Productively Managing an Executive’s Calendar

Whether you’re an intern, assistant, or helping out a friend or family, you may be asked to help manage someone else’s calendar. That responsibility should never be taken lightly. They need their day to run as smoothly as possible to protect their business, reputation, and well-being. Here’s how to productively manage an executive’s calendar.

But, what if you’re new to calendar management? Well, here’s how you can effectively achieve that. And, as a perk, you can take this experience and apply it to your own life. Who knows? It may even help transform you into an effective leader yourself someday.

And, if you’re an executive who still manages their own calendar, then these tips will also apply to you.

Get to know your executive.

Imagine that it’s finally time for you to host your friends and family for a holiday feast or reunion. In all of your excitement, you probably didn’t take into consideration the dietary needs and preferences of your guests. Maybe someone is a vegan, while another suffers from celiac disease.

Did you also think about the distance that everyone has to travel to? If someone had to drive two hours to get to your house, having dinner at 8 p.m. may be too late for them if they weren’t staying over.

The point is, it takes a lot of planning to throw together a successful event. And, the same is true when it comes to an executive calendar.

You may be tempted to start filling their calendar however you like. But, remember, it’s your executive’s valuable time. That means you need to respect how they wish to spend it.

Spend some time shadowing them so that you know what their daily routine is like. Ask your boss when they prefer to have meetings or eat lunch. How do they prioritize their lists? When are they at peak productivity? How does your exec make time for their own well-being?

You could also review their past calendar to see how they spent their time.

Besides their individual inclinations, the rules of time management are undoubtedly different for employees and executives. But, you won’t know that if you don’t get actually to know your executive.

Think strategically.

There’s a misconception that when managing an executive calendar that you’re merely taking orders. They ask you to add a lunch date or schedule a team meeting, and that’s it. The thing is, to effectively manage an executive calendar, it’s the opposite.

You need to think broader and more strategically. Before filling up your boss’s calendar, you need to consider the bigger picture. Do the task event have a purpose. Does it align with their goals? What is the time commitment attached to the time request?

What’s more, you also have to realize that just because a slot is open doesn’t mean it’s available. For example, let’s say that there’s a blank block from 1 p.m. to 2 p.m. Because there isn’t anything scheduled, you book a conference call. But you didn’t notice that your boss has a meeting at 3 p.m. that’s on the other side of town. They wanted to leave that block open so that they could prepare and travel for that meeting.

Before adding something to their calendar, make sure that it’s not interfering with anything else on their calendar. You should also take into account travel time, jet lag, breaks, and work-life balance. For instance, avoid scheduling an urgent meeting on the day after they arrive home from an international trip or when it interrupts with their downtime.

Use a shared calendar.

There’s really no excuse for not having a shared calendar. A shared calendar should be readily accessible and come packed with benefits like keeping everyone in the loop. Besides, if your organization uses Office 365 or G Suite, then you already have a shared calendar at your fingertips.

Whenever someone asks what the executive’s availability is, send their calendar via email. Better yet, embed their calendar somewhere like the company’s website. It just avoids those lengthy back-and-forth communications when scheduling.

It’s essential to keep in mind, though, that you don’t want to share too much information. There’s no need for anyone else to know what your executive’s life is like outside of work. You should also customize the calendar by using the executive’s preferred view. You can also use color-coding or different fonts so that they can quickly identify calendar entries.

And, integrate the calendar with tools like Calendar. It works with Google, Outlook, and Apple calendars. But, it also used machine learning to make smart suggestions on how to schedule your executive’s time.

Run a better medical practice appointment schedule.

You don’t have to be involved with a medical practice to run your schedule like one. After all, medical practices must maximize their schedules to keep patients satisfied and keep the office running smoothly.

