Well, hello again! 👋

It's been three months since my last newsletter. THREE. Between life, raising a toddler who apparently has more opinions than most executives I've supported, and working on a few things behind the scenes, it's been a busy few months. But I'm back, and somehow we're already planning for 2027.

Seriously, how?

I was scrolling through Reddit recently (as one does) and came across a post from an EA who had finally gotten their company's board meetings scheduled for the year. Every date coordinated, calendars aligned, everyone on the same page. A beautiful sight.

And then a board member asked to move one of the meetings because of a dentist appointment.

A dentist appointment, people!!

Listen, I'm all for good oral hygiene, but I would've needed a minute.

After 16+ years supporting executives, from Saint Laurent to being the first EA at Uniswap, I've learned that getting ahead of the calendar is one of the easiest ways to save yourself a massive headache later. I've always been the EA who starts booking next year's big meetings before the current year is even over. Not because I'm particularly excited about planning another board meeting, but because I know what happens when you don't.

There's nothing quite like trying to coordinate eight executives, three board members, and five assistants in February, only to discover the CEO is traveling, two board members have conflicts, and the only date everyone can agree on falls during spring break.

And then someone suggests June. ..Lovely. 🫠

So before we all disappear into holiday parties, year-end reviews, and the inevitable "can we squeeze this in before everyone leaves?" requests, let's talk about getting ahead of 2027.

I'm not suggesting you plan every minute of your executive's life for the next 12 months (please don't). But there are a handful of meetings that have absolutely no business being scheduled at the last minute.

You get first dibs on everyone's calendar. Board members sit on other boards, executives have competing priorities, and their EAs are probably doing exactly what you're doing right now. The longer you wait, the fewer options you have. I'd much rather be the person proposing dates than the person begging for whatever's left.

January is already chaotic enough. Everyone comes back from the holidays refreshed, ambitious, and suddenly full of ideas that apparently need to happen immediately. The last thing I want to be doing is chasing six assistants to schedule a meeting we knew was coming six months ago.

Moving one meeting usually means moving another ten things. Anyone who's had to reschedule a board meeting knows what I'm talking about. It's never just changing the calendar invite. It's the travel, the venue, the pre-reads, the prep meetings, the catering, and the executive who's somehow already booked a flight. No, thank you.

And please, put YOUR vacation on the calendar. I'm serious. Before you spend the next two months protecting everyone else's time, protect your own. You deserve to take a vacation without discovering that someone scheduled a leadership offsite smack in the middle of it.

Here's what I'd tackle before Thanksgiving…

Start by opening your executive's 2026 calendar. Search for the recurring big-ticket meetings and make a list of what needs to happen again next year.

🏕️ Leadership and team offsites

📊 Quarterly business reviews

📣 Company all-hands

🗓️ Annual planning and budget sessions

⚖️ Performance review calibration

🎤 Major conferences and speaking engagements

🌴 Executive vacations (and yours!)

Don't worry about finding the perfect dates just yet. First, figure out what needs to happen, how often, and whose attendance is actually required. Then work backward from the non-negotiables: quarter close, reporting deadlines, holidays, school breaks, and major company events.

One more thing: if you're booking an offsite, start checking venues now. Nothing hurts quite like finding the perfect property, getting everyone excited, and then learning the only available dates are in August.

Can I tell you about something I've been working on?

Over the years, I've spent an embarrassing amount of time coordinating availability. You know the drill. You send five dates, three people respond, two ignore the email, someone replies to an entirely different thread, and another person says they're available only to realize they were looking at the wrong month.

And somehow, you're the one who has to make sense of it all.

I got tired of it. So I built Quorum, a free availability polling tool designed specifically with EAs in mind.

The idea is simple: create a poll with your proposed dates, share one link, and let everyone indicate what works. No account required for respondents, no asking a board member to download another app, and you receive an email notification whenever someone responds.

That's it. Nothing complicated.

Here's how I'd use it for 2027 planning:

Create a separate poll for each major meeting. Start with three to five realistic dates that you've already checked against holidays and major conflicts.

Send it to the assistants. If you're coordinating with executives or board members, their EAs are usually your best bet for getting accurate availability.

Give everyone a deadline. Otherwise, that poll is going to sit in someone's inbox until Valentine's Day. 💔

Confirm and send the hold. Once the required attendees are aligned, get it on the calendar before another meeting steals the slot.

You can try it at quorum.officeoftheea.com. It's free, and because I built it for people who do this work every day, I'd genuinely love your feedback. If there's something missing, let me know by replying to this email and I’ll add it!

Once you've landed on a date, don't overcomplicate the calendar invite. Here's what I'd send:

That's all you need for now. You can always update the invite as details are finalized.

Before you go, a few dates worth flagging

For those planning U.S.-based meetings, here are some 2027 dates to keep in mind:

🎉 January 1 — New Year's Day

✊🏽 January 18 — MLK Day

🇺🇸 February 15 — Presidents' Day

🐣 March 28 — Easter Sunday

🇺🇸 May 31 — Memorial Day

❤️💛💚 June 18 — Juneteenth observed

🎆 July 5 — Independence Day observed

🛠️ September 6 — Labor Day

🦃 November 25 — Thanksgiving

🎄 December 24 — Christmas observed

Don't forget religious holidays, school breaks, and company-specific closures. You can reference the official federal holiday calendar as a starting point.

Before you log off next Friday, pick ONE major meeting for 2027 and get the scheduling process started. Just one. Whether it's your first board meeting, a leadership offsite, or that quarterly planning session everyone dreads coordinating.

And if you use Quorum, come tell me how it went in our Office of the EA Slack community. I want to know what worked, what didn't, and what would make your life easier.

It's good to be back. I've missed writing these, and I've got plenty to share over the next few weeks.

Now, if you'll excuse me, I have a toddler who's apparently running his own Halloween planning committee.

With love, and lots of coffee,

Chrissy

From now through the end of December, we'll be sharing some great holiday gift ideas to make your shopping a little easier. We're partnering with some amazing brands to help you find gifts for everyone on your list, whether that's your executives, colleagues, family, or yourself (because why not?).

And in early December, we'll be releasing our Office of the EA Holiday Gift Guide, packed with gift ideas, brands, and special offers curated for this community.

Consider it one less thing on your holiday to-do list. We've got you!

Because apparently working 9 to 5 also means planning meetings for a year that hasn't even started. Dolly really understood the struggle.

Full playlist linked here.