boss's calendar

It’s responsible enough being in charge of your own calendar, but when you’re in charge of someone else’s calendar schedule — it can be an overwhelming experience. If you want to save time, reduce stress, and ensure that everything in your life runs smoothly, then proper calendar management is a must. Here’s how to manage your boss’s calendar.

If you’ve recently been given the awesome responsibility of managing your boss’s calendar, you may feel a lot of pressure. I mean, if you make one mistake, they could do irreversible damage to their reputation. It may even put their career or business in jeopardy.

Before you have a panic attack, the good news is that if you properly manage their calendar, you have nothing to worry about. And, here the best ways that you can keep your boss, and yourself, on track.

Who are you?

Managing someone else’s calendar is like running a business. To be successful, you have to know your clientele. If you don’t know anything about your boss, then how can your efforts at their calendar business provide them any value?

Take the initiative to get to know your boss better. You can get to know your boss by reviewing their past calendars to see what their daily routine is like. Check the calendars used both inside and outside of the office. Shadow them for a couple of days. Walking with your boss around the workplace converse with them. And, don’t be afraid to ask them questions about preferences and what your boss considers most important for the day.

After getting to know your boss, you’ll be able to manage their calendar more effectively. You’ll know when their biological prime-times are. You’ll also know the days and times they want to schedule meetings. And, you’ll know how they like to maintain a healthy work-life balance.

Help them strengthen their scheduling skills.

Making sure that your boss stays on schedule is probably the most important responsibility you have when managing their calendar. Of course, that’s an uphill battle when facing last-minute changes or working with someone who has unhealthy habits.

The good news is that since you know your boss pretty well now, you can help them bolster their scheduling skills.

  • Constant questioner. Does your boss always ask what’s on their schedule? That can be exhausting for you. But, you can help them out by using a multi-calendar system that uses paper and digital calendars for them. Now they can quickly access their schedules. You could send them reminders via text before a meeting. But, most online calendars have this built-in. So, use this technology to your advantage.
  • Constant re-arranger. Here we have someone infamous for making last-minute changes. You can’t force them to change. But, you could stay ahead of this by frequently meeting with them to review their calendar. Also, send their daily schedules to them the night before. And, try to stress the importance of maintaining their schedules. For example, if they had to meet with an investor, remind them that it took months to set this meeting up and if they cancel if it will take several more months to reschedule.
  • Out of sync-er. Create and share your boss’s calendar with others. It’s a simple and effective way to keep everyone on the same page. You could also place a large wall calendar in the office. Or, utilize tools like scheduling and project management software.
  • Late arriver. Leaders should never be late. It’s disrespectful and sets a bad example. Set up reminders on they need to leave so that they’re on time. Also, include buffers in their calendar so that they have the right amount of time to travel and prepare for events.
  • People-pleaser. An open-policy isn’t a terrible idea. It’s a great way to build trust and rapport between your boss and their time. But, it can also interfere with your boss getting their work done. Block out specific times in their calendar for drop-in appointments to resolve this problem.

Create a calendar template.

Why create a new calendar for your boss each week? That sounds like a tedious and time-consuming task. Instead, create calendar templates for them.

For instance, you could quickly generate their monthly schedule just by inputting recurring events. Let’s say their maker’s day is on Monday, while Tuesdays are dedicated to meetings. Wednesdays are set aside for marketing, Thursdays for networking, and Fridays fro admin.

Being aware of this, you could just plug these entries into their calendar. Then, you could build the rest of their schedule around these repeating activities.

Mi calendario, es tú calendario.

I’ve already alluded to this, but creating and sharing your boss’s calendar is vital. Most online calendars allow you to do this action through email. But, you can place your boss’s schedule on a website like the company’s website or right within the Calendar.com app.

The reason why you would do this is that it lets others know when your boss is available or not. As such, it eliminates lengthy back-and-forth communications when scheduling. And, it also keeps others in the loop. For instance, if they’re going out of town for business, you could share their calendar with their family so that they’re aware of his or her’s itinerary.

However, make sure that you share the right information with the right people. Employees, business partners, and board members do not need to know everything that your boss has planned in this personal life.

Avoid double-booking at all costs.

