Outrageous assistant tasks

Executive and celebrity assistants tell all.

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By Blake Ellis, contributor

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NEW YORK (Fortune) -- Becoming the assistant to a CEO or star may sound glamorous to some, but the job can be more trouble than it's worth (just ask anyone who has watched VH1's "I Want to Work for Diddy"). And it can make the people who do it feel like thankless "punching bags," as one assistant put it.

While the big names enjoy fame and fortune, it's the often Herculean labors of assistants who support them behind the scenes that make things work so well under the spotlight. So to find out just how demanding this job can be, Fortune asked elite assistants from across the country to share their most outrageous stories.

Conversations with ... cats?

As an assistant, even the strangest requests start to seem normal after a while. But being ordered to talk to the boss's cats was crossing the line for this assistant, who worked for an executive producer of a major national news show.

Notoriously bizarre, the producer asked the assistant to go to his house and have conversations with each of his cats. He even pre-scripted the chats, listing questions and specific statements he wanted his assistant to pose to the cats. This boss then asked his assistant to report back in full detail, telling him exactly how each cat "responded."

Power pampering

While working for the CEO of an investment bank, assistant Hector Rosario -- a member of the New York Celebrity Assistants professional association who has worked for actresses Fran Drescher and Kim Raver, and music mogul Diddy, among others -- was in charge of planning everything for her. And "everything" in this case included making sure her housekeepers were available at any given moment to put lotion all over her body directly after she stepped out of the shower.

High on e-mail

Being a Hollywood assistant has its drawbacks -- assistants have complained about such unexpected tasks as holding ice packs on their bosses' newly augmented breasts -- but for one assistant to a well known Hollywood manager, cocaine was the cause of the problem.

She forwarded one of the many nonsensical e-mails she received from her boss over one weekend, when he appeared to be under the influence, to Lilit Marcus, a co-founder of savetheassistants.com, who will use it in her upcoming book, "Save the Assistants: A Book for the Beleaguered."

This particular note ordered the assistant to "get socks" multiple times, to "move my 1:00 lunch to 1:03," and to "pre-order a yarmulke for Hanukkah" -- all in one e-mail. And the highlights continued: "My alarm clock rings funny -- find one that's more soothing." "Are bagels different with LA water? They seem different. Find out!" And finally, "Book a lunch with Pamela. Then cancel it two hours before. (hate her!)"

A man and his sheep

Even farm animals can play a role in the life of an executive assistant: The president of a major venture capital firm ordered his assistant to bring a sheep to his partner's birthday party, according to Leni Miller, the founder of executive assistant search firm EASearch. When the assistant finally got her hands on a sheep and brought it to the hotel where the party was being held, the doorman wouldn't let her take it onto the elevator because of health concerns. It wasn't long before the animal was in a crate on its way back to its farm, courtesy of the assistant, of course.

Fatal attraction

Booking a boss's travel isn't always as easy as it seems for some assistants. The CEO of a private company was on his way to Australia to spend a vacation with his girlfriend, and naturally, his assistant arranged his trip. But while he was in Australia, the CEO suffered a heart attack and died. And as if that wasn't bad enough, the CEO was legally married -- to someone else.

So to spare the family more heartache, not only did the assistant have to deal with the CEO's actual death, she also had to fly his girlfriend back home and handle the situation. "Even after he was gone," says an executive assistant recruiter who knows this assistant, "she was still taking care of him."

Ski trap

Whatever the hijinks, the bond between an executive assistant and her employer is a vital one -- in ways one might never expect.

The assistant of a Silicon Valley-based CEO had booked her boss on a weekend ski trip to Colorado. But when she arrived at the office Monday morning, he hadn't returned. His cell went straight to voicemail when she called, and his hotel told her that he had checked out. Just to be safe, she called the car rental company -- and found out he hadn't returned his car.

In a panic, the assistant quickly phoned one of the other skiers on the trip, only to find out that her boss had taken one more run down the mountain alone after his friends left for earlier flights.

So the assistant contacted the ski patrol, and finally -- around 11 a.m. the next day -- they found him, frostbitten and huddled in the woods with a dead cell phone. He'd gotten lost and disoriented because of the cold, and to this day, he credits his assistant with saving his life.

Bonnie Low-Kramen, assistant to Olympia Dukakis and author of "Be the Ultimate Assistant," heard this story from the hero assistant. But she maintains that all identities must remain anonymous -- because this particular CEO's wife still feels badly she didn't find him first. To top of page

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