This week, Atlassian announced it’s laying off about 1,600 employees (roughly 10% of its workforce) as part of its push into AI.

They’re not alone.

Earlier this year, Block, Inc. cut thousands of roles as CEO Jack Dorsey pushed the company toward an AI-first operating model.

The headlines frame this as an AI boom, but what’s actually happening is bigger than that: companies are redesigning themselves around software.

Fewer people, more automation, entire layers of work handled by AI systems instead of teams.

That doesn’t mean Executive Assistants are going away, but it does mean the role is evolving. The EAs who thrive in the next phase of work won’t just manage calendars and inboxes.They’ll orchestrate systems, humans, tools, automations, and AI agents all working together.

In other words, they’ll run the operating system of the executive’s office.

And the shift has already started. Which is why the real question isn’t “Will AI replace administrative work?”

It’s, are you learning to use it, or ignoring it?

Because the assistants who approach AI with curiosity will move faster, operate at a higher level, and create leverage their peers simply don’t have.

The ones who don’t? They’ll feel the squeeze. So today I want to share one automation that can immediately make you look like a wizard in your executive’s office.

With love and lots of coffee,

Chrissy

AI will eliminate 300 million jobs in the next 5 years.

Yours doesn't have to be one of them.

Here's how to future-proof your career:

Start learning AI now

Here's something nobody tells you when you take this job:

You will become world-class at managing someone else's time. And absolutely terrible at managing your own. 🫠

It's not a flaw. It's a feature of the role. We're trained to be reactive. To respond. To catch things before they fall. By Wednesday, half of us have no idea how the week got away from us, we're just surviving it.

So here's the fix, and it takes five minutes on Monday morning.

👉 Read the full guide

Plus, I added a bonus automation that makes your exec look ridiculously prepared for every meeting.

Trust me, you'll send me an email thanking me later. 😉

While we're talking about working smarter… here are three free tools OOTEA built specifically for EAs, EBPs, and Chiefs of Staff. No BS, no paywalls, no "book a demo." Just open and use. ✨

One search. 21 platforms. Built for EAs, EBPs & Chiefs of Staff. Instead of toggling between LinkedIn, Indeed, and eight other tabs, search everything in one place, filtered by title, location, and how recently it was posted.

EA-approved restaurants, curated by the community. 48 cities and counting. When your exec says "find somewhere good for a client dinner" and you have exactly 20 minutes to figure it out, this is where you start. Every recommendation comes from someone who's actually been there on the job.

Find your team's perfect offsite- in minutes. Free, always. Add your team's home cities, pick destinations you're considering, and get a scored analysis with flight data, neighborhood guides, hotel ranges, and an exec-ready brief you can copy, PDF, or draft straight to Gmail. Under 2 minutes to a full brief.