Stuck with Copilot
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Sales · 10 min

Find a fair upsell from what the customer already bought

Copilot Chat

Jump to the prompt ↓

Short answer: Paste the customer's past orders and what they've asked about since. Add a short list of what you could offer. Ask Copilot for up to two add-ons that solve something they've actually raised, and one reason each might not fit. Then ask for a short check-in email that leads with their problem.

Last checked against Microsoft docs: Oct 21, 2026

The best upsell is the thing the customer was going to need anyway. Copilot helps you connect what they bought with what they've been asking about. Growing an account the honest way builds trust and pipeline at the same time, and pipeline is what you get paid on.

A common situation (composite)

They bought the starter plan in March.
They've emailed support three times about the same limit.
I want to bring it up without sounding pushy.

What you get

  • Data: their past orders, recent requests, and your product list.
  • Does: matches their requests to add-ons and drafts a check-in.
  • Output: up to two upsell ideas with reasons, and a short email.
  • How often: at quarterly check-ins or before renewal.

Before you start

  1. Needs: Microsoft 365 Copilot Chat. Not sure what you have? Start here.
  2. Where: Copilot Chat.
  3. Access: Copilot only uses content you already have permission to open. Use only information your company allows in Copilot.

The steps

  1. Gather what they bought and when, plus the requests or issues they've raised since.
  2. Paste a short list of add-ons with one-line descriptions.
  3. Run the prompt and cut anything that doesn't tie to something they said.
  4. Run the follow-up for the email.
  5. Check pricing and availability yourself before you mention them.

Copy this prompt

This customer bought [products] on [date].
Since then they've asked about or had issues with: [list requests, tickets, comments]
Our add-ons: [paste options with one-line descriptions]

Suggest up to two add-ons that solve something they've actually raised. For each:
- Which request it solves
- How, in one sentence
- One reason it might NOT be a fit

If nothing fits, say so. Don't invent features or prices.

(Prompt from stuckwithcopilot.com/guides/upsell-from-last-order/)

Make it better

Run this next, in the same chat.

Draft a short check-in email to [name] that leads with the problem they raised, not our product. Mention the add-on in one sentence as an option, and ask a question that's easy to answer. Under 100 words, no hard sell.

(Prompt from stuckwithcopilot.com/guides/upsell-from-last-order/)

Data tip: use this with your work Copilot, and leave out passwords, payment details and anything your company marks restricted.

What a good result looks like

Each suggestion ties to something the customer said. The email reads like a check-in, not a pitch, and it has one easy question.

If a feature is missing

With a Microsoft 365 Copilot license, ask Copilot Chat to list what this customer asked about in your emails and meetings over the last 90 days, then use that as the input.

Make it smarter

Keep a short "What it got wrong" note. Paste it above the prompt next time, like "Don't invent dates".

Not sure what to ask? Copy the quick note for your Copilot admin.

Questions people ask

Find a fair upsell from what the customer already bought?

Paste the customer's past orders and what they've asked about since. Add a short list of what you could offer. Ask Copilot for up to two add-ons that solve something they've actually raised, and one reason each might not fit. Then ask for a short check-in email that leads with their problem.

What do I need for this?

Microsoft 365 Copilot Chat. With a Microsoft 365 Copilot license, ask Copilot Chat to list what this customer asked about in your emails and meetings over the last 90 days, then use that as the input.

What if the honest answer is that they don't need anything?

Then say that and ask how it's going. Customers remember the rep who didn't push. That trust is worth more at renewal than a small add-on now.

Can Copilot see what they bought?

Only if that information is in emails or files you can open, or your company connected your CRM to Copilot, for example through the Sales agent or a custom agent. Otherwise, paste it in.

Can I use this for a whole book of accounts?

Do it one account at a time. Batch versions turn into generic offers, which is exactly what this guide helps you avoid.

Next step

Try it once, then make it yours.

Run the prompt on one real task this week. Then pick your next workflow.

See the workflow library ↗

Cite or share this guide

Find a fair upsell from what the customer already bought. Stuck with Copilot. https://stuckwithcopilot.com/guides/upsell-from-last-order/ Last checked Oct 21, 2026.

Official references

Last checked against Microsoft docs: Oct 21, 2026.