Here's what this gets you: one prompt in Copilot that reads your last two weeks of email and lists every time you promised somebody something and never got back to them, with the person, the promise and the date. Then it drafts the top three follow-ups, you read them, and you set the whole thing to run every Monday so you never have to remember to remember.
I think the job goes to whoever followed up. So this guide is the whole setup: the exact prompts, the license you need (the free Copilot Chat can't read your whole inbox), what it costs on Microsoft's own pricing page, how to schedule it, and the stuff that breaks. One heads-up on names: Microsoft renamed Microsoft 365 Copilot to Microsoft Copilot, and some of its pages still use the old name. Same thing.
Start here: paste this into ChatGPT or Claude
This setup happens in Outlook and Copilot, not in code, so the easy way is to have ChatGPT or Claude sit next to you and walk you through it. Paste this prompt into either one. It goes one step at a time, explains every word, and stops before anything costs money, reaches a customer or deletes something. Rather do it yourself? Everything it does is under “The manual way” below.
Hi. Please be my patient setup helper. I run a business and I'm not technical, so go one step at a time, tell me exactly what to click or type, and wait for me to say done before the next step.
Goal: set up Microsoft Copilot in Outlook so it finds every email where I promised something and didn't follow up, drafts the follow-ups for me to read, and runs that search every Monday on its own. Follow this guide; it's the source of truth for every step, menu name and price:
https://receiptsgroup.com/guides/copilot-outlook-follow-ups
Words to explain to me in plain English the first time you use them: Copilot, Copilot Chat, license, add-on, Microsoft 365 admin center, Exchange Online mailbox, scheduled prompt, connected experiences.
Steps:
1. Ask me which Microsoft 365 business plan my company has and who manages it (me, or an IT person). Ask whether I already have the paid Copilot license. If I don't know, tell me how to check: in the Microsoft 365 admin center, Users > Active users, select my name, then Licenses and Apps.
2. If I don't have the paid Copilot license, show me the guide's price table and stop. Buying the license or starting the free trial costs money or needs a credit card, and that's my call, not yours.
3. Tell me how to open Copilot: the Copilot button near the top of Outlook, or copilot.cloud.microsoft in a browser, signed in with my work account.
4. Give me the guide's find prompt to paste. When I paste the answer back to you, help me check three of the results against my Sent folder, so we know it's reading the right emails.
5. Give me the guide's drafting prompt. Remind me that Copilot only shows drafts; I read every one before I send.
6. Before I send anything: stop. These go to real customers. Help me read each draft and check it against what I actually promised. Flag any date, price, install time or discount in it that I didn't give.
7. Help me schedule the Monday prompt: hover over the prompt in the Copilot chat, select Schedule this prompt, pick Monday morning, set how many times it runs, turn on the email notification, and Save.
8. Show me where the results show up (Chats, on the left in Copilot) and where to change or stop the schedule (the ... Settings and more menu, then Scheduled prompts).
Rules: Never send, forward or delete an email for me. Never put a customer's name, email address or phone number anywhere outside Outlook and Copilot. If a menu on my screen doesn't match the guide, tell me what you expected to see and ask me what I see; don't guess. Never ask me for a password, key or code.
House rules for this setup:
- If you use a technical word, explain it in plain English the first time.
- Ask me before you assume anything about my business, my accounts or my setup.
- Stop and check with me before anything that costs money or spends credits.
- Stop and check with me before anything that sends, posts or publishes to real people.
- Stop and check with me before you delete or overwrite anything.How the pieces connect
This is the manual way: every step, every prompt, and where each button is.
- 1Your mailboxOutlook, on an Exchange Online mailbox→ the last 14 days of email
- 2The find promptCopilot Chat, with the paid Copilot license→ a list: person, promise, date
- 3The draftsCopilot drafts the top three→ three follow-ups to read, nothing sent
- 4Your readYou, in Outlook→ fixed drafts, sent by you
- 5Every MondayA scheduled prompt in Copilot→ a fresh list in Chats, plus an email that it's ready
Every Monday the scheduled prompt runs the search again. You open the result, read the drafts, and send the ones that are right.
Words you'll see
- Copilot Chat: Microsoft's AI chat for work. Every eligible Microsoft 365 business plan gets it.
- The paid Copilot license: the add-on that lets Copilot read your whole inbox, calendar, meetings and files. Microsoft sells it to small businesses as Microsoft 365 Copilot Business.
- Exchange Online mailbox: Microsoft's cloud email, the kind a Microsoft 365 work account uses. Copilot needs it to read your email.
