confidential.

Their logic?

If AI can eventually figure it out, it's not a secret worth protecting.

As a result, they were already feeding her frameworks, methodologies, and specialized knowledge into AI systems to scale and commercialize her expertise.

Without her permission.

Without compensation.

The irony here is that while I was fighting for my client's right to control how AI uses her intellectual property, I was simultaneously using AI to practice better law than I've ever practiced before.

What AI Actually Did (In Real Legal Work)

The timeline was brutal - the entire process took less than three months.

In traditional practice, that timeline would mean compromise: incomplete analysis, surface-level preparation, or burning out my team - especially if I was going up against a bigger law firm.

That's why I made a decision: use AI as my junior associate, applying everything I'd been theorizing about for months to gain access to capabilities I've never had before.

These capabilities included:

  1. Generating complete summaries of each day's hearing transcript within hours of receipt. While a junior associate would take at least eight hours to identify key testimony, contradictions and strategic implications, I was able to complete in less than two hours - with better results.
  2. Cross-referencing each witness testimony with evidence in hand to compile a credibility analysis framework. These credibility frameworks showed me exactly where witnesses were vulnerable and informed my strategy in crafting a closing statement.
  3. Building dynamic cross-examination roadmaps that evolved based on each day's testimony. When a witness said something unexpected, I had a new cross-examination strategy ready within hours.

Looking back, the real breakthrough wasn't only speed - it was depth.

With AI, I uncovered weaknesses in both my case and the Company's case that I never would have identified through traditional analysis.

Patterns emerged across hundreds of pages of testimony that human review simply misses.

Strategic options I hadn't considered became obvious when I could test them against complete information.

Put simply, I had complete confidence in my preparation. Not because I knew I'd win, but because I knew that with AI, I had the analytical capability of a ten-person BigLaw team.

The traditional solo and small firm disadvantage? It's over.

What This Means for Your Practice

Over the next few weeks, I'll break down exactly how I used AI for each phase of this arbitration. Not just the theoretical frameworks, but the workflows and tools I used in real, high-stakes litigation.

To that end, I'd love your feedback on which tools you'd be most interested in hearing about first.

Just click the picture below to complete this quick survey!

Also I'll be doing the first quarterly strategy session for 2026Q1 on Monday (December 29 at 10am).

Let's map out how you're going to integrate AI into your practice into 2026 by covering:

  • The AI tools that actually matter for lawyers (and which ones are hype)
  • How you can get started using AI this month without overwhelming yourself

Space is limited.

Lets get you ready for the first quarter of 2026.

​You can sign up for the workshop here.​

It'd be great to see you there πŸ™Œ

Questions? Reply to this email. I read every response personally.

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Have a great week,

p.s. Want a free resource to help you use AI effectively? Our Strategic AI Toolkit shows you exactly how to integrate AI tools safely into your practice, including

  • Simple rules for secure AI usage in legal practice
  • Ready-to-use prompts for client communications and task delegation
  • Complete setup guide for your AI workspace
  • Role-based prompts for different practice functions

​All you need to do is become a subscriber to our Substack.

About Lawtrepreneur

Modern legal practice requires more than just legal expertise - it demands smart systems, efficient workflows, and sustainable growth strategies.

Our mission is simple: support solo lawyers and lawyers at small law firms on their journey building sustainable practices aligned with their wellness.

Whether launching a practice or optimizing an established one, we provide ideas, resources and strategies needed to master three essential components of a thriving legal practice:

  • clear blueprints key to building a legal practice aligned with their personal priorities;
  • systems to delight clients and further practice growth; and
  • workflows to ensure smooth practice operations and minimize stress.
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πŸ’Ό 10+ Years In Legal Practice 🎯 Helps entrepreneurs & solo lawyers build modern businesses & balanced lives ✍🏽Writings about business, law, habits & tech