Why You Should Give Your Calendar To Your Executive Assistant

With all the thought, attention, and detail an Executive Assistant can bring to your calendar – delegating this can revolutionize the way you work.

When it comes to offering advice, I try not to be too direct. But, in this case, I have to make an exception: 

You really need to give up your calendar to your executive assistant.

A few years ago, I asked Kristie, my executive assistant at the time, to document all the different personal and strategic considerations she used to manage my calendar. When I first saw what she had written, I was blown away by the depth of her thought processes and attention to detail, and I benefited tremendously from her incredible calendar prowess during the season we worked together.

Kristie now serves on our Emmre Advisory Board where she shares her experience and insights as a seasoned executive assistant. I decided to take her “Notes on Calendar Management” from our time working together and craft it into this blog post to encourage you to rethink your relationship with your calendar. As you’ll be able to tell by reading Kristie’s notes below, allowing your executive assistant to manage your calendar can free up a considerable amount of mental space, alleviate a ton of stress from your workday, and add a new level of strategy for getting things done.

Additionally, if you’re an executive assistant reading this article, I hope you uncover some useful tips from Kristie’s notes and apply them to your own calendar management process.

Kristie’s Thoughts on Calendar Management

Kristie Webber

My overarching philosophy toward calendar management revolved around arranging all the different puzzle pieces of Don’s schedule to help him be better at his job. I took a very strategic approach to managing Don’s calendar – and for good reason.

Meetings are a crucial element of making things happen and effectively managing those meetings enables those things to happen more efficiently. From coordinating with other stakeholders to negotiating the value of Don’s time in specific circumstances, calendar management was the cornerstone by which he got his work done. For this reason, strategically managing an executive’s calendar should be one of the most critical aspects of an executive assistant's role.

Preparing for the Day

As an executive assistant, my goal for the start of each day remains the same – ensuring my executive has everything they need for their meetings so they’re prepared and not lacking anything.

There are several ways I accomplish this goal, starting with asking a series of questions.

• What meetings are scheduled for today?
• Which emails would Don need to reference to prep for these meetings?
• Do these meetings need an agenda?
• What information does Don need to be aware of before the meeting begins?

These questions often extended to myself as well. I saw my role as helping Don think as little as possible about what he needed to do that day which required prep work on my end. I made a “weekly resource folder” in which I collected all the emails, agendas, and information that Don would need for his upcoming meetings, and I ensured that every meeting space was cleaned and prepped for an effective meeting experience (i.e. room was reserved, all technology was ready to go, whiteboard was clean, name tags were printed, etc.).

It’s important to think of an executive as a whole person – they aren't a machine. They need space in their day for bathroom breaks, lunch, and brief periods of reflection. For some executives, if these breaks aren’t worked into their schedule, they’ll blow right past them without realizing it. If the day is going to be packed with back-to-back meetings, I make sure to order lunch and always keep their office well-stocked with snacks and drinks.

I also compiled a list of Don’s “go-to” orders at local restaurants, so if we unexpectedly had to order lunch, I could ask, “Do you want me to order [restaurant name]?” Depending on his answer, I could order his go-to meal without offering him a menu to peruse.

I also made personal considerations when I set up Don’s schedule. For example, if I knew someone he was scheduled to meet with had a reputation as a “talker,” I’d make sure to schedule a hard stop. In addition, there were some types of meetings that Don told me he found physically and emotionally draining, while other meetings were life-giving and invigorating. If possible, I tried not to schedule anything after a “draining” meeting that required intensive participation, and I did my best to protect the “life-giving” meetings.

Another consideration was the building’s layout. If meetings throughout the day had to happen in different rooms, I tried to make sure the rooms were close to one another (or at least on the same floor). It was very easy for people to intercept Don as he moved between meetings, and I wanted to try to mitigate that as much as possible on his busy days.

Meetings With Other People

Executive meetings can be broken down into two broad categories: external (meetings with people outside your company) and internal (meetings with people inside your company). While there is often a lot of overlap between external and internal meetings, I made some special considerations regarding meeting prep.

If someone from outside the company was coming onsite for a meeting, it was important to show them we were expecting (and anticipating) their visit. I always had someone available to meet the guest when they arrived. I also made sure the meeting space was stocked with snacks and drinks as I wanted to create a hospitable atmosphere around their meeting. Additionally, I found the LinkedIn profile of the guest and gave Don a quick rundown of their professional resume. I scheduled buffer time before and after the meeting to ensure Don could make it to the meeting on time and gave a little bit of margin in case the meeting ran long.

If the meeting was taking place over the phone or Zoom, it was vital to be aware of different time zones and schedule appropriately. When it came to setting up meetings for Don, I began with the availability of the most senior (or VIP) person and worked my way down.

I approached internal meetings a little differently than external meetings, but not much. For starters, since employees don’t always meet with the CEO, I’d often “soften” a meeting invite with additional details in the event description to ease any anxiety that might arise from a meeting request from the CEO.

I also tried to determine if the meeting would be more productive (or personable) as an offsite meeting (often lunch) or by having lunch brought to the office. If the meeting was with a direct report, I’d make sure they knew what the meeting would be about and if they needed to have any materials prepared beforehand.


Specifically addressing local travel (in which Don returns to the office), I always built-in additional buffer time to account for traffic and other uncontrollable factors. Sometimes, I’d schedule a meeting for myself with Don to fill out that time slot.

I’d also frame out Don’s calendar with vital information – like hotel address, meeting locations, flight numbers, agendas, etc. – so all he needed to do was pull up the event in his calendar for all the information he’d need while away.

If Don was traveling to a different office, I’d try to connect with their executive assistant to see if there was anything I needed to let Don know (i.e. how to enter the building, etc.) and to share important information that would be helpful to them (i.e. food preferences/aversions).

All of these considerations made a huge difference in helping Don be more prepared and more effective throughout his day.

Don's Conclusion

If all of this doesn’t convince you to give up your calendar, then I don’t know what will. I really want to emphasize the fact that Kristie did all of this, and she’s very good at what she’s described above. Prior to handing over control of my calendar, I had no idea how much time and energy I was expending trying to accomplish not even a fraction of what Kristie was capable of. Kristie’s calendar management skills became seamlessly integrated into my day-to-day operations, and I heavily relied on her to help keep my schedule going smoothly. If you haven’t already, now is the time to hand over calendar management to your executive assistant.

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