ChatGPT training for employees in Chicago

FitTeams on ChatGPT · 5–500 people

• Staff on personal accountsusing ChatGPT for work before anyone set rules
• Owners about to buy Business seatsand wanting them used from week one
• Workspaces already on Business or Enterprisewith admin settings nobody has reviewed
• Teams that built custom GPTsand now need a plan for their retirement
• Mixed groupsFree, Plus and Business in one room

The curriculum is the two-day program on the AI training hub, with every setting and exercise inside ChatGPT. If your people use several tools or haven’t picked one, start with tool-agnostic generative AI training; if you live in Outlook and Teams, Microsoft 365 Copilot training fits better.

Summarized from OpenAI’s help center, November 2026. OpenAI changes plans and prices often; check openai.com/chatgpt/pricing before you buy.

ChatGPT Team was renamed ChatGPT Business on August 29, 2025, a name change only. Seats are bought from OpenAI and are not part of our fee.

A personal Plus subscription paid for by the company is still a personal account: the history leaves with the employee and nobody else can check its settings. Our note on shadow IT in small business covers moving that usage into a company workspace. For a side-by-side of the four main assistants, read ChatGPT vs Copilot vs Gemini vs Claude for small business.

Prompts for common roles

The HR row is deliberate. Since January 1, 2026, the Illinois Human Rights Act covers employers’ use of AI in hiring, promotion, discipline and other employment decisions, with a notice requirement. Drafting a handbook is fine; ranking applicants is what the law addresses. Our Illinois AI employment notice kit explains the obligation.

What does a good ChatGPT prompt look like?

One that names the role, the task, the source and the format, then states the rules. The first reply is a draft you improve by saying what to change.

ACT AS   A customer service lead at a Chicago distributor.
TASK     Draft a reply to the customer message below.
SOURCE   Our delivery policy (pasted below). Use nothing else.
FORMAT   Under 150 words. Apologize once. One clear next step.
RULES    Don't promise a refund or a date the policy doesn't allow.
         If the policy doesn't cover it, say "I'll check with my
         manager" instead of guessing.

Everyone runs the same prompt, compares replies, changes one part and runs it again; the source line turns out to do most of the work. Our post on prompt engineering basics for employees goes further on the structure.

A good team Project has one narrow job (“proposal first drafts”), instructions written once and tested, and only the files that job needs. Owners manage instructions, files and members; workspace admins decide who may share Projects. Each role group builds one around a recurring task, runs it on three fictional examples and fixes the instruction that failed.

You draft proposals for [our company], a Chicago IT services firm.
Use the files in this Project: our service descriptions and two past
proposals. Follow their structure and tone.
For every price, scope item or date, copy it from the brief I paste.
If the brief doesn't state it, write [CONFIRM] instead of a number.
Never name another client. End with a list of every [CONFIRM].

What happens to custom GPTs?

OpenAI is retiring them. Its help center lists December 11, 2026 as the scheduled retirement date for custom GPTs (later for some Enterprise workspaces with an approved deferral), and creators are being moved to plugins, which package instructions as skills along with reference files and connected apps.

According to OpenAI, a GPT’s instructions become a skill and its knowledge files become reference files; the selected model, sharing settings and custom actions do not carry over, the plugin starts private, and a migrated plugin may respond differently. Timing varies by account, so check the notice in your workspace.

1. List every GPT your people use and who built it; only the creator can migrate it.
2. Decide what each one becomes: a shared Project for most document work, or a plugin where it needs connected apps.
3. Migrate or rebuild from the latest published version; drafts and unpublished edits do not transfer.
4. Retest on three real-shaped examples and compare against the old GPT’s output before anyone relies on it.
5. Reshare deliberately, since migrated plugins start private.

• Passwords, API keys, card or bank numbersin any plan, ever
• Client files on a personal accountuse the company workspace or nothing
• Health, Social Security or biometric dataunless your policy and contracts explicitly allow it
• Material under an NDA or client contractcheck what the contract says about third-party processors
• Applicant or employee records for decisionssee the Illinois note above
• Anything you can’t checkif you can’t verify the answer, don’t paste the question

The ChatGPT settings we walk through

These rules go into your AI acceptable-use policy; start from the free AI acceptable use policy template.

Illustrative example. We agree the final agenda with you once we know the plans in the room and the tasks people bring.

The workshop is the core of Day 1. Day 2 (reusable workflows, three labs on your processes with fictional data, multi-step and scheduled tasks) comes with the two-day program; the AI workshop page compares formats, and before-and-after confidence results are on 312 AI Training.

Typical price, not a quote. Every engagement gets a written scope and quote before work starts. ChatGPT subscriptions are bought from OpenAI and are not included.

Tailoring drives the price most: standard curriculum, labs on your processes, or fully custom Projects per role. The guide to AI training costs in Chicago has market benchmarks and the questions to ask any provider.

Can Illinois help pay for it?

Possibly. Through ETIP, the Chicagoland Chamber of Commerce reimburses up to 50% of eligible training costs for qualifying Illinois employers, with pre-approval before training, at least two trainees, and a certificate of completion for workshops (we issue one to every attendee). See Funding AI training in Illinois.

General information from 312 IT Consulting, not legal advice. Confirm legal requirements with counsel and program availability with the agency before relying on it.