325: Copilot Doubt To Power

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Apr 14, 2026

Brandon Siegel, a Canadian tax litigator and AI-savvy law firm founder, explains why Microsoft Copilot moved from flop to useful. He talks Wave 3 Word editing, deep research and model-critique features. Brandon outlines his “braiding” method of combining multiple LLMs and argues Google Gemini is an underrated workhorse for long-doc legal drafting.

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ANECDOTE

How One SHRED Case Turned Brandon Into An AI Believer

Brandon Siegel first used ChatGPT to simplify a PhD-level expert explanation into a first-year university level summary for a SHRED tax pleading.
The expert confirmed the simplification was accurate, which convinced Brandon AI would be central to his practice.

INSIGHT

Copilot Now Edits Word Directly

Wave 3 adds agentic editing so Copilot can directly edit Word documents rather than only chat beside them.
Brandon recommends enabling Track Changes because Copilot sometimes alters formatting or content without obvious prompts.

INSIGHT

Copilot's Built In Model Council Improves Research

Copilot Wave 3 bundles 'deep research' by running OpenAI research then having Claude critique it, producing vetted results.
It also shows a side-by-side Model Council comparing outputs and a merged synthesis automatically.

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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.

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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 Cowork23:54 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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