The 15Five AI Outlook Calendar integration connects your Microsoft 365 calendars to 15Five AI, enabling agents to surface insights such as meeting load, focus time, availability patterns, and early capacity signals. The integration syncs calendar events with a sensitivity level of Normal across your Microsoft 365 tenant. Events marked Private in Outlook are automatically excluded before any data is ingested. To set up the integration, a Microsoft Global Administrator or Privileged Role Administrator must grant tenant-wide admin consent.
Access and Availability
| Role | Requirement |
|---|---|
| Microsoft Global Administrator or Privileged Role Administrator | Required to grant tenant-wide admin consent during setup |
| 15Five Company Admin, HR Admin, or IT Admin | Required to initiate the connection from Agens Hub |
The same person can hold both roles, or two people can coordinate the setup.
15Five AI respects Outlook privacy controls and only syncs events with a sensitivity level of Normal. Events marked Private in Outlook are automatically excluded before any data is ingested.
Note: To ensure the highest level of security, 15Five is continually investing in our overall information security program, resources, and expertise. To review 15Five's security documents, and how we handle your company data, see our Trust Website.
Feature Structure
The integration is configured from Agents Hub > Integrations > Outlook Calendar.
How Access Works
The integration uses application permissions granted once at the tenant level — no individual employee sign-in is required. It reads from every user's calendar in the Microsoft 365 tenant, subject to Outlook's sensitivity settings.
Data Synced
Calendar events (Normal sensitivity only):
- Event subject and description
- Start time, end time, and time zone
- Organizer and attendee details — names, email addresses, response status
- Meeting locations and online meeting links
- Recurrence patterns
- Files attached to events
- Calendar metadata — categories, free/busy status
User and directory data:
- User profiles — names, email addresses, job titles, reporting relationships
- Directory data — groups, organizational hierarchy, reporting structure
Excluded by default: Any event marked Private in Outlook. Private events are filtered out before any data is ingested — 15Five AI never sees the subject, description, attendees, or location of a private event.
Backfill and Sync Cadence
On first connect, up to one month of calendar history is backfilled across all user mailboxes. Backfill typically completes within 24 hours, after which events sync on an ongoing basis.
Permissions Requested
These are application permissions granted once at the tenant level during setup:
| Permission | Purpose |
|---|---|
Calendars.Read |
Read calendar events from all mailboxes in the organization. Private events are filtered out before processing. |
User.Read.All |
Read user profiles — names, email addresses, job titles, and other directory fields — to attribute events to the right people |
Directory.Read.All |
Read directory data — groups, org hierarchy, reporting structure — so insights reflect how teams are organized |
People.Read.All |
Add context on event attendees not in your org directory and surface working relationships beyond the formal org chart |
Access can be revoked at any time from Microsoft Entra ID or by disconnecting the integration in 15Five.
Key Rules
- Only events with a sensitivity level of Normal are synced — this is the Outlook default for any event.
- Events marked Private are excluded automatically before any data is ingested; 15Five AI never processes their content.
- All permissions are application permissions — they apply tenant-wide with no per-user sign-in required.
- Tenant-wide admin consent must be granted by a Global Administrator or Privileged Role Administrator.
- The integration reads from all user mailboxes in the tenant; scope cannot be narrowed to specific users or groups today.
- The integration can be disconnected from Agents Hub > Integrations, or by revoking consent in the Microsoft Entra admin center. Revoking from Microsoft Entra ID ends access immediately, even if the integration has not been disconnected from 15Five.
WHAT YOU CAN DO
Set Up
Manage
Analyze
Common Questions
Who can set up the Outlook Calendar integration?
A user with the Company Admin, HR Admin, or IT Admin role in 15Five can initiate setup. A Microsoft Global Administrator or Privileged Role Administrator must grant tenant-wide admin consent.
What calendar events are synced to 15Five AI?
15Five AI syncs Outlook events with a sensitivity level of Normal, including event details, attendees, locations, and related calendar metadata.
Are private Outlook events synced?
No. Events marked Private in Outlook are automatically excluded before any data is ingested by 15Five AI.
How much calendar history is imported when the integration is connected?
15Five AI backfills up to one month of calendar history during the initial connection.
How often does Outlook Calendar data sync?
After the initial backfill is complete, calendar events sync on an ongoing basis.
Can I disconnect the integration?
Yes. You can disconnect the integration from 15Five or revoke access through Microsoft Entra ID at any time.
Does each employee need to sign in to connect their calendar?
No. The integration uses tenant-wide application permissions and does not require individual employees to sign in.
RELATED ARTICLES
- Set up Agents (Admin)
- Add and manage Company Context (Admin)
- Google Calendar Integration- Feature Overview
- MS Teams Integration - Feature Overview
- Connect work system integrations (Admin)
- Feature Overview - Agents & The Context Layer