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How to Effectively Manage an Executive Calendar 101: The Essential Guide

Calendar management for Executives
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Effective calendar management is a very crucial component of the role of executive assistants. At least a third of an assistant’s day is spent, making their own schedule and organizing their executive’s calendar.

The fundamental scheduling rule states that all scheduling must pass through you. You are solely responsible for scheduling all direct reports, appointments, other meetings, phone calls, and other calendared things. If a meeting must be canceled or postponed, you make the necessary adjustments. Only you have complete control of the calendar.

However working with a busy, well-connected person maintaining the perfect scheduling process can be a daunting and time-demanding endeavor. As a result, you’re likely to make some errors along the road until you discover how to effectively manage your boss’s calendar.

That’s why we created a list to give executive assistants a breeze to their schedule management. These best practices, techniques, tools, and tactics complement your intrinsic knowledge, save time and stress, and make it appear effortless to create calendar magic.

Key Takeaways

  1. Prioritize projects according to their significance and urgency.
  2. Collaborate on related tasks.
  3. Allocate particular time slots throughout the day for specific tasks.
  4. Continue analyzing and customizing the calendar to meet your specific demands.
  5. Ascertain that your boss’s calendar does not interfere with your work-life balance.

What is Executive Calendar Management?

Executive Calendar Management is the methodical process of planning meetings, activities, and assignments to maximize the return on investment, which you may obtain from our valuable limited resource time.

The process includes hectic but vital work, including addressing requests and organizing meetings and long-term strategic work, such as establishing day-to-day priorities for executives and implementing best practices for time management.

The importance of calendar management can be seen in the question posed by Chip and Dan Heath in Decisive: How to Make Better Choices in Life and Work

“If forensic analysts confiscated your calendar and e-mail records and Web browsing history for the past six months, what would they conclude are your core priorities?”

A well-managed calendar should reflect and make key priorities possible. It has the potential to influence both an executive’s daily and long-term success. This is why calendar management is one of the most critical abilities a manager can have.

The Advantages of Effectively Managing a Calendar ✨

Managing calendars correctly creates the groundwork for obtaining a variety of other business benefits, including achievement, efficiency, organization, cooperation, and insight.

  • Calendar management enables you to prioritize critical goals 🎯 (both your executive assistant goals and your boss’s goals) while still covering everything else. This helps to focus on your achievements and makes it much easier to reach your goals. 🏆
  • Developing a systematic calendar management approach paves the way for the discovery of automation and solutions that boosts efficiency and saves time. ⌛
  • By centralizing calendar management, administrative and executive assistants have the power they require to keep the organization on track. 🗂️
  • Effective calendar management enables leaders to collaborate with others by spending time efficiently, without skipping a meeting, double booking, or forgetting critical collaboration or growth opportunities. ✔️
  • Effective Calendar Management is about more than today and tomorrow. It focuses on the bigger picture and helps to deliver unwavering business insight . An organized executive calendar gives a fully documented account of where and for what purpose time has gone and how time will be spent tomorrow. 📈

What is the best way to effectively manage an executive’s calendar? General Practises

1. Prioritize Work with a Handy Matrix

Strategically pursue priorities with an Action Priority Matrix to filter your exec’s calendar. This enables you to determine the “return on investment” of your executive’s time on a particular task and to identify possibilities to balance the time portfolio. Advise against any activities that do not produce a return on investment proportionate with the time invested.

2. Use Calendars for More Than Just Scheduling Meetings and Events

Fill the schedule with memoranda, deadlines, time offs and time blocks for brainstorming, exercises, and other wellness and vision activities important for the success of your executive.

3. Design Your Perfect Color Coding System

Use labels, folders, or color-coding(s) to develop a scheme for the calendars you administer. This facilitates all calendars for you and everyone else to skim for essential pickups. For example, in these categories, you may establish and color code folders: internal, client, personal, recurrent, recall, and trip.)

