Your Progress
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Foundation
Quick Wins + Exec Ops
Automation
Advanced
Core expectation: Alyssa owns automating as much of this role as possible end-to-end — while keeping Alex aligned, informed, and focused on high-value decisions.
Essential Skills (Ongoing)
These aren't phases — they're foundational skills to develop throughout your onboarding.
Alex's Preferences
Time zones, titles, attention to detail
AI Security & Confidentiality
What NEVER goes into AI tools
Stakeholder Mapping
Know the players and relationships
Gatekeeping & Time Protection
Protect the Alex's calendar
Autonomy Ladder
Know when to decide vs. ask
Alex's Calendar Rules (Must Know)
Calendar Hierarchy
Tori → SLT → Direct Reports → Board
Meeting Request Rules
Required vs. Optional handling
Phase 1
Foundation
Days 1-10
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✓Shadow & DocumentShadow Alex for 10 days, document all recurring tasks
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✓Office Dynamics AI TrainingPrimary course — most practical for day-to-day EA workOffice Dynamics AI Training →
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✓
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✓Internal Platform TrainingLearn the internal AI chat (email + calendar access)
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✓
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✓Task InventoryComplete task spreadsheet with AI potential ratings
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✓Who’s Who in the Zoo (VP+ & Board)Alyssa builds and maintains a living stakeholder map to navigate VP+ leaders, board members, priorities, and best channels while partnering with Alex on context.
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✓Sales/Support/Product ImmersionBuild deep context on what LeadsOnline does, why it matters, who we serve, and how teams deliver outcomes for agencies.
Phase 1 Outcome (Day 10): Tools set up, AI foundations complete, and Alex workflow baseline documented.
Phase 2
Quick Wins + Exec Ops
Days 11-30
Phase 2 focus order: 1) Core AI workflow setup 2) Executive operating rhythm 3) Logistics + communication SLAs
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✓Email Triage SystemAI categorizes inbox by urgency, drafts responses
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✓Email TemplatesBuild 10+ templates matching Alex's voice
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✓Meeting Prep AutomationAuto-generate briefings with attendee info
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✓Meeting SummariesTranscription → summary → action items
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✓Follow-up DraftsAuto-draft post-meeting emails
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✓Exec Review Readiness SLARun a one-week-ahead readiness system for standing executive reviews so nothing is last-minute.Corporate Governance Schedule & Owners (Word) ↓
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✓Trip Briefing PacksComplete travel briefings for multi-day tripsView Example → Download Template →
Day 14–30 Additions (Executive Operating Layer)
Workflow Core AI Workflow Setup
- 30-Day Alex Calendar Analysis Report: Every 30 days, analyze Alex’s calendar/time by category (strategy, people, customers, travel, admin), identify optimization opportunities, and deliver recommendations (AI-assisted synthesis allowed).
Operations Executive Operating Rhythm
- SLT Cadence & Protected Blocks: Maintain recurring SLT rhythm and protected strategic work blocks.
- Exec Review Readiness SLA: Use corporate governance schedules, confirm each review has a clear owner, and ensure Alyssa gathers pre-reads to Alex 7 days before standing executive reviews.
- Follow-up Accountability Tracker (Optional): Owner tracking for follow-ups tied to due dates.
- Meeting Discipline System: Confirm required attendees only, clarify purpose/outcomes up front, avoid over-inviting, and maintain constructive sense-check quality standards.
- Weekly Lunch Cohorts Reset: Re-launch small-group company lunches with target cohorts of 10–15 people.
Travel Travel, Calendar & Stakeholder Ops
- Travel Operating Plan (US-first): In first 7 days review Alex’s travel agenda PDF and preferences; build draft goals map (MTL 4x, Largo 1x, Denver 1x tentative, DC 3x) and track tentative international items (IFFIS Dubai, SAPS, MX, BR, Vietnam/Bangkok, Dublin).
- Seasonal + Priority Travel Windows: Track spring/fall exec offsites (Apr/Sep), IACP (Oct, confirm), and top-customer travel priority (ATF + TBD accounts).
- Personal + Family Calendar Operations: Ensure integrated support across family/work calendars, including FL vacation (Jun 19–21), MT summer trip (Jun 27–Jul 11), July 4 week MT trip, spring skiing (Mar 4–9), Neptune Beach trip, and board meeting (May, Boston).
Service Levels Service Levels, Events & Coordination
- Expense Catch-Up + Receipt Workflow (with Andrei): Partner with Finance Director Andrei to clear Alex's expense backlog and implement a fast drag-and-drop receipt process Alyssa manages for Alex.
- Visitor + Office Coordination with Kelsey (Office Manager): Keep this simple — coordinate directly with Kelsey on visitor arrivals, interviews, onsite logistics, and maintain a tight weekly sync with Kelsey + HR.
- Health, Home, and Life Ops: Set healthcare cadence (primary doctor, annual physical, any biannual specialist cadence) and build home maintenance owner/vendor tracker with renewals.
Phase 2 Outcome (Day 25): 5+ hours/week saved with repeatable email + meeting workflows, plus an operating cadence across stakeholder map, calendar quality, travel planning, and executive support systems.
Phase 3
Automation
Days 31-45
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✓Internal Chat WorkflowsMaster email/calendar automations via internal platform
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✓Custom GPTsBuild Alex Communicator, Meeting Prep, Decision Support
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✓Weekly ReportsAutomated compilation from multiple sources
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✓Travel CoordinationAuto-parse bookings, create itineraries
Phase 3 Outcome (Day 45): 8–10 hours/week saved with stable automation, executive alerts, and weekly reporting cadence.
Phase 4
Advanced
Days 46-60
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✓Daily Briefing SystemCalendar + email + news + metrics morning brief
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✓Proactive IntelligenceRelationship reminders, news alerts, follow-up tracking
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✓Document SOPsCreate playbooks for all automated workflows
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✓Measure & ReportTrack time saved, document wins
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✓Expansion PlanPlan rollout to other executives
Phase 4 Outcome (Day 60): 10+ hours/week saved, full operating rhythm in place, and playbooks ready for scale.
Your Tool Stack
Prompt Library
Email Triage
Categorize emails as 🔴 URGENT, 🟡 ACTION, 🔵 FYI...
Meeting Summary
From this transcript, create: 1. Executive Summary...
Research Brief
Prepare a briefing on [Name] from [Company]...
Email Draft
Write an email from [Alex] to [Recipient] regarding...