Happy (almost) Halloween! 🎃

Halloween is hands down one of my favorite times of the year. There's something about seeing everyone's creativity come to life that makes it so much fun. The costumes, the decorations, the people who somehow manage to turn a completely ridiculous idea into something brilliant. Love all of it!

And naturally, we started thinking about what Halloween would look like if Executive Assistants were in charge of the costumes. Let's just say we came up with some pretty horrifying ideas. 😂

But before we get to those, I want to talk about something that's been on my mind this week.

We spend a LOT of time teaching EAs how to become strategic partners. But who's teaching executives how to be good partners in return?

I've been having some really interesting conversations on LinkedIn this week about influence, trust, and what it actually means to be a strategic EA. And one thing has become pretty clear: We can't keep putting the entire responsibility for building a successful partnership on the EA.

We'll get into that today, along with a few things I think great executives do differently.

And make sure you stick around until the end because I'm sharing some hilarious EA-inspired Halloween costume ideas for anyone who's still scrambling to find something to wear. Consider this your last-minute costume rescue mission. 👻

We're constantly telling Executive Assistants to think bigger.

Be proactive, anticipate needs, understand the business, have an opinion, speak up, stop being “just” an assistant.

And while I agree with much of that advice, after more than 15 years in this profession, I have a question.

Why does so much of the responsibility for building a strategic partnership fall on the EA?

Think about it… We're encouraged to earn a seat at the table, but what happens when the executive isn't willing to pull out the chair?

I've worked with executives who gave me very little direction but plenty of context. They trusted me to figure out how to accomplish something because I understood what we were trying to achieve. Those were some of the partnerships where I was most effective.

I've also seen the opposite. Executives who say they want someone proactive but require approval for every decision. Who ask their EA to anticipate needs but rarely share what's happening in the business.

And here's where I think we need to make an important distinction.

There's nothing wrong with wanting excellent administrative support. But that's not the same thing as building a strategic partnership.

If an executive needs someone to manage their calendar, coordinate travel, process expenses, and keep everything organized, that's a valuable role in its own right.

But if they're asking for someone who can think strategically, identify problems before they happen, and make decisions on their behalf, they have to be prepared to create an environment where that can actually happen.

You can't ask someone to think like a partner while treating them like an order-taker, and I think it's time we started acknowledging that.

I've been trying to work with Ryland, the founder of Sundial, for a while now because I've been dying to introduce this tool to the Office of the EA community. So I'm SO excited we're finally partnering on this issue!

I use Sundial literally every single day, and I'm not exaggerating when I say it's changed the game for me.

My favorite feature? Proposing meeting times. I select available slots directly in Google Calendar, Sundial formats them exactly how I need them (including time zones), and I'm done. No manually typing out dates and times or doing time zone math.

And can we talk about the UX for a second? It's so intuitive and easy to use. Everything lives right inside Google Calendar, which means I'm not constantly jumping between different tools. It just makes my life easier. Period.

But here's what really sold me on Sundial. I once reached out to Ryland with a request for something that would make my workflow easier, and within a couple of hours, he came through. That kind of responsiveness says a lot about the person behind the product. He's genuinely eager to listen, improve the experience, and help EAs get things done.

And listen, don’t just take my word for it, EA teams at OpenAI, Snowflake, and Indeed.com are already using Sundial, too.

Here's what else you can do with it:

🌎 Unlimited time zones: See different time zones directly in Google Calendar with automatic conversions.

📅 Calendar overlays and bulk holds: Make managing busy schedules a whole lot easier.

👀 Calendar Watch: Catch missing meeting details before they become a headache.

🔒 Security-conscious options: Custom setups for companies with strict security requirements.

🎁 A little something just for our community!

Subscribe to Sundial's Scheduler plan during November and get 20% off your first three months. Just reach out to their team and mention Office of the EA to claim your discount.

And if you'd rather see it in action first, you can even request a demo from Ryland himself, just email him at [email protected] and tell him I said hi! 👋

👉 Explore Sundial for EAs

So, what does a genuinely successful executive and EA partnership look like?

In my experience, the best executives I've worked with weren't necessarily the ones who gave me the most instructions. They were the ones who gave me the tools, information, and trust to do my job well.

Here are five things they did differently.

1. They explained the why, not just the what.

Telling your EA to schedule a meeting is one thing. Explaining what you're hoping to accomplish in that meeting is another. When we understand the bigger picture, we're better equipped to anticipate obstacles, identify opportunities, and make decisions without constantly asking for direction.

