01“Is this plan any good?”
The question underneath every other question, and the one you cannot get answered. Judging a plan now means weighing the roadmap, the model, the architecture and the customer experience against each other, and almost everyone you can ask is fluent in only one of the four.
02Everyone qualified to answer has a stake in the answer.
Your team wants the headcount, the vendor wants the contract, the integrator wants the follow-on, and every one of them is competent without any of them being neutral. I am most useful in the engagements where the answer turns out to be don’t.
03Four questions decide the deal.
Whether the technology is real, whether the team can ship what they showed you, whether the architecture survives the next model, and whether customers will actually adopt it. Any one is a comfortable afternoon with a specialist, and all four together is a different job.
04There is a product only you could build.
Rarely the one already on the roadmap, because roadmaps get built from what people thought to ask for. Finding it means going through what you already know and what customers trust you to hold, and that search is how most of my innovation-focused engagements start.
05Good ideas are rarely rejected. They get averaged away.
Scoped and staffed and reviewed and softened until nobody quite remembers what was interesting about them. Part of my job is holding the shape of an idea steady and saying out loud which parts are load bearing and which can be traded.