Welcome to the July edition of Not a Newsletter, a monthly, semi-comprehensive, Google Doc-based guide to sending better emails! I’m Dan, the founder of Inbox Collective, an email consultancy, and the former Director of Newsletters at The New Yorker and BuzzFeed. Every month, I update this doc with email news, tips, and ideas. Sign up here to be notified when the next edition goes live!
This month, Yanna-Torry Aspraki is back with a new Ask a Deliverability Expert — she’s sharing four strategies that are actually worth trying to make sure you stay in the inbox. Plus: Best practices and A/B testing ideas for your subject lines; tips for getting started with SMS; ideas for using animation in your emails; and more!
Want to read a previous edition of Not a Newsletter? Find the full archive at this link.
-Dan
This Month in Email Headlines
- Google Is Going to Let Politicians Spam Your Inbox (Bloomberg)
- And here’s how one industry expert, Jennifer Nespola Lantz of Kickbox, responded to the news.
- WeChat Is China’s Most Beloved (and Feared) Surveillance Tool (Bloomberg)
- Rise of subscription sleepers (Axios)
- You can read the full report from Piano here — There’s a lot in here, and I’m going to try to unpack it in detail in a future Not a Newsletter.
- European Firms Launch Email Newsletter Ad Network for Switzerland (MediaPost)
- New Gmail rolls out to everyone, and you can hide that big sidebar now (Ars Technica)
- Industry Dive to sell to U.K.-based events firm Informa (Axios)
New on inboxcollective.com
As one of your subscribers scrolls through their inbox, looking through the emails they’ve been sent that day, they’re always asking two questions:
- Who is this email from?
- Did they give me a reason to open their email?
The subject line is your answer to that second question. It’s your opportunity to catch a reader’s eye, to tell them: This is why you should take a moment to focus on what I have to say.
Writing a great subject line is harder than you’d expect. Subject lines should be a little like fingerprints: unique to you and the emails you’re creating. There are several best practices to implement, but there’s no one right way to write a subject line — it’s up to you to figure out what your subject line style should be.
So let’s talk about subject lines: Rules for writing a great one, ways to get more out of the preheader space, and ideas for A/B testing. You might just find a few new ways to improve your newsletter’s subject line strategy.
Other recent stories on Inbox Collective:
- A scrappy news startup plows a new (and profitable) model for local news, by Alex Hazlett
- Creating accessible emails: A guide for marketers and journalists, by Jason Rodriguez
- How I Built a Welcome Series for My Newsletter, by Dan Oshinsky
Ask a Deliverability Expert
I get a lot of questions about deliverability, and I don’t always have the right answers. But I know someone who does: Yanna-Torry Aspraki, a true deliverability expert. She’s been working in the email space since 2014 in all sorts of roles — at ESPs, with brands, and as a consultant. She really knows her stuff!
So let’s get to this month’s question:
There are so many tactics I see newsletters use to stay out of the spam folder, like asking readers to move their emails to the priority inbox or instructing them to whitelist their newsletter email address. Are any of these actually worth doing?
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Email is still pretty young, but it has grown and changed quite a lot over the past 50 years. From spam filters making decisions by looking at an IP all the way to new forms of authentication to protect senders from spoofing, getting into the inbox is no easy feat, especially if you don’t follow all best practices.
Over the years, senders have identified certain tricks to get their emails into the inbox. The mailbox providers, spam filters, and various blocklists then adapted to stop some of those tricks from working.
Still, you’ve probably seen an email like this land in your inbox:
That’s an email sent for one purpose: To try to keep their newsletters in your inbox. But does it work? We often talk about red flags — tactics that might hurt your deliverability — but there are also green flags out there— tactics that help you land in the inbox. So let’s talk about some of these tactics, and figure out which might be worth trying with your newsletter.
Which tactics actually work?
Deliverability is all about knowing what your subscribers want to receive and sending that type of content to them. Spam filters and mailbox providers are looking to catch emails that are malicious or annoy their users, and if they spot one of these emails, they’ll stop them from landing in the inbox. But any tactic that generates a positive, organic action will help your sender reputation — and your deliverability.
