Seventy years of AI in five generations, taught one at a time with your company as the case study. The skill reuses your other deliverables or researches your company first, maps your departments, then walks rule-based expert systems, classic machine learning, deep learning perception, generative AI, and agentic AI: how each works, what it was good at, what it was not, and what actually drove the value. For every generation it builds examples in your own departments, each carrying the systems it would take, the skills it would take, the benefit, the limitation, and the risk. It records which generations already run in your company, and it teaches the rule that governs all of them: the right generation is the earliest one that clears the bar, and sometimes the answer is no AI at all. It ends with a live challenge and an animated deliverable with a quiz your team can take.
- Company grounding: sibling deliverables and your knowledge graph reused where they exist, otherwise research from your website, ending in a department map you confirm.
- The five generations, one at a time: the lesson, the systems and skills each demands, examples in your departments, and your estate read on whether it already runs here.
- The example bank at the depth you choose, from fifteen examples to well over a hundred, every one carrying its benefit, limitation, risk, and the honest verdict on whether it needs AI at all.
- The live challenge: a sorting round, a defense round where the skill argues the other side, and four calls on your own company, then the animated deliverable with the quiz.
You provide
- Your website, or the sibling deliverables that already describe your company
- Corrections to the department map before anything is generated
- How deep the example bank should go: Quick, Standard, or Deep
- Your estate read per generation, and your answers in the challenge
You receive
- An animated learning deliverable: the timeline, all five generations with the systems and skills each requires, and your estate map
- The example bank for your departments, filterable by generation, department, and whether AI is needed at all
- A playable quiz that prints as a full answer key for your team
Download this skill and its install guide: https://exec-skills.paulcheek.com/skills/cheek-five-generations-of-ai
How to use this skill
Once installed, start a new conversation and paste this prompt. The slash command invokes the skill directly; everything after it is your opening brief, so edit it to fit.
Sample output
A completed run of this skill for a sample company, Mastercard, exactly as the deliverable would arrive. Open it in a new tab.
The samples are illustrative demonstrations of the output format, built from public information. Mastercard is not affiliated with and has not endorsed these materials.