Calendar management is an underrated skill with big impact potential. Depending on how well you execute, it can critically impair your executive’s schedule or immensely increase efficiency and long-term sustainability. That’s why it’s imperative that you have as much information and insight into what makes up your boss’s calendar before even making the first decision. 

When you manage their schedule, you are not just prioritizing their time, but also your executive’s energy and relationships. So, it’s imperative you navigate it right.

“Strategic calendar management should be recognized and valued as it is critical to the success of executives and organizations.”

That inspiring excerpt comes from none other than Tiffany Nguyen. She is the Manager of Administrative Operations at Onit, and has over 10 years of experience supporting CEOs across various industries. Highly regarded speaker when it comes to productivity and calendar management, she has shared her expertise on Executive Calendar Analytics in a segment at the High Performing EA Summit with the topic: Executive Calendar Case Study.

Calendar analytics can take every executive assistant’s schedule management to a whole new level. So, we’re giving you a rundown on all there is to know about auditing your executive’s calendar and the steps you can follow to do it right.

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WHAT IS CALENDAR ANALYTICS AND WHY DOES IT MATTER?

Executive calendar analytics is the analyzed data taken from your executive’s calendar that is used to do a data-driven approach to managing their schedule. Upon performing an audit, you will have a more in-depth idea of the aggregate pieces that drive your executive’s day-to-day priorities. The analysis results can be summarized through data illustration which will enable you to see exactly what meetings your executive is devoting majority of his/her time to.

Instead of trying to navigate their priorities daily, performing an audit can allow you to get out of the micro view and have a holistic, macro view of their calendar. It’s through this that you can easily identify weaknesses that might, otherwise, get missed when you’re in the weeds. This allows you to be more proactive, rather than reactive.

This insight is the key to effectively managing their schedule and making sure that you are creating enough breathing room, funneling your executive’s energy to high-value responsibilities, and preventing decision fatigue. 

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HOW TO PROPERLY AUDIT AN EXECUTIVE CALENDAR

The key to successful executive calendar management is a thoroughly executed audit. Analyzing your executive’s calendar isn’t just about pulling a CSV file of what meetings are listed, rather it’s about getting a deep understanding of the purpose and intent behind each one. 

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STEP 1: ANALYZE THE DATA

Your first goal is to understand what exactly is happening with your Executive’s calendar and how it is impacting their productivity. As you pull all the data from the calendar, you should be able to identify three main meeting categories:

• Strategic meetings. These are high-value meetings that require your Executive’s attendance and participation in decision-making.
• Tactical meetings. These are typically recurring meetings focused on the daily activities of the team and may not necessarily require any participation from the Executive. They are mostly intended for information or supervision.
• Personal time. This is the rest, thinking, or any form of personal time. Including this in your analysis is vital to creating a schedule that is sustainable and healthy for them in the long run. 

Considering the information you have, there are four essential questions you would need to consider:

• What are the key challenges you can identify?
• Why do they exist?
• How are they impacting the Executive in terms of availability, accessibility, and productivity?

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STEP 2: GATHER THE FACTS

This is the part where you dig deeper and work on getting a solid understanding of each meeting’s purpose. There are three ways you can do this:

1. Color code their calendar based on priorities. By doing so, you can get a pretty good idea of where overlaps happen, how many recurring meetings are occurring, and which are led by specific departments.
2. Categorize them into buckets/themes. The theme or buckets can vary depending on what type of information you want to organize. However, the most common ones are split between: recurring, non-recurring, and 1:1s. If you want to further break this down, you can continue to consolidate them into tactical, strategic, and personal buckets.
3. Interview meeting owners. While data can provide a macro overview of how your Executive’s calendar is being scheduled, it won’t necessarily provide you a complete picture of the meeting’s intent and purpose. This is where interviewing meeting owners can be extremely helpful.  Some questions you can ask are:
   
   a. Who are the owners of the meetings in the Executive’s schedule?
   b. What is their purpose?
   c. What is the Executive’s participation in these meetings?
   d. Is his/her attendance truly required?

In conducting your interviews, remember to be sensitive to the meeting owners. These are relationships within your Executive’s ecosystem that you need to steward properly. So, continually reaffirm to them that you are not trying to push them back, but instead properly manage your Executive’s calendar to provide more availability in a sustainable manner.

4. Interview your Executive. Because one of your goals in calendar management is sustainability, it’s important to also get the thoughts of your Executive on what they think the purposes are of the meetings, how important it is for them to be in those meetings, and which ones they dread but necessary for them to be in, and finally, which ones they enjoy.

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STEP 3: IDENTIFY PROBLEMS

Depending on the data you pull from the history of their schedule and insights you gather from interviews, you can identify the problems with your Executive’s calendar. To help you spot them easier, we’ve listed some common challenges that you might encounter:

• Too many recurring meetings. Are there meetings that the Executive doesn’t necessarily need to attend weekly or bi-weekly? Can they be moved to a monthly basis or re-directed to weekly written updates, instead?
• Too many tactical meetings and too few strategic meetings. Having the Executive be present in every weekly progress meeting can be counterproductive. Is there an option to empower or assign a team lead to run them instead?
• Frequent overlap of meetings. Are there meetings being booked that are not being funneled through you? As their executive assistant, it’s imperative for better organization and execution that every appointment is scheduled through you especially if there are a handful of ad hoc meetings being communicated last minute.
• Little to no “personal time”. Executives are humans, too. If they complained of feeling burnt out or fatigued during the interview, that’s an indicator that you might want to schedule more personal time for them.

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STEP 4: PROPOSE SOLUTIONS

The best solutions are ones grounded on data, tested by experience, and inspired by practicality. Here’s how you can do that:

• Lean on your data and present your analysis using data illustration. This is especially helpful if you have an Executive who prefers data-driven explanations.
• Pull in from different experiences and expertise. Remember that you don’t have to do this alone, sometimes tapping other executive assistants and getting their insights can be quite helpful in figuring out the best solution. EA communities like Cabinet provide access to a big network of executive assistants from different industries and experiences, and can be a goldmine for getting the perspective of other EAs.
• Be practical and think long-term. Your solutions are only successful if they can continue to be successful in the long run. When the company grows, will your solution grow with it? Lean toward a sustainable roadmap when it comes to managing the calendar.

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