The best tactic to use: Sending great emails that readers love to open and click. (Of course, that’s easier said than done.) But there are four other tactics you might want to try, too:
Tactic #1: Asking subscribers to move your emails to their priority inbox
Asking a customer to move your brand’s email to the priority inbox is a great way to let spam filters and mailbox providers know that your emails are valuable. But it’s not always the quick fix it seems like. First, not every inbox offers different tabs, and not everyone uses them. (Many still see their emails in a chronological order.) Second, if you are sending emails to people who don’t have a strong relationship with you, prompting them to move your email to the inbox won’t save you from the spam folder, since they probably won’t take the action.
Having emails moved to a different tab, in the long run, should help with deliverability, as your most active readers will continue to see your emails where they want to receive and, hopefully, continue to interact positively with them. This tactic is great when you are looking to stabilize or grow your engagement ratio — the ratio of engaged readers to emails sent.
I’ll also note that this works great for certain business cases, but not in all situations. For example, if you are selling online courses and you have new students actively taking your course, asking them to move your emails from the Promotions tab to their main inbox tab will allow them to see your educational content among all their other important emails. But let’s say over time, your students finish the course, and now you’re mostly sending promotional emails to get them to purchase another course. Don’t be surprised if those emails land in the Promotions tab — that’s where the inbox believes that type of content should be.
Tactic #2: Adding the sender email to an address book
Asking your subscribers to add your email in their address book is a great way to show mailbox providers that your subscribers want to have a relationship with your brand. Some inboxes will prompt their users to do this when downloading the content of an email. That makes it easy for readers,as you don’t have to do anything — the mailbox takes care of it for you! In other cases, you have to prompt your subscribers to do this.
As every mailbox provider is different, so there isn’t a one-size-fits-all trick to help your subscribers do this in one click. I have seen brands ask this of their customers at sign up or within the first few emails. The thing to keep in mind is that having a passive sentence in your email that prompts your subscriber to perform this action probably won’t be enough. It’s just too big of an ask, even though it’s a simple one. Some readers won’t understand how to take this step, or they don’t have the time to do it, or they don’t clearly understand the benefit of why they should take the step. (The main benefit: They’ll see more of your emails, but that may not be enough for them.)
If you’re going to ask a user to do this, try to make it clear why you’re asking. The more clear the benefit, the easier it will be to get a subscriber to perform this action. For instance, a reader might take the time to add an airline’s email address to their address book if they’re first reminded that they don’t want to miss important flight updates.
Tactic #3: Asking subscribers to star or save an email for future reference
This action is one of the easiest for your audience to do. The star/save option is easy to find and is done in one click in most mailbox providers. Unfortunately for us senders, getting subscribers to star all of our emails is probably an impossible feat! Not every single email we send should be saved for future reference anyways. When using this tactic, we want to ensure that we are using it when it makes the most sense. For instance, stores can send coupons in their emails that can be scanned when someone shops in person. Prompting a reader to star that kind of email so they can find it faster in store would make sense. Prompting someone to star a “reset password” email might not!
Tactic #4: Asking subscriber to reply back
It’s easy to forget as senders that our subscribers can write back to us right from their own inbox. Getting them to reply back to your email is a great green flag, even if it’s a tactic that’s underutilized. Let’s be honest: How many conversations in your inbox start from a marketing email you’ve received? Personally, the only times I can remember replying back was if I saw an issue within the email, content or otherwise, and wanted to politely let the brand know!
Replies are great because they show that you’re a brand that cares about its customers and are open to starting a conversation with them. Replies boost your engagement ratios, and if subscribers are prompted correctly and see the value in replying back to your email, you can use this tactic to get reviews, pictures, comments, or other useful feedback! (The Not a Newsletter welcome series, for instance, uses replies as a way to learn more about subscribers, which helps steer the Google Doc’s content strategy.)
Don’t forget, email is a two-way street, and replies are a great way to engage directly with readers and improve deliverability all at once.
