Thursday Things — Sep 4th, 2025

In case you’re new here, CCing my EA is a bite-sized newsletter dedicated to Executive Assistants like yourself.

Every Thursday, we deliver a quick email with 5 new job listings, 3 fun posts, and 1 helpful tech tip straight to your inbox. 📬

5 new job listings

1. Dropbox, $118k-$179k, Remote (excluding SF, NYC, and Seattle)

2. Autodesk, $73k - $126k, Remote

3. National University, $62k - $84k, Remote

4. QUIGG Capital, $95k - $145k, Remote

5. Geron Corporation, $120k - $130k, Remote

We only post jobs under 7 days old, but some may expire before you open this email.

3 posts you might’ve missed

#1

“A great EA doesn’t just keep things moving. They make sure the RIGHT things are moving.” 👏👏👏

#2

Calendar Tetris’d to perfection.

Text from exec: “Running 20 min late.”

…and there goes the first domino. 🫠

#3

I just absolutely love how Debbie has leaned into her “The Office Rockstar” brand. 👩‍🎤

This is part 3 of 7 of Brett Trembly’s “Behind every legendary CEO is a badass Executive Assistant.” thread.

Since this is a longer thread, I’m breaking it up into a limited “Weekly EA Spotlight” sort of thing across the next few newsletters.

But if you’re impatient, you can click in now to read the full thing.

1 Tech Tip

The 95% Rule: Make ChatGPT ask you first

A while back I shared the long “Lyra” prompt. It’s helpful, but in practice I use a totally boiled down version where I effectively just tell ChatGPT to ask me clarifying questions until it’s 95% confident it can deliver the task with total accuracy.

ChatGPT has a habit of speaking with conviction, so it’s tough to gauge what it actually understands and what it’s hallucinating. Forcing clarifying questions makes its confidence visible and your results wayy better.

Pro tip: Ask ChatGPT to rate its confidence in delivering the task accurately out of 100. This puts on a number on an otherwise totally qualitative task.

Here’s an example of something I might include in my prompt:

Before you answer, rate your current confidence out of 100 in delivering this task perfectly. Then ask me any clarifying questions needed until you’re at least 95% confident you can complete the task with 100% accuracy.

Pro tip 2: To keep the “numbers on qualitative tasks” theme going, try asking ChatGPT to “Grade this output out of 100 like an expert [role: comms lead / chief of staff] and tell me what’d you improve to get it to 95+.”

For a refresher on past Tech Tips without digging through your emails, they’re all available in a single post right here.

Thank you for reading!

Double thanks if you completed last month’s very lengthy survey! I’m genuinely taken aback by how engaged you are, and it makes keeping up with this newsletter every week incredibly worthwhile.

I’ll see you next Thursday~

- Johnny Wu

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