Jacqueline Leib explains her method for managing multiple calendars

Managing your executive’s calendar can be challenging. Managing several executives’ calendars can be exhausting! I manage 29 calendars (not including my own) on a 165-acre school campus and it is only a portion of my responsibilities as the Executive Assistant to the CFO of Lake Forest Academy in Lake Forest, Illinois, USA.

Anyone who knows me knows how passionate I am about this school, my executive, and my position at the school. Now to be clear, I do not manage 29 executive’s calendars, rather I manage 27 room calendars, two of which encompass several rooms across our campus. I have learned a few things about the logistics of keeping a calendar and thought I would share what I have learned as the self-proclaimed “Queen of Calendars”.

1. Color Code

I might be Capitan Obvious here, but I like to use colors to determine the different calendars. In Google Calendar, there are several preset colors. There are not 29 colours, so I need to be a little creative. My calendars are disbursed between seven buildings, plus I have a calendar for Miscellaneous.

I take the colors of the rainbow – red, orange, yellow, green, blue, indigo, violet – and change the variances depending on the calendars within the building. I also choose colors for the direct reports for my executive. He is responsible for seven departments so the rainbow works well for his direct reports.

Though you may not have to vary the colors of the rainbow, using colors as systems helps you to see who is busy when, and can even help you to determine two different schedules without having to use Google’s “More Options” to “Find a Time”. Google Calendar, when opened on my computer screen, looks like a bag of Skittles has been spilled all over it. Should someone come by when I have Google Calendar opened, interesting comments are usually made such as “Whoa!”, “Yikes!”, or “how do you control that beast?!”

2. Logistics is the name of the game

I have all calendars open all the time. In fact, I have it pinned as a tab so it always opens when I turn my computer on. On a good day, it may be that I have only two events going on at one time, but if the ice rink has a hockey tournament which will bring in hundreds of cars and the Armour Mansion has a wedding with 200+ people in attendance, parking will be at a premium.

Should the team parents from the girls Varsity field hockey team want to have a team dinner this same evening, we will suggest that we find a different night for that. If my CFO wants to have a meeting with the auditors on our campus, we will need to consider a different time or maybe suggest the meeting be held at the auditor’s office.

If our Head of School Symposium Committee wants to bring entertainment for the students to our campus, we will want to look for a different date. Or if we have the Dance Group from our local town wanting to put on their dance recital, where not only mom and dad will attend but both grandparents and aunt and uncles will be coming, we will have nowhere for them to park even though the Cressey Auditorium is wide open.

3. Communication is Key

It is important to communicate effectively when booking a meeting. I am responsible for three committees of our Board of Directors. I will send out an email two weeks in advance with all the information including the Zoom meeting ID, phone number to call in if not attending in person, and computer access. In that email, I indicate that I will follow up shortly with a calendar invite with all this information in it.

I will send out another email to the committee one week in advance and again include all of the information.

My last email will be a day or two prior to the meeting with all of the information. I will indicate that all documents (minutes from last meeting, agenda, financials, etc.) have been posted on the website in the Trustee portal so that the Trustees can review these documents prior to the meeting.

4. Details, Details, Details

When I book a room, I ask as many questions as possible, including the nature of the meeting.  I put this information in the title of the meeting along with the person’s name who is booking the room and the date of the contact. This comes in handy if you have any questions or if someone else is looking to use that room. I can suggest to the new person to contact the person who already has the room to see if we can find a different room/time/date. I also indicate any changes made including who made the changes and on what date. This has saved me, many times, from a colleague not remembering what they had requested and when.

If a person is looking to use our Auditorium, which requires that our Tech Director be present, I include him in the email to make sure that he is aware of this event happening. This meeting information is also added to my Executive’s calendar. I indicate the reason for the meeting, the location of the meeting, who will be attending, and any documents that pertain to the meeting will be embedded into the appointment itself.

I set up email reminders to hit both my Executive’s inbox as well as my inbox, 15 minutes, 10 minutes, 5 minutes and 1 minute prior to the start time of that meeting. You might think this is excessive, but I know that I get the first ping at 15 minutes prior and think “I can finish this last thing” and before you know it, I am late for the meeting.

Also, we are a large campus and it takes several minutes to walk from one building to another. It helps to have these reminders as well as what building the meeting is in so that we can plan accordingly.

5. Training others

I have a request of all who want to reserve a room which is “Look then Book”.

I have given our faculty and staff view-only capabilities for all the calendars on campus. When they want to reserve a room for a meeting, they can look to see what is available. Once they find what they are looking for, they either call or email me with their request. When I receive a request for a meeting that will need a specific room set up (e.g. add 6 feet round tables that would not normally be in a room) or will need food and/or drinks, I will attach an event form that allows the event planner to request these items from our facilities or catering departments.

Being a school, all of our doors are locked for security and are opened with an ID. If parents are coming for a parents’ meeting, there is a place on the event form to ask our security department to open the doors 30 minutes prior to the meeting and keep them open 30 minutes after the meeting is set to be over.

6. Why be the middle woman?

I have had people ask me why we do not allow people to book the rooms themselves? Why do I need to be the middle woman? There are a few reasons, but the main one is the logistics of parking and people on the campus. Someone needs to be the logistics manager of traffic on campus.

There is also a hierarchy of need. Being a school, our students come first. Next in the hierarchy are our Head of School and the Board of Trustees. After that, we accommodate faculty and staff and any requests from the community.

The Armour Mansion, a historical building on our campus, and our Formal Gardens are very busy during April through October with weddings. We also have corporate event planners booking our space for meetings such as kick-off meetings, team building and holiday parties during winter months in the mansion.

We are a school first and the mansion houses our English department and classrooms. Two of the English rooms are used for the wedding parties. These events help bring in income to support the school. It is a fine line that we need to play in organizing the calendars so that the students do not feel they are being rushed with their teacher and that the bride-to-be is happy.


Managing our multiple calendars can be a full-time job on certain days; just like managing an executive’s calendar or travel can take up a full day.

I hope that some of the tips that I use to keep our campus calendars (and oh yeah, my Executive’s) in order help you in your pursuit to tame the beast we politely call “the calendar”.

Jacqueline (Jackie) Leib, CAP, Dean of Positivity (not an official title), and Calendarist. What is a calendarist? Merriam Webster’s definition of a Calendarist is one devoted to the study or making of calendars. I prefer the definition given by a ... (Read More)

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