4. Document Your Exec’s Priorities

An Executive assistant should do their best to ensure that their boss spends time on the most important things.  As an executive attends more than one meeting each day, you need to keep a tab on the detailed record of each and identify essential priorities. Make sure that the executive’s schedule reflects these priorities and even use your documentation to justify rejecting invitations that are not in line.

5. Clarify Calendar Roles and Permissions

We all heard the saying: too many cooks spoil the soup in the kitchen. The same applies to having too many executive assistants to manage a calendar. With calendar control and monitoring, calendar management is simple and strategic. Make it easier to create and document who may accept most meetings and other priorities on behalf of your executive.

6. Mentoring and Shadowing

This includes shadowing or allowing your executive to mentor you throughout the initial training period. This will help you in becoming more acquainted with your executive’s calendar. By regularly monitoring your executive’s timetable, you’ll quickly learn how they spend time and who are their most important and professional contacts.

You will discover their preferred personal items, apps, other priorities, what they would like to be added or removed from their executive calendar, or when not to schedule or accept meetings or. Possessing this knowledge will assist you in creating the perfect daily routine such as finding the ideal time to receive phone calls and return phone calls for any off-site meeting request without making your boss angry. Hence, this makes calendar management easier.

7. Set Multiple Time Zones

If your executive’s schedule includes external meetings or recurring meetings in different time zones, organizing your executive calendar to include all relevant time zones will make it easier to plan events quickly and without making embarrassing errors.

8. Optimize Your Executive Calendar for Different Meetings

Executives spend 80% of their day, attending various kinds of meetings such as status meetings, client meetings, upcoming meetings, board meetings, and so forth. Rather than scheduling an hour for each meeting, optimize your executive’s schedule by finding the best times for different types of meetings. For instance, a ten-minute phone call is more than sufficient for introductions and guidance. 45 minutes is ideal for an out-of-office meeting. Additionally, weekly staff meetings should not exceed 30 minutes in duration.

9. Group all Meetings Together

If your executive has to attend meetings on the same day(s) of the week, like every Tuesday and Wednesday afternoon. This way they’re not leaving the office every day. The same goes for receiving phone calls for meeting requests. If a recurring meeting is scheduled, the likelihood of it being canceled or rescheduled is high. Block time for ‘building’ tasks such as preparing for a board meeting, brainstorming, or strategic thinking. This helps you to put similar tasks within the same time block.

Having a good balance between work and leisure will make both you and your boss’s lives much your calendars more efficient.

Executive Calendar Management Tips & Tricks: Automating Your Executive’s Calendars

1. Setup automation to receive text reminders for upcoming events

Set a time and a phone number for text-based event reminders. This is particularly beneficial for extremely busy CEOs who receive so many email reminders that the default setting is to disregard them. You can use apps like Zapier that allow you to automate your processes without a developer or knowing how to code.

2. Streamline Follow-Ups

Establish automated email follow-ups so you don’t have to spend all of your time nagging people to react so you can secure dates and move on with your life. Best of all, because of ReBump’s automation capabilities, follow-ups appear more human than robotic.

3. Gather Bulk Data

Create forms (for example, Google Sheets) that you can use to send in bulk data and that will funnel data into a spreadsheet. So that you can save time by not having to email every coworker and sort through their responses. You can also use TimeTackle’s automated Google Calendar to Ms Excel exporter to export all your excel, spreadsheet, or CSV files in bulk in just under 3 minutes. This saves loads of time and allows you to format and filter calendar data in different intuitive ways to streamline your process very easily.

4. Use Automations to Connect Unrelated Apps

Use IFTTT to connect apps that often do not integrate well with one another. For instance, you can send items from your Outlook calendar to your Google calendar, or from your iOS calendar to your Google calendar, and so on.

5. Transform Emails into Conversations

Spike will transform your approach to reading and responding to emails. This service converts emails into a more conversational text-based application. Finally, it enables you to produce concise, courteous, and effective emails that drive results and reduce your traffic.

