Training Design8 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.

By Shubham Chandra, Head of Curriculum

Key Takeaways

  • The most effective AI training opens with frustration, not technology: "What do you hate about your job, why, and who do you wish could do it?"
  • When an entire room realizes they all waste hours on the same kind of task, skepticism turns into urgency.
  • Participants build tools for the specific problems they just named: custom assistants, automated workflows, role-specific playbooks.
  • Organizations with the highest AI ROI started with workflow pain points, not "AI awareness."

The question that starts every program

Nobody opens with "what is a large language model." The first thing participants hear is three questions: What do you hate about your job? Why do you hate it? And who do you wish could do it?

The answers are consistent across roles and industries. Repetitive work that someone wishes they could hand off. Reformatting data between systems. Writing the same status update in three formats. Drafting boilerplate that nobody reads carefully but everyone demands.

That "someone" they wish could do it? More often than not, an AI can. But nobody has drawn the line between "I hate writing weekly status reports" and "a custom assistant can generate those from your project notes in ninety seconds."

Why the Socratic method works for AI training

Borrowed from the University of Chicago tradition. Discussion, not lecture. Questions, not slides. The instructor's job isn't to hand people answers. It's to set up the conditions where they work through it themselves.

When a room full of professionals shares their pain points out loud, two things happen. First, they realize the frustration is universal. The operations manager hates the same kind of work the marketing director hates.

Second, that shared recognition creates energy. The room shifts from passive audience to active problem-solvers. That energy carries people from "I'm not sure AI is relevant" to "I built a custom assistant for my team" in a single day.

The moment a room realizes they all waste three hours a week on the same kind of task, skepticism turns into urgency.

From pain to product in 8 hours

The first hour is frustration and discovery. The next two are calibration: what AI is good at, what it isn't, why your first attempt probably disappointed you. The rest is building.

By the end of the day, three deliverables walk out the door:

  • An AI integration blueprint: mapping where AI fits in their team’s actual processes, not generic templates
  • A workflow map: showing where AI fits in their daily work, which tasks to automate, which to augment
  • A 90-day AI strategy: concrete actions with timelines, no IT approval needed

Why this scales

Organizations with the strongest AI ROI share a starting point. They didn't begin with "AI awareness" campaigns. They started by identifying repetitive, time-consuming tasks and working backward to the solution.

The Socratic method scales from ten people in a room to a thousand-person rollout. The question is always the same: what do you hate, and who do you wish could do it? When people name their own problem, they own the solution.

Why this is the article to forward to your boss

If your team can answer "what do you hate" but can't answer "what AI tools have you built to fix it," that tells you where the gap is.

The AI training market is projected to grow from $1.2 billion to $6 billion by 2033. Most of that spend will go to platforms nobody finishes. The programs that deliver ROI start with real problems and end with tools people use the following week.

The gap isn't awareness. It's the bridge between "AI could probably help" and "here's the tool I built last Tuesday that saves me three hours a week."

Want to try a different approach?

See what the program looks like.

Forward to your team

Spring 2026 Cohort

Limited Spots Available

Get proposal