Purpose
Resolve competing calendar demands by scoring each conflicting request against the executive's stated priorities, then recommending exactly which meeting wins, which move, which delegate, and which decline — with rationale the executive can approve at a glance and language ready to send to every affected party.
When to Use
Invoke this skill when the user asks to:
- Resolve two or more meetings that overlap on the executive's calendar
- Decide whether to accept a high-priority request that lands on an already-full day
- Rank competing requests when the executive has more asks than available hours
- Determine which recurring meetings to protect, shorten, delegate, or drop
- Draft reschedule or decline messages for the losing side of a conflict
- Recover a day thrown off by a last-minute urgent request
Inputs Required
Before starting, collect:
- Conflicting events: Each competing meeting with title, requester, time, duration, and stated purpose
- Executive priorities: The exec's current top objectives or a ranked list of what matters this quarter
- Attendee stakes: Who is in each meeting and their relationship (board, direct report, external client, internal peer)
- Immovable anchors: Meetings, travel, or personal blocks that cannot move under any circumstances
- Decision authority: What the assistant can resolve independently vs. what needs the exec's sign-off
- Reschedule window: How far out meetings can be pushed and any blackout dates
- Delegation options: Who on the team can attend in the executive's place, if anyone
If executive priorities are not provided, default to a standard hierarchy (board/legal/regulatory > revenue-generating external > direct report 1:1s > internal cross-functional > optional/FYI) and flag the assumption.
Instructions
Step 1: Inventory the Conflict
List every competing event in a single view with time, duration, requester, purpose, and attendees. Identify the exact overlap window and whether the conflict is a true collision (same time) or a capacity conflict (day is over-full). Flag any immovable anchors upfront — these are removed from contention before scoring.
Step 2: Score Each Request on Five Factors
Rate each conflicting meeting 1–5 on each factor, then total (max 25):
- Strategic alignment: How directly does this advance a stated executive priority? (5 = core objective; 1 = tangential)
- Stakeholder weight: Who is asking and what is the relationship cost of moving them? (5 = board/key client; 1 = optional internal)
- Reversibility: How hard is this to reschedule? (5 = one-shot, external, hard to rebook; 1 = recurring internal, trivially moved)
- Time sensitivity: Does a decision or deadline hinge on this happening now? (5 = deadline-critical; 1 = no urgency)
- Executive-only necessity: Does this genuinely require the executive, or can it be delegated? (5 = only the exec can do it; 1 = fully delegable)
Step 3: Rank and Assign a Resolution
Order the meetings by total score. Assign each a resolution verb:
- Keep — highest-scoring meeting holds the slot
- Move — reschedule into the nearest acceptable window
- Delegate — hand to a named team member with a briefing note
- Shorten — compress to fit around the winner (e.g., 60 → 30 min)
- Decline — remove entirely with a graceful reason
Break ties in favor of the least reversible, most externally-facing meeting.
Step 4: Propose the Reschedule Mechanics
For every "Move" or "Shorten," propose 2–3 specific alternative slots within the reschedule window, respecting blackout dates and existing anchors. Note buffer time so the executive isn't stacked back-to-back. For every "Delegate," name the substitute and list the 2–3 briefing points they need.
Step 5: Draft the Communications
Write ready-to-send messages for each affected party:
- Reschedule note: acknowledges their time, states the new proposed slots, keeps warmth
- Delegation note: introduces the substitute and frames it as attention, not a downgrade
- Decline note: gracious, offers an alternative path (async update, future date, delegate) so the door stays open
Step 6: Summarize for Executive Sign-Off
Produce a one-glance recommendation table so the exec can approve or override in seconds, plus a flag for any decision that exceeds the assistant's authority.
Output Format
- Structure: Conflict inventory → scoring table → ranked resolution → reschedule mechanics → drafted communications → sign-off summary
- Length: 700–1,000 words
- Format: Scoring and resolution as tables; communications as copy-ready message blocks; summary as a compact approval table
- Sections: Conflict Inventory, Priority Scoring, Recommended Resolution, Reschedule Options, Ready-to-Send Messages, Executive Sign-Off
- Tone: Chief of staff — decisive, discreet, protective of the executive's time and relationships
Quality Checklist
Before delivering output, verify:
- [ ] Every conflicting event received a score on all five factors and a resolution verb
- [ ] Immovable anchors were excluded from contention, not scored
- [ ] Each "Move" or "Shorten" includes 2–3 specific alternative slots within the reschedule window
- [ ] Each "Delegate" names a specific substitute and their briefing points
- [ ] A ready-to-send message exists for every affected party
- [ ] The sign-off summary flags any decision requiring the executive's approval
Notes
- When priorities conflict with relationships, protect the relationship on the low-stakes meetings and protect the priority on the high-stakes ones — never trade board goodwill to save a movable internal sync.
- Recurring internal meetings are the most common source of hidden capacity conflicts; a standing meeting that could be shortened or made async is often the cleanest thing to move.
- Always leave the executive a visible override — recommend firmly, but present the ranking transparently so they can adjust in one line.
- For last-minute urgent requests, score the incoming request the same way; urgency is only one of five factors and should not automatically win.
How to use this skill
This file is a Claude Code skill in Anthropic's standard format — markdown with YAML frontmatter at the top.
Installing in Claude Code:
~/.claude/skills/<folder-name>/SKILL.md— auto-loads in every session anywhere on your machine (recommended for skills you'll use across multiple projects)<your-project>/.claude/skills/<folder-name>/SKILL.md— auto-loads only when working in that project (recommended for project-specific skills)
Restart Claude Code or open a new session to register.
Using in Claude.ai, ChatGPT, Gemini, or other AI tools:
- Drag this file into a new chat, or copy and paste its contents
- Send your task or request as your next message — the AI will apply the skill where it fits
For Claude Code skill details: https://docs.anthropic.com/en/docs/claude-code/skills