- Scheduled prompt: a Copilot prompt you save to run on its own at a time you pick.
- Connected experiences: a Microsoft privacy setting. If it's off, scheduled prompts disappear.
Check you have the paid Copilot
This is the part most of these videos skip. Copilot Chat comes with an eligible Microsoft 365 business plan, but Microsoft's own comparison says that without the paid Copilot license, its reach into your work data is limited to files you upload. With the license it's full: meetings, emails, chats, files and more. Scheduled prompts need the license too.
Check what you have
WhereMicrosoft 365 admin center: Users > Active usersSelect your name, then Licenses and Apps, and expand Licenses. You're looking for a Copilot license next to your Microsoft 365 plan. Not the admin? Ask whoever set up your company email.
PermissionsAssigning licenses takes at least the License Administrator or User Administrator role in the admin center.No Copilot license? Pick one
For a business with up to 300 users, Microsoft sells the Microsoft 365 Copilot Business add-on on top of Microsoft 365 Business Basic, Standard or Premium (also Apps for Business and Teams Essentials), or the Business Standard and Business Premium plans with Copilot built in. Prices are in “What it costs” below. Microsoft's pricing page has the Buy now and Try for free buttons; the free trial needs a credit card and turns into a paid subscription after a month unless you cancel.
Assign it to yourself
WhereMicrosoft 365 admin center: Users > Active usersSelect your name, then Licenses and Apps, expand Licenses, tick the Copilot license and select Save changes. Or go to Billing > Licenses, pick the Copilot product and select Assign licenses.
The four steps
1. Ask Copilot to find the promises
WhereThe Copilot button near the top of Outlook, or copilot.cloud.microsoft in a browser, signed in with your work accountPaste the prompt from the video. It works as is. The longer version underneath is the one I'd actually use: it looks at what you sent, skips threads you already followed up on, and gives you a link to each email so you can check it.
Find every email from the last 14 days where I promised something and didn't follow up. List the person, the promise and the date.Look at the emails I sent in the last 14 days. Find every one where I promised something: a quote, a call back, a date, a document, a price, a visit. Leave out the ones where I already followed up later in the same thread. Give me a table with: the person, what I promised, the date I promised it, and a link to the email. If you're not sure about one, put it in a separate list called Maybe instead of guessing.2. Have it draft the top three
In the same chat, right after the list, paste this. The rules are what keep it from making promises for you.
Draft follow-ups for the top three. Rules for the drafts: - Keep each one under 100 words and sound like me: plain, friendly, straight to the point. - Say what I promised and where it stands. - Don't promise any new date, price, install time or discount. Where I need to give one, leave a blank like [DATE] for me to fill in. - Don't send anything. Just show me the drafts.3. Read every one before you send
Open the original email, hit Reply so the follow-up stays in the same thread, and paste the draft. Then read it like a customer would: is that what I promised, is the date right, did it make up anything? Fill in every [DATE] blank yourself.
Rather draft inside the reply? In new Outlook and Outlook on the web, select Help me reply in the message area. In classic Outlook, Microsoft documents it on a new email: Home > New Email, the Copilot icon, then Draft with Copilot.
4. Schedule it for every Monday
WhereCopilot Chat, Copilot in Teams, or Outlook on the web and desktopRun the Monday prompt below once. Then hover over your prompt in the chat and select Schedule this prompt. Pick when it runs (Monday morning), how many times it runs, and whether you want an email when the answer is ready (yes). Select Save.
Microsoft's page doesn't list every repeat option, and its own example is a prompt that runs every Wednesday. If your screen only lets you pick a number of runs, take the most it offers and redo the schedule when it runs out (“When it breaks” has where).
Look at the emails I sent in the last 14 days. Find every one where I promised something: a quote, a call back, a date, a document, a price, a visit. Leave out the ones where I already followed up later in the same thread. Give me a table with: the person, what I promised, the date I promised it, and a link to the email. If you're not sure about one, put it in a separate list called Maybe instead of guessing. Then draft follow-ups for the top three, under 100 words each, in my voice. Don't promise any new date, price, install time or discount: leave a blank like [DATE] where I need one. Don't send anything.
First test: one run, checked by hand
Before you trust it with Mondays, run the find prompt once and check its work. This costs nothing beyond the license. No license yet? The one-month free trial on Microsoft's pricing page is the cheapest way to test it; put a reminder on your calendar to cancel before it turns into a paid subscription if you don't keep it.
Look at the emails I sent in the last 14 days. Find every one where I promised something: a quote, a call back, a date, a document, a price, a visit. Leave out the ones where I already followed up later in the same thread.
