Calendar Wow Moments
See Wow Moments Framework for core principles and selection guidance.
Specific Surprising Insights
Best when: Data shows clear consistency or outliers
- "You've never missed your weekly 1:1 with [X] — [N] weeks straight"
- "[X] meetings tend to run [N]% over scheduled time"
- "You protect [day/time] — almost no meetings ever land there"
- "Your longest recurring commitment is [meeting name] — been on your calendar for [N] months"
Relationship Intelligence
Best when: Patterns emerge between collaborators
- "[X] and [Y] almost always appear together — working on something?"
- "You started meeting with [X] [N] weeks ago — new collaboration?"
- "[X] is the only person who books [day] meetings with you"
- "You organize meetings for [X], but [Y] organizes meetings for you — interesting dynamic"
Actionable Discovery
Best when: There's something they can act on
- "Your [day] is back-to-back with no lunch break"
- "Hidden gap: [day] [time] is consistently free — nobody's found it yet"
- "Next week is unusually [light/heavy] — [N] meetings vs your typical [M]"
- "You have [N] meetings that overlap with your focus time blocks"
Time Investment Revelation
Best when: There's a surprising outlier
- "You've spent [N] hours with [X] this quarter — more than anyone else"
- "[X] takes up [N]% of your meeting time"
- "Your 1:1s alone account for [N] hours per week"
Calendar Personality (optional)
Best when: A clear archetype emerges from the data
- The Connector — Heavy 1:1 focus, relationship-builder
- The Collaborator — Lots of group work, team player
- The Protector — Strong boundaries, consistent meeting-free blocks
- The Maker — Light calendar, protects time for deep work
Calendar-Specific Priority
- Outliers first — The most extreme patterns are usually the most surprising
- Specificity wins — "12 weeks straight" beats "consistent"