Flow Alt Delete – Josh Cook [Microsoft MVP]

Category: M365

  • How I Keep Copilot Cowork Sessions Alive with a requirements.md File

    How I Keep Copilot Cowork Sessions Alive with a requirements.md File

    Copilot Cowork is strong at creating files. Documents, markdown files, HTML files, specs, plans, summaries, all of it.

    So I started using that strength against one of the biggest pain points in agent work: losing context.

    1. The Problem
    2. The Workaround
    3. The Prompt I Use
    4. What I Want Cowork To Track
    5. The Recovery Flow
      1. Step 1: Open the Output Folder
      2. Step 2: Copy the OneDrive Link
      3. Step 3: Start a New Cowork Session
    6. Why This Works
    7. My Recommendation
    8. Final Take

    The Problem

    Sometimes a session can glitch, freeze, or reach a point where starting fresh is easier.

    The painful part is not starting a new session.

    The painful part is rebuilding the context.

    You have to explain the goal again. Rebuild the requirements. Re-upload or reconnect files. Remind it what decisions were already made. Recreate the mental map of the work.

    That burns time.

    So I started giving Copilot Cowork a job before it does any other job:

    Keep the context alive.

    The Workaround

    At the start of the session, tell Cowork to create a requirements.md file and keep it updated while you work.

    That file becomes the session brain.

    It gives you a portable record of the work that can move from one Cowork session to another.

    Think of it like a handoff file.

    Not a final deliverable. Not a pretty summary. A working memory file.

    The Prompt I Use

    Create a requirements.md file and keep it updated throughout this session.
    Use it to track the full context of our work, including:
    - requirements
    - decisions made
    - open items
    - files created
    - key conversation details
    - risks
    - assumptions
    - and next steps
    I want to be able to pass this file to another Copilot Cowork session
    so it can continue with full context.

    You can change the file name if you want.

    For some sessions, I might use project-context.md, demo-notes.md, or handoff.md.

    But I like requirements.md because it forces the session to stay grounded in what is actually being built.

    Note

    This works best when the requirements.md file is updated throughout the session, not only at the end. When decisions change, files are created, or blockers appear, tell Cowork to update the file.

    What I Want Cowork To Track

    The file should not be a fluffy recap.

    I want it tracking the stuff that matters:

    • Session goal
    • Current objective
    • Requirements
    • Decisions made
    • Files created
    • Important assumptions
    • Open questions
    • Risks or blockers
    • Next actions
    • Anything another session would need to continue the work

    That last one is the key.

    Do not just ask Cowork to summarize.

    Ask it to prepare the next session to continue the work.

    The Recovery Flow

    If the session glitches, breaks, or you want to continue in a fresh session, here is the flow I use.

    Step 1: Open the Output Folder

    In Copilot Cowork, open the details pane and look for the Output folder.

    Click the folder icon to open the generated files in OneDrive.

    Once the folder opens in OneDrive, click Copy link.

    This gives you a link to the folder that contains the files from the previous Cowork session.

    Step 3: Start a New Cowork Session

    Open a new Copilot Cowork session.

    Paste the OneDrive folder link into the new session and tell Cowork:

    Im continuing the <Project or task name>.
    Use the files from our previous session. ( <Paste OneDrive Link> )
    Start by reading the requirements.md file.
    Then continue the work from there.

    Now Cowork has a fighting chance at picking up where the previous session left off.

    Why This Works

    Agent workflows are only as strong as the context behind them.

    If the context is trapped inside one chat session, you are exposed.

    If the context is written into a file, you can move it.

    That changes the way you work with Cowork.

    You are no longer relying only on the chat thread.

    You are creating a portable project trail that can survive a new session.

    My Recommendation

    Make this part of your normal Copilot Cowork workflow.

    Before you ask it to build the document, analyze the data, write the plan, or generate the assets, tell it to create the context file first.

    Then keep pushing Cowork to update that file as the session evolves.

    When a decision is made, tell it to update the file.

    When a requirement changes, tell it to update the file.

    When a file is created, tell it to update the file.

    Small habit.

    Big protection.

    Final Take

    Copilot Cowork can generate the work.

    But you should also make it generate the trail.

    The requirements file keeps the important context outside the chat window, inside the actual working folder, where another session can use it.

    That is the move.

    Use Cowork to build the output.

    Use Cowork to protect the context.

    This is currently a limitation on the product, which I assume the Team will fix in the future. But for now, this is how I manage long running tasks and work with Copilot Cowork.

  • Boost Productivity with Planner and Copilot Cowork

    Boost Productivity with Planner and Copilot Cowork

    Copilot Cowork Prompt of the Day: Planner + Cowork

    Most people open Planner, see a wall of tasks, and then burn time figuring out where to start.

    Bad move.

    A better play is to use the Planner (Frontier) agent to pull everything due this week, then hand that full output to Copilot Cowork so it can start moving the work immediately.

