How an AI rollout usually goes, one article per step. Budget: bought as a line item, measured by no one. Training: taught to prompt, never to build. First try: used like a search engine. Week three: the novelty fades and nobody checks. These four are where rollouts break, and the path waits at each of them. The question: start with the work people hate. There the path becomes a stream.
Why this works
Most AI rollouts break in the same four places. Each piece below takes one apart, and the last shows where the program starts instead.
Written by Shubham Chandra, who teaches AI-driven entrepreneurship at the University of Chicago and builds AI automation systems at Digital Realty.
- Budget8 min read
Your AI training budget is a line item, not a strategy
84% of companies plan to spend more on AI. Only 35% have a mature program for teaching people to use it. - Training8 min read
Stop teaching people to prompt. Teach them to build.
Prompting is a tactic. Building an agent that runs part of your own job is the skill that sticks. - First try7 min read
The same mistake everyone makes with AI
It happens in university classrooms and Fortune 500 conference rooms. The error is the same. - Week three8 min read
Why AI adoption dies in three weeks
The pattern is predictable. The fix isn't more training. It's a different kind. - The question8 min read
What do you hate, why do you hate it, and who do you wish could do it?
The best AI training doesn't start with AI. It starts with a question.
Bring us one process.
The one that waits at every handoff. In two days your team rebuilds it as a stream.
Bring us one process