A hands-on AI workshop for Chicago teams

FitOne group · up to about 15 people

• A department starting from zerosales, finance, operations, HR or a front office
• A team already using AI on its ownpersonal accounts, no shared rules
• A leadership groupdeciding whether to fund a wider rollout
• Teams on Microsoft 365see the dedicated Copilot workshop
• Whole-company rolloutssee corporate AI training

The workshop is the core of our Day 1 Foundations curriculum, compressed. It teaches the habits that make any AI tool useful at work: asking precisely, giving it the right source, checking what comes back, and knowing what must never go in. Those habits carry across tools, which is why we can run the same session on ChatGPT, Copilot, Claude or Gemini.

The case for a short session with practice built in is in the research. In Boston Consulting Group’s AI at Work 2025 survey of more than 10,600 employees, regular AI use was sharply higher among people with at least five hours of training and access to in-person training and coaching, and only a third said they had been properly trained. Microsoft’s 2024 Work Trend Index found 78% of AI users were bringing their own tools to work. A workshop is the cheapest way to replace that guesswork with shared habits.

What attendees practice

• How AI produces an answerask the same question in three new chats and compare what changed
• Tokens and contextask once with unrelated text pasted first and once without
• The five parts of a promptact as, want, context, what good looks like, rules
• Checking the workpull two numbers from fictional notes and verify both
• Working from your own material“quote the line you used” and “say not stated”
• AI as a thinking partnerask it to argue against an idea from your own work

Privacy runs through every block. Attendees open their own settings and find the controls for chat history, memory and model training, and learn when to use a temporary chat. On business plans the defaults differ: OpenAI states that data from ChatGPT Business and Enterprise is not used to train its models by default. We explain which plan your team is on and what that changes, so nobody leaves thinking a free personal account is the same as a company workspace.

BEFORE   Write a follow-up email to the client.

AFTER
ACT AS   An account manager at a Chicago accounting firm.
WANT     A follow-up email after today's kickoff call.
CONTEXT  [paste the fictional meeting notes]
GOOD     Under 150 words, friendly, lists the three documents
         we still need with the dates we agreed.
RULES    Use only what is in the notes. If a date is missing,
         write "date not stated" instead of guessing.

The rebuilt prompt is longer, and the answer usually needs far fewer rounds of edits. People see the difference on their own screen.

How we prepare a workshop

Preparation takes about a week and roughly ten minutes of each attendee’s time.

1. Free first call. We agree on the group, the tool your team already pays for, the date and whether we are on-site or online.
2. Task collection. Each attendee sends one recurring task that eats their week. We use the list to choose examples for the room, and we write fictional versions of anything sensitive.
3. Account check. Everyone confirms they can sign in to the AI tool on the laptop they will bring. Free accounts work for every required exercise.
4. The session. 2–3 hours, hands-on from the first block, with a short “your turn” after each topic.
5. Certificates and a check-in. Certificates of completion go out after the session, and we check in a few weeks later to see which prompts people kept using.

Illustrative example. The final agenda is agreed with you after we collect tasks from the group.

For a two-hour slot we keep the same order, shorten the prompting and source blocks by ten minutes each and drop the thinking-partner block. If you want the reasoning behind this structure, our guide to what AI training should include explains why checking and privacy sit in the middle of the session instead of at the end.

How does a workshop compare with a full-day AI program?

The workshop is the shortest of three formats built on one curriculum. It covers the core of Day 1; the longer programs add depth and labs on your own processes.

The full curriculum and both days, module by module, are on the AI training hub, and the training results from the two-day program are on our training results page.

Why is a workshop capped at about 15 people?

Everyone in the room is working on a laptop. With about 15 of them open, one trainer can see who is stuck and fix a prompt in under a minute; with 30, half the room waits.

If your team is larger, we split it into groups and run them back to back or on separate days. Splitting by department usually helps: a finance group and a sales group bring different tasks, and each group sees examples that look like its own work. For companies planning sessions across many departments, cohorts, a policy and a way to measure adoption, see corporate AI training.

On-site travel and industry-specific preparation can move the price above the starting point. How we price, and what other providers publish, is in our guide to what AI training costs in Chicago.

Why does the certificate of completion matter for Illinois ETIP?

Illinois ETIP excludes conferences, workshops and seminars from reimbursement unless a certificate of completion is issued. Without certificates, a short workshop would not qualify at all.

The Employer Training Investment Program, funded by the Illinois Department of Commerce and Economic Opportunity and administered in Chicagoland by the Chicagoland Chamber of Commerce, reimburses up to 50% of the cost of eligible training for Illinois-based, full-time employees. The conditions that matter for a workshop:

• Pre-approval firstsubmit the Training Pre-Approval Request before the session
• Two or more traineesa workshop clears this easily
• Certificate of completionwe issue one to every attendee
• A roster and an invoicethe invoice must be issued directly to your company
• Skills, not awarenessawareness-style training is ineligible; this is hands-on tool training
• First come, first servedpre-approval does not guarantee reimbursement

We provide the invoice, agenda, roster and certificates the paperwork needs. The approval decision is the Chamber’s. The full picture, including the current quarterly deadlines and the Chicago Cook Workforce Partnership route, is in funding AI training in Illinois.

This is general information from 312 IT Consulting, not legal or funding advice. Confirm eligibility and program availability with the Chicagoland Chamber of Commerce before relying on it.