
What's your scariest email moment?
It's that time of year: all things pumpkin spice, rotting our teeth with candy corn, and rewatching Nightmare on Elm Street for the twentieth time. Yep, it's Halloween. So, I'm curious: what is your scariest moment as an email designer?
I'll go first. Years ago, I worked at an agency that handled a fair amount of email marketing. I had just uploaded a test to ExactTarget to send out to a group of stakeholders for approval. Instead of selecting the stakeholder list, I unknowingly selected the actual subscriber list and hit send. Which it did. To about 14,000 people. It was one of those moments that I realized what I'd done about five minutes too late. Then, with my heart in my throat, I proceeded to walk to my boss' office to tell him the bad news.
Fortunately, he didn't mind. The stakeholders were informed (good thing there weren't any mistakes in the campaign) and the subscribers just got that email about a week early. I kept my job and was the butt of many a joke for the next month or so.
Anyone else care to share?
Two come to mind.
I circulated an event email test to some internal stakeholders. One had several small text edits, so the easiest way to get those edits into the email was just to copy and paste her version into my editor and move on with my life. ... Of course, I neglected to acknowledge that the email copy had a first name personalization in it, so, I ended up calling ~5K people in Seattle "Catherine" which I didn't realize until the replies started coming in. This was my first major email fail, so, it was super scary to realize what sort of power the Send button can hold.
Also...being the guy who presses Send for Litmus is impossibly scary just about all the time, mostly because I know how ruthless the Litmus community will be if anything we send ever contains an error ;) On one of our recent sends, I noticed one of the variants had a typo in it. (Which, interestingly, none of your beloved Litmus marketing team caught in the review process—calling you out, Jason, Justine, Kevin and Lauren!) The email was already scheduled, and set to go out 2 minutes later. Luckily, I was able to cancel the send and get the typo fixed...but had about 67 heart attacks in the span of those 2 minutes.
This is how nervous he gets before he sends emails:

To our credit, it was a teeny tiny typo. In fact, a small missing word. The kind your brain inserts for you while you're reading.
Email to potential investors: Font color was set to #333333 background-color was set to #333333. Yeah, I didn't see anything either. needless to say had to resend with font-color #ffffff
Also, somebody get Cori Hemmah in here. I want to re-hear all of hers again.
Just recently programmed a newsletter to be sent out. The business owners were on us to get it done quick (even though they were super slow in approving) so I programmed it, got it done in plenty of time and was just waiting for the go ahead to upload it. I stepped away from my desk for a bit, forgot my phone, and when I came back a huge storm hit me. They wanted to upload and send the email for approval but that was 15 mins ago so now it's too late and it won't go out. (This because another department decided to go home early). I turned it in apologizing profusely. I went home only to discover my phone and email blowing up that the email wasn't working. They'd sent a test and it wasn't rendering completely in Outlook 10. I had thought this was just a glitch in litmus due to some previous experiences so I tried to explain it away, but come to discover after several phonecalls and hours of research that Outlook 07 and 10 have an Image Height Limit at 1728 (or something like that). The way I code emails now forces background images to render in Outlook but also makes every section read as an image so the email was being cut off at 2/3. I had to do some quick testing and research and the only way we could fix it was to change the design (I offered several options but every one got shot down because the manager didn't want to go back to the business owners telling them we needed to redesign basically two small sections). After more discussion and back and forth we decided to make two small changes to the design which solved everything. I was up late recoding and testing and testing until it was done. And even then the next morning there were still corrections and issues that had to be fixed until finally they just sent it out.
This has been a common issue lately with new designs and code to better render in Outlook (which in turn causes problems among all the other ESP).
My brain was fried, my heart was in my throat, my stomach was twisted and it was just all around a bad couple of days that all got put on me even though a lot of it just came down to unknown factors that are now quite well known and taken into account.
My philosophy has always been: Code for Outlook and IE and all other things will fall into place.
O, and, business owners/sales guys/marketers/"those who approve" always know better, don't they?
We ended up asking the business owner if redesigning would be ok and the response was do what you need to do to make it work. As expected. Not a bad philosophy, and that's usually what I adhear to, I always check them first and if they render right, generally everthing else renders right.
I know this post is a little old, but for anyone still subscribed, we just opened up our latest Community Contest that's asking everyone to share their biggest email mistakes and talk about what they learned from the experience. Check it out here.
A couple of years ago at my previous employment, we were switching from one ESP to another which involved the transferring of all assets - yep, fun! We got the emails, images and documents all in, set up the auto-responders and basically had everything ready to go. As we had the previous setup linked to our website for new subscribers, we waited until after business hours to export the subscriber list and import to the new ESP, while simultaneously switching the website signup form to send to the new ESP. After exporting and then importing the 90,000 subscribers from the old to the new ESP, we tested to make sure everything was set up, ran a few auto-responder tests, deemed everything was good and headed home for the night.
The next morning, our customer support line, which goes into voicemail mode after business hours, had a large number of messages from some very confused customers - with some equally confused employees listening to them. After we all checked our inboxes, we realised why. It turned out that the list at the new ESP had default settings which triggered our welcome email for every new addition to the list. Normally this is what we would expect but we didn't expect it to send to the 90,000 imported subscribers - which it did! Cue a flurry of activity as the business heads decide how best to respond, and me trying to figure out how and why it all happened, while trying to keep my job and my face from turning red.
Needless to say, the ESP we moved to has since changed how they approach welcome emails and now turn it OFF by default, instead of ON. I am now extra cautious when adding any new subscriber list to our ESP, old and new, just incase they decide to play another trick on me.
The silver lining of this story is that our welcome email included a money-off coupon for our website, which more than a few decided to take up, so we actually ended up with a spike in traffic and sales. I don't intend on trying this again though!
Recently, we (meaning me) sent a high profile email to a list of C level execs with First_Name personalization without properly inspecting the data, which did not have a column for First_Name. Sending an email with "Dear ," as the personalization was not the highlight of my career. Scraping together an "oops, we screwed" up email wasn't either.
I love commiserating over email marketing fails. Add this one to the reel...
I had just started working with a sports and entertainment company and was sending a post event email to a list of folks who purchased tickets for Cirque du Soleil Michael Jackson. Unfortunately, I sent it to everyone who went to a Coldplay show earlier in the week. What resulted was multiple phone calls to our lawyers and reports to the better business bureau for illegally charging credit cards (which didn't actually happen).
It was my first ever email marketing fail, my team's response? "Welcome, you're officially an email marketer".