Mastering the Calendar: An Intro to Time Management 

When I started supporting Dick Costolo at Twitter as an executive assistant, day 1 on the job was my first experience calendaring for someone. Hard to believe they trusted me with so little experience and without any training. Make no mistake, I quickly realized that an organized and well-managed calendar is the foundation to successful time management which leads to a successful executive.

There is no doubt that we have all seen the pitfalls of a disorganized calendar. One-on-one meetings get scheduled over or meetings getting double booked. Having your executive go in and out of the office wastes a ton of time. If you have a fire drill, everything gets pushed to later in the week.

Time organization is the most critical component to calendar organization. I also advocate for healthy calendar habits in Do Not Schedule time, commonly referred to as DNS. This will allow you to break the bad habits and to create room for the good ones.

Dick and I had a great process we established early on to communicate setting up meetings. I’ll share with you our pro-tips, broken down into three comprehensive parts.  

Getting Organized Starts with Proper Time Organization

First and foremost, no one should be allowed to book anything on your executive’s calendar, including the executive. Anything that goes on without your permission should get declined. Without this element of control the calendar is out of control. I am not asking you to be a gatekeeper. Quite the opposite. I am asking you to create the right boundaries to ensure your success, and the success of the person you are supporting, Once people know you are their advocate and want to help them find time with your executive, they start going through you for everything. This builds trust with other team members all while giving you the control you need to create well organized days and weeks for your executive. 

Prioritizing the days of the week is your first step at a well organized calendar and exercising your responsibilities as an administrative executive. When we have a hierarchical approach to the week, we can easily find times that work and what will not. This will make room for the meetings that matter the most. 

Most of the executives that I have worked with find Mondays to be overwhelming. They are backlogged with emails from the weekend, have a ton of requests they need to sort through for the week, and also a list of to do’s on their mind. Imagine feeling this way, and then finding out you have to be out of the office on a Monday?

Make Monday the highest priority day. This means everything scheduled on Monday is a meeting your executive needs in order to accomplish their priorities for the week.

Move all Tier 1 one-on-one meetings to Monday

  • This requires you to discuss with your exec to distinguish their top-tier players. You most likely need to divide their direct reports and put tier 1 on Monday and tier 2 on Tuesday.
  • Staff meetings should always fall on a Monday
  • High priority project check-ins
  • Most importantly, create a time block (30 mins to 1 hour) for DNS time to catch up from the weekend. If you need to give that time away for a meeting, you have a time slot to provide weekly.

Tuesday becomes a day for Tier 2 one-on-ones and allows for rescheduling one-on-ones from Monday. You can easily reschedule over Tier 2 meetings without feeling a huge sacrifice. 

The key is to create a program that works for your executive. A weekly routine creates what I like to call FLOW.

Flow is when a day is set up to make sense and the exec has smooth transitions from one thing to the next. I often spent my early mornings at Twitter trying to create flow before Dick got in to review his schedule. If there was something out of the ordinary, such as a quick coffee meet up outside the office that wasn’t moveable, and he only had five minutes to get back to the office, we discussed it ahead of time. He knew what to expect and we agreed on the madness together. This sets the expectation that disorganization is not the norm and you aspire to have a daily FLOW that works. How else can anyone get anything done!?

Designate days your executive can easily have meetings out of the office. For example, if that is Tuesday and Thursday afternoon, the executive will start to catch on to the routine and will start to offer up those days to their business partners. As we know, going outside the office wastes a ton of time. Once you have designated days, you will offer up those days first when scheduling with other EAs. 

There will always be fire drills and meetings will need to be rearranged.

By having a prioritized calendar, you can move a group of high priority meetings over to a day that has easily moveable meetings. Here are some additional ways prioritized days of the week can drastically improve the flow of your executives calendar:

  • Creates clear openings for booking travel 
  • Time optimization for being in and out of the office
  • High priority meetings and projects don’t get rescheduled over
  • Creates openings for deep work 

Your executive’s schedule is often dictated by inbound requests and your decisions dictate the flow and organization of their day. Be rigorous about the schedule, only prioritizing the meetings your executive needs to have to move the company’s strategic initiatives forward successfully. In other words, what the exec NEEDS vs what people WANT. 

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