Leading from the Sky (And Writing a Book)

Once upon a time I was a flight attendant. OK, just for one day, but I passed training, and that is a story for another day.

We had the best trainers and they were both named Jennifer. One of the Jennifers always said her grandfather called stewardesses “waitresses in the sky” and we all rolled our eyes and giggled. And while that is true to a degree, those biscotti cookies from Delta ARE delicious and there is an entire day of training on service during an international flight, the real job of a flight attendant is safety. They are leaders and public speakers and servers and the kindest people to nervous first-time fliers and babies on planes. They give out wings. And when it matters, they are the people trained to get you out alive.

To keep you safe. That’s actually the whole job.

I think about that a lot when someone gives me “the look.” You know the one. The “oh, she’s just the water girl” look. I got it earlier this year at an offsite when I did what I always do: made sure the executive presenters had water or tea at the podium. And I looked up and there it was. Then I watched a guy bring his executive something, and I looked around the room and there was no look. Just a guy doing a thing for his person.

We did the same thing. The only difference was who got credit, and more importantly, how they got credit.

Executive assistants do more than schedule travel and move things on calendars. We have hard conversations. We notice things and we carry context, and those are two very different things. Most executives I know hate gossip, but sometimes what looks like “the scoop” on a team member or a situation isn’t gossip at all. It’s context. Something the executive should keep their eye on. Knowing the difference, and knowing when to say something and how to say it, is a skill that doesn’t show up in any job description. Neither does knowing which meeting your executive should skip, or what the person across the table really wants, or when to say the thing nobody else will say.

You cannot automate that.

Earlier this week I posted on LinkedIn that I am (gasp) writing a book. If you missed it, you can read it here. [Caroline's LinkedIn Post]

The response kind of surprised me. I’ve been sitting on this for a while, and I think part of why is that I love this job so much that I’m used to the “oh she just does calendar stuff” thing. I don’t always clock how much that matters. But it does. CNBC dropped an article just this week about whether AI will disproportionately replace women in administrative roles. They traced it back to telephone operators in the 1940s. Then secretaries in the 1980s with PCs. Then clerical workers today. They’re not wrong. The work that gets automated first has always been the work women do.

Are we making the same mistake again?

Quick resume moment: thirty years in this work. I’ve been the receptionist, the secretary, the admin, the EA. I left corporate and started my own company, and these days I support 16 executives at 7 companies. I’m not writing this book from the outside looking in. I’m writing it from the podium, holding the water.

Short version: this job has been underestimated for a long time, and I went looking for why. I’ve been digging back to the 1790s, and the pattern is right there in the archives, names and all. Same work, different person, totally different headline.

I’m sharing the stories, the research, and the journey right here as it all comes together. Come along and help me find the title.