Use Outlook's Copilot to Draft Subcontractor Follow-Up Emails

What This Does

Outlook Copilot drafts follow-up emails to non-responsive subcontractors, pulling context from your email thread so you don't have to manually summarize the history every time you chase a missing quote.

Before You Start

• You have Microsoft 365 with Copilot enabled (Business or Enterprise plan)
• Outlook is open with the sub's email thread visible
• You know the bid deadline and what you're waiting on

Steps

1. Open the email thread

Open the existing email thread with the subcontractor, even if it's just the original bid invitation you sent. Having the thread open gives Copilot context about the project and what you asked for.

2. Start a reply and activate Copilot

Click Reply on the thread. In the compose window, click the Copilot icon (purple sparkle) above the compose area. Select Draft with Copilot.

3. Describe what you need

In the Copilot prompt box, type what kind of follow-up you need. Examples:

• "Write a polite but firm follow-up asking for their quote by Friday. We're chasing their mechanical bid."
• "This sub hasn't responded in 2 weeks. Write a final reminder with a deadline of [date]. After that we'll move forward without them."

4. Review and adjust

Copilot drafts the email using your thread context. Read it carefully, verify the project name, deadline, and tone are correct, then click Keep it to move the draft into your compose window and edit before sending.

5. Build a template sequence

For bids with many non-responsive subs, draft your three standard follow-up emails (day 7, day 14, day 21) using Copilot once, then save them as Quick Parts in Outlook (Insert → Quick Parts → Save Selection) for reuse on future bids.

Real Example

Scenario: You sent bid invitations to 12 electrical subs 10 days ago. Seven have responded. You need to chase the remaining five before your bid is due in 4 days.

What you do: Open each thread, click Reply, activate Copilot, and type: "Write a brief follow-up asking them to confirm they're bidding and to submit their quote by [bid date minus 1 day]. Mention the project is a 150,000 SF office building in [city]."

What you get: A professional, appropriately urgent follow-up that references the project and deadline, drafted in 10 seconds. You review, adjust as needed, and send. Five emails done in under 5 minutes.

Tips

• Set your follow-up tone based on the relationship: "friendly reminder" for preferred subs, "formal final notice" for new subs who haven't engaged
• Ask Copilot to "make this shorter, under 75 words" if it generates something too long for a quick check-in
• For subs you call frequently, Copilot's drafts work well as a script for voicemail messages too

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