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Microsoft Copilot Cowork: What Chicago businesses should know

If you run a business anywhere from Chicago to the smaller towns across the Midwest, you already know the drill. Half your day gets eaten by email, meetings, and shuffling documents around. Microsoft Copilot Cowork is built to take a real chunk of that off your plate. 

Here’s what makes it different from the Copilot you might already know: Cowork doesn’t just suggest things. It actually does them, start to finish. You describe what you need, it builds a plan, works through it step by step, and hands you a completed result. Not a draft. Not a recommendation. Done. 

A few things set it apart under the hood:

Here’s the plain-English rundown of how it all works. 

What is Copilot Cowork?

Copilot Cowork is an AI agent that lives inside Microsoft 365. The big difference from regular Copilot? It doesn’t just suggest things. It actually does them. 

You tell it what you need, and it goes to work:

Think of it less like a spell-checker and more like a capable coworker you can hand a task to. You stay in charge the whole time, but Cowork handles the busywork.

What are the Cowork features?

Cowork covers a lot of ground. Here’s what it can do, sorted by the kind of work you’re dealing with.

Communication

Documents and files

Calendar and meetings

Research and search

Automation

Copilot Cowork vs. Copilot Chat: key differences

FeatureCopilot ChatCopilot Cowork
Best used forQuick questions, drafts, and summariesComplex, multi-step tasks that span several tools
How it worksYou prompt, it respondsYou describe a goal, it builds a plan and executes it
Takes real actionsNo, you act on its suggestions manuallyYes, it sends emails, posts in Teams, books meetings
Works across M365 appsTypically one app at a timeMoves across Outlook, Teams, SharePoint, and more in a single task
Runs in the backgroundNoYes, tasks keep running even when you step away
Supports recurring tasksNoYes, you can schedule prompts to run automatically
Requires your approvalNo, you stay in control manuallyYes, it pauses and asks before taking sensitive actions
Typical task lengthSeconds to a few minutesMinutes to hours for heavier work
Access and pricingIncluded with eligible Microsoft 365 plansRequires a Microsoft 365 Copilot license plus usage-based billing

How do you use Cowork?

Nervous it’ll go rogue and email the wrong client? Don’t be. The whole thing is built around you approving each step. Here’s how a typical session goes.

Want a tip? Start with low-risk stuff like internal summaries and draft emails. Once you see how it handles your workflow, you can hand it bigger jobs. 

How does Cowork pricing look like?

This part trips people up, so let’s keep it simple. 

First, you need a Microsoft 365 Copilot license. That’s a flat per-user, per-month fee, and it covers the core Copilot experience across Word, Excel, Outlook, Teams, and more. 

Cowork sits on top of that with usage-based billing. Instead of a flat rate, you pay for what you actually use, measured in something called Copilot Credits. The cost of each task depends on how much work it takes. 

Tasks generally fall into three buckets:

You also get two ways to pay:

The nice part for budgeting? Admins can set spending limits at the company, team, or individual level, plus alerts when spend crosses a threshold. So there are no surprise bills at the end of the month.

Ready to put Cowork to work for your business?

Cowork handles the coordinationYou handle the calls that actually need a human. If your team already lives in Microsoft 365, the foundation is already there. As a Microsoft Partner, iwx can help you figure out where to start, what to watch, and how to scale it in a way that fits your business, not just the product sheet. Start with one workflow. Build from there.

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