So, how can this be achieved? Well, here are some tips that accomplish this goal:

  • Always start on time. If meeting beings at 1 p.m., then that’s precisely when it should start. To prevent a late start, suggest that everyone arrives ten minutes early. Even better, the meeting invite could have a start time of 12:50.
  • Plan appropriately. A doctor’s office typically sees a bump during specific times of the year, as flu season. Knowing this, they make sure that they have enough help and resources to handle the increase in patients. For you, review past calendars to see when your executive is most in-demand so that you don’t fill their calendar with less essential objectives.
  • Forge a timeline. Medical practices know in-advance how many patients they can see per day. For you, be real on how much you and your executive can accomplish realistically every day — including how many meetings can be scheduled.
  • Group similar patients. It’s more useful for medical professionals to see patients with similar conditions or histories at the same time. Mainly because it keeps your boss in the right mindset. Also, it prevents them from continually putting away and getting right the same equipment. We call this batching. It’s pretty much the same concept where you group similar activities together.
  • Schedules should reflect the patient mix. “If you have 70% Fee for Service (FFS) patients and only 30% are insurance-based, then your schedule should reflect that,” explain the team over at liveClinic. “Block out only 30% of your daily schedule for capitated patients and leave the rest for open Fee-For-Service patients.” How does this apply to you? It’s similar to the Pareto Principle, where 80% of your executive’s outcome is produced by 20% input.
  • Create organized triage. Medical professionals also have to handle emergencies. In other words, they will only see a patient at the last minute, depending on the “the symptom, appointment urgency, and appointment length.” On your end, learn how to prioritize so that your boss doesn’t fall into the urgency trap.
  • Be open all day. Of course, this isn’t possible. Even though leaders are always “on,” they need downtime to recharge and rest. To protect this time, without completely neglecting their responsibilities, use automated tools that could take care of customer service inquiries. You could also create an out-of-office message informing the other party when to expect a response or what steps to decide if it’s an absolute emergency.

Update their calendar in real-time.

An employee asks if they can schedule a one-on-one. You look at the calendar and see that the executive is free next Wednesday at 3 p.m. Both of you agree on that date and time. Unfortunately, you get sidetracked and don’t add this to their calendar. In the meantime, someone else requests this same date and time. It’s free, so you go ahead and book that event. That’s definitely disrespectful to the employee.

The sooner you had a calendar entry, the better. It’s a surefire way to prevent conflicts.

Also, if an event has to be canceled or rescheduled, make a note of that in the calendar and notify the other people it impacts.

Bonus tip: Even if something hasn’t been set in stone, maybe the other party has to double-check their availability, add it to the calendar anyway.

Foresee the future.

Obviously, you don’t possess this power. But, there are simple ways to make it appear as if you do.

Stay on top of traffic and weather reports. I would just set up Google Alerts so that this doesn’t slip your mind. The reason you want to do this is that both can impact travel.

But, there’s more to this then being weather or traffic reporter. You also need to be their timekeeper. Do they have a conference call in fifteen minutes? Either shoot them an instant message or set up a calendar reminder to give them a head’s up. If they’re in a meeting, provide them with a signal when they have five minutes to bring the meeting to an end.

You could even do small things like having lunch ideas prepared. And, know which calendar entries can be pushed back or rescheduled. Knowing and understanding the motivations of your exec can be tricky when everything is a priority. But, date-specific entries or essential and urgent tasks usually take place before anything else.

One final word of advice here. Allow for some flexibility in your exec’s calendar. That means not overbooking the boss’s schedule where every minute of their day has been scheduled. Instead, leave some blank spaces so that they can attend to an emergency or have some free time to spend with their employees.

Review. Then review again.

Be proactive by reviewing their calendar frequently. Ideally, you should double-check your exec’s calendar every evening (right when you check your own calendar — or at least first thing in the morning. That may sound like overkill. But, it’s always better to be safe than sorry. For instance, let’s say you notice that a meeting invitee had to cancel at the last minute. You need to let your executive know the information as quickly as possible so that they’re not still planning their day around this event.

I’d also suggest that you review their calendar for the next two weeks. It allows you to address any possible conflicts and make sure that everything is still on track.

And, most importantly, make sure that their calendar has been successfully synced across all of their devices.

Find a system that works for both of you.

Finally, find a system that works for both of you. Even though you might do everything digitally, the other person may not be as tech-savvy. As such, you may want to print out their calendars for them so that they can still access their schedules offline.

While this takes some trial and error? Certainly. But, once you get into a groove, it will make managing an executive calendar much easier.

About John Rampton

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