2. They gave their EA room to make decisions.

If you hire someone for their experience and judgment, let them use it. Agree on boundaries, clarify what they can own, and trust them to make decisions within those parameters. Otherwise, you're creating a bottleneck, not a partnership.

3. They made their trust visible.

This one is especially important. An executive can trust their EA behind closed doors, but if nobody else on the leadership team recognizes that trust, the EA's ability to influence outcomes will always be limited. Great executives make it clear that their EA has their confidence and support.

4. They included their EA in the right conversations.

No, your EA doesn't need to know every confidential detail or attend every leadership meeting. But they do need enough visibility to understand priorities, recognize what's changing, and connect the dots. You can't expect someone to stay three steps ahead when they're missing half the information.

5. They welcomed a different perspective.

Some of the best executive partnerships I've experienced were with leaders who didn't expect me to agree with everything they said. They wanted my perspective, even when it challenged their own thinking. That's what happens when you hire someone you trust instead of someone who's simply going to tell you what you want to hear.

And to my fellow EAs, this doesn't mean the responsibility is entirely on the executive.

We still have to earn trust, develop good judgment, understand the business, and demonstrate that we can handle greater responsibility.

But a strategic partnership is exactly that. A partnership.

Both people have to show up for it.

And maybe it's time we spent as much energy teaching executives how to develop great EA partnerships as we do teaching EAs how to become strategic partners.

Ever tried coordinating a meeting across five different people at three different organizations? Yeah, that’s what I thought!

We built Quorum, a completely free availability polling tool that makes coordinating meetings a whole lot easier.

Propose a few dates and times, share one link, and let everyone vote on what works. Participants don't need to create an account.

No endless email chains. No back-and-forth. Just find a time and move on with your day.

Holiday gifting season is right around the corner, which means the annual hunt for thoughtful, professional, budget-friendly gifts is officially beginning.

We're putting together our Office of the EA Holiday Gift Guide, featuring gift ideas, brands, and services worth knowing about for executives, colleagues, teams, and clients.

Stay tuned. We've got some fun things coming all November and December! 🎅

I asked our LinkedIn and some slack communities a very important question: What are some funny, slightly unhinged, EA-inspired Halloween costume ideas?

Here are some of my favorites, brought to life with a little help from AI.

🧾 The Expense Report

My personal contribution to this nightmare.

A dress made entirely of receipts, none of them itemized. Somewhere in there is a $900 dinner labeled "business" with no attendees listed.

Truly terrifying. 😱

🚨 The Urgent Notification

Courtesy of Nicole Motles in the EAs to the Rescue Slack community.

Dress as a giant red exclamation point that follows people around yelling "URGENT!" Better yet, dress as an app notification bubble with 9,999 unread alerts.

Nothing says Halloween horror quite like opening Slack after a day off.

📅 The Calendar Invite From Hell

Courtesy of Kelly Muñoz on LinkedIn.

A giant calendar invitation stamped DECLINED in red, with the reason: "Conflict with the meeting I declined last week."

I feel like this one might be a little too realistic. 😱

🗳️ The Doodle Poll Nobody Can Agree On

Another masterpiece from Kelly.

Wear a sheet covered in people's names, empty time slots, and one giant message: "No time works for everyone."

📧 The Out-of-Office Auto-Reply

Also from Kelly, who clearly came prepared. 😂

A giant out-of-office message that reads: "Thank you for your email. I am currently away. For urgent matters, please contact my EA."

Because apparently even an executive's vacation is an EA's problem.

🧣 The Never-Ending To-Do List

Courtesy of Hillary Robertson.

An impossibly long scarf covered in tasks, reminders, and deadlines. Every time you think you've reached the end, another five things appear.

Bonus points if someone adds a task to your scarf while you're wearing it.

📌 The Human Post-it Note

Also mine, because I apparently have too much time to think about this.

A dress covered in Post-it notes because remembering absolutely everything is apparently part of our job description.

🤔 I have enough Post-it’s all over my desk to actually make this happen…

And to everyone who shared an idea, THANK YOU. You reminded me why I love this community. We're all dealing with some version of the same chaos, but at least we can laugh about it together.

If you actually show up to a Halloween party dressed as a declined calendar invite, please send me photographic evidence. I need to see it. 😂

Happy Halloween! 🎃

Chrissy 🧡

It's Halloween, so you already KNOW we had to go with a classic. 🎃👻 This week's pick is Monster Mash by Bobby “Boris” Pickett. A little spooky, a little ridiculous, and impossible not to sing along to. It was a graveyard smash, after all. 🧟‍♀️

Full playlist linked here.