We are being pitched a highly custom, six-figure AI operational system that promises to automate our entire field dispatching. How do we use Keith Cunningham's concept of the dumb tax and specific business questions during a Thinking Time session to evaluate this proposal before signing the contract?

Question

Tyler Smith · Accepted Answer

Before committing to a six-figure custom AI software contract, you must perform a disciplined Thinking Time session to avoid paying a massive dumb tax. Software sales representatives are experts at selling future promises while hiding current operational realities.

To cut through the theater, sit down with a blank notepad for forty-five minutes and answer these three questions.

First, what is the exact problem we are trying to solve, and can we solve it with a simple, off-the-shelf automation tool for a fraction of the cost?

Second, what are the hidden operational costs, including employee training time, system maintenance, and data integration, that are not included in this quote?

Third, what happens to our business if this custom software provider goes bankrupt or fails to deliver a working system on our timeline?

If you cannot answer these questions with absolute clarity, you are about to make a highly speculative bet. Demand that the software vendor provide a working prototype using a small sample of your actual data before you sign a long-term contract. If they refuse, walk away. It is always better to lose a potential efficiency gain than to lock your company into a complex, expensive system that does not work.