Keep in mind…
Now, all these tactics won’t save you from the spam folder if you’re not a good sender following all best practices. These green flags, as powerful as they can be, will never compensate for spammy or clickbaity tactics. You still need to have explicit permission from subscribers to email them, and still need to provide real value within your emails — inboxes are going to look at clicks and engagement after someone opens your email. Don’t underestimate how proper list practices and marketing strategies based on engagement can help you stay out of the spam folder, or how useful it can be to reduce your overall email volume by sending your marketing emails in a more targeted manner.
So, yes, you can try these four tactics, but don’t forget to focus on a few other key strategies to make sure you stay in the inbox:
- Authenticate your domain with SPF, DKIM, and DMARC
- Show the value of your emails during the signup process
- Create a killer welcome email series
- Review how you segment and target your subscribers over time
- Make it easy to unsubscribe
- Create a sunset policy to automatically remove subscribers who’ve been on your list for a certain period of time and who haven’t engaged with a certain number of emails
- Clean your lists with list cleaners and by segmenting non-openers out
Do all of this — and send great emails on a regular basis — and you should consistently land in a reader’s inbox.
Yanna-Torry is a Canadian-born, Netherlands-based email and deliverability specialist at EmailConsul, a new deliverability monitoring tool. In 2020, Litmus gave her their first-ever Coach Award for her work serving the email community. You can follow her on LinkedIn or Twitter. She also has a free deliverability course on Udemy.
Have a question for a future edition of Ask a Deliverability Expert? Submit it here.
For Your Reading / To-Do List
- You’ve heard me talk often about the importance of using automations, like a welcome series, to get the most out of your email strategy. But what email automations are worth setting up, and which emails should you send as part of these? I love this resource from Mailmodo, which details dozens of different automated flows, including examples of the copy to send in each email.
- A few other useful how-tos that might be helpful to your long-term email success:
- Aweber’s Sean Tinney wrote a useful guide to different types of confirmation emails. These emails, which might be sent after a reader makes a purchase or donation, get incredibly high open rates, so it’s worth investing time into making them great.
- Postmark’s Bettina Specht wrote about dunning emails — the emails a customer or subscriber might receive when their credit card payment fails. These are crucial for any subscription business, and there are good examples here you can use as templates for your own email program.
- Oracle put together a handful of checklists with ideas for newsletter acquisition, website optimization, and automated campaigns. Again: Lots of ideas in here for you to learn from and build off of!
- Really liked this, from SailThru, about when to use SMS vs. email, plus specific tactics to try to encourage opt-ins for SMS.
- Ayaz Nanji of MarketingProfs dug into data from a recent survey of business owners and users about their SMS habits. I thought this was interesting: Among the marketers surveyed, 88% said they saw click-through rates of 10% or better on their SMS campaigns. Only 36% could report similar rates on email.
- That being said, I see SMS and email as complementary tools. I like to describe the inbox as a living room — it’s a personal space where readers might let in their family, friends, co-workers, and a handful of trusted newsletters. If the inbox is a living room, then your text messages are like the bedroom — an incredibly private space reserved for only the closest people in your life. Be careful about what you send. Trust is hard to win and easy to lose, especially with SMS.
- Here’s a good example of using targeted messages in a smart way: Germany’s Kölner Stadt Anzeiger Medien found that targeting readers who were at risk of cancellation with messages featuring recent top stories reduced churn by 5 percent. (This example is actually one where they used push notifications, not SMS, but it could easily be applied to SMS, too.)
- One more SMS story: What’s New in Publishing chatted with the Nevada Independent about their SMS strategy to engage readers around the Nevada primary elections. If you’re a newsroom thinking about using SMS for the first time, this might be a good SMS idea to test out.
- I always love a good story about how a newsletter reached a specific subscriber milestone. Here’s one from John Bardos of Idea Economy about reaching 2,000 subscribers, including a breakdown of some of his paid subscription tactics and costs.
- Nieman Lab’s Hanaa’ Tameez wrote about Prism, an interesting pop-up newsletter about wellness that changes themes every few weeks. (Full disclosure: I’m working on an Inbox Collective project with Evelyn Crowley, who’s the GM of Prism.)
