Microsoft 365 Copilot training for Chicago teams

001/ FitMicrosoft 365 teams · 5–200 people

• Microsoft 365 Business Standard or PremiumCopilot licenses assigned, or a pilot group about to be
• Owners who just bought licensesand want usage, not shelfware
• Teams drowning in email and meetingsOutlook and Teams recap are the fastest wins
• Admins responsible for the tenantpermissions, labels and settings are on the agenda
• Firms handling client dataaccounting, legal, insurance, professional services
• Not on Microsoft 365?see the Gemini and ChatGPT sessions on the hub

Licensing, briefly: Microsoft sells Copilot for business as an add-on. Microsoft’s published list price for Microsoft 365 Copilot Business in 2026 is $21 per user per month on an annual subscription, with bundles that fold it into Business Standard or Premium; the enterprise add-on is priced separately. Check microsoft.com for the current price before you budget — it has moved more than once this year. The free Copilot Chat that comes with Microsoft 365 answers from the web; only the paid license works across your own mail, files and meetings, which is what this workshop is about.

If you are still deciding whether to buy, read our Microsoft Copilot guide for small business first — it covers plans, high-ROI use cases and the permissions audit in detail — and our comparison of Microsoft 365 vs Google Workspace if the platform itself is in question.

Prompts that work in Copilot

Copilot does best when you name the source. “Summarize this” is vague; “using the last five emails from this client and the attached SOW, list open commitments with dates” is a task.

GOAL     Prepare me for this week.
SOURCE   My inbox since Friday and my calendar for this week.
TASK     List emails that need a reply from me, grouped by meeting
         they relate to. Flag anything with a deadline before Thursday.
FORMAT   A table: sender, topic, deadline, suggested one-line reply.
RULES    Don't draft replies yet. Say "none found" if a group is empty.

Every entry in your prompt library is written once: it names the app, the source Copilot should use, what good output looks like and the rules, and it is tested on a few real inputs before anyone relies on it. The library lives where the team already works — a Teams channel or a shared OneNote — and grows from the workshop onward.

What not to paste in, even inside your own tenant

Copilot stays inside your Microsoft 365 tenant, which removes the biggest risk of consumer chatbots. It does not remove the need for rules.

• Data from outside the tenanta client’s files or personal data you were sent, not given
• Passwords, keys, card numbersnever, in any tool
• Other people’s confidential filesif you can open it by accident, don’t prompt on it
• Anything under a “Highly confidential” labelunless the policy says that role may
• Personal Copilot or ChatGPT accounts for workbusiness accounts only
• Output nobody checkedCopilot summarizes; a human signs

These rules become part of your written AI acceptable-use policy, which we draft as part of a full rollout. Start with the free AI acceptable use policy template, and if staff are already using personal AI accounts, our note on shadow IT in small business explains how to bring that into the open without a fight.

1. Licenses assigned to every attendee’s work account, at least 48 hours before the session, and sign-in tested on the laptop they will bring.
2. SharePoint and OneDrive oversharing audit. Find sites and folders shared with “Everyone” or “Everyone except external users”, and old project libraries holding HR, finance or client files, and restrict them.
3. Sensitivity labels in Microsoft Purview for at least your most sensitive categories (“Confidential”, “Highly confidential”), applied to the files that matter most, so Copilot respects them.
4. Teams transcription enabled in the meeting policy, otherwise meeting recap — usually the first win — has nothing to work from.
5. Copilot settings reviewed in the Microsoft 365 admin center, including web grounding and any plug-ins or agents you want on or off.
6. An AI acceptable-use policy, even a one-page interim version, so the rules in the room match the rules on paper.
7. A pilot group and a measure. Three to five people, two or three use cases, and one number you will watch in the usage reports for 90 days.

If your tenant has never had a permissions review, that work is usually a half day and belongs before the workshop, not after. We can scope it with you as part of an IT strategy engagement or point your existing IT provider at the right reports.

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

What your team leaves with

• Saved instructionsfor the tasks each person practised, tested on real inputs
• A shared prompt libraryin Teams or OneNote, with owners and one current version
• Rules everyone understandswhat Copilot may and may not touch
• A cleaner tenantoversharing found and fixed, labels applied
• A pilot measureone number to watch in usage reports
• Certificates of completionfor every attendee

We don’t promise hours saved. Before the session we agree on one workflow you will watch in the usage reports — meeting recaps, proposal drafts, inbox triage — and we check back a few weeks after it to see what people actually kept using.

Typical prices, not quotes. Every engagement gets a written scope and quote before work starts. Copilot licenses are bought from Microsoft or your reseller and are not included.

ETIP: Illinois may reimburse up to half

The Illinois Employer Training Investment Program (ETIP), funded by DCEO and administered in Chicagoland by the Chicagoland Chamber of Commerce, reimburses up to 50% of eligible training costs for Illinois-based full-time employees. It requires a physical Illinois location, at least two trainees, a pre-approval request submitted before the training starts, and — for workshops — a certificate of completion, which we issue to every attendee. Funds are first come, first served. The arithmetic, the Chicago Cook Workforce Partnership route and the caveats are in Funding AI training in Illinois; the full price picture is in What AI training costs in Chicago.

This is general information from 312 IT Consulting, not legal advice. Confirm requirements with your employment counsel and program availability with the agency before relying on it.