Email Automation

Automate email drafting, scheduling, and follow-ups with Sidekick and Gmail.

Overview#

This walkthrough shows how to use Sidekick with a Gmail connection to automate email workflows with full governance.

Prerequisites#

  • Gmail connection active in workspace settings
  • Governance rules configured for email actions

Scenario: Weekly team update#

Step 1: Create the workflow#

Tell Sidekick what you want:

Every Friday at 4pm, draft a weekly update email to the engineering
team summarizing: PRs merged, issues closed, and blockers raised
this week. Pull data from our GitHub connection.

Step 2: Review the proposal#

Sidekick proposes:

  1. Query GitHub for the week's activity
  2. Summarize into categories
  3. Draft the email
  4. Send to engineering@company.com

Each step appears as a proposal card in your chat.

Step 3: Set governance rules#

For recurring workflows, consider:

RuleSetting
GitHub readsAuto-approve
Email draftingAuto-approve
Email sendingRequire approval

This lets Sidekick prepare the email autonomously but wait for your sign-off before sending.

Step 4: Monitor#

Check Observe → Activity each Friday to see the workflow execute. Approve the final send step, or edit the draft first.

success After a few weeks, if the drafts consistently meet your standards, you can auto-approve the send step too.