The Seven Deadly Sins of Email Marketing Management

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Published on March 27, 2007

It’s a common belief that email marketing is dead, and that we’ve now entered a Web 2.0 era of blogs, buzzing social networks, and podcasting, but the reality is that email marketing is alive, kicking, and more powerful than ever.

It’s cost-efficient—its ROI (return on investment) is one of the highest out there—and it’s easy to use. It’s also a great branding tool and a trusted way to get your name in front of your customers.

As with most technologies, email marketing can be a double-edged sword. As a communication channel, it is easily abused by ill-willed spammers, giving it a dirty name. To avoid being painted with the same brush as the bad guys, there are a few pitfalls to avoid when it comes to maintaining your most precious treasure, your list of opted-in addresses.

The Seven Deadly Sins

The signs of a successful and long-lived relationship with your email readers are high open rates, clickthroughs that convert into actions, low unsubscribe and complaint rates, and active feedback from your readers. Just like maintaining your car’s engine keeps it running nicely, a little TLC for your email list means you’re less likely to find yourself broken down by the roadside.

Sin #1: Failing to test the design of the email in multiple email clients

Every web designer knows that Internet Explorer likes to be different. Well, start mixing IE with email clients, and you’re in for a lot of fun.

To put it bluntly, email clients are bullies, and your design will need all the help it can get to stay clean and shiny when it arrives at the inbox. Clients can automatically disable images, ruin your efforts to align things, and generally ignore any fancy code you’ve included.

Recently, Microsoft delivered the final blow when it announced that Outlook 2007 will use the Word HTML rendering engine. Yes, you heard me right—welcome back to 1998. SitePoint’s Kevin Yank has recounted his experiences with Outlook 2007.

In practice, this means shunning most advanced CSS and HTML, and sticking to more basic designs and tables. Good designers will plan for the graceful degradation of the email’s design by ensuring that widths and alt text are set correctly, and that the email’s structure and key elements continue to communicate your message effectively, even when images are turned off.

There are plenty of resources available to guide designers in the creation of new email templates that are compliant with the current limitations. Mark Wyner writes a great summary of the current conditions of image blocking in email clients, and sets out best practices in dealing with the limitations of these different clients.

When hiring a designer to produce a new email design, choose someone with experience in designing for the email channel. Once created, “Test, test and test again,” should be the mantra of any email designer, to ensure the different key mail clients on all operating systems render the email correctly.

Tools such as Site Vista can make the task of testing new designs easier, but there is no replacement for manual testing.

All manual testing requires is:

Access to a Windows computer and a Mac (or an Intel Mac running Windows emulation software such as Parallels), and possibly a Linux platform if you have a more technically minded audience.
Suitable email clients: The web-based ones are mostly free to sign-up for, so create yourself a set of test accounts with Gmail, Yahoo!, AOL, Hotmail, etc. You’ll also need Outlook 2003, Outlook 2007, Outlook Express, Apple Mail, Thunderbird, Eudora, and Lotus Notes, a number of which come either with the operating systems or free to download.
Time and patience.

There is no question that it’s possible to create striking designs for the email medium; it just takes patience and a fair bit of tweaking. The first time, in particular, it’ll take some time to get the design to work across all platforms and clients, but once you get the hang of it, it’ll be a breeze!

Sin #2: Failing to spam-check the email copy before sending

As essential as testing the design of the newsletter, the content of the newsletter should be spam-checked before sending. Any email message you send is scored with a number of points when it is received on a mail server equipped with spam-detection software. The lower a message scores, the better.

So what makes the spam filters twitch? Messages containing unusually high ratios of images or HTML tend to score higher, as images or HTML can often be used to disguise spammy content. The use of capital letters, excessive punctuation (!!!), and certain keywords can also trigger spam filters—words such as free, trial, money, as seen on tv, and so on, so it is essential to test your copy before each send to evaluate how much impact it has on the scoring.

Services such as SpamCheck can be used to quickly score your emails, and can help to guide you towards better word selection.

Sin #3: Putting hurdles in the way of unsubscribing

First off, it’s a legal requirement to have a clearly visible unsubscribe link on any emails sent to an opt-in list: It’s not a maybe, it’s a must-do. But it’s not just about making unsubscription possible, it’s about making it easy.

People change, needs change, and sometimes, a good inbox spring cleaning is the only way to get back on top of things. If users decide to unsubscribe, it doesn’t necessarily mean they’re unhappy with your business or what you have to say, so don’t cause them to be bitter because the breakup was difficult. In accordance with the CAN-SPAM regulations, when you receive an unsubscribe request from permission-based mailouts, you’re given ten days to honor it, but it’s good practice to take all unsubscribes into account before you send out your next mailing.

If you’re concerned about losing readership, here are some suggestions:

Allow them to reduce email volume without unsubscribing completely: “Would you prefer to receive a monthly news digest instead of the weekly newsletter?”
Offer a change-of-address option: Maybe a reader doesn’t want to receive your newsletter at a business address, but won’t mind reading it in a personal inbox.
Offer an alternative: If you have a blog or publish your newsletter online, offer them the opportunity to bookmark it or sign up via RSS.

Sin #4: Neglecting to maintain the list’s invalid addresses

The older your list grows, the more regularly you’ll see invalid addresses. Email delivery or email broadcast systems such as eCircle, MailChimp, or Campaign Monitor generally detect soft and hard bounces and will deal with these addresses automatically. (Hard bounces are categorically invalid addresses, such as a closed mailbox, while soft bounces are of the, “Mailbox currently unavailable,” or “Mailbox over size limit” variety) .

