Keep Your Boss on Task with These Calendar Management Strategies

Last-minute changes or late arrivals can throw your boss’s calendar out of whack. Try these strategies to better maintain their schedule.

Organizing your boss’s calendar is one of the toughest parts of your job — but keeping them on that schedule might be even more challenging. For a variety of reasons, some bosses just don’t focus on their schedule, frequently showing up late or making disruptive changes. As you know, even small changes can wreak havoc on everyone’s day.

The good news is that you might be able to help break that pattern. Research from the University of Southern California found that repetition and reinforcement can build better habits, so planning a new course of action and sticking to it may lead to fewer last-minute schedule adjustments.

Look at the following list of boss types for the one that matches your boss. Then, use the tips to help them build stronger scheduling skills.

The Constant Questioner

Working with a boss who is never quite sure what’s on their calendar on any given day saddles you with a heavy load of support and organizing.

To shift some of the schedule questions off of your plate, try building a multi-calendar system that includes a paper reference for quick access. Assuming your boss already has a digital version of his or her calendar, purchase a non-digital planner — like a wall calendar — for reinforcement and quick reference. Display the calendar prominently so you or your boss can quickly jot down meetings and notes.

If needed, consider having multiple calendars — for example, one for in-office meetings and another for business travel. Including times, addresses and other necessary details on these calendars can minimize information scrambles.

Extra reminders, whether by texting, emailing or simply popping your head into their office, can help cut down on questions and keep everything on track.

The Constant Re-arranger

Last-minute scheduling changes are challenging for you, frustrating for other team members and inefficient for everyone involved. Each time a meeting moves, you likely have to notify attendees of these changes and work to find another meeting room and dial-in number, and settle other logistics.

If your boss is inclined toward last-minute shifts, consider getting ahead of it by establishing regular times to review upcoming meetings. Use this time to get a heads-up on meetings your boss wants to move while there is still time to do it efficiently. Also use this time to reinforce the importance of attending upcoming meetings, and get your boss to double down on his or her commitment to important events.

When a retooled meeting doesn’t come together — either due to lack of attendance or an inconvenient reschedule time — find a nice way to remind your boss that their schedule shifting is the reason.

The Out of Sync-er

Some people are not inclined to sync up with others, and this can create work for the person managing group coordination — which is usually you. For example, your team may rely on a large wall calendar to reflect important updates, but your boss goes by what is on a digital calendar. Or, your entire organization works digitally, but your boss gets by with a tried-and-true day planner.

In a case like this, converging both methods is your best bet. Get out in front of miscommunications by scheduling weekly sit-downs to review your boss’s paper calendar. During this time, you can update your boss based on the team’s digital calendar shifts and gather details they may be tracking on paper.

If you think a common paper calendar will help you or your boss, download a free printable calendar and either fill it out yourself or ask your boss to write down meeting time updates for an easier sync up.

The Late Arriver

This boss may attend every meeting and know what’s coming up, but has a habit of arriving late each time. This can leave attendees frustrated — and leave you fielding questions about where your boss might be. Not to mention that late-meeting starts, for any reason, can cost companies time and money.

It may seem like micromanaging, but the fix for this type of boss is constant reminders. Start by putting reminders on their calendar to notify them 10 or 15 minutes before a meeting is set to begin. If your boss is typically in back-to-back meetings, suggest a company-wide policy that ends meetings 10 minutes before the hour to give them time to transition.

If meetings are offsite, provide your boss with all of the necessary details to get them there on time: for instance, travel directions, addresses and which materials to bring.

The People-Pleaser

Your boss might be proud of an open-door policy, but frequent visitors can cut into meetings and work time. The result: It throws off their schedule. Delays from impromptu visits can have a ripple effect across the day’s meetings and deadlines.

The first step toward a solution is to tactfully flag the problem for your boss, so that they understand the need for a new approach. Suggest retaining the open door policy, and designating blocks of time for handling drop-in appointments and last-minute meetings. Suggest time limits or guidelines too. For example, schedule 10 minutes for a quick problem-solving drop-in meeting, or 30 minutes for more in-depth employee conversations.

With your boss’s permission, simply swing by their office if these impromptu meetings run long, or look like they might overlap with an upcoming event. Ask people who want to see your boss outside of these specific time blocks to schedule through you.

Keeping your boss on task requires time and effort in the beginning, but once you have set a routine, your job will become easier. Ongoing communication is crucial, so be sure to talk with your boss to figure out what is working and what’s not. Adjust your approach based on what you learn. You may be surprised at how a few tweaks to the way you and your boss maintain schedules can gradually have a big payoff.