Watch the full walkthrough
Setup, global instructions, permission modes, and a real task run start to finish.
Full transcript
Spoken by Scott Midgley, Chief Information Officer & Co-Founder, Wellforce IT. Lightly edited from the recording for readability; wording is otherwise unchanged. Timestamps link to that moment in the video.
What Claude Cowork is 0:00
In this video we're looking at Claude Cowork: what it is, how it differs from regular Claude chat, and why it matters if your work involves turning scattered notes, files, and follow-ups into something organized and useful. I'll walk through the basic setup, then show a real example so you can see what it looks like when Cowork handles multi-step tasks instead of just answering one prompt at a time.
My name is Scott Midgley and I'm the co-founder of Wellforce IT. We're a managed IT and cybersecurity firm serving professional services organizations across the DC metro area and central North Carolina. A lot of what I do day to day is helping firms and organizations figure out where AI tools fit into their workflows, and where they don't.
This is the first in a short series walking through these tools, and we're starting with Claude Cowork.
Chat versus Cowork 1:35
If you've used Claude before, the basic flow is familiar. You ask a question, get an answer, copy it somewhere else, then come back with the next question. That works well for quick tasks, but most of the real work inside a professional services firm isn't quick. There are layers. You might need to read through several sets of notes, find the important pieces, organize them, write them up, and get the result into the right document. That's exactly the gap Claude Cowork is designed to close.
Think of Cowork as a different way to use Claude desktop. Chat is for basic back-and-forth conversation. Cowork is for getting work done. You give it the outcome you want, it reviews the files you connect, figures out the steps, and works through them so you can come back to a finished result.
Under the hood it uses the same agent-style approach behind Claude Code, but it's packaged for normal desktop work. You don't need a terminal, you don't need to write code, and you don't need to think like a developer to use it.
Installing the desktop app 2:50
To use Cowork you need the Claude desktop app. It works on Mac, Windows, and Linux. You will also need a paid Claude plan, either Pro, Max, Team, or Enterprise, and your computer needs to stay connected to the internet while a task is running.
After it is installed, open the app and look for the mode selector. Chat and Cowork appear side by side. Choose Cowork and that puts you into task mode.
Setting global instructions 3:55
Another part of the setup is global instructions. Go into settings, then click Cowork, and there are the global instructions. Whatever you put in here is read by Claude before every single Cowork session.
You could use yours to specify things like preferred document format. If you want it to open in Word, you can set that here so you're not repeating yourself every time you start a new task.
How it protects your files 5:00
Before you hand Cowork a real task, it's worth knowing how it's built to protect your files. It runs code inside an isolated virtual machine, separate from your operating system. Claude can only read and write files in the folders you have specifically connected. It doesn't have free run of your computer.
There's also a permission mode selector. You can set it to ask before every action, which is what I'd recommend when you're just getting started, or you can let it act without asking once you trust the workflow. Either way, Claude will always stop and ask before permanently deleting a file. There are no exceptions to that.
Running a real task 6:00
Let's start with our example. Inside this folder there are four files. These are the same kind of scattered notes I usually end up with during a work week. There are client check-ins, voice memos that I dictate, and a catch-all file of things I don't want to forget. It's useful information, but it's not organized and it's not ready to share.
I'm going to point Cowork at that folder and ask it to read through everything, then turn the notes into a clean weekly recap grouped by client, with one follow-up list at the end, and anything time-sensitive clearly flagged.
Here is the prompt: "Read through the notes in the input folder and turn them into a clean weekly recap I can use internally. Group by client, pull out anything that needs follow-up into a single action list at the end, and flag anything that seems time-sensitive or risk-related."
Before it touches anything, it lays out a plan. This is worth looking at a little closer, because we can see exactly what it intends to do before it does it. If something looked off, we could stop the process right now. Now it's telling us it has everything it needs from the four notes, and it's going to set up the tasks and build the recap.
There's a progress bar as well. It's going to read and consolidate the notes, then build the weekly recap into a Word document because I asked for that in my settings, and at the end it will verify the recap against the source notes.
Reviewing the output 8:20
Here we go. Notice it grouped everything together by client on its own. I never told it which notes belonged together. It also caught two things that are easy to miss when you read through these casually: a compliance concern buried in a voice memo about staff using personal email for client correspondence, and an overdue letter mentioned almost as an afterthought. Both of those made it into the action list.
The top three are customers I had calls with. Bright Futures, listing out the issues they reported to our team. A call with the office manager at Hartwell Bryce, the same information given for our staff to address. Whitfield Health, where our staff went on site, updated a router replacement, and checked some of the Huntress alerts. There is a potential HIPAA issue listed right there. And then it gives us an action list and follow-ups.
That's the walkthrough. If you're trying to figure out where Cowork fits into your own day, start with something small and familiar. An inbox you need to clean up, a folder of notes you need to organize, or a rough draft that needs to be turned into something more usable. The goal is not to hand Cowork your most complicated workflow on day one. It's to see how it handles a real task you already understand, so you can compare the output against your own expectations.
