How NOT To Write a Prospecting Email, Part III

I woke up this morning knowing I would be writing a blog post today. I wasn’t sure what the topic was going to be, and then, voilà! … a new message hits the inbox from a total stranger. The subject line read:

RE: quick question…thanks!

subject line debacle

So begins Part III of my latest blog series on prospecting emails gone awry. How can one little subject line inspire a 700-word post from me, anyway? Well, it starts with the rich depth in this deceptively short subject line.

Error #1
Let’s start with the use of “RE:” … of course, this represents the conventional email default setting for replying to someone else’s message. There are also cases for using it to refer exclusively to your own previous message, but these tend to be messages that are first forwarded and thus carry the notation: “FW: Re:”. With or without the “FW” mark, the tactic only works when you know the person you’re messaging, because it implies time will eventually be taken to look if the message was initially missed (by your busy colleague, for example).

So, this message implies two distinct interpretations for a would-be buyer: A conversation or at least a previous relationship with the recipient. Cold senders offer neither. This tactic just signals they’re trying too hard to convey a sense of familiarity. Mr. Outbound Emailer, I don’t know you, and your use of a couple characters at the beginning of your second, third or fourth message do nothing to change that.

What else is wrong?

Error #2
How about the very next part, quick question? Again, you’re probably reaching when you say quick. If nothing else, the conversational nature of the expression is too casual for a first-time email contact. The bigger problem I have with it is that I as the reader have no incentive to answer this question. I still don’t know you, and if I don’t know you, what would motivate me to even consider your quick question, let alone answer it?

Error #3
Yes, this 28-character subject line contains a third flaw—amounting to an astounding density of 1 error for every 9 characters. That flaw is: “thanks!” What’s wrong with politeness, you’re wondering? See my earlier remarks about familiarity and authenticity, which might have prompted me to click through despite the overall error of vagueness. Plus, the exclamation point at the end is a little much. Think about it, he’s enthusiastically thanking me in advance for a faulty assumption (i.e., that I’ll respond) … now that’s confidence! Also, assuming no relationship with you or your company, your subject line needs to carry all the weight in order to reach me. Otherwise, what indicates I would take the time to read the rest of this message and actually answer the quick question when the subject line lacks essential info-carrying microcontent?

Reputation and popularity
I don’t pretend to work in outbound sales, and I admire the thick skin and tenacity of those who do. However, if I did, I would not resort to attention-grabbing parlor tricks that ultimately make me look bad. Mind you, I understand the marketing value of getting people’s attention, but if you leave any negative impression whatsoever, you have wasted your time and potentially your reputation. And reputation is a terrible thing to squander.  If you think others’ impressions of you don’t matter, read Robert Greene’s ‘reputation’ chapter in The 48 Laws of Power: “Much Depends on Reputation: Guard it with Your Life.” (In fact, read the entire book … it will change the way you look at the world forever.)

Finally, my new prospector friend is not alone. I see this subject line in my work email all the time. It seems to be in vogue with sales folks these days. In fact, within an hour another random outbound message tried to sell me Hubspot subscriber data by dropping another “RE:” subject line on me.

subject line debacle II

Maybe she thinks that suddenly I’ll want to read her message on Monday after ignoring it Friday? Better still, as pictured above, she opened it with “How are you?” (Public service announcement: If you don’t know somebody and you want to sell them, never start a cold email with “How are you?” It’s so patently false. Nothing screams ‘used car salesman’ more than forced intimacy.)

Thanks to my latest outbound prospecting friend for inspiring today’s contribution to these ongoing spotlights of sales messaging gone wrong. For other popular miscues deconstructed, check out:


Paul Richlovsky

About Paul Richlovsky

Paul purposefully merges a creative writing and teaching background with his decade-long marketing career. He advises clients on content strategy, editorial direction and PR/distribution. He is a perpetual critical thinker who has written/edited hundreds of blog posts and multiple long-form marketing guides, including those aimed at audiences as varied as healthcare, higher education, financial services, B2C brands and manufacturing. With a BA in English from the College of Wooster, he is also the author of a collection of poetry, "Under the Lunar Neon."He gets really excited about the science of elite performance, usability, brand voice, headlines, digital governance, ballroom dancing, bachata, racquet sports, and romping with his niece and nephews.

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