A Guide To Executive Calendar Management

Executive Assistants are pros at calendar management – and rightfully so! Managing an Executive’s calendar takes a copious amount of skill and savvy. It’s more than simply adding meetings and tasks. For the assistant, Executive calendar management is about designing a schedule that aligns with the high-level priorities and goals of their leader. With these effective calendar management principles, you can streamline and strengthen your skills to keep your Executive happy and on track.

Get organized ✍️

Executive calendar management is one of the best ways you can lean in to support your leader’s productivity. When your Exec’s calendar is working for them without any heavy lifting, they are free to focus on what matters most! An initial step you can take towards great calendar management is to organize your own calendar first. You’ll instantly build credibility with your leader when you personally use the calendar management tools you champion your Executive to use. Plus, your own days will be more productive because you’ll both be on the same page. 

To get started, make sure you’re using basic calendar management tools like color coding, task batching, themes, white space, etc. These simple tools will help you stay organized and on task, which will free you up to do the same with your Executive’s calendar. Also remember to set clear boundaries, dream up your ideal work week, and hold yourself accountable to what you put on your own calendar. Accountability in the calendar is a must-have for both you and your Executive.

Free Guide: Download Calendar Management 101 for an in-depth look at how to manage your leader’s calendar

Learn your leader’s preferences 🙋

Before you dive into managing your Executive’s calendar, make sure you have aligned with them about their personal preferences, priorities, and work style to find the right calendar management tools. Some great questions to ask:

  • What time of day do you work best?
  • Do you want transition time between work and home? 
  • What are your priorities for work and personal? (i.e. logging off by 6 pm, no meeting days, build external relationships, etc)
  • What’s your preferred meeting duration?
  • Zoom or phone calls for meetings?
  • How much time between meetings do you like for both virtual and in-person meetings?

Think through what motivates your leader, what frustrates them, and what makes their life easier. Then, find additional ways to incorporate calendar management tools that will reflect their preferences. For example, if you know your Exec hates taking calls right after their lunch block, schedule a recurring break or email block at that time.Take a look at how Base can help you simplify scheduling and maximize your Executive’s time!

Update and ask for feedback 💬

Executive calendar management is not a one and done approach. Instead, it will require your ongoing maintenance. Pay careful attention to your Executive’s shifts in work and adjust accordingly. For instance, if a staff member transitions off their team, think through how this will impact their schedule and proactively plan for it by adding holds and work blocks to accommodate the additional workload.

Ask for feedback periodically about what is working well and what can be improved. As you listen to their feedback, take the lead in finding ways to implement calendar management tools that can alleviate any pain points they may be experiencing.

For instance, if you are color coding your leader’s calendar already, but they voice that they want to know which meetings align with their priorities, add a label to the calendar events so you can view its type, (meeting, work block, email, travel, etc) and its priority (staffing, new donors, annual planning, fundraising, etc). For more help on color coding, read ‘The Small Details: Color Coding Calendars’ to help you visualize the week ahead! 

Being ready to adapt to your leader’s ongoing needs in the calendar will show them exactly how much you value keeping their schedule as fine-tuned as possible. 

Build the ideal schedule 🗓️

Once you’re equipped with your Executive’s preferences, needs, and work rhythms, you can build out their ideal work week! For this exercise, think about your leader’s ideal week: no last minute meetings, no sick kids, no crises – a perfect week. Include personal appointments they want to keep, like picking up the kids from school, working out, dinner with friends, book club, etc., and add those into the calendar, too.

Quick tips for ideal schedule creation

  • Identify and call out working hours and offline hours.
  • For working hours, identify the priorities and the non-priorities. 
  • Add ‘startup’ work blocks at the beginning of the week. These work blocks will help your leader settle in before jumping into any work.
  • Add a ‘shutdown’ work block at the end of their day as a prompt to wrap up any remaining work. 
  • Add in any non-negotiable appointments or activities they may have, like standing meetings and check-ins.
  • Build around non-negotiable appointments with additional work blocks, call blocks, email blocks, and meeting blocks.

One note on work blocks – be strategic when scheduling them. For instance, if your Exec mentions they are sharpest in the afternoon, schedule the work blocks for afternoon instead of first thing in the morning. 

With the ideal schedule complete, review it with your Exec and make adjustments (if they really want only 30 minutes for lunch, go ahead and dial back that block).

Having an ideal schedule as a framework allows you to be a stronger gatekeeper in Executive calendar management. It also frees up your Executive to say no to things as they pop up.

As with any change, there will be a learning curve. When there are some weeks that feel challenging, don’t give up! Remember that the ideal schedule is a foundation, and there will always be competing priorities and times you need to shift. 

Embrace the gatekeeper role 🔐

As your Executive’s right hand, they will look to you for Executive calendar management. This means filtering appointments and meetings they need to take, and more importantly, saying no to the ones they don’t need to take. It can be hard to say no. Remember that saying no can be vital to a sustainable and productive work/life balance for you and your Exec.

Before adding meetings to your leader’s calendar, ask the requestor clarifying questions to get to the heart of the purpose:

  • I know you have your regular check-in on Wednesday, is this Tuesday meeting something that could be covered in your check-in?
  • Is this a request that can be reviewed first, then a meeting scheduled for any questions?
  • I noticed you requested a 60-minute meeting, could this be covered in 30 minutes?
  • Is there another leader better equipped to take this meeting, or who could make this decision instead?

If it’s a meeting that needs to happen, work your calendar magic to make it happen. If it doesn’t need to happen, your calendar management will protect your leader’s time! You’ll also influence others, helping them make more strategic meeting decisions in the future.

Gatekeeping also means managing up. If your Exec continues to use their workblocks for meetings or ignores the calendar management tools you agreed to, speak up! Avoid assumptions and start with seeking to understand why: is there a specific reason or project that is taking more time? Is the time of day not good for a work block? Do they need one full day of no meetings?

Many times, Executives simply have a hard time saying no. If that’s the case for you, coach them on how to politely decline, and most importantly, hold them accountable. It may feel intimidating to coach your leader at first, but with clear and respectful communication, you can do so in a way that enhances their work-life instead of burdening it. 

Next steps ▶️

Executive calendar management is a skill that you develop over time with constant refinement. It can be easy to put it on autopilot and stop looking for new tools and methods. Remember to be open to trying new things! Even if you think you’ve got all the bases covered, try assessing your Executive’s calendar right now. Chances are, there’s at least one method above you can start using to improve their workflow. Bring it to your next meeting and impress your leader with your proactivity!

Need to review the basics? These fundamentals of effective calendar management will help you build a solid foundation as you move forward.

Streamline your calendar management with Base!

At Base, we know how hectic and time consuming it can be for EAs to schedule meetings for their Executives. That’s why we created Scheduler, a fast, friction-less way to manage the ins and outs of your leader’s appointments, meetings, and more. Get a demo and see how you can use Scheduler to streamline your current processes and make calendar management a breeze!

Written by Bryn Smith

Bryn is the Senior Manager of Brand and Product Marketing at Base, where she is on a mission to build a world-class EA community by connecting them with top-notch thought leaders, invaluable resources, and cutting-edge insights.