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How To Solve Your Complex Scheduling Heachaches With A Remote Executive Assistant

Written by: Sandra Lewis

For most executives, their schedules are either tightly woven or in a complex tangle.

Even with the increase in virtual meetings in recent years, an exec’s schedule is as tricky as ever. Cutting out in-person travel has removed some planning factors, but added new ones in their place. With all the digital platforms and the ease of requesting meetings, the virtual factor may have made scheduling more complex.

Suddenly, it became easier to meet more often, for everything, all the time. 

In general, studies show that most people—over 75%, in fact—feel like their meeting schedules are out of control. When you realize that those same people rank scheduled meetings as a disruption, right up there with email and office chit chat, but before social media, you can see there’s a significant problem. 

And that’s just meetings. Think of everything else that ends up on your calendar! 

If you don’t have an executive assistant helping you with your complex schedule, you’re wasting time and getting frustrated.

While you can’t always clear your schedule, you can shave some of that frustration and wasted time off by using an executive assistant to help control your calendar.

Why Executives Have Complex Schedules

For many executives, their entire business revolves around meetings with multiple parties. Meetings grease the wheels; without them, nothing moves.

Even if that’s not the case for some execs, just about everything they do has to end up on a schedule or it won’t get done, whether it’s blocking out time to respond to emails, travel, attend personal appointments, or meet with investment partners. 

A schedule is partly about time management and partly about filtering who gets access, but no matter what ends up on it, there’s a ton to do with limited time for it all.

Let’s put that into perspective. On average, an executive works about 62 hours a week. Of that time, 75% was scheduled in advance, with only 25% made up on the fly. 72% was spent in meetings, with the rest spent alone doing work or regrouping.

It’s safe to say that most schedules have to do with meetings.

Financial meetings. Planning meetings. Team meetings. Then there are the cascading meetings; those meetings that are generated from a meeting and it forces adjustments to an already tight calendar. After a while, it feels like you’re being chased by the schedule. 

But why does this happen to so many executives?

Maybe their company is experiencing growth and they don’t have enough help to manage it. They might be poor time managers. Perhaps they’re not doing a good job saying “no” to people who want access to their time, particularly if they’re managing their own schedule. They might even confuse being busy with being productive.

Whatever the reason, there’s one solution, and it isn’t working harder. It’s getting a skilled executive assistant.

How An Executive Assistant Handles A Complex Schedule

Some execs have four or five assistants who do nothing more than handle their schedule. It’s that big of a deal. If you’re still trying to do it yourself, or have a system that’s supposed to help but isn’t effective, you’re already losing ground.

When you understand that your schedule—being the key driver of activity for an executive—is like the Holy Grail for productivity, it’s easy to acknowledge the need for a high-end executive assistant who does more than simply look at the calendar and drop meetings in.

A top-shelf executive assistant understands scheduling inside and out.

1. They understand the buffer zone around meetings.

You can pack a calendar perfectly full, but no human can make that happen. There need to be buffer zones for things like travel time or regrouping.

A great executive assistant plans some wiggle room into the schedule for meetings or events that might run over. They might even schedule some meetings that have a tendency to run long or get sidetracked with “safeguards” in place, such as planning them over lunch, or just before a natural cut-off time, for example.

They also know when to block out time for their executive to work or simply get some breathing room from a packed schedule. Even if their exec isn’t aware of overwork taking place, a great executive assistant can spot it and adjust the schedule to reduce unnecessary meetings.

2. They understand what their executive prefers.

A good executive assistant gets to know their exec.

Each person has their own personality, work style, and daily schedule preferences. A schedule that works for one executive won’t for another.

Not everyone likes afternoon meetings, for example, while others prefer it. Some refuse meetings on Mondays or Fridays, while others are indifferent. Some need mental space between meetings while others like to charge forward and work through a solid chunk of meetings at once.

An executive assistant also has to understand the executive’s personal schedule, since that affects the work schedule. It might include workouts at the gym, picking kids up from school, or an anniversary dinner reservation.

The executive relies on the assistant to know and remember these things. They’re the structure that the schedule hangs on.

3. They understand the executive’s priorities.

You can have a perfect schedule, but not for long. 

Something is going to come along that will blow it apart, and a great executive assistant can handle it as long as they understand what takes priority.

They know which items on a schedule are flexible and can be adjusted or moved if something more important pops up. They know which meetings, investors, or clients are VIP and take priority. They know how to filter out requests for access to the executive, and can say “no” so the exec doesn’t have to.

4. They take an active approach to understanding.

And perhaps most importantly, they take the time to learn these priorities and preferences with an active approach: they schedule time with the executive themself.

It doesn’t have to be daily or even weekly; it might be once a month for planning and an overview of the upcoming calendar. It’s about touching base on what’s coming up that might affect the schedule, and reviewing any past scheduling hiccups to avoid repeating.

A great executive assistant understands that clear communication—both about what already happened and what’s coming—makes scheduling much easier.

How To Find An Executive Assistant Who’s A Scheduling Expert

Thinking of hiring this kind of scheduling rockstar? It can seem like a daunting task.

You’re basically looking for a partner, someone who nearly reads your mind and can think on their feet, even as your calendar shifts around. Where do you even look for someone like that?

You’ll be glad to know you don’t have to put “hire an executive assistant” on your schedule, because we already found one for you.

At Boldly, we’ve sourced and hired the most talented people available. Our executive assistants are the best from thousands of applicants, people with experience at Fortune 500 companies and top-level executives. 

From that, we use a custom matching process that sets us apart from other executive assistant services. We don’t just assign someone to you, we match you with someone. We make sure it’s a real partnership. That means you’ll have an assistant who works and thinks like you do.

How busy do you have to get before you do something to get rid of all the complicated scheduling headaches? When you’re ready to control your schedule instead of having it control you, contact us. We can connect you with a scheduling expert in just a few days.

Topic: Remote Executive Assistant

Updated on October 12th, 2023

About the author: Sandra Lewis is the Founder and CEO of Boldly. She's passionate about helping Businesses, Organizations and Executives increase productivity and move their work forward with the right skills and resources. Setting an example of the efficiencies gained working remotely, she’s been leading her entire team on a virtual basis for the past decade.