- Chus Naharro put together a study of independent, Spanish-language newsletters after surveying nearly 150 writers in the space. There’s some interesting data in here, but I was particularly excited to see someone seeking to gather more data on non-English-language newsletters. (We’ve got a few Inbox Collective stories in the works from newsletter writers operating outside the US or in languages other than English. Lots more to come on this front!)
- Adam Piore of CJR profied the team behind Punchbowl, a newsletter-first site covering American politics. (Punchbowl also got a shout-out in my piece on subject lines — they do a really nice job with their subject line strategy.)
- Two stories about animation in email that might be useful for you:
- Lily Worth wrote a fantastic post for Animatedly about best practices for including animations in email, including tips for creating accessible animations and a tutorial on how to reduce file size. If you’re a designer or just thinking about including animations in email, save this post.
- And this was fun from Al Iverson, who shared a neat little trick for creating an animated logo to display in Gmail. (If you’re a small brand that won’t be applying for BIMI, you might want to give this a read.)
- You don’t need to design a beautiful email to make it one readers will engage with. For MarketingProfs, Chad S. White walked through a few cases when plain-text emails might be a better option than HTML.
Stuff I Loved This Month
- Here’s a fascinating launch that caught my eye: ConvertKit’s rolling out a sponsor network to make it easier for advertisers to buy advertising across several different creator-driven products. (They take 20% of the advertising revenue, which I think seems like a pretty good deal for the indie writer who otherwise wouldn’t have time to sell ads.) They’re the first ESP I’ve seen that’s tried something like this — but based on my conversations with others in the industry, I don’t think they’ll be the last.
- Research and experimentation should be part of the process of developing any new product or newsletter. I loved this, from Stephanie Ho for the News Product Alliance, about how to get started with the research process.
- Deborah Carver of The Content Technologist wrote about how she took Gmail’s tabbed inbox and made it a better experience for her.
This Month in… Mel Brooks Quotes That Are Also Good Rules to Follow for Email Marketing
Mel Brooks is a comic genius, and also a surprisingly good source of inspiration for those of us in the email space. So in 2022, I’m closing the Google Doc with a brand new feature: Mel Brooks Quotes That Are Also Good Rules to Follow for Email Marketing! This month, let’s turn to the wisdom of the 2000 Year Old Man.
Some background here: The 2000 Year Old Man was a comedy routine with Carl Reiner and Brooks. Reiner played an interviewer; Brooks played a man who’d been alive for 2,000 years. Brooks had allegedly lived and seen everything, but never answered questions quite the way you expected him to. (“I have over 42,000 children — and not one comes to visit me!”)
One of my favorite bits involved Reiner asking Brooks about his first job. Brooks replied that he was in manufacturing — he was one of the first to make and sell the Star of David:
Interviewer (played by Reiner): How did you make them? Did you have tools?
2000 Year Old Man (played by Brooks): Well, we didn’t have lathes. I employed six men, see, each with a point and they used to run together in the middle of the factory, and in the great speeds they would fuse the thing…
Interviewer: …thus making a star.
2000 Year Old Man: Yes. We would make two a day because of the many accidents. We had six men running at high speed.
Interviewer: You never thought of going into anything else?
2000 Year Old Man: No, I had an offer once. A fella came to me, Simon.
Interviewer: What did Simon ask you to do?
2000 Year Old Man: He said we have a new thing, a new item, a winner. It looks like a winning item. It’s going to be a big seller. It’s called a cross. And I looked at it, and I turned it over, and I looked at all sides of it, and I said, “It’s simple. It’s too simple.” I didn’t know that it was eloquent! I didn’t know it would be such a hit!
I’ve been in the email space for a decade, and sometimes, that experience can work against me. I’ll hear a new idea and think: I’ve seen it all, and I’ve never seen that work before — so it definitely won’t work! I’ll dismiss an idea before I’ve given it a chance.
And then someone else will come along and try that idea and do great things with it.
The challenge in this business is staying curious. Are you open to trying new things? Are you willing to test out new ideas, even if you might be proven wrong? Are you OK with the idea that everything might change one day, and you might have to change with it?
Be open to all sorts of new ideas, and see what happens. You never know what’s going to work next.
That’s all for this edition! Want to be notified when next month’s edition of Not a Newsletter is live? Sign up here:
