Section 1: Availability & Preference Management
1.1 Preferences Cannot Be Changed via Natural Language
Skej doesn't modify scheduling preferences based on conversational requests via email, Slack, text, or WhatsApp.
Examples of requests that won't work:
- “Only book me meetings after 10am.”
- “Never schedule me on Fridays.”
- “Add a 30-minute buffer before meetings.”
- “Reduce my daily meeting cap to 3 hours.”
These changes must be made in settings. Even if the assistant confirms the change, it will only apply to that specific meeting. Users must save preferences in the dashboard instead.
1.2 One-Off Freeform Instructions Do Not Persist
Instructions like these won't create long-term rules:
- “Always schedule meetings with John at the Coffee Shop.”
- “When I meet with Paul, always title it 'Pizza Party'.”
- “If someone suggests an hour meeting, always tell them only 30 minutes.”
- “You can always reschedule over my 1-1 with Beck on Fridays.”
While Skej may apply such instructions to the current interaction, they won't persist. To create lasting rules, users should add them to their Instructions/Memories settings.
1.3 Availability May Appear Open — But Skej Says Busy
If Skej indicates unavailability while the calendar appears open, it may be enforcing:
- Daily meeting limits
- Buffer settings
- Minimum notice rules
- Time-of-day constraints
- Scheduling window rules
Skej enforces these consistently without overriding them automatically. Users should check their settings if something appears incorrect.
1.4 No Automatic Meeting Prioritization
Skej does not:
- Prioritize one contact over another
- Automatically bump lower-priority meetings
- Reshuffle existing meetings to accommodate new ones
If conflicts exist, Skej requests direction rather than making autonomous decisions to prevent unintended calendar disruption.
1.5 Custom Instructions
Skej supports open-ended custom instructions allowing nuanced scheduling logic.
Examples:
- “Don't schedule Fridays unless it's the only time available.”
- “If I tell you to offer times starting at a future date, never offer times before that date.”
- “Always prefer mornings for internal meetings.”
- “Avoid back-to-back meetings with external clients.”
Custom instructions layer supplemental logic on core availability rules.
Important Considerations:
- Custom instructions are flexible and open-ended
- They are not pre-structured toggles
- They may not behave perfectly initially
- They should be tested in real scenarios and refined over time
Edge cases can occur depending on phrasing and context.
Contact-Specific Instructions
Instructions referencing specific people (e.g., “Always prioritize John” or “Never offer late afternoons to Sarah”) should be used carefully.
Custom instructions evaluate for every scheduling interaction without automatic contact scoping. This means:
- Instructions may influence meetings beyond the intended person
- Overlapping rules can create conflicting logic
- Behavior may become difficult to predict with layered person-specific rules
Best practice: “Keep custom instructions general when possible. If contact-specific logic is necessary, test thoroughly and monitor behavior.”
Avoid Conflicting Logic
Conflicts can occur when:
- An instruction contradicts a core setting
- Multiple custom instructions overlap
- A temporary instruction conflicts with a global one
When conflicts exist, Skej attempts logical reconciliation, but behavior may not always align with expectations.
Section 2: Channel-Specific Guardrails
Skej behaves differently depending on communication channel.
2.1 Email
Email is the most flexible interface. However:
- Complex, multi-layered instructions may require clarification
- More requests in a single message make parsing harder
Users can batch requests but should keep instructions clear and focused when possible, breaking into multiple tasks if needed.
2.2 Email Thread Consistency
Skej operates based on active scheduling thread context. Meeting-specific instructions should remain within that thread.
Avoid Mixing Thread + 1:1 Instructions
A problematic pattern:
- A scheduling thread is active with multiple participants
- A user emails Skej separately 1:1 with additional instructions
- The user expects those instructions to silently influence the active thread
This can cause inconsistency because thread context, participant visibility, and state maintenance differ.
Best practice: “Keep all meeting-specific instructions within the original scheduling thread. If you need to modify logic privately, clearly reference the meeting and confirm behavior before assuming changes were applied.”
2.3 Assistant Will Not Act Unless the User Is Included
Skej will only act on scheduling requests when the user it represents is included on the email thread.
If someone emails the assistant saying, “I'd like to meet with Justin,” but doesn't include Justin, the assistant won't respond.
This limitation exists because automatically searching the user database and selecting people based on name or context creates risk of:
- Representing the wrong user
- Accessing the wrong calendar
- Acting without proper authorization
One assistant can represent thousands of people even within a single company.
To ensure accuracy and protect privacy:
- The intended user must be included on the email thread, or
- The user must explicitly instruct the assistant to begin scheduling
If a contact emails both assistant and user, the assistant will ask for user confirmation before proceeding.
This adds friction but serves as a deliberate safeguard based on Skej's architecture. Improvements are actively being explored.
2.4 Slack
Slack scheduling is designed for internal coordination.
Works:
- Internal DMs, channels, and group DMs
- Internal meeting scheduling
- All participants are Skej users
Does not work:
- Slack Connect channels
- External contacts
- Mixed Skej/non-Skej Slack scheduling
Slack lacks the routing and identity infrastructure required for external coordination.
2.5 Text / WhatsApp
Designed primarily for personal calendar control.
Works:
- Blocking time
- Moving existing meetings
- Solo scheduling actions
- New requests with external contacts can be DM'd but will be relayed via email
Does not work:
- Group SMS threads
- WhatsApp group chats
- Group scheduling (even if all members are Skej users)
If users request meetings with others via text/WhatsApp, Skej coordinates externally via email, ensuring reliability and auditability.
Section 3: Contact Memory & Context
Skej currently:
- Does not prioritize specific contacts
- Does not store long-term relationship context
- Does not track VIP status
- Does not remember past preference patterns
It only stores timezone and required scheduling metadata. Each request evaluates independently against current rules.
Summary
Skej is an autonomous scheduling assistant operating within clearly defined system boundaries.
It is designed to:
- Coordinate intelligently
- Enforce availability consistently
- Operate across email, Slack, and SMS
- Execute calendar actions automatically
- Respect configured rules and enterprise constraints
When Skej asks for clarification or enforces rules, it's applying configured scheduling settings logic, not malfunctioning.
Understanding these boundaries ensures:
- Fewer surprises
- Cleaner coordination
- More predictable outcomes
- Higher trust in the assistant
How to Get the Best Results
To maximize effectiveness:
- Update availability rules in settings (not conversationally)
- Keep multi-step scheduling instructions clear and structured
- Use Slack for internal meetings only
- Use email for external coordination
- Use SMS/WhatsApp primarily for personal calendar control
- Review buffers and meeting caps if availability seems incorrect
“Skej performs best when its autonomy is paired with clear configuration.”
Looking Ahead
As Skej evolves, expansion areas include:
- Structured natural language preference updates
- Contact prioritization logic
- Enhanced group messaging support
- Context-aware scheduling improvements
The goal is to increase autonomy without compromising predictability.