Calendar management for executive assistants: best practices and top tools

There are about 55 million meetings held each week in the United States. That’s about 11 million meetings a day and more than one billion per year. The numbers are insane, aren’t they? 

According to Fellow, about 50% of executives attend between 6–15 meetings a week. Provided an average meeting lasts one hour, they spend up to 15 hours of their working time in meetings or phone calls. However, in addition to on-site and off-site meetings, C-level executives have many other daily tasks.

Obviously, effective calendar management is essential for executives to stay productive and focused. And that’s exactly what executive assistants do — they skillfully manage the executive’s calendar, scheduling meetings and tasks most efficiently.

This article discusses the best practices for effective executive calendar management, provides tips for managing an executive’s calendar, and lists the top tools for calendar management. Read on to learn how to effectively manage an executive calendar. 

What is executive-level calendar management?

An executive assistant spends at least a third of their daily working time organizing an executive’s schedule and making their own schedule. 

However, an executive assistant role presupposes not only scheduling meetings but also finding time for certain tasks, pre-meeting activities, and managing the time executives spend outside meetings.

Managing an executive’s time is a complex process requiring attention to detail. An assistant must be “on the same page” with an executive and ensure that the executive isn’t stressed and performs their responsibilities effectively. 

It’s worth noting that it’s an assistant who is responsible for planning meetings and other tasks. That means that all meeting requests should be directed to an assistant. Therefore, ideally, an executive shouldn’t ever edit the schedule.

Advantages of effectively managing an executive’s calendar

Effective calendar management leads to productive decision-making that inevitably benefits the business. Besides this, based on our observations, an executive’s schedule planning allows for:

• Prioritizing critical goals and making it easier to achieve them
• Keeping the organization on track and allocating time and resources wisely
• Collaborating efficiently with others, which significantly boosts productivity and decision-making
• Gaining better business insights by leaving more time for productive work
• Boosting efficiency by saving time for truly important tasks

Calendar management skills for executive assistants

Considering the fact that one of the main responsibilities of an executive assistant is to manage the boss’s calendar and time wisely and efficiently, a great executive assistant should have the following:

• Strong organizational skills
• Ability to multitask and prioritize
• Attention to detail
• Perfect time management skills
• Problem-solving skills
• Critical thinking
• Punctuality
• Excellent communication skills
• Tech-savvy skills
• Ability to make independent decisions

11 best practices of calendar management for executive assistants

Here’s what an executive assistant should do for an executive to have a well-managed calendar and stay productive while avoiding stress.

1. Prioritize tasks correctly 

One of the core responsibilities of an executive assistant is to prioritize tasks for an executive so that the boss doesn’t waste time on unimportant meetings and focuses on things that truly matter instead. However, you shouldn’t agree with every meeting request your director gets.

There are many approaches to task prioritization, and the Eisenhower Matrix is one of them. The Eisenhower Matrix is named after Dwight D. “Ike” Eisenhower — the 34th President of the United States. He once said there are basically two kinds of problems — urgent and important. And according to Eisenhower, urgent problems are not important, and important problems are never urgent.

The picture below shows what should be done with each type of problem/task according to the Eisenhower Matrix. 

2. Note executive’s meeting preferences

When you first start working with your executive, it’s highly recommended to learn his or her meeting preferences to make sure you use the boss’s time most efficiently. Moreover, it’s essential to let the executive’s direct reports know about those preferences as well. This is what you should know:

• Time. Learn what time of the day an executive feels most productive and eager to attend meetings. Pay attention to the time zone, as executives often need to communicate with professionals from multiple time zones.
• Duration. There are many kinds of executive meetings in your boss’s schedule, and each of them has a different average duration depending on their purpose.
• Location. Though most meetings are now conducted online via various software tools like board portals, in-person meetings still take place. Knowing an executive’s preferred locations for different types of meetings is also essential.
• Non-meeting time. Some executives prefer having at least 15 minutes of rest between meetings, others don’t mind jumping from one meeting to another. Ask your boss if a short pause between meetings is required.
• Restricted time. An executive might require some time when no meetings should be conducted. Make sure you know about this preference and never schedule meetings during this time slot.
• Meeting preparation. Some meetings, like board meetings, require preparation. You should be aware of when your boss needs extra preparation time before adding a meeting to an executive’s Google Calendar.

3. Allocate time for non-meetings

Having a well-managed calendar doesn’t mean you should fill it with meetings. For better efficiency and stress reduction, an executive should also have non-meeting tasks added to the calendar. This is what you can add to the schedule:

• Focus time
• Personal appointments
• Lunch
• Gym time
• Doctor/dental appointments
• Deadlines
• Family commitments 
• Networking with colleagues

4. Color code meetings

To help an executive better understand their daily schedule, add some visual planning tricks. 

