Outlook lead follow-up workflow for contractors

If your contracting business runs on Microsoft 365, most of the automation tutorials on the internet aren’t written for you. They assume Gmail, Google Sheets, and the friendly OAuth flow that comes with them. Outlook is different. It’s not worse — it’s actually more capable — it’s just less documented for small businesses.

Here’s the Outlook lead-follow-up workflow, written for the real world.

Outlook’s equivalents, translated

Gmail concept	Outlook equivalent
Label	Category
Filter	Rule
Gmail API	Microsoft Graph API
OAuth in GCP	App registration in Azure AD
Drafts folder	Drafts folder (same name, same idea)

If you’ve done a Gmail workflow and someone asks you to do the Outlook version, the mental model maps 1:1. The plumbing is different.

The five-step flow

1. Outlook trigger in n8n — polls your mailbox every 2 minutes for new messages with the Leads / New category.
2. Classifier — same LLM call, same prompt. Outputs structured JSON (service type, intent, urgency).
3. CRM upsert — write a row to your Sheet or your Airtable.
4. Drafter — composes a reply based on service type.
5. Create draft in Outlook — lands in your Drafts folder with category Leads / Drafted.

You never leave Outlook. You scan Drafts in the morning, send the good ones.

The Azure AD piece

Connecting Outlook to n8n requires registering an app in Azure AD. The choke point most people hit:

• Permission type: Delegated, not Application. You want the workflow to act as you, not as a service account.
• Scopes: Mail.ReadWrite, Mail.Send (only if you’ll auto-send), User.Read. The offline_access scope is required for the refresh token.
• Consent: an admin might need to approve the first time for some tenants.

If you’re an admin on your tenant, this is a 10-minute exercise. If you’re not, loop in your IT person before you start — getting that approval can otherwise drag a week.

Why categories are underrated

Outlook categories don’t just color-code emails. They’re searchable, rule-triggerable, and syncable across every Outlook client you use. A well-structured set:

• Leads / New
• Leads / Hot
• Leads / Warm
• Leads / Drafted
• Leads / Sent
• Leads / Don't reply

Pair this with a rule that auto-applies Leads / New based on subject or sender patterns, and you’ve effectively built a lightweight CRM view inside your inbox. Sort by category, done.

The follow-up piece

The reason contractors lose deals isn’t that they don’t reply. It’s that they reply once, don’t hear back, and never ping again. The follow-up workflow is an n8n scheduled trigger that:

1. Runs at 2pm local every weekday.
2. Reads your CRM for rows with status = followup_pending and last_touch_at < today - 1 day.
3. Drafts a short “checking in” email.
4. Drops it in your Outlook Drafts folder.

You scan Drafts at 2:15pm. Send the good ones. Most are good.

The short version

If you want a pre-built Outlook + Google Sheets or Outlook + Airtable workflow — with the Graph API connection, the categories, the follow-up scheduler, and the prompts tuned for contractor businesses — that’s what Inbox Autopilot for Landscapers is. The “landscapers” label is the first niche; the plumbing works identically for cleaners, roofers, and similar trade businesses.