Year-Round Property Maintenance Playbook

As the EA, you oversee the end-to-end property maintenance process. This includes coordinating service providers, setting recurring schedules, tracking payments, and ensuring quality standards are consistently met. You also proactively anticipate seasonal and preventive maintenance needs so the property remains in optimal condition all year.

All documentation and coordination should be tracked in GuideLayer > Task comments and in the designated tracking system (e.g., Asana, Sheets, Airtable). Use AI Copilot to research vendors, draft communications, troubleshoot issues, and generate seasonal/preventive recommendations.

Why this matters:

Maintaining a property is detail-heavy and time-sensitive. By handling logistics and vendor management, you reduce stress on the executive and ensure the property stays in excellent condition without their active involvement. Proactive planning prevents costly, urgent repairs later.

EXPECTED OUTCOMES

• Property is consistently maintained with minimal executive involvement.
• Reliable, vetted service providers engaged and managed by the EA.
• Recurring service schedules established (weekly, monthly, seasonal).
• Payments tracked and processed according to client-specific guidelines.
• Vendor and service records fully documented in the designated tracking system.
• Seasonal and preventive maintenance recommendations proactively shared with the executive.
• AI Copilot used to support communication, planning, and troubleshooting.

Use this playbook whenever you are responsible for ongoing property upkeep, including:

• Primary and secondary residences.
• Rentals or investment properties the executive owns.
• Common areas, outdoor spaces, and specialized systems (e.g., pool, HVAC, security).

Pre-conditions

• Property details and access protocols confirmed (address, gate codes, lockbox, security).
• Executive expectations and standards for property condition clearly discussed.
• Tracking system agreed (Asana, Sheets, Airtable, etc.) and set up.
• Spending/approval thresholds and payment process clarified.

Executive Assistant

• Owns property maintenance coordination end-to-end.
• Identifies, vets, and manages service providers.
• Sets and maintains recurring schedules.
• Tracks invoices and payments per protocol.
• Documents services, feedback, and decisions in GuideLayer and tracking system.

Executive

• Provides initial standards, priorities, and budget guardrails.
• Reviews major vendor choices or larger maintenance projects, if required.
• Shares feedback on property condition and service quality.

Service Providers / Vendors

• Deliver services according to agreed scope, schedule, and standards.
• Communicate issues (access, constraints, extra work needed) promptly.

Finance / Operations (if applicable)

• Processes payments and reconciles invoices.
• Maintains contracts and legal/compliance documentation.

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Tools:

• GuideLayer (task + comments)
• Asana / Airtable / Google Sheets (property maintenance tracker)
• Google Calendar (service schedules)
• Yelp, Google Reviews, Nextdoor, Angi/HomeAdvisor (vendor research)
• Email / SMS for provider communication

AI Copilot Power Prompts:

• “Draft a professional email requesting quotes from three local HVAC providers for annual servicing.”
• “Generate a preventive maintenance checklist for [spring/fall/winter] property care in [city/region].”
• “Compare these two vendors side by side for reliability, cost, and reviews. Highlight any red flags.”
• “Summarize this quarter’s property maintenance activity and flag any recurring issues or risks.”

Client Feedback Template:

Hi [Client], I’ve coordinated [service] for your property and updated your maintenance tracker with all details. Could you share quick feedback — was the quality and timing up to your standards, or is there anything you’d like me to adjust for future visits?

• 100% of recurring services completed on schedule.
• Service provider database maintained and current (contacts, agreements, notes).
• Invoices tracked with zero missed or late payments.
• Executive satisfaction consistently confirmed via feedback loop.
• Seasonal/preventive recommendations shared at least 2 weeks before the relevant season or due date.

Pro Moves

• Maintain a living vendor database with ratings, notes, and feedback history.
• Always present 2–3 vendor options with side-by-side comparisons for new services.
• Add all major service appointments to the executive’s calendar if presence or awareness is needed.
• Negotiate bundles or loyalty discounts (e.g., HVAC + duct cleaning, lawn + landscaping).
• Provide seasonal “look-ahead” reports so the executive knows what’s planned (without needing to ask).

Top Mistakes to Avoid

• Vague or undefined scope of work with providers.
• Not maintaining accurate vendor contact info, contracts, or access instructions.
• Skipping feedback, allowing dissatisfaction or poor performance to continue.
• Waiting for breakdowns instead of planning preventive work.
• Escalating to the executive too early instead of using AI Copilot to troubleshoot first.

CLIENT FEEDBACK LOOP

After each major service or a quarterly maintenance review, send:

“Hi [Client], I’ve coordinated [Service] and documented everything in your property maintenance tracker. Could you share quick feedback: Was the service up to your standards? Is there anything you’d like me to adjust for future visits?”

Log responses in your AI Tool / Project Management Tool, and use them to refine standards, vendor choices, and future scheduling.

• Vendor no-shows: Confirm appointments the day before; keep 1–2 backup vendors on file.
• Overlapping service schedules: Cross-check the executive’s calendar and property access before confirming times.
• Payment delays: Track invoices weekly and set reminders in Asana/Sheets.
• Executive unavailable for access: Arrange alternative access (lockbox, concierge, trusted local contact).
• Emergency repairs (plumbing, electrical, storm damage): Use pre-vetted emergency vendors; ensure immediate containment, then brief the executive.
• New property or service type: Use AI Copilot + online reviews to identify potential vendors; validate using references.
• Multiple properties: Maintain separate tabs/lists for each property, plus a master overview sheet for the executive.
• Disputed invoices: Use AI Copilot to draft escalation messages and propose solutions before involving the executive.