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  • Dan Albert S. de Padua

Emailing the Boss

My editor threatened to kill me if I fail to submit an article each week. He whispered the threat to me under his breath as we shook hands after lunch. My problem is I am currently traveling abroad and I really don’t want to spend my time staring at my laptop instead of taking in the sights. I’d rather be having leisurely meals in well-reviewed restaurants than drowning in coffee while pounding out words for an article. How do I tell my boss this in a friendly but firm email that won’t get me fired?

Dear Boss, - Nobody uses “Dear” in emails. It’s archaic and I’m glad it is because a boss who threatens to murder you is not really a dear.

Hi Boss, - Too familiar. I might as well use his first name and I’d do that if we were both

Millennials but we’re not.

PCJ: - The initials of my boss who, for purposes of this article, I’m calling Peter Charles Jennings. Anyway, this salutation seems a little too cold, especially with the colon, but I think I can settle on a compromise here.

Hi PCJ, - Ok. We have a beginning.

Greetings! - I would never ever start an email or a letter or anything with “Greetings!” but I see a lot of correspondence that starts that way, and I put it here so that I can rant about it. Beginning with “Greetings!” is stilted, stupid and a waste of time because you already said “Hi”. If some sort of special greeting is appropriate for the season and the subject matter of your letter, then go ahead and kick off with “Merry Christmas” or “Happy Fall of Bataan Day” but a generic “Greetings!” is plainly stupid. Especially in an email, get right to business.

You said you’d kill me if I missed a deadline. – Take note of how I started the body of my email with “You”. This is a very subtle signal that tells my boss how important he is. Most people start practically every sentence with “I” and it comes off as egotistic. I, however, am extremely good at writing emails; therefore, I invariably start with some other word, preferably “You”.

You said you’d kill me if I missed a deadline. I hope you’ll reconsider this decision not to permit me to go on leave from writing my column. I’m in the U.S. now spending a very limited period of time with my one and only son whom I have not seen in almost a year. I would like very much to be able to spend some quality time with my family, especially considering that I’m retired and in the twilight of my life. Please, please, allow me to skip just two weeks of writing for you. - See what I did there? I stated very clearly at the outset what I wanted. I laid out my arguments logically with just a little bit of an appeal to emotion. Then, I begged. Even the most jaded, grizzled veteran editor will certainly grant my request, what more my wonderful, all-around-great-guy boss.

All that remains to be done is close the email properly.

Very truly yours, - This is how lawyers end their letters, and yet at every career orientation seminar I give, some smart ass high school student asks, “Are all lawyers liars?”

Thanks! - I’ve used this in the past, but I read somewhere that it’s presumptuous to thank someone before he has even had a chance to respond to your request. Valid point, I guess.

Many thanks. – Strikes me as obsequiously presumptuous, if there’s such a thing. Anyway, I don’t like it.

Nagmamahal, - I’m kidding.

Text, text – Nice casual, digital way to say bye-bye, but according to my Millennial son with whom I’m trying to spend quality time at this very moment, this is what you say when you secretly have no intention of contacting the other person ever again. Since I don’t want to be misinterpreted, maybe I shouldn’t use this.

All the best, - This I like, but it’s a little too much for this occasion. I generally use it to close messages to people for whom I really do wish only and all the best things, especially those I don’t get to see very often. Yeah, it’s excessively sentimental for an email to the boss.

Best, - A popular email closing these days, and there’s nothing really wrong with it. Whenever I see it, however, I keep asking myself rather irrationally, What best? And Best what? It seems ambiguous and incomplete, but that’s just me.

Regards, - My go-to closing, because I don’t want to overthink these things, as if I haven’t done so already. Hahaha. Since I want to up the ante a bit for this particular email, I think I’ll end with:

Best regards,


P.S. Please consider this my article for this week. Therefore, even if you decide you will still kill me if I miss a deadline, I effectively have another week to live.


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