Stop managing your own calendar — that's not what your time is for

Every hour you spend wrangling meeting requests, chasing confirmations, and resolving scheduling conflicts is an hour you're not doing the work only you can do. Trusty Oak EAs have logged 330 time entries in calendar and scheduling support alone — handling the back-and-forth, buffer times, prep reminders, and rescheduling so your week is structured before it starts. Delegating this isn't a luxury; it's a basic leverage decision.

300+ tasks completed in this service category across our client base.

What your executive assistant handles

Concrete tasks our team takes on — not vague promises.

Meeting Request Intake & Coordination

Your EA monitors incoming meeting requests, applies your scheduling rules (time blocks, no-meeting days, buffer preferences), and confirms directly with attendees — so you never touch the back-and-forth.

Calendar Audits & Weekly Structuring

Before each week begins, your EA reviews your Google Calendar or Outlook for conflicts, overloads, and missing prep time, then makes adjustments that reflect your actual priorities.

Recurring Meeting Setup & Management

Your EA builds out recurring events in Zoom, Google Meet, or Microsoft Teams — including agenda templates, dial-in details, and reminders — so standing meetings run without you setting them up each time.

Scheduling Link Configuration & Maintenance

Your EA manages your Calendly or Acuity Scheduling account, keeping availability windows, meeting types, intake questions, and confirmation emails current and aligned with how you actually want to work.

Travel & Multi-Timezone Coordination

When meetings span time zones or require travel, your EA accounts for transit time, local time conversions, and prep windows — reducing the chance you show up late or underprepared.

Pre-Meeting Prep Reminders & Briefings

Your EA compiles relevant context before key meetings — pulling CRM notes from HubSpot or Salesforce, prior email threads, or agenda items — so you walk in ready instead of scrambling.

$Trusty Oak fractional talent services$

How the handoff works

After onboarding, your dedicated Client Success Manager documents your scheduling preferences, time boundaries, and communication style in a Strategic Delegation Plan before your EA ever touches your calendar. In the first week, you'll grant calendar access (Google Calendar or Outlook), share your Calendly or scheduling tool credentials, and walk your EA through one or two real scheduling scenarios so they can match your standards exactly. By week two, most clients are fully hands-off — your EA is fielding requests, resolving conflicts, and keeping your calendar structured without you being in the loop on every exchange. You stay informed through a lightweight check-in cadence that fits your preference.

Tools our team works with

We adapt to your existing stack — no forced migrations.

Microsoft Outlook

Acuity Scheduling

Microsoft Teams

Google Calendar

Calendly

Zoom

...and many more!

What calendar & scheduling support costs

Drag the sliders to build a monthly plan that fits your workload.

Executive Assistants

~$35/hour

25 hours $875

Specialists

~$50/hour

5 hours $250

Fractional Executives

~$95/hour

0 hours $0

Your monthly budget

$1,125

Starting at $1,000/month. One-time $300 onboarding fee includes your Strategic Delegation Plan.

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Frequently Asked Questions

How do I give an EA access to my calendar without compromising security?

Most clients share access through Google Calendar's delegate feature or Outlook's shared mailbox permissions, which let your EA manage scheduling without having your login credentials. Your Trusty Oak Client Success Manager will walk you through the exact setup during onboarding so access is scoped appropriately from day one.

What if my scheduling needs are inconsistent month to month?

That's exactly what the flexible hour model is built for — you're not locked into a fixed number of scheduling hours each week. Unused hours roll over monthly, so a lighter month doesn't mean wasted spend, and a busier stretch is covered by your existing balance.

Will the EA communicate directly with my clients or colleagues to schedule meetings?

Yes — most clients have their EA communicate directly on their behalf, either from a shared email alias or by being CC'd on threads. Your Strategic Delegation Plan will define exactly how much autonomy your EA has and what requires your sign-off before anything is confirmed.

How long does it take before an EA can manage my calendar independently?

Most clients reach a fully delegated state within the first two weeks. The onboarding process is designed to front-load the context your EA needs — your preferences, recurring commitments, and communication norms — so the ramp-up is fast and the handoff is clean.

Get your calendar off your plate

Starting at $1,000/month with a one-time $300 onboarding fee, you'll have a US-based EA managing your schedule within days — not weeks. Let's build your delegation plan.