Calendar Management Tools, Software & Apps

1. TimeTackle

TimeTackle is a time tracker which allows you to measure your time spent on tasks in real-time and then analyze whether you’ve achieved them or not. TimeTackle provides an easy calendar integration to construct timelines from your calendar data directly so that you will be able to track hours and time spent in new and inventive ways.

What makes TimeTackle special is that it caters to all types of users’ time management needs. You can sign for yourself as well as for your entire team so that your organization can stay on the same page and achieve true-time efficiency.  Audit and adjust your schedules to make your team time efficient. It utilizes machine learning to explore and analyze your key performance indicators (KPIs) and priorities and assists you and your team members in getting the most out of your workday and maximize your free time.

Additionally, you can also measure your meeting health with TimeTackle. TimeTackle allows you to understand the overall meeting load across your organization and lets you identify and eliminate time sinks.

Key Features: 

  • Calendar Analytics
  • Export Google Calendar to Excel
  • Categorize and Tag Events
  • Custom Reports
  • Sync with Google Sheets
  • Fast and Simple Meeting Scheduler
  • Easy to use Chrome Integration

2. Monday.com

This is an online application that gives you an overview of how all work, meetings, and activities fit together.

How does monday.com help manage calendars? It provides you with visibility on key dates and tasks for every calendar you manage. Stay tuned while also decreasing the time you spend on telephone calls or browsing email for updates.

Key Features:

  • Real-time see and relay scheduling changes
  • Use helpful templates for calendars
  • Use several perspectives (including kanban, timeline, and Gantt) to see all the tasks you require.

3. Office Otter

Office Otter takes all the communication channels, email, slack, and text that are used to make requests, assign tasks to you, etc., and detangles and organizes them by urgency into ONE to-do list! It removes the time and energy you normally would have to spend to stop and write something down. It saves you from having to recall what was said to you and allows you to focus time on your job and duties instead of stopping, losing focus, and then having to scramble and write something down and shift back to the task at hand.

With the number of tasks and the number of people you manage, the time it takes for you to get on back on track after being interrupted with a new action item really adds up. By using Office Otter you can end your work week knowing that all my important timely items are completed without anything hanging over your head.

Key Features:

  • Prioritize painlessly with built-in features
  • Turn your “done” list into a detailed report
  • Integrate with text, email, Slack, and Siri

4. Calendly

Calendly is a very clean and attractive and user-friendly app. It is a very easy-to-use meeting or appointment scheduling solution for you to send a link to a client and for them to select the best time for you to meet. It allows you to avoid many back-and-forth emails with your clients coordinating this kind of thing. You can easily integrate it with Zoom; you can select your work hours and save slots of time that you are unavailable due to different commitments. And it also helps you a lot by syncing the time zones and avoids the back and forth communication with your client located in a different time zone, asking “your time or my time.”

Key Features:

  • Customized schedule blocking for seamless appointments
  • Integrating with multiple platforms
  • Extremely user friendly

5. Cogsworth

Cogsworth is smart scheduling software that syncs with your calendar and enables you to quickly schedule meetings, appointments, and bookings. Cogsworth supports a number of teleconferencing solutions for virtual appointments and allows for customization of just about every single thing the customer will ever see from you. Cogsworth prevents time-wasting in update meetings by providing instant SMS text when a new appointment comes in, which is extremely useful. The software is easy to run for multiple businesses and is easy to engage with for Staff members. Cogsworth is that one software that really captures just about everything you would need in a scheduler in one product.

Key Features:

  • Great interface
  • Amazing support
  • Extremely affordable


Keep in mind that your boss’s schedule — like your own — is not absolute and needs to be constantly updated. You’ll have to check their schedule and make any adjustments periodically. For instance, they may require more time for extracurricular activities or the recurring team meetings maybe have become redundant.

This may be a time-consuming task but you must examine what works and what does not work in their calendar. You’ll make the necessary adjustments to ensure that your employer has extra time on his or her schedule. Health and productivity are directly proportional. If one is flushed down the toilet, the other will follow suit.

Related Reading: Tracking And Analysis With Google Calendar Time Tracking

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