Managing a calendar will be more than just a routine task for your new remote executive assistant. This will become an integral part of their job and ensure one of the primary needs for you to leverage their help: to stay organized and optimize your time more efficiently. It isn’t just about scheduling appointments; it’s about ensuring smooth business operations and a conflict-free personal life. In fact, according to a study by the American Management Association, effective time management can boost productivity by up to 25%. That’s why you need to ensure you delegate calendar management in the most effective way possible so your EA can make your existence ten times easier. At A Team Overseas, we have extensive experience helping our clients understand how to delegate this part of their work, so we’ve decided to put together a bite-sized playbook to aid you in nailing this part of EA delegation. In this guide, you’ll discover practical strategies for setting up everything for your assistant to best organize your calendar, techniques for delegating calendar management effectively, and best practices to enhance your scheduling efficiency. Keep reading to learn more!

Key Starting Goals When Delegating Calendar Management

What You Should Work Towards

• Identifying the fixed parts/items of your life.
• Assigning specific times for their non-negotiables such as sleep, exercise, date nights, weekly planning, etc.
• Reviewing and evaluating progress toward their ideal schedule.
• Understanding how to delegate calendar tasks effectively will help you streamline operations and prevent overlap. Clear communication and proper access permissions are key to ensuring that everyone involved is on the same page.

What Your Remote Executive Assistant Should Achieve:

• Your EA should develop a system that will save you from having to go through or look for emails to get clarity regarding your schedules. Almost every task, event, and meeting discussed in emails or other channels should be on the calendar.
• Your calendar should become your single source of truth where you can easily find your schedules and any information related to those. This helps to avoid context switching and wasting time jumping around different tools like emails, CRMs, etc.
• Regularly review and update your calendar to keep it relevant.

How To Define Calendar Management Preferences

1. Clarify Your Priorities To Your EA:

Path A) If you already have a system or certain priorities, you can proceed to this:

• Confirm main priorities as these will be deciding factors in prioritizing schedules and ensuring your EA can develop into stretch goals down the road. This is helpful whenever there are conflicts. As the primary protector of your time, your EA should be able to determine which events, tasks, or meetings should be plotted and which ones can be rescheduled.
• If there are new events or meetings that haven’t been discussed yet, your EA should have a 5-minute call to inform you and confirm if it’s a new key priority or not.
• Any emails requesting for a meeting or other plans should be taken care of by the EA. By default, EA should step in and communicate with the sender for availability.

Path B) If your calendar is all over the place, you can start from scratch and work on the core pillars and priorities: 

• Determine the pillars or central values on which their life is built. This can be work and/or personal-related. Include meeting priorities (e.g. Senior execs, Investors/clients, Company/team, Applicants, Family/friends).
• Recommended categories: Relationships | Business | Health | Lifestyle
• You, as the client, can choose to have different categories or focus on one or two.

2. Analyze the Current Calendar Pain Points:

You Should Think of Any Pain Points in Your Calendar:

•  Is there anything that seems to be chaotic or anything that you feel frustrated about in your calendar?
•  Is there anything you want to change or be done this time around?
•  In a perfect world, what would your most impactful and fulfilling days looked like?

Your EA Should Study Your Calendar and See Which Dates or Events Look Messed Up:

• Are there any meetings that seem to be scheduled at the same time?
• Are there meetings that look like they’ve been plotted twice?
• Does your client want to have buffer times or gaps in between meetings or major tasks?
• Are there any meetings or tasks that serve no real purpose?
• Are there tasks that you can take on or can be delegated to someone else?
• Are there any activities that the client wants to start implementing?
• Any inconsistent activity that needs to be reviewed?
• How is the inbox currently being handled?
• Is there an apparent system of organization?
• Compared to the priorities and ideal week-to-week schedule, how different is the current reality of the calendar?

3. Have Your EA Program Your Calendar: 

They should main or most-valued activities first.

Since they should already know your pillars (those that you want the calendar to be based on), they can now program them into the calendar first and everything else will be set up around them.

Example: 

*Schedule a weekly meeting with the Sales team.* 

*Schedule a recurring activity of playing badminton with Jane every Saturday at 2:30pm until June.

• Input your other activities.
• Determine which items from the previous calendar should be carried over (EA can also ask which ones you do NOT want to be carried over).
• Assign uninterrupted blocks of time for focus time or deep work ‣ depending on your priorities, they can also categorize this as one of the main priorities.
• Know your focus and energy levels as this will help you maximize productivity.
• This might not be easy and will take some maneuvering, but your EA should remember to set up a schedule that caters to what you want and need to do in order to optimize your time.
• Present the changes for the next 2 weeks and beyond.
• Since you already shared the typical calendar pain points, your EA can work around this and make changes.

