THE LONG GOODBYE

Dear @work reader,

There’s little doubt that you – a richly rewarded professional working in the tri-state area – spend much of your day churning out e-mails like a frantic butter maker at the Wisconsin State Fair.

As soon as one hits your inbox, you whip together a crisply worded reply designed to improve your business with clients, smooth relations with co-workers, or kiss your superiors’ buttocks like Smithers on Mr. Burns. Your “Collected E-mails” could be a textbook at Wharton.

Until you hit the home stretch, that is, and it’s time to supply a pithy sign-off – that final “Best,” “Cheers,” or “Toodles” that goes before a comma and your name. You need something that’s respectful but not stiff; friendly but not overly familiar; not too dull but not trying too hard.

“Yours truly”? Too buttoned-down. “Peace out”? Too goofy. “Love and kisses”? Too actionable.

Pick the wrong one and all your painstaking work can be cut at the heels. It’s enough to make you as paranoid as a High Times editor at a surveillance convention.

“People obsess about it,” says Will Schwalbe, co-author of “Send: The Essential Guide to Email for Office and Home,” a book held by some e-mailers in the same reverence as bongo players hold “On the Road.”

The biggest dilemma, Schwalbe and co-author David Shipley write, is “to make sure you aren’t being inappropriately formal or informal.” But there are any number of other minefields one can step in, ranging from the message sent if you “de-escalate” – going, for example, from a warm “all best” to the relatively frosty “sincerely yours” – to the need to match your correspondent’s tone.

“One of the things that really freaks people out is when they send a ‘sincerely’ and they get a ‘love’ back,” says Schwalbe. It’s “like an unexpected Valentine – did it go to the whole class or just to me?”

Robert Smith, an Internet search engine marketer, figures using something less straitlaced than the usual sign-offs helps lighten up his e-mails, and brand himself as “a down-to-earth guy, cool to do business with.” So, with a whiff of irony, he likes to dispense with “best regards” in favor of “rock on,” “dude” or “bro.”

“I like to be more creative. Not to be too off the wall, but anything that could make me sell myself,” he says, adding, “My feedback has been pretty much positive. Sometimes it gives people a chuckle.”

On the other hand, it pays to play it a little straighter when he’s starting a business relationship, he says, imagining the reaction he might get from a potential client: “I’m going to give this guy 20 grand, and he’s like, ‘Rock on, dude’?”

A big part of the issue is the amount that can be read into a word or two – and the subtle way a sign-off can go from courtly to ironic, or gracious to passive-aggressive depending on the wording and the context. Throw in the need to take into account the exact nature of your relationship with the recipient (boss? client?) and the message being delivered (complaint? apology?), and the quandary deepens.

“I think about it every time,” says Eve Bayer, an account planner for an interactive ad agency, who notes,”It’s so hard for any sign-off to sound sincere.”

“Regards” is too formal, she figures; “best,” too nebulous. “That’s not even a complete thought,” she says. “It’s like, best what?”

Her go-to sign-off is “thanks,” “but sometimes I’m like, what am I thanking this person for, especially if you’re doing them a favor.” On those occasions she might go with a “cheers,” having landed on it as the “least weird” of the alternatives.

Better not to send that one to David, an exec at her firm, though.

“Cheers is the one that really bugs me,” he says. “Unless you’re British, my advice is, don’t.”

What gets under the skin of Dorothy, who works in the music business, is the X’s and O’s increasingly used by the publicists who write her.

“I think it’s weird,” she says. “It’s too familiar. It means hugs and kisses, for crying out loud. It’s like, why are you saying this to me?”

Figuring “thanks” sounds rote, and “warmly” sounds “queer,” she’s settled on “cheers” or “cheerio” as her standards, deeming them “just friendly enough without being too friendly.” But hitting the sweet spot is a never-ending dilemma.

“It’s hard to navigate what you should do,” she says.

To add to the challenge, looking to experts for some advice can yield mixed signals. Judith Kallos, author of “E-Mail Etiquette Made Easy,” says her “guiding principle is: If you wouldn’t do it on a business letterhead, don’t do it in an e-mail.”

“All business is formal,” says Kallos, who usually bids adieu with “at your service,” but will opt for “take care” if the relationship is more familiar. “Don’t pretend this person is a friend.”

But Cherie Kerr, co-author of “The Bliss or ‘Dis’ Connection?: E-mail Etiquette for the Business Professional,” argues that e-mail requires something more casual and breezy.

“You want to change it up. You want to make it friendly, a little funny,” she says. “I think there’s so much to be said about how we make each other feel each day.”

Business etiquette expert Ann Marie Sabath says your telephone relationship with the correspondent offers a good idea of what you can get away with. Her rule: “The ending should be based not on what you like, but on how the other person will take it.”

The play-it-safe approach of mirroring the other person’s closing takes much of the guesswork out of the game, says Schwalbe – if he closes with “all best,” do the same.

Personally, he’s partial to “as ever,” an ending he finds “instantly reassuring. Whatever we were before, we are now. There’s a little touch of intimacy.”

So, give your e-mail closings the thought they deserve by making them a reflection of your personality and the nature of your relationship – and don’t sweat the odd closings you get in return.

Rock on,

B.M.