A Guide To Executive Calendar Management

Anyone can drop into an executive’s calendar and simply add meetings and tasks. But what sets an Executive Assistant apart is the ability to design a schedule that not only accomplishes meeting and task management, but that designs a life aligned with high-level priorities and goals. Using these simple but effective calendar management principles will help you streamline and strengthen your executive calendar management skills, which will translate to a happy executive!

Organize Yourself First

Executive calendar management is one of the best ways you can lean in to support your client’s productivity. When they have a calendar that works for them without any heavy lifting on their part, they are free to focus on what matters most. However, if your own calendar is disorganized, it will be difficult to organize theirs! It’s like trying to make breakfast for the family when you woke up late: scattered, frustrating, and not fun at all. . You will build credibility when you personally use the calendar management tools you champion with your client, and your own days will be more productive as well.

Ensure you are 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 client. Set clear boundaries for your calendar and dream up your ideal week as well. Hold yourself accountable to your calendar so you can do the same with your executive calendar management!

Learn Your Client’s Preferences

Before you dive in, make sure you have aligned with your client about their personal preferences, priorities, and work styles to find the right calendar management tools. A few examples of great questions to ask:

  • What time of day do you work best?
  • Do you want transition time between work and home? Especially helpful for your clients who work from 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 they like—both virtual and in-person?

Those are just a few to get you started, and one list of preferences will not fit everyone! Think through what motivates your client, 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 client hates taking calls right after their lunch block, schedule a recurring break or email block at that time.

Continually Update the Calendar and Ask for Feedback

Executive calendar management is not one and done, it will require your ongoing maintenance. Pay careful attention to your client’s shifts in work and adjust accordingly. 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.

Periodically, ask for feedback about what is working well and what can be improved. Try not to take the feedback personally and find ways to implement calendar management tools that can alleviate the pain point.

One example, if you are color coding your client’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 not just its type, (meeting, work block, email, travel, etc) but also its priority (staffing, new donors, annual planning, fundraising, etc)

Building the Ideal Schedule

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

Quick Tips for Ideal Schedule Creation:

  • Identify and call out working hours and offline hours.
  • For working hours, think through their workweek and what priorities they have.
  • Add startup work blocks at the beginning of the week to get your client settled before they jump into work.
  • Add a shutdown work block at the end to close out anything lingering.
  • Add in any non-negotiable appointments or activities they may have, like standing meetings and check-ins.
  • Finally, build around those non-negotiable appointments with additional work blocks, call blocks, email blocks and meeting blocks.

Once complete, review with your client and make adjustments (if they really only want a 30 min lunch break 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, and frees your client up to say no to things. However, like with any change there will be a learning curve. When there are some weeks that feel challenging, don’t give up! Remember that an ideal schedule is a foundation, but there will always be competing priorities and times you need to shift. That is okay!

One note on work blocks: be strategic. If your client mentioned they are sharpest in the afternoon, schedule the work blocks there instead of first thing in the morning.

Be the Gatekeeper

As their right hand, your client looks to you for executive calendar management which means filtering appointments and meetings they need to take and, more importantly, saying no to the ones they don’t need. It can be hard to say no, and your client may not be used to it, but it is vital to a sustainable and productive work/life balance.

Before adding meetings to your client’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 Joe can review, and schedule a meeting if he has any questions?
  • I noticed you requested a 60-minute meeting, could this be covered in 30 min?
  • Is there another leader better equipped to take this meeting, or who could make this decision instead?

If it is 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 client! You’ll also influence others, helping them make more strategic meeting decisions in the future.

Gatekeeping also means managing up. If your client continues to use their workblocks for meetings or ignores the calendar management tools you agreed on, 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 clients simply have a hard time saying no. If that’s the case, coach them on how to politely decline and, most importantly, hold them accountable. It may feel intimidating to coach your client 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 get set in your ways, avoiding 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 client’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 executive with your proactivity!

Written by Bryn Smith

Bryn is Digital Marketing Manager at Base, where she helps serve the assistant community through virtual events, social media, and more.