Scheduling conflicts like double-booking are embarrassing, unprofessional, and stressful. Because so, they should be avoided at all costs.

Don’t overcommit your boss’s time. If they already are attending an event, then don’t accept an RSVP for another function on the same day. Are they attending more than one meeting or event in one day? Add buffers between them.

If a scheduling error has occurred and there was a double-booking, reschedule one of the events as soon as possible.

Don’t overbook their calendars.

Those in a leadership position have a mentality where they believe they can do it all. Likely because these individuals are entrepreneurs, a boss thinks that they must do everything and be everywhere 24/7.

While this is true to an extent, the fact of the matter is that this just isn’t possible. A boss requires breaks to eat or catch their breath — just like everyone else. Your boss needs to unload some of their workload to focus on their priorities. And, to avoid burnout, they need boundaries when it comes to work-life balance.

Even if your boss is a workaholic, there are some ways that you can avoid overbooking their calendar. Interject breaks throughout the day. Leave an hour or two of blank space that can be used to address the unexpected. Don’t permit meetings to be scheduled close to the end of the workday. And, add buffers in-between events.

You should also make suggestions on which tasks can be delegated or outsourced. And, most importantly, be realistic with their time. If they have ten things on their to-do-list, spread them out for several days since it’s unlikely they’ll complete them all in just one.

Schedule their calendar like a medical office.

For those in the medical field, scheduling, as pointed out in an article published on Medium, is “the lifeblood of your practice. ” When schedules are maximized, it reduces stress, improves time management, and keeps patients satisfied. After all, when someone doesn’t feel 100%, the last thing they want to do is sit around in a waiting room for the doctor to see them.

While you may not see a similarity, you can take some cues from medical appointment schedules when managing your boss’s calendar:

  • Don’t keep people waiting. Always start and end on time.
  • Plan ahead. Medical professionals know that certain times of the year are busier than others. As such, they plan accordingly. For example, their office may be packed in the fall and winter, but less so in the summer. Analyze previous appointments to see when your boss’s time is most in demand so that you can plan accordingly.
  • Forge a timeline. Doctors can only meet so many patients per week. Likewise, your boss can only have so many meetings or put in so many hours per day. Knowing this information will help you more easily create and manage their calendar.
  • Group similar patients. When a medical staff can see patients with similar conditions or medical histories on the same day, it creates a rhythm. Mainly this is because they’re able to maintain a specific medical mindset. They also can keep all the same resources and equipment out all day. You can take this concept by batching similar tasks and meetings on your boss’s calendar.
  • Your schedule should reflect your patient mix. For example, if a medical professional has around 70% Fee for Service (FFS) patients and 30% insurance-based, they’re schedule should reflect that. As for your business, make sure that they’re schedule follows the Pareto Principle, where 80% of their outcome is produced by 20% input.
  • Create a triage. Emergencies happen. Doctor’s realize this by creating a triage scheduler in their chart. Depending on the symptom, urgency, and appointment length, a physician may accept occasional patients’ last-minute. Know how to prioritize so that your boss doesn’t fall into the urgency trap.

Be their weather/traffic person and timekeeper.

Sure. You already have a million things to do. But, this is a part of your job. Gridlocks and inclement weather can cause them to arrive late to a meeting. That’s why you need to keep tabs on traffic and weather if your boss is out and about.

Also, another task that’s not the most exciting is to keep your eye on the clock. For instance, when in a meeting, let your boss know that there are five minutes left so that they can wrap things up on-time.

Double-check synching.

There usually aren’t too many problems with synching. But they can happen. And, the last thing anyone needs is to have a situation where your boss’s calendar didn’t sync with their smartphone or personal agenda. Just take the extra couple of minutes and make sure that there aren’t any issues.

Meet weekly.

Finally, block out time at least once a week to review their calendar. Although this may seem like a waste of time, it’s necessary.

For one, it lets your boss know their schedule ahead of time so that they can prepare or adjust their schedules if needed. It also gives you a chance to adapt. For instance, maybe they no longer attend a weekly networking event. Instead, they’re attending a public speaking class. You’ll have to adjust to their new schedule. And, it also gives you a chance to discuss what systems and process work and which ones that don’t.

Tags: ,