325: Copilot Doubt To Power

In this episode, we talk with tax litigator Brandon Siegal about why Microsoft Copilot has gone from a disappointing experiment to a genuinely useful AI tool for legal work. We unpack what changed with Microsoft's latest updates, including direct Word editing, deeper research capabilities, and new ways to connect AI with the documents and systems lawyers already use every day.

You'll also hear Brandon explain his "braiding" approach—combining multiple AI tools so they strengthen each other's output—and why he believes Google Gemini remains one of the most overlooked options for lawyers. Whether you are testing Copilot, comparing AI platforms, or building a smarter workflow, this conversation offers practical ideas for getting more value from the tools available right now.

Chapters

0:05 Copilot Skeptic To Believer
2:00 Brandon's AI Journey
7:18 Wave 3 And Word Editing
13:02 Braiding Multiple AI Tools
14:46 Deep Research And Cowork
23:54 Why Gemini Stands Out

Resource Links

• AI Lab (a weekly AI workshop for lawyers)
• LinkedIn post by attorney offering AI chatbot that protects privilege
• The Inner Circle (my online community for lawyers)
• The 80/20 Principle (my techlaw newsletter)

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