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Leading an AI Rollout: Pilot, Measure and Train Your Team

Leading an AI Rollout: Pilot, Measure and Train Your Team is a self-paced AIvanced Academy course (20 lessons, 5h 2m).

Run a small, safe AI pilot with your team, measure what really changed, and decide with real numbers whether to expand it, fix it or stop.

Length: 5h 2m
20 lessons in 6 modules
Level: Advanced
Certificate of completion
Price: $29.99 one-time, lifetime access

Also included with Academy Membership ($29.99/month or $249.99/year) and with a Teams plan. See pricing

About this course

You've been asked to get your team using AI. This course shows you how to do it the careful way: one task, a small group, a set time, and honest numbers at the end.

You'll pick a good first use case, get the tool approved, take a baseline, and design a short pilot with a finish line and stop rules. You'll choose a champion, plan hands-on training and answer worries honestly. Then you'll read usage reports without turning them into watching people, work out time saved without fooling yourself, report results to leadership, and decide Go, Adjust or Stop. You finish with your own Rollout Kit of templates.

Every exercise uses one made-up company, Ashgrove Print & Sign, with made-up data, a model answer and a way to finish it with no AI tool at all. Most lessons fit a short sitting, and the final exercise has 3 parts you can save one at a time.

What you need: any AI chat assistant, such as ChatGPT, Microsoft Copilot, Google Gemini or Claude. Free plans work for every exercise. You don't need admin access. To run a real pilot later, you'll need a work plan your company's approver has approved, and someone who can add and remove people. Real company information only goes into a tool your company has approved for it. No approved tool yet? Practice with the made-up data. No AI policy yet? Take Write Your Company's AI Policy first or alongside this course.

Before you start: this is an advanced course for managers, owners and operations leads. Take AI for Managers and Team Leaders first, or have the same experience. AI Privacy, Safety, and Responsible Use is a good course for your pilot group.

Not legal advice: This course is general guidance, not legal advice. For your AI policy, use Write Your Company's AI Policy. For legal questions, ask your HR professional or lawyer.

Topics: ai rollout, ai pilot, managers, small business, team training, change management, measuring results, usage reports, ai policy, approved tools, human approval, employee training

What you'll learn

Pick a first use case with a five-question check and label it Go, Adjust or Stop.
Write a pilot request and a one-page pilot plan with a finish line and stop rules set before day 1.
Take an honest baseline, and keep timing data about the work, not the worker.
Choose a champion, plan short hands-on training and answer worries without promises you can't keep.
Read a usage report for what it is, and give every number a note: measured, estimated or self-reported.
Work out time saved fairly, including checking time and what would have happened anyway.
Write a results report leaders can trust, and decide to scale, fix or stop each use case.
Build your own Rollout Kit of reusable templates.

A Try It exercise called "Your first prompt": a short scenario about moving a team meeting from 2 p.m. to 3 p.m., then numbered steps to send a prompt in ChatGPT, Copilot, Gemini or Claude, paste the reply, and note one thing to keep or change. — An example from AI Foundations, Lesson 1. Lessons in Leading an AI Rollout work the same way: you do the task in your own AI tool, then a quick check explains the answer. Try this course's first lesson free

A quick check question about an AI tool that confidently states a rent late fee. The answer "It may be a guess, because the tool can't see Fernhill's leases" is marked correct, with an explanation of why asking again proves nothing and the fact should be checked in the lease. — An example from AI Foundations, Lesson 1. Lessons in Leading an AI Rollout work the same way: you do the task in your own AI tool, then a quick check explains the answer. Try this course's first lesson free

Course outline

Module 1: Start With a Plan

Your Rollout Starts Here: Ready Check and Game Plan (free preview)
Find Out Where Things Stand Today
Guided Check: Is This a Good First Use Case?

Module 2: Tools, Guardrails and Your Baseline

Choosing and Approving the Tool With IT and the Approver
Keeping People in Charge of Decisions
Baselines: Clock It Before You Change It

Module 3: Set Up the Pilot

Designing Your Pilot
Champions and Peer Help
Training Plans That Stick
Handling Worries Honestly
Guided Check: Ready to Launch?

Module 4: Run It and Measure It

Usage Reports and Feedback: What They Can and Can't Tell You
Structured Simulation: Week Two of the Pilot
Measuring Time Saved Without Fooling Yourself
Structured Simulation: The Numbers Look Too Good

Module 5: Report and Decide

Reporting Results to Leadership
Guided Check: Scale, Fix or Stop?
Scaling Up, or Stopping Well

Module 6: Your Rollout Kit

Final Practice Exercise: Your Rollout Kit
Final Knowledge Check

Start with the free preview lessons, no account required. Questions about buying