Closing Out The Calendar

As assistants, we sometimes work more than anyone else in our organizations – at least more than anyone else sees. We do our work in the shadows, just behind the halls of power, but remain an indispensable component of a properly functioning organization.

Confidence is a state of being that is realized only when our other skills are fully honed. It’s the emotional outpouring of being prepared. It’s a prerequisite of joy.

As we assistants march towards “The Most Wonderful Time of the Year”, it can be tough for us to let go and really sign off. There always seem to be lingering questions floating around, and loose ends yet to be tied. If you really want to enjoy this break, you have to prepare so you can confidently unplug during this well deserved time away. 

Closing out the calendar is more than tying up loose ends. It’s one of the most important things you can do to set yourself up for success in the New Year. It represents the mindful reflection and purpose-driven preparation it takes to effectively adapt to the changes every new annum brings.

(Re-)map out the scope of your executives’ Operational Purview.

Your boss’s operational purview represents all of the things she oversees in her job function. Say, for example, your boss is the EVP of Supply Chain. They likely manage a lot of moving parts: inventory, shipping, warehouses, etc. While they likely have people under them supporting that effort, they stand as the ultimately responsible party before the CEO and the broader executive team. 

This is where the expert analytical skills you boasted about in the “Core Competencies” of your resume come into play. You’ll need to map out all of these moving parts. Understanding is necessary for your own edification in addition to ensuring alignment between you, your boss, and her team. Tools like Asana can be extremely useful in helping to get a birds-eye view of all that falls under their (and by extension your) operational purview. During this process, labeling the priority level for each of these workstreams will provide deeper insight into how to best utilize the limited amount of work hours in the day. 

One of the primary reasons to do this is to identify gaps in ownership and/or communication. Perhaps the new “Town Hall” initiative your boss is eager to get off the ground does not have an explicitly identified owner. Has the “Director” been informed? Do they have a clear understanding of the expectations around this? For example, attendance is mandatory, it should incorporate team building elements with the informational components, etc. Demonstrating your acumen by flagging the lack of clarity about who knows “the what and how” is a huge win! This is how you effectively manage expectations so your team can execute at the highest level.

Review recurring meetings

The activities done above, while not calendar specific, represent essential, foundational work. They’re necessary to achieve the kind of calendar administration that reduces stress and increases productivity.  

Recurring meetings have the potential to be the most important and productive touchpoints that happen in your organizational sphere of influence. We can’t be stuck on “autopilot”. Proactive calendar management means refreshing our outlook (no pun intended) as priorities also shift around the organization. 

If you don’t have a running spreadsheet to track and edit recurring meetings, it’s a good idea to start one. This artifact will help you stay organized and ensure nothing slips past you. Keep a record of:

  • Type: 1:1, small group, large group
  • Cadence: how often
  • Time: how long
  • DRI: Directly Responsible Individual who ensures the agenda gets drafted. They also decide if and when to cancel the meeting, along with other org-specific jobs
  • Workstream: what particular initiative does this support, if any?

Implement Best Practices

Find out what recurring meetings might need to be deprecated. Determine what was working and where there are opportunities for improvement. Did the product meeting on Thursdays struggle because there was a lack of preparedness? This is a great time to implement and share new best practices that will maximize time in the new year. It can take many forms. For example, reminder emails or Slack messages 24-48 hours before the meeting to ensure the team has had an opportunity to review the material.

Did the finance meeting run long more than 80% of the time this year? You may need to schedule more time or communicate that going forward there’s a need to ensure this meeting stays on time. Do you know who owns the agenda for the Supply Chain bi-weekly meeting? When you don’t know who owns the agenda, it’s difficult to act as a point of accountability. Being a POA means checking in on behalf of your exec to see whether or not the agenda is complete and when it will be disseminated.

Most importantly you need to align with your exec. Document and implement these changes to ensure your recurring meetings much more productive and efficient.

Prepare for Presentations

For most of us, the experience leading up to public speaking engagements could only loosely be referred to as “preparation”. We all have (or had) that boss who refused all admonitions for preparation in advance. Instead, they decide to draft slides the week – or even day – before the big presentation.

Given the prevalence of this eleventh-hour phenomenon, I’ve become convinced that many CEO’s and executives are the kind of people who find creativity under pressure. I’ll qualify this by stating categorically that finding creativity under pressure isn’t an excuse to procrastinate. That’s because it doesn’t work under all kinds of pressure. In her book “The Progress Principle”, Harvard Business School professor Terresa Amabile analyzes the conditions under which pressure can produce creativity. She describes the “On a Mission” phenomenon when the task or job is high pressure and high meaning. This elusive combination, even when present, can be difficult to capitalize on. Let’s not be tempted to throw in the towel here.

Work Backwards

Work backward from the goal of nailing down an awesome presentation seven business days in advance. This will help you strategize on when to put this at the top of your executives’ ever-expanding todo list.

Start a presentation draft. If you don’t have a presentation template, draft one of those first. This is a skeleton presentation that includes slides or placeholders for key ideas your boss will likely cover in a given talk. Depending on the engagement you may or may not be able to leverage this resource.

Next, plug in the dates and locations of conferences you already know your boss will be speaking at. I suggest placing all-day headers in here as well to ensure you have a birds-eye view when scanning the calendar in the weeks ahead. Doing this will help ensure you can effectively manage their time and energy in the lead up to these events.

Finally, ensure you have contact details and requirements for presentations. This always comes in handy. I usually check in one month out to see if anything’s changed and where on the schedule my boss has landed. This will save you a lot of running around and confusion as the date get’s closer.

Ultimately, the exact process might look a bit different for every assistant depending on how your organization opportunities. The main takeaways here are around clarity and preparation. (In that order, making preparations before you are clear on the best way forward can only result in more confusion). This way when you leave for your Holiday Break, it’ll truly be a break rather than a stressful exercise.


I’m Ebony, I’ve been an Executive Assistant in San Francisco and Los Angeles for over 10 years. I’ve had the unique opportunity of supporting the CEO of Sephora, a globally loved cosmetics brand, working for Founder & CEOs in the tech space, including Twitch (an Amazon company), and currently working on the cutting edge of cryptocurrency. I’m passionate about innovative learning and growth centered development. The A List is a labour of love to share practical wisdom and tips on the trickiest parts of #LifeInAssistantLand


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