4. Determine Meeting Support & Other General Preferences:

For both you and your EA

• Visual preferences (color coding)
• Optimal meeting size
• Preferred tool for video meetings
• Preferred meeting duration based on the type of meeting ‣ e.g. Daily standup: 15 minutes, Internal 1-on-1: 40 minutes, etc).
• Buffer times ‣ back-to-back meetings or have a break in between meetings? How many minutes?
• Preferred naming convention ‣ one naming convention across the board or varies by meeting type? (e.g. [Name of Guest] - [goal of meeting])
• Video meeting preferences ‣ use a password for entry? EA to join & assist?
• Attachments/links ‣ include links to docs (e.g. slide deck, meeting bio, agenda checklist) within meeting invitations.
•  In-person meeting preferences (Preferred meeting types ‣ e.g. lunch for personal, coffee for business & Preferred locations ‣ e.g. local or frequently-visited locations when traveling).

Best Practices to Help Your EA Manage Your Calendars More Efficiently

Clear Communication: 

Establish open lines of communication as soon as you hire a remote executive assistant. You should take the time to have in-depth discussions about your priorities, needs, current challenges, preferred meeting times, and any recurring commitments. Try to ensure they understand your goals and preferences and make it clear to them that they should approach you if they have any questions.

Regular Updates: 

Keep your EA updated on any changes to your schedule or priorities. Having regular check-ins can help avoid confusion and ensure that your calendar remains current. You can also encourage them to do a weekly or bi-weekly review together to ensure nothing is missing and you’re both aligned on any upcoming commitments.

Well-Defined Priorities: 

Right off the bat, you should clearly define which meetings or events are high-priority and which are less urgent. This will help your EA make informed decisions when it comes to both scheduling and rescheduling any commitments you have. This also applies for your personal life if you;re comfortable with your EA handling that side of your calendar as well.

Set Working Hours & Contact Boundaries: 

Define your working hours and preferred times for meetings, as your assistant will use this information as a baseline to schedule anything into your calendar. Let your EA know if there are times you prefer to be free from meetings or if there are specific times when you’re most productive and would rather do focus time sessions.

Use Calendar Tools Effectively: 

Utilize shared calendar tools like Google Calendar, Microsoft Outlook, or other scheduling platforms. Ensure that your EA has the necessary access and understands how to use the features, such as color coding, reminders, and scheduling assistant tools. If you want to learn more about the best tools for working with a remote executive assistant, go to this article of ours!

Automate Scheduling: 

Leverage scheduling tools like Calendly, Doodle, or Microsoft Bookings to automate meeting scheduling. These tools can sync with your calendar and allow others to book meetings within your available time slots.

Include Buffer Time: 

It’s best to build buffer times between meetings to accommodate overruns and provide time for preparation. Your EA should schedule these buffers to ensure you have time to transition between meetings or tasks.

Be Clear About Recurring Meetings: 

You and your ea should regularly review and update recurring meetings. Make sure they are still necessary and valuable, and have your EA adjust the frequency or timing as needed so you can ensure your calendar is as optimized as possible.

Communicate Travel Times: 

Your ea should be informed of your upcoming travel schedule in advance in order to move around any conflicting commitments. Moreover, if you have business or personal events that require travel, ensure that your EA schedules adequate travel time and accounts for potential delays.

Share Key Information: 

Provide your EA with essential details for each type of meeting, such as agenda items, attendees, and any preparatory work required. This helps them manage your schedule more effectively and ensures you are well-prepared. Over time, they’ll be able to create and handle these items for you.

Be on The Same Page Regarding Confidentiality: 

If there are confidential or sensitive meetings, ensure your EA understands the importance of discretion and handles these meetings with the appropriate level of confidentiality.

Establish a Feedback Loop: 

Regularly review how the scheduling process is working and provide feedback to your EA on what’s working well and what might need adjustment. This iterative process helps refine the system and improve efficiency over time.

Set Up Emergency Protocols:

Establish procedures for handling last-minute changes or emergencies, as well as times where you’ll be unavailable. Make sure your EA knows how to manage these situations and communicate changes to you effectively.

Delegate Related Scheduling Tasks: 

For large-scale events or complex schedules, consider delegating specific scheduling tasks to your EA. For instance, they can handle booking meeting rooms, coordinating with multiple parties, or managing travel arrangements.

Ready To Delegate Calendar Management? Hire a Remote Executive Assistant With Us!

We hope you found our calendar management playbook helpful and are now able to confidently delegate this part of your work to your remote executive assistant. Remember to always prioritize clear communication and be transparent regarding your scheduling preferences to get the most value out of your EA partnership. Now, if you still haven’t found the right assistant for you, don’t worry. At A Team Overseas, we specialize in connecting the top remote executive assistants in the Philippines with clients who are looking to stop work from falling through the cracks. Ready to take some tasks off your plate? Contact us today to schedule a free discovery call!