Drawing on our own experience, using different colors for different kinds of meetings maintains a better structure. This is easily done in such apps as Google Calendar, for instance. You can color-code events by:

• Type of the meeting
• Location (virtual, on-site, or off-site meeting)
• Internal or external meetings
• Priority level
• Recurring meetings (for example, recurring team meetings)

5. Make sure there are meeting reminders and confirmations

Each of the meeting’s attendees should receive a reminder of the upcoming event. You can set an automatic reminder sending in a preferred time (15 minutes, for example) or send reminders manually prior to the meeting. 

Additionally, there should be an option for all attendees to confirm their attendance. It can be extremely demoralizing when someone doesn’t show up at a meeting without warning. Moreover, it can significantly influence the success of a deal or project.

6. Avoid double booking

The whole purpose of calendar management is to make the most out of the executive’s time and expertise and avoid stress. Make sure there are no situations when events overlap. It would be highly unprofessional for a director to choose one meeting over another if double booking appears.

7. Create invitation and confirmation templates

Based on our experience, you can significantly reduce the hassle and save a great deal of time by having templates. Create a separate invitation template for each type of event and send them without spending extra time filling in the required information. 

Additionally, you can create templates for confirmation emails on your director’s behalf which would also greatly simplify the email management process.

8. Allocate time for document review

If your director has upcoming board meetings, it’s essential that he or she has enough time prior to the meeting to review documentation. 

Allocate time blocks for document review and make sure all meeting attendees prepare the required documents before the meeting. You can add a list of documents required for a meeting to an invitation template.

9. Daily review the executive’s calendar

For effective calendar management, it’s important to keep track of all the executive’s meetings and make appropriate changes when needed. 

Review the executive’s next day’s schedule at the end of the day to have enough time to notify other parties if there are any changes to the planned event.

10. Allocate meeting-free time 

To reduce stress and encourage productivity, arrange meeting-free time blocks in an executive’s calendar. 

For this, discuss with a director how much time he or she needs for deep work without being interrupted by meetings every day. Also, clarify whether this meeting-free time block presupposes no meetings at all or whether there can be certain exceptions. 

11. Mind privacy

When sharing an executive calendar with others, you should be careful about not disclosing specific meetings with others. It relates, for example, to any kind of legal meetings or those dedicated to complex financial transactions. 

Additionally, avoid adding personal appointments to the executive calendar as well. It’s not professional for others to know when and where a director is planning a vacation, for example. Only you should know this kind of information.

Fortunately, most calendar management tools like Google Calendar offer various privacy settings that allow for keeping certain information private. Moreover, you can create several executive calendars with different privacy settings and manage multiple calendars simultaneously. 

Note: The same privacy recommendations are also valid for a corporate secretary or board administrator responsible for managing the board. For this, they can use board portal software since it provides the services needed to ensure high-end security and privacy.

Calendar management tips for executive assistants

Our investigation has shown that calendar management can be even easier when following these executive assistant calendar management tips:

• Use automation add-ons. With the help of such extensions as Zapier, you can automate the process of sending reminders so that your executive never misses a meeting.

• Make follow-ups automated. Follow-ups can also be automated with the help of such solutions as Rebump. This program automates follow-up emails, saving you time.

• Have a meeting with your executive. Yes, meetings again. For effective calendar management, you need to timely discuss all the executive’s tasks and events. To stay on top of this, it’s best to hold regular quick recurrent meetings with your executive at the start (or end) of every day.

4 calendar management tools for executive assistants

The market for calendar management tools is huge. When deciding on the one that best suits your needs, make sure it offers the most relevant services. We recommend paying attention to these four when managing calendars for executives:

• Calendly. One of the most popular calendar management tools. It has a modern and pleasant design, a number of integrations for streamlined collaboration, and various automation possibilities.

• Monday.com. This is a great tool for executive assistant calendar management since it provides the ability to see the bigger picture. You can see all the dates, tasks, and meetings to make the most out of meeting planning.

• Fellow. This is another modern calendar management application that allows for a bit more than simple meeting scheduling. With its help, you can build an agenda, create templates, assign action items, and exchange feedback.

• Google Calendar. Probably the most well-known calendar management solution, though not as modern as the previous ones. Google Calendar has everything you need for successful executive-level calendar management — from the ability to create multiple calendars and set working hours to various privacy settings.

Pro tip: Board portals are great for calendar management since they not only allow you to manage executive meetings but also ensure all the information shared on the platform is secured. They offer a variety of data and user management services, collaboration tools, and data security features.

Conclusion

Executive calendar management is an extremely time-consuming task. An executive assistant spends at least a third of their day managing the executive’s schedule. 

For effective executive calendar management, the executive and assistant should be on the same page. An assistant should be aware of the executive’s meeting preferences and use his or her time in the most productive way that, at the same time, reduces stress. 

The process of executive calendar management can be significantly streamlined when using dedicated tools such as Calendly or Google Calendar. However, when using board portals, executive assistants can ensure a higher level of privacy.