However, in some cases, the only way to detect that an account is unused is through the permanent out-of-office messages you’ll receive. They’ll range from, “John Smith is no longer employed by Widgets Inc.,” to, “I’ve moved to a new email address, john@smith.com,” and are common both in personal and business addresses. While neglecting to maintain this list won’t affect your subscribers, for your own good, you should clear out the trash every few months. It’ll allow you to maintain a clearer idea of your active readership and list size, and probably save you some costs in the long term by avoiding sending to dead addresses.

If your customer base is small and the ties with your readers are solid, you might want to consider contacting the owners of invalid addresses by mail with, for example, a postcard asking, “Where have you gone? We miss you!”

If you haven’t sent to your list in a few months and suspect there may be a large number of invalid addresses, you might want to consider trickling your first newsletter over a number of days or weeks. Your recipients’ ISPs might have tight delivery requirements, and could blacklist you for sending to too many invalid addresses. (Derek Harding from ClickZ has more on the topic of blacklisting as a result of bounce rates.)

Sin #5: Becoming complacent

Once you’ve been sending for a few months, you’ll be able to go through the process of creating content, managing data, and sending with your eyes closed and your hands behind your back. Ironically, at that point, it’ll become more important than ever to keep your eyes open and have all hands on deck.

It’s great that you’re finding a comfort zone, but if routine sets in, it’s easy to start rehashing content, turning a blind eye to list management for a few weeks, or not checking stats for any odd list behavior. If you’re not vigilant, it’ll catch up with you at some point.

Most email delivery systems will provide more or less in-depth reporting of the activity around your newsletters, from how many emails were delivered to who forwarded the newsletter to a friend. This allows you to benchmark your latest email against the past ones you’ve sent, and track whether any changes are improving your response rate.

Think of the process as a funnel:

Total number addresses in your list
Delivered emails
Opened emails
Clickthroughs to your site
Your reader taking action on your site

In each step of the process, some users will drop out. Either the subject line will fail to grab their attention, or they’ll be too busy to click through to your website and make a note to read it later (which, as busy people, we all know never happens).

What looking at your stats might tell you is that a large percentage of your list has clicked through, but few have answered your call to action once on the site. Could it be that the call to action is unclear and users don’t know what to do? Or maybe you’ll discover that a different subject line has piqued your recipients’ interest more than ever before?

There’s an immense caveat that accompanies email marketing stats, and it is that they can be terribly misleading. For example, when sending a multipart message (containing both the HTML and text-only versions—the email client decides whether it is able to display the HTML version), those opening the text version won’t generally be counted as part of your opens. Quite the opposite, mail clients with a preview pane (such as Outlook and Mail.app) will count your message as opened mail, even if it’s only previewed quickly, as long as the images are turned on. For these reasons (and many more), stats should be used to establish trends, rather than as absolute numbers.

The bonus, which I didn’t include in my funnel, is the pass-along activity. This is when someone reads your newsletter and finds it so insightful or funny that the reader chooses to pass it on to a friend. Always make it easy for a friend to subscribe by having a link to the effect of, “Did someone forward this to you? Why not subscribe to the newsletter yourself,” at the bottom of the email. This is an effortless way to grow your list.

Sin #6: Sending content that isn’t relevant to what the user signed up for

I’m now getting into the two biggest no-nos of email marketing. These last two can make or break not only your success in email marketing, but affect your business as a whole.

Users like to know what they sign up for; the frequency, the topics covered, the benefits they’ll get out of it. But first and foremost, they need to be confident that you’ll respect them. They need to know they’ll be able to unsubscribe if they realize they’ve made a mistake and the newsletter is of no interest, and that you won’t go distributing their email address like candy on Halloween night.

Mathew Patterson of CampaignMonitor says it well in an article about permission:

It’s all about setting expectations, so that when that first email arrives, your subscriber is happy, not surprised or angry.

If you feel you are straying from your original topic of discussion—for example, you create a newsletter broadly discussing technology, but find yourself focusing on mobile technology in every newsletter—it might be worth considering starting a new group specifically for the topic. Not only will you show your users you respect the fact that they may not want to hear about mobiles, but you also create a second, more direct point of contact with those who are interested.

Failing to do this is likely to result in rising unsubscribe rates, or worse, getting marked as spam by your recipients—if it’s easier and quicker than unsubscribing, they’ll often take that route. If enough users flag you as spam by, for example, clicking the Report Spam button in Gmail, you’ll find yourself blacklisted from that ISP, which not only means your newsletters may not get through to your recipients, but your colleagues’ emails to anyone with the same ISP may not get through either.

Sin #7: Most importantly, emailing a user without their permission

It doesn’t get any lower and scummier than this. Sending email to people who haven’t subscribed is what has given email marketing a dirty name. “Oh, so you’re a spammer?” is a low shot most email marketers will have heard a few times at least.

The solution is simple: Don’t send to a customer unless they’ve expressed interest.

There are exceptions to this rule. (Aren’t there always?) In a business-to-business context, if you’ve attended an event as an exhibitor and were given the list of all attendees’ email addresses, there is no harm in sending them a one-off email inviting them to join your mailing list or find out about your business. Just remember that it’s a one-off communication, and those who do not respond should not be added to your list without permission. And as far as business-to-consumer is concerned, there should be no reason for you to email users without their permission.

In conclusion

The bottom line is, be passionate. Don’t do a half-assed job: Write great content, manage your list well, and the results you’ll get will be both rewarding and motivating. Relationship management is all about common sense and respect, so take a step back if you’re unsure, and treat customers how you’d like to be treated.

Anything that is created with passion is a form of art, and if you love what you’re doing and believe in it, it’ll show. We’ll be able to read it between the lines of copy you write, sense it from the way you deal with your readership, and it’ll ooze out of the designs you create.