Most law firms buy AI tools backwards: slick demo, firm-wide deal, then discover it is brilliant at the demoed thing and mediocre at what the firm does all day. - Start with the job, not the tool: contract review, legal research, deposition summaries, intake. A great research assistant can be a clumsy contract reviewer. - Compare the tier you would actually buy: per-seat math gets ugly fast, and demo features often live one tier above the advertised price. - Ask the confidentiality question before signing: where do documents go, how long do they stay, do they touch training data. In writing. - Pilot one tool with five power users for a month. The tool that survives real matters is the one to buy. - Train people. A tool nobody knows how to prompt is shelfware. I compare 207 AI tools across 40+ professions, and PrivateLLM deploy sets up a private LLM on AWS for $50 plus usage when firm data must stay in-house.