The Miss Jobless Chronicles: You Had Me At ‘Hello’

Ed. note: “The Miss Jobless Chronicles” is a weekly series written by Caitlin O’Toole.

When it comes to getting a job, I’m thinking that first impressions are everything, and that the first impression really begins before the in-person meeting. It begins on the phone, with that initial “hello.” I figure it’s kind of like the dating game.

So today, I am practicing my ‘hellos.’ For the flurry of job calls I’ll be getting. Any day now. Tick, tock, tick, tock.

When I answer the phone, do I say, “Hello???” Eager, curious, hopeful?

“HELLLOOO??” Kind of annoyed — like, why are you interrupting me?

Do I put on an English accent and say “Caitlin O’Toole’s office. Who’s calling? I’ll see if she’s out of her meeting — please hold.”
Or is my hello sexy-like, breathy, sultry, seductive?

I practice this into a tape recorder ad nauseam.

I figure keeping my phone’s outgoing message fresh and somewhat interesting is key too. I record and re-record it. Once with background noise, once without, once with Vivaldi playing in the background, and once sounding rushed and somewhat frazzled. I record and re-record and re-record again. I ask my friend Laura to call and check it. How does it sound? How did my outgoing message make you feel as a potential employer? Were you intrigued, turned off, turned on?

Laura pointed out that each situation is different. I mean, if you’re expecting a call from NPR or the New York Times (and if you are, then lah-dee-da for you), you may not want to mess around. Be straightforward. But if i’s from Rolling Stone or MTV, act busy and too cool for school.

She also offered this small piece of advice: AVOID RINGBACK TONES AT ALL COSTS. No employer wants to hear “Hollaback Girl” while they’re waiting for you to pick up.

I’ve picked up a lot of tricks from my friend Laura. She’s probably been unemployed as many times as I have, but she’s much smarter about it. First of all, she ALWAYS wears a suit, even if she’s just going to Starbucks. Because it’s that little bit of extra confidence that could make or break that initial “hello.” Secondly, whenever anyone calls, she always says she just got out of a meeting. Translation: I just left Starbucks with a skinny chai latte and now I’m smoking a cigarette. Third, she always acts slightly pissed off when you call her — even rumples her face a little. People are scared of Laura. And goddammit, I want them to fear me, too. So I embrace every tip I can.

Please hold — phone.

OK, back.

Laura’s also a name-dropper, and that’s always impressive. She always drops names very casually.

“Yesterday at lunch with Phylicia Rashad — “
“Wait — you had lunch with Phylicia Rashad? Like, Mrs. Cosby?”
“Yes, well, Bill and I used to work at NBC together.”
“You worked at NBC with Bill Cosby?”
“Wow, Laura, that’s so cool.”

Turns out she was an intern on The Cosby Show and never had any direct contact with Bill Cosby — only saw him once — but no one needed to know that. She massaged the story to make it seem like she used to work with Bill Cosby. She didn’t actually HAVE LUNCH with Phylicia Rashad; they were both at Chipotle, across the room from each other. (Chipotle? Really?)

I try the same thing on my friend today.

“Well, when Kurt Loder and I used to lunch together in the MTV cafeteria –“
“Wait, you used to eat lunch with Kurt Loder?”
“Did all interns used to eat lunch with him? Was that, like, part of the internship program?”

Busted. Oh, well. We can’t all be as cool as Laura. We can only try.

Caitlin O’Toole is a New York City-based writer and editor. A native of Washington, D.C., she began her illustrious journalism career as a Washington Post paper girl. She has since written and edited for Sesame Workshop Digital, Star Magazine, The National Enquirer, Glamour,, and Washington’s City Paper. Her work has also been featured on Fox News, ABC, MTV and VH1. She lives in Chelsea with her two cats, Lucy and Ethel. She can be reached for work at her LinkedIn page.