Would You Hand a Stranger Your Baby? How's Your Calendar Any Different?

Effective time management is crucial for executives, as they often have a wide range of responsibilities and must balance competing priorities.

I have a theory. A contentious one at that. Wanna hear it?

As a leader or manager, the #1 culprit consistently compromising your emotional health at work is handing over your calendar to someone else to manage. The converse is true for those managing your calendar.

Now before you charge for the exits or bust out your classic eye roll and hit the "next" key, hear me out.

Only You Know How You Show Up Best

Think about it. You've lived with yourself all your life. You know what you like and dislike, what makes you tick, when and what you like to eat, when you're tired or energetic, when you need some silence or when you want to engage. Your mother probably knows you second best. Your partner, a distant third. Where does your Executive Assistant fit into that hierarchy? Do they truly know you? Or do they just use whatever information you give them about your preferences in the hopes that they will magically figure out who you are and innately know what you want?

Having been a damn good, highly intuitive Executive Assistant for almost 30 years I can assure you I was about as close to the human manifestation of AI as they come. I've been called a "CEO whisperer" more than a few times throughout my career. The truth of the matter is that I figured out the connecting thread that weaves its way through all the CEOs I supported. Each CEO's role was not that different from the others. They had similar challenges and needs and operated in similar ways, seeking similar outcomes, specifically where my role was concerned. While I'd love to think I was pretty high up on each of their "Knows Me Best" hierarchies, the truth is I only knew them well enough to do my job to the best of my ability. Unfortunately, most remained a bit of a mystery and frequently surprised (and disappointed) me with some rather bizarre behavior at times.

So Let's Circle Back

One of the primary responsibilities of an Executive Assistant is to "do the calendar." This is, essentially, a complete stranger whom you hire, rarely train, never truly onboard, and who is immediately tasked with getting to know (and like) you, quickly absorbing your tastes, whims, personality, expectations (expressed and implied), favorite foods, seats on planes, sports teams, business associates you like/hate, secrets to keep, lies to tell on your behalf, etc. The one thing that takes time to gauge and gather a comprehensive understanding of is someone's physical and mental energy reserves. While I was pretty good at this innately, many EAs aren't. And until you're high up on that "Knows Me Best" hierarchy which could take years or possibly never happen you'll never truly master how the person for whom you plot their day will feel day to day or moment to moment.

As an Executive, how often have you flamed your Executive Assistant for f*cking up your calendar? As an Executive Assistant, how often have you thought to yourself, "WTF was that about?!?" when you got flamed for literally duplicating the same calendar timings as the day before, only with different players? On the surface, nothing changed except the day. However, if you dive a bit deeper, the chasm of understanding widens. I'll explain.

The Lack of Context Plague

One of the silent killers of any Executive/Executive Assistant relationship is the lack of communication and context between the two. When there is a lapse of communication from the Principal to the EA, assumptions are made. In fact, they have to be in order to keep the train moving down the tracks. Here's an example. Your EA books your Tuesday just as fraught as they did your Monday. You didn't seem to complain. You weren't late to any meetings. You weren't moody or short. Smooth sailing and permission to proceed, right? However, Monday night you, Mr. CEO, missed the PTA meeting, again, and spent the night in the doghouse just after being assigned drop-off duty for the kids the following morning as penance, which means you will likely be about 10 minutes late for your first meeting on Tuesday. AND you forget to email/text/Slack your EA until the morning of instead of the night before when it all went down. Little do you know, it took your EA a month of back-and-forth emails, across three different time zones, to nail down a time with the people you're meeting with first thing on Tuesday. Your hastily crafted message to push the first meeting 1/2 hour is met with resistance (read: attitude) you neither expected nor appreciate given the frazzled beginning to your day so you snap on the one person you feel should say, "how high" anytime you request levitation. See where I'm going with this?

Managers often make assumptions of their Executive Assistants that simply aren't fair, especially when crucial context and communication aren't shared. This often leads to the kind of subtle abuses EAs have to deal with every day and normalize as part of the job.

The Calendar is the Culprit

After all of these years, I've come to the conclusion that managers handing off their calendars to their Executive Assistants is one of the biggest mistakes in business. Expecting someone who only sees you several hours per day (even less now) in a setting that only provides you with certain context to know you well enough to schedule your day in perfect synergy with your mood, energy level, attention span, hunger/caffeination level, and focus is foolish. Officially.

As controversial as it sounds, I believe all managers should handle their own calendaring. Think about it. They know all the context. They know the players and where they fit in the game. They know who should be in the room and why. Most importantly, they know firsthand how they will show up on the day. By booking their meetings they subconsciously prepare themselves for what's to come and will pre-allocate the exact amount of energy, focus, and preparation they'll need to crush the meeting. Or they'll tap out if they know ahead of time they're not ready or if it innately doesn't feel right. Often, they'll call, text, or send that email anyway to request a postponement.

The New Rules of Engagement

AI-powered calendaring has revolutionized the way calendar management is done. While more and more EAs lament their bosses f*cking up the beautiful calendars they've created, I'm now one of the biggest proponents of managers handling their own calendars. This would, in turn, free up Executive Assistants to help with the research, information gathering, and even sitting in on the meetings to get more context, potentially provide a different perspective, and partner more effectively with their Executive vs. doing the calendar, being left out of the conversation, and handed a bunch of tasks and subsequent calendar requests with little-to-no shared context...again.

As AI becomes more integrated into our operating systems both in the office and at home calendaring will become less dependent on an Executive Assistant to manage effectively. We're already at, "Alexa, what's my day look like?" stage. Quite soon we'll be at, "Alexa, please cancel my 8:30am and 9am meetings with my regrets and reschedule each for next available times on our calendars, text Emily's teachers for her first and second period classes and let them know I'll drop her at school right after her dental appointment. Also, Slack my Assistant and let her know I'm running late and ask her what she wants from Starbucks. Oh! And order hers and my normal latte for pickup at 9:45am."

I hate to inform you, but we're kinda here already. The 1950s have been over, kids. We've been operating with an archaic model for decades, not because of efficiency, but because we've tied this warped idea of status to having an Executive Assistant at the helm vs. truly utilizing and empowering them in a way that force multiplies them and the people they support. As such we've created a culture of running through EAs, assigning impossible expectations, and treating and compensating them differently than every other employee in the building with singular accountabilities.

In Conclusion

We've now reached that chasm. On one side: where we are now. EAs handle calendaring and rarely do it exactly as expected since the goalposts move daily with little-to-no context provided and often on a whim. On the other side of the chasm, we have a future with far fewer Executive Assistants in the mix thanks to our new bestie, AI. As uncomfortable as this may be, it's time to start ripping off the BandAid.

Executive Assistants now need to find a new way of operating that leverages AI. Those who follow me already know I'm pushing the transition into a Junior Chief of Staff role, which will require higher levels of training, education, exposure, access, and partnership with their Executives. NOT calendaring.

Executives should now leverage AI to manage their own calendars. They'll quickly find that it's much more efficient and requires less explanation and micro-management. Additionally, they can start re-engaging their intuition in the process and align their energy, focus, and desire to engage in all the meetings they schedule themselves into.

Executives handing off their calendars has created unnecessary anxiety and scapegoating for decades. Think about it, if you're too busy to effectively govern yourself in your own life perhaps you're doing too much. Executives hiring EAs to enable their poor self-governance has led us all to where we are today. The time has come to lean into the technologies at our disposal and reimagine roles and functions so that they are effective, efficient, and equitable. This simple shift will enable this long-overdue transition toward the business practices of the future.