A software vendor is pitching us an AI-powered contract review tool that promises to save our operations team hours of legal review, but the setup costs are massive. How do we use Keith Cunningham's Thinking Time to evaluate if we are paying a dumb tax before we sign the contract?

Question

Tyler Smith · Accepted Answer

High-pressure sales pitches for custom or premium AI tools often lead owners to pay a massive dumb tax on software they do not actually need. To protect your cash flow, you must step back and analyze this proposal objectively.

Schedule a thirty-minute Thinking Time session. Sit in a quiet room with a pad of paper, turn off your phone, and focus on this core question: How might we achieve eighty percent of these legal review savings using our existing tools before spending a single dollar on new software?

During this session, write down the actual number of complex contracts your team reviews each month. If you only review five contracts a month, buying an expensive AI tool is a classic dumb tax. The manual human time saved will never offset the licensing and integration costs.

Consider if you can use a simpler, low-cost solution, such as a templated contract guide or a basic, secure version of a public LLM. If your Thinking Time reveals that your contract volume is truly high enough to justify the tool, formulate three strict performance metrics the vendor must guarantee before you sign. This disciplined thinking process ensures you only invest in technology that drives a clear, hard return.