    That is exactly what I did here.

    I had 6 tasks due in the upcoming week. Instead of manually opening each one, rewriting the context, drafting emails, setting meetings, and creating documents one by one, I used Planner to extract the full list and Copilot Cowork to help kick things off.

    The scenario

    I had a packed week ahead with multiple tasks already assigned to me in Planner. I needed a fast way to get organized and get the work moving before the week started tightening up.

    So I used the new Planner (Frontier) agent to give me a full view of what was due, then I passed that output directly into Copilot Cowork.

    That gave Cowork real context to work with: due dates, notes, priorities, task titles, and the actual work that needed to happen.

    Step 1: Pull the weekly task list from Planner

    First, I asked Planner to show me everything due this week and give me the full details.

    Show me tasks that are due this week.
    Give me full details.
    I will be giving your output to Copilot Cowork to do the tasks.

    Planner returned the task list with the details I needed. Then I asked it for one more thing: put the output into a code block.

    Can you output this in code block

    That extra step is smart. It makes the output much easier to copy and paste cleanly without wrecking the formatting or losing structure. Also AI loves it.

    Step 2: Hand the extract to Copilot Cowork

    Next, I dropped that Planner output into Copilot Cowork with a very simple prompt.

    I pulled the list of items I need to get done this week coming up.
    Get these things going and started, so I can get them done on time.
    Here is the extract from Planner:
    <Paste output from Planner agent from step 1>

    No complicated framework. No giant system prompt. Just the actual task extract from Planner and a direct ask.

    That is where this gets good. Cowork is no longer guessing what matters. It has the real list in front of it.

    Step 3: Let Cowork start the work

    Once Cowork had the context, it started breaking the workload down and pushing the execution forward.

    In my example, the work included:

    • Drafting emails and Teams messages to align what was still left for the team to build
    • Setting up workshop meetings to gather more requirements
    • Checking availability and scheduling the right people
    • Creating a procedure document
    • Helping move general dev work forward

    That is a strong workflow because it cuts out the dead time between seeing the work and starting the work.

    Instead of looking at six tasks and thinking, I should probably get on this, Cowork starts lining up the actual actions that move those tasks forward.

    Teams message sent to group chat:


    Procedure document generated:

    Meeting scheduled:

    Recap

    Planner and Cowork each do a different job, and that is exactly why this combo works.

    • Planner gives you the structured workload
    • Planner gives you the dates, notes, priority, and task details
    • Cowork uses that context to help draft, schedule, create, and coordinate

    You are not starting from a blank chat. You are starting from actual work that already exists inside Microsoft 365.

    Prompt recap

    Planner prompt

    Show me tasks that are due this week.
    Give me full details.
    I will be giving your output to Copilot Cowork to do the tasks.

    Planner follow-up

    Can you output this in code block

    Copilot Cowork prompt

    I pulled the list of items I need to get done this week coming up.
    Get these things going and started, so I can get them done on time.
    Here is the extract from Planner:
    <Paste output from Planner agent from step 1>

    Why I like this prompt

    This one is simple, practical, and dangerous in a good way.

    You take a task list that usually just sits there, and you turn it into momentum.

    That is the real win. Less dragging. More movement.

    If you are already using Planner, this is one of the easiest Copilot Cowork workflows to start using right now.

  • Copilot Cowork Is Coming: Here’s How to Get Your Tenant Ready on Day 1

    Copilot Cowork Is Coming: Here’s How to Get Your Tenant Ready on Day 1

    Get Your Tenant Ready for Day 1: Joining Microsoft 365 Frontier for Copilot Cowork

    If you’ve been following the buzz around Copilot Cowork, you already know it’s going to change how we work inside Microsoft 365. But here’s the thing — Day 1 readiness doesn’t happen on Day 1. It happens now.

    In this post, I’ll walk you through exactly how to get your tenant set up: the right licenses, how to join the Frontier program, enabling the Anthropic sub-processor, configuring pilot groups, and locking down governance before you open the floodgates.

    Copilot Cowork is expected to be available for Frontier customers late March or later.

    Step 1: Make Sure You Have the Right Licenses

    Before you can enable anything, your tenant needs the right foundation.

    RequirementDetails
    Microsoft 365 Copilot licenseRequired for all end users who will access Copilot Cowork. Available as an add-on on E3, E5, Business Standard, and Business Premium plans.
    AI Administrator roleRequired to make changes in the Copilot settings area of the Admin Center.
    Microsoft Entra ID P1 or P2Needed for group-based access control and conditional access (P1 minimum).
    SharePoint OnlineIncluded in most M365 plans — required for Cowork’s document grounding.

    Admin tip: Before you go further, run a license audit. In the Microsoft 365 Admin Center, go to Billing > Licenses and confirm Copilot licenses are assigned — unassigned licenses won’t show up in Frontier eligibility checks.

