Why is Microsoft 365 setup (Groups + SharePoint + Domains) still so complex?

Microsoft 365 Setup Feedback Summary

Summary of Experience:

Setting up two small business workspaces (Cork & Clarity and Stone Clarity Consulting) in Microsoft 365 required navigating multiple disconnected systems including the Admin Center, Outlook, SharePoint, and an external DNS provider. The process was significantly more complex than expected and not intuitive for a non-technical user.

Key Issues Encountered:

1. Identity and Account Confusion
- Unclear whether to create separate users or use one account with aliases
- Creating multiple users caused login confusion, broken permissions, and access issues

2. Domain and DNS Setup Complexity
- Required switching between Microsoft and external DNS (Looka)
- Instructions were unclear and required manual troubleshooting
- No clear distinction between required and optional DNS records

3. Default Domain Confusion
- New groups defaulted to the wrong domain
- No visible option to change domain during group creation
- Required changing global default domain (non-intuitive)

4. Inconsistent Group Behavior
- Outlook groups and Teams-backed groups behave differently
- No indication of differences or consequences
- Groups appeared in some places but not others

5. Membership and Ownership Issues
- Group creator was not consistently added as member
- Ownership did not always persist after changes
- Groups existed but were inaccessible or invisible

6. Outlook UI Limitations
- Groups not visible despite existing and being correctly configured
- No clear instructions on how to 'activate' or 'follow' groups

7. SharePoint Site Not Created Automatically
- SharePoint sites were not created when groups were created
- Required hidden steps: Outlook → Files → Open in SharePoint
- No indication that the site did not exist yet

8. SharePoint Discovery Issues
- Sites do not appear until manually accessed or followed
- No onboarding or guidance for discovering sites

9. Ghost/Deleted Items Still Visible
- Deleted group (Cork & Clarity Hub) remained visible
- No clear distinction between deleted vs followed sites

10. Fragmented User Experience
- Required switching between multiple platforms
- No single place to manage or understand setup status
- High cognitive load for basic configuration

Conclusion:

While Microsoft 365 is a powerful platform, the initial setup experience is overly complex and fragmented, especially for small businesses. Simplifying group creation, making SharePoint provisioning automatic and visible, and improving UI consistency across apps would significantly improve usability and adoption.