Why AI fails in midsized law firms: the one-IT-guy problem, told through a consultant's story
jkubicki · x · 2026-10-01
A consultant who has worked with midmarket law firms for years sums up why legal tech stalls: these firms typically have a single IT veteran ("Paul") who cut his teeth on Windows NT, hates AI, and makes every implementation painful. In the anecdote, Paul dies at his desk from stress; replacements last months, and the cycle repeats until the firm gives up and moves to an MSP, shifting email and core systems to the cloud. The darkly funny takeaway: law firm culture itself kills young tech talent, which is the real blocker for AI adoption in traditional professional services.
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