    Step 2: Join Microsoft 365 Frontier

    Microsoft 365 Frontier is the early adopter program that gives your tenant access to upcoming Copilot features before general availability — including Copilot Cowork.

    What you’ll need first

    You must have AI Administrator access to complete this setup. If you don’t have this role, work with your Global Admin to get it assigned before you start.

    How to join Frontier

    1. Start from office.com and open the Admin Center.
    2. Navigate to Copilot → Settings → Frontier.
    3. On the Frontier settings page, enable early access.
    4. Under Web Apps, select the users who should be included.
    5. Click Save.

    That’s it — your tenant is now enrolled in Frontier.

    Step 3: Enable Anthropic as an AI Provider

    After Frontier is enabled, you need to turn on the AI providers that power the new Copilot experiences. This is the step most admins don’t realize is required.

    How to enable Anthropic

    1. From the same Copilot settings area, navigate to Data access.
    2. Enable the available AI providers — the recommendation is to enable as many as possible.
    3. Specifically, find Anthropic and enable it for Copilot.

    Step 4: Set Up Pilot Groups (Optional)

    Don’t roll Frontier out to your entire organization on Day 1. A phased pilot protects your environment and gives you time to validate the experience before broad deployment.

    Recommended pilot structure

    PhaseGroupPurpose
    Wave 1 — Champions5–10 power users (IT, Copilot champions)Validate setup, surface issues early
    Wave 2 — Early Adopters50–100 users across key departmentsReal-world workflow testing
    Wave 3 — Broad RolloutAll licensed usersFull deployment

    How to configure

    1. Create security groups in Microsoft Entra ID — for example, SG-CopilotCowork-Wave1 and SG-CopilotCowork-Wave2.
    2. In the Frontier settings from Step 2, assign early access to your Wave 1 group first using the Web Apps user selection.
    3. Expand to Wave 2 once Wave 1 has validated the experience.

    Pro tip: Set up a Microsoft Teams channel for your pilot group — something like #cowork-pilot-feedback — so you have a central place to collect issues and wins before you scale.

    Step 5: Governance — Lock Down Oversharing Before You Start

    This is the step most organizations skip — and regret. When Copilot can surface content from across your tenant, oversharing becomes a data exposure risk, not just a governance annoyance. Lock this down before you enable Cowork broadly.

    Key controls to review

    ControlWhere to set itRecommendation
    External sharingSharePoint Admin Center → Policies → SharingSet to “Existing guests only” or “Only people in your org” during Frontier rollout
    Default sharing linksSharePoint Admin Center → Policies → SharingChange from “Anyone with the link” to “People in your organization”
    Site-level permissionsIndividual site settingsAudit “Everyone except external users” — this is the #1 oversharing culprit
    Sensitivity labelsMicrosoft PurviewApply labels to classify and restrict access to confidential content
    Guest access expirationEntra ID → External collaboration settingsSet guest access to expire after 90 days

    SharePoint Admin Agent Prompt: Oversharing Audit

    Use this prompt directly with the SharePoint Admin agent in the Microsoft 365 Admin Center to get a fast, prioritized oversharing assessment:

    Review my SharePoint environment for oversharing risks before a Copilot rollout. Specifically:
1. Identify all sites that have 'Everyone' or 'Everyone except external users' granted any level of access.
 2. List sites where external sharing is enabled but shouldn't be (e.g., HR, Finance, Legal).
 3. Show me any files or folders shared via 'Anyone with the link' in the last 90 days.
 4. Flag any sites with more than 500 unique permissions (permission explosion).
 5. Recommend which sites should have sensitivity labels applied but currently don't.
Format results as a prioritized remediation list — highest risk first.

    This gives you an actionable list to work through before any end user asks Copilot Cowork a question about a document they shouldn’t be able to see.

    Your Day 1 Readiness Checklist

    • [ ] M365 Copilot licenses assigned to target users
    • [ ] AI Administrator role confirmed
    • [ ] Tenant enrolled in Frontier (Copilot → Settings → Frontier)
    • [ ] Early access enabled and Web Apps users selected
    • [ ] Anthropic enabled under Data access → AI providers
    • [ ] Pilot security groups created (Wave 1, 2, 3)
    • [ ] SharePoint oversharing audit completed using Admin agent prompt
    • [ ] External sharing policies tightened
    • [ ] Sensitivity labels deployed for confidential content
    • [ ] Pilot feedback channel set up in Teams

    Final Thought

    Copilot Cowork is a new way of working. The organizations that will get the most out of Day 1 are the ones doing this prep work right now. Join Frontier, enable Anthropic, run your oversharing audit, and start small with a tight pilot group.

    The foundation is simple: Frontier starts with admin enablement and provider access. Once that’s in place, you’re ready for everything that comes next.