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Writing about building legal tech — the pain points, the technical decisions, and the honest reality of replacing legacy software.
There's a term for it — the empathy gap. Most legal software is built by engineers who've never practiced law, which is why so much of it is technically complete and practically unusable. Three things you only understand once you've sat in the seat.
Vendors pitch a clean three-week migration. The real switch unfolds in three predictable phases over 90 days — dual-system, behavior change, and reconciliation. Here's what actually works in each, and the three questions to ask a vendor before you sign.
Vendor demos promise seamless integration. Three months later, data is disappearing between platforms and nobody can explain why. Here's why legal tech integrations fail — and the architecture that makes them unnecessary.
On June 1, New York's Part 161 took effect: use an AI tool to prepare a filing and your signature now certifies that a human reviewed it. The exposure isn't whether you used AI — it's whether you can prove the review happened.
Sullivan & Cromwell apologized to a federal bankruptcy judge last month for filing a brief with citations that didn't exist. In the same month, two lawyers in Oregon were hit with $110,000 in sanctions for the same problem.
Anthropic launched Claude for Legal last week. The legal tech world treated it as a category event — and it is — but it also surfaced a question I keep hearing from small-firm partners.
The productivity gain from eliminating software friction isn't just about hours — it's about what becomes possible when your team isn't exhausted by their tools.
In two years, every legal tech vendor will claim to be "matter-centric." Most will be lying. Here's how to tell the difference.
Legacy legal tech vendors are facing a structural problem, and some of them know it. The response will follow a predictable playbook — here's exactly how it'll unfold.
I've sat through demos from dozens of legal tech companies. Every single one is built around documents, calendars, or contacts. But lawyers don't think that way — they think in matters.
I timed an attorney filing a single document across his firm's systems. Fifteen minutes. Four different systems. Three different folders. Metadata entered three separate times.
I recently helped a 20-attorney firm discover they're spending $147,000 annually on legal software. They thought it was maybe $60K.
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