Risk management
What Law Firm Leaders Should Ask Before Buying AI Tools
May 15, 2026
By Stephen Walther, founder of DraftWorks, former Microsoft product manager, and State Bar of Texas approved MCLE sponsor.
A checklist for evaluating vendor claims, data handling, workflow fit, and the places where AI should fail fast.
AI tool evaluations often start with impressive demos. Law firm leaders should start somewhere else: the actual workflow the firm wants to improve.
Before buying a tool, ask what documents or tasks it will support, what data it needs, how that data is handled, and what review steps the firm can enforce.
The most important question is not whether the tool can generate fluent text. It is whether the tool can fit into a controlled legal workflow where lawyers remain responsible for judgment, confidentiality, and final work product.
A useful tool should make the firm more consistent. If a product cannot explain its data practices, preserve review boundaries, or fit the way lawyers actually work, it should fail fast in the evaluation process.