When should a CEO get a second opinion on a technology decision
When should a CEO get a second opinion on a technology decision? Not on all of them. There are thresholds, and they are worth writing down before the next proposal arrives, because after it arrives the answer is always "this one is different."
Money. Anything above what you would spend a week thinking about if it were a truck or a building. For most owners that is somewhere between $50k and $100k, all-in, including the years of running it.
Irreversibility. A decision you could unwind next quarter does not need a second opinion. A data model, a platform, a contract with a three-year term, a custom build you will own: those cannot be undone cheaply, and the review is cheap by comparison.
Lock-in. If the answer to "how do we leave" is a project, the entry deserves scrutiny.
Disruption. Anything that changes how more than one department works every day. The software cost is the smaller number in those.
Uncertainty. If you cannot explain to your CFO in two sentences why this option beat the alternatives, you are not deciding. You are trusting.
Any two of those, get a second look. Three or more, do not sign until you have one.
The test is not whether you understand the technology. It is whether anyone in the room would lose money if the answer were no. If nobody would, you may not need a second opinion. If everybody would, you do.