Give me a table with: the person, what I promised, the date I promised it, and a link to the email.
If you're not sure about one, put it in a separate list called Maybe instead of guessing.Then check three by hand. Open your Sent folder, find the emails it listed, and see if it got them right. Then think of one promise you know you forgot and see if it's on the list.
Good: real people, real promises, the right dates, links that open the right emails. Bad: it says it can't see your email, or it answers from the web. That's almost always the license (see “When it breaks”). Also normal: it misses one. Copilot reads and judges, it doesn't keep a ledger, and anything you promised on a phone call or a text was never in Outlook.
Real use: three more prompts
Find emails from the last 30 days where someone asked me for a quote, an estimate or pricing, and I haven't sent one yet. List the person, what they asked for and the date. Don't draft anything yet.Summarize every email between me and [CUSTOMER NAME] in the last 60 days: what they asked for, what I promised, what's still open. Link each email.Which emails from the last 7 days ask me a direct question I haven't answered? List the person, the question and the date, oldest first.Same rule on all of them: Copilot finds and drafts, you read and send.
What it costs
| Plan | Paid yearly (a user a month) | Paid monthly (a user a month) |
|---|---|---|
| Microsoft 365 Copilot Business (add-on to a Business plan you already pay for) | $21.00 ($18.00 first-year promo, offered July 1 to December 31, 2026) | $25.20 |
| Microsoft 365 Business Standard with Copilot | $23.50 | $28.20 |
| Microsoft 365 Business Premium with Copilot | $32.00 | $38.40 |
The fine print, from that page: the add-on is only for existing Microsoft 365 customers on an eligible Business plan. The promo needs an annual commitment, applies to the first year only, and isn't available on trials. Subscriptions renew on their own. After a paid subscription starts there's a 7-day window to cancel for a prorated refund. Microsoft also says some advanced AI features bill by usage on top of the license. Copilot Business covers up to 300 users; bigger companies buy the enterprise version.
When it breaks
Copilot says it can't see your email, or answers from the web
No “Schedule this prompt” option
The Monday prompt stopped running
It won't let you schedule another prompt
It lists a promise you already kept, or misses one
A draft promises a date, price or install time you never gave
Draft with Copilot is greyed out or missing in the reply
You scheduled one back in the preview and can't find it
That's the setup
One prompt finds the promises, you read every draft, and Monday does the remembering. The job goes to whoever followed up, so make it you.
Checked on Oct 31, 2026 against
Every claim about a third-party tool in this guide (plans, prices, menu paths, commands, limits) was checked against these official pages on Oct 31, 2026. These screens change often: if something looks different, trust the page over this guide.
- Microsoft Support: Schedule your most used Copilot promptsSchedule this prompt, the run time, run count and email notice, results in Chats, the Scheduled prompts page (Run now, Edit Schedule, Turn off, Delete), up to 10, license required, connected experiences.
- Microsoft Learn: Manage scheduled promptsAdmin controls (the connected experiences policy), scheduling only in the Work IQ tab, legacy preview prompts in Power Automate.
- Microsoft Support: Chat with Copilot in OutlookThe Copilot button in Outlook, what you can ask about your inbox with and without the add-on license.
- Microsoft Support: How Copilot Chat works with and without a Microsoft Copilot licenseWork data reasoning: limited (uploaded files) without the license, full (meetings, emails, chats, files) with it.
- Microsoft Support: Draft an email message with Copilot in OutlookDraft, Generate, Keep it, Help me reply, Draft with Copilot in classic Outlook and on a Mac, the plain text and Mac version limits.
- Microsoft Support: Summarize an email thread with Copilot in OutlookSummary by Copilot at the top of a thread, numbered citations, attachment summaries, mobile.
- Microsoft Learn: License options for Microsoft CopilotCopilot Business: an add-on for up to 300 users on eligible Business plans, with an annual commitment.
- Microsoft Learn: Microsoft Copilot requirementsThe rename to Microsoft Copilot, copilot.cloud.microsoft, Exchange Online mailbox, supported Outlook versions, no group mailboxes.
- Microsoft Learn: Assign or unassign licenses in the Microsoft 365 admin centerUsers > Active users > Licenses and Apps, Billing > Licenses > Assign licenses, the admin roles needed.
- Microsoft: Copilot plans and pricingCopilot Business $21 ($18 promo) paid yearly or $25.20 monthly; Business Standard with Copilot $23.50 / $28.20; Business Premium with Copilot $32 / $38.40; the trial and refund terms (checked 2026-10-31).
Questions people ask about this
