Calendaring Tips for Assistants

Managing the Madness: Calendaring Tips for Assistants

Administrative assistants wear many hats. While their duties range wildly, one of the most important elements of their role is calendar management. This often overlooked and commonly minimized task is so critical that it represents one of the most frequent questions I receive. How do I help my executive maximize their time? How can I avoid scheduling conflicts? What systems will help make calendar management more seamless? In this week’s blog, we’ll cover some helpful tips for assistants who manage appointment scheduling and calendaring.

Why calendar apps alone just don’t cut it

First, let’s address the elephant in the room. Do assistants really need to spend their time and use their talents to manage their executive’s calendar? The short answer: Yes! Calendar management is truly a cognitive task that takes understanding, empathy, and strategy. While there are some great calendar applications on the market, they alone cannot effectively and intelligently juggle an executive’s busy schedule, ensuring no balls get dropped and the executive is set up for success. That app just doesn’t exist.

Why? Because scheduling appointments, meetings, and project-focused time requires an ability to see the big picture. Stellar assistants who have learned to master calendar management for their executive have adopted a strategic approach. Before they ever put something on their executive’s calendar, they first consider a huge number of factors, carefully weighing all key elements that need to be considered and serving as the protector of their leader’s time. This is a holistic approach to calendar management.

Now, there are some super tech-savvy executives who have shared with me that they think it’s just easier for them to manage their calendar than to delegate that duty to their assistant. However, I’ve seen some huge issues with this approach that serve to accumulate over time. Consider this:

  • When meetings change, the executive is responsible for constantly updating their calendar to reflect the new meeting time/date/location. This can often become tedious and cumbersome, draining precious minutes every day. Those minutes add up!
  • If their assistant doesn’t have access to their calendar, they can’t help them prepare for meetings or appointments. Top-level leaders often attend meetings that require some significant information download prior to the meeting. When an executive manages their own calendar, they don’t have anyone to ensure they are prepped and ready.
  • If an executive is managing their own calendar, they are wasting their time and skills on a task that could be more efficiently and effectively handled by their assistant. It’s as simple as that.

The first thing an assistant/executive team needs to do is decide who is in charge of the executive’s calendar. I strongly recommend this role be taken on by the assistant. The assistant can truly devote the energy, brain power, and skill needed to ensure calendar management is a strength of their partnership, not a hindrance.

Find one home for your executive’s calendar

Once the assistant has been formerly delegated the task of calendar management, they need to evaluate the current system and, if necessary, identify one home for all appointments and meetings. I often find that many teams, as they begin to hone a solid calendar management system, are utilizing more than one calendar to house their schedule. This may include various applications, desk calendars, or hard copy planners. A system that uses more than one calendar is ripe for missed appointments and mismanaged time. First, consolidate those systems into one. Typically, a digital calendar is best since most modern communication occurs via email. If an executive prefers to see their appointments on paper, most applications provide a plethora of printable reports to display their daily, weekly, or monthly schedule.

Think before you book it

Once one calendar system has been identified, it’s time to start approaching meeting and appointment scheduling as a cognitive task. This means that a schedule is thoughtfully constructed, one that provides a deep understanding of the executive. From there, a calendar strategy can be developed. This strategy should go far beyond what just one day looks like. It should have both short-term and long-term considerations, ensuring that the leader is set up for success on an ongoing basis. The assistant must first consider factors like the executive’s current workload, personal commitments, the impact of travel, and the schedule for the weeks ahead before adding anything else to their leader’s calendar.

Prepare, prepare, prepare

Exceptional assistants also help their executives successfully and thoroughly prepare for their meetings, speeches, appointments, and pitches. This task requires anticipation, preparation, and forethought. Preparation in this area will equate to success for the executive/assistant partnership.

For example, many meetings include materials that need to be reviewed before the leader walks into the room. If the assistant has effectively managed the calendar, they know what materials need to be reviewed, and they allot time for their leader to review them. They also keep a close eye on last-minute communications about a meeting and immediate relay any changes, updates, or need-to-know information to their executive. Top-notch assistants also anticipate busier-than-usual times. This may be associated with specific project, time of year, or important task. Be ready for these times! Think about what may be needed ahead of the expected crunch time and, if possible, take advantage of additional resources that can help support the assistant/executive partnership.

Top-tier leader/assistant teams understand that there are three parts to meeting planning: pre-meeting, meeting, and post-meeting. While the meeting element is, of course, important, the pre-meeting and post-meeting parts help to really ensure the time spent was productive and the executive is well represented. They add critical value to the meeting itself.

The pre-meeting element includes essentially everything that happens before the meeting:  scheduling the meeting, handling critical communication, obtaining needed information and materials, reviewing those materials, and blocking prep time for the meeting. The importance of this part of meeting planning is huge! If the pre-meeting part is not done well, the leader can’t walk into any meeting confidently and thoroughly prepared.

The post-meeting element is also important but, unfortunately, frequently dismissed. The stress of a big meeting can build, but once it’s complete, the instinct can be to move on quickly. Don’t make that mistake. Successful assistant/executive teams huddle up post-meeting to discuss action items that need to be documented, research that needs to take place, assignments that need to be delegated, and any associated details that need to be noted. This post-meeting part allows your leader to ensure the time spent in the meeting was productive, and that forward progress continues.

Communication is key

For the last quick tip in this blog, I’d be remiss if I didn’t address how important communication is in mastering the art of calendar management. It’s critical in almost every area of our professional lives. When executive/assistant partnerships focus on developing their communication, they find that they are better able to connect and become a much more effective team. In the realm of calendar management, it will be important for the assistant to gain an understanding of their leader’s appointment/schedule preferences. This will help to better guide them through the scheduling process. Important nuggets could include whether or not they are a morning person if they have personal commitments to consider, or when their most productive work time is. Learning these preferences about a leader through effective communication allows an assistant to hone their calendar system, serve as their leader’s gatekeeper, and strategically plan out the days, weeks, and months ahead.

If communication is a struggle between an executive and their assistant, a good way to start forging a path toward solid communication is to begin having daily huddle meetings. These meetings should focus on the day to come, including meetings, deadlines, and appointments. Over time, the executive/assistant partnership will begin to deepen because these huddle meetings serve as a connection point at the beginning of every day and put you both on the same page. That’s powerful stuff!

Ready to become a Calendar Management Master?

Office Dynamics has developed a library of resources that focus on helping administrative assistants master all the key functions required in their role, including calendar management. In our essential eBook, Mastering Your Executive’s Calendar, I introduce you to creative techniques, impactful skills, and revolutionary concepts. Find out how powerful you can become when you conquer calendar management. This eBook, along with the rest of the Success Store, which includes a massive library consisting of books, certification courses, eBooks, live virtual training, and on-demand training, can help assistants level up and reach new heights in their careers. Click here to learn more! 


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