In the next few videos in this series we go deeper on specific workflows, starting with practical examples for law firms and nonprofits.
Eight steps from zero to a working habit
The same sequence we run in paid engagements, compressed to a checklist.
Get on a paid Claude plan
Claude Cowork is included on Pro, Max, Team, and Enterprise. Team Standard is $20 per seat per month on annual billing or $25 billed monthly and includes central administration.
Open Cowork on the right surface
Use Claude Desktop for local files and supported computer use. Web and mobile can run remote Cowork sessions where available. Sign in with your work account and select Cowork from the message box.
Give it a working folder
Create one folder for your first project and point Cowork at it. Start narrow: copies of the files for one task, not your whole drive. You can widen access once your rules are set.
Describe one real task in plain language
Skip the toy demos. Try the report, cleanup, or draft you actually owe someone this week. Say what you want, what the inputs are, and what the finished product should look like.
Review the plan before it works
Cowork proposes its steps before it starts. Read them. If the plan touches files it should not, or skips a step you need, say so. Correcting the plan is faster than correcting the output.
Review the output like a manager, not a fan
Check what changed, verify numbers against sources, and send back edits the way you would with a new hire. The quality of your feedback in week one sets the quality you get in week ten.
Save the winners as Skills
When a task works, save it as a Claude Skill so it runs the same way every time: same format, same checks, same voice. Skills are how one good workflow becomes a team asset.
Set team rules before you scale
Write a one-page policy: what data Cowork may touch, what never gets pasted or connected, and when to disclose AI help. Then train the team on your two or three proven workflows.
What a good first week looks like
Day 1–2: one folder, one task
Pick the weekly task everyone dreads. Run it through Cowork with copies of the real files. Time it against how long it usually takes.
Day 3–4: iterate and template
Rerun the same task with your corrections applied. Once the output is right twice in a row, save it as a Skill.
Day 5: show one colleague
Adoption spreads by demonstration, not memo. A five-minute "watch this" beats an hour of training slides.
The five mistakes we fix most often
Pointing it at everything on day one. Start with one folder; earn your way to wider access with rules in place.
Treating it like search. Cowork shines on multi-step production work, not quick lookups; use regular Claude chat for those.
Skipping the review step. It is a strong drafter and a fast worker, and your team is still the editor of record.
No data rules. Decide what is off-limits (donor SSNs, client matters, student records) before staff decide for themselves.
Buying seats without training. Unused seats are the most expensive version of AI. Two hands-on sessions beat any memo.
Not sure what it should cost to do this right? See Claude Cowork pricing, or skip straight to having us run the rollout.
Using Claude Cowork, answered
How do I get started with Claude Cowork?
What should my first Claude Cowork task be?
Can Claude Cowork access all my files?
What are Claude Skills and why do they matter?
How long does it take a team to get real value?
We install Claude Cowork for teams in DC & Raleigh
Design, setup, connected tools, hands-on training, and a one-page AI policy. Live in two weeks, from $2,500 flat. Nonprofit pricing available.
Or just tell us what you're trying to do — we'll point you the right way, free.
More Claude Cowork guides
What is Claude Cowork? The plain-English guide
What it is, what it actually does, who it is for, and how teams use it.
Read the guide →Claude Cowork pricing
What Claude Cowork costs, plan by plan, plus what a real team rollout runs.
Read the guide →Claude Cowork vs Claude Code
Two Anthropic agent products, two different jobs. Which one fits yours.
Read the guide →Claude Cowork vs OpenClaw
Managed knowledge-work agent or self-hosted personal assistant: the practical choice.
Read the guide →Is Claude Cowork free?
The direct answer, what each paid plan includes, and what can cost extra.
Read the guide →Claude Cowork use cases
Eighteen real workflows, by team type: nonprofits, legal, and growing businesses.
Read the guide →Claude Cowork vs Microsoft Copilot
An honest comparison for SMB stacks, from a Microsoft shop that deploys both.
Read the guide →Claude Cowork security & data privacy
What it can touch, what it cannot, and the controls that make it safe for real data.
Read the guide →Claude Cowork for nonprofits
Grants, donor emails, and board packs: the nonprofit playbook.
Read the guide →Claude Cowork for law firms
Intake, review, and records work with the controls partners expect.
Read the guide →Legal intake automation, step by step
Four intake files to a reviewed matter summary, with the conflict surfaced, in under five minutes.
Read the guide →Claude Cowork for small business
Official workflows, Team plan costs, and a rollout that prevents AI shelfware.
Read the guide →Claude Cowork Dispatch
Assigning desktop tasks from your phone: what it needs, which plans have it, and the trade-off.
Read the guide →Claude Cowork change log
A dated record of Cowork releases, plan changes, platform support, and fact checks.
Read the guide →Claude Cowork plugins & Skills
Skills, connectors, and plugins: what each one is, when to build, and how to govern them.
Read the guide →Claude consulting for SMBs
Implementation, training, and managed Claude operations in DC & Raleigh. Live in two weeks, from $2,500 flat.
See the service →