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Considerations when planning a newsletter

There are many reasons to start an email newsletter, for instance to help with a membership campaign, drive traffic or, heaven forbid, serve your readers! Whatever it is, this guide will help you think through your daily newsletter product.

First things first: Who is your audience? Yes, it’s your website audience, but give some thought to which segment of your overall audience you’ll be targeting. Newsletters lack discovery (Gmail doesn’t recommend newsletters, for instance) so you’ll be looking at users who already have some measure of loyalty. Try to break them apart. Perhaps there is a cohort of regular homepage-checkers; maybe mobile traffic spikes at different times. Use what you know about your web audience to inform how you think about your newsletter audience.

Content strategy & niche targeting can play a big role in planning a newsletter, but it’s common to have at least one general newsletter product in addition to newsletters that may be more tightly tied to a specific section or beat. Even so, defining the target audience upfront will let you better plan your general effort.

Even on a small beat, taking the general operation to sustain an entire outlet is becoming more possible thanks to startups like Patreon and Substack. As far as the jobs to be done, “catch me up” comes to mind; “share our insight” might be another.

Ben Thompson, publisher of Stratechery, explains how insight played a part in the phenomenal success of his own $10/mo ($100/yr) subscription business:

The internet enables niche in a massively powerful way, where you can focus and be really good at one thing. And because you’re not constrained to a geographic area, you can reach the entire world. I have subscribers in 30 countries.

Ben Thompson, Stratechery (2017)

Thompson thinks there’s advantage in the clarity of a single daily email:

What I am selling will be much clearer and easier to explain: a daily email, with my opinion on the most important stories and articles of the day. It’s something that doesn’t exist now, but will if you pay for it.

Ben Thompson, Stratechery (2014)

Another newsletter impresario is D.C.’s Mike Allen, formerly Politico but now at Axios. Mike Allen’s Playbook was quintessential high-twitch reading for Beltway insiders, and Axios AM has similarly seen popular success. Allen explained (also to Recode):

People are starving, hungry, desperate for illumination about the Trump White House, about what’s going on, and we’re able to do that. [The daily newsletter] got us off on an incredible start, we’ve taken off like a rocket ship. And a big part of it is, we can help people understand this crazy world.

Mike Allen, Axios (2017)

Headline roundups, driven by feeds, are giving way to a new generation of insight-first products that might refer to content published on the website, but with different context and possibly additional analysis.

The newsletter no longer exists as a secondary product, meant to promote your main asset; no, the newsletter is today a first class product, up there with your website and print edition. As CNN host Brian Stelter reveals in a pinned tweet, daily production of the Reliable Sources email can take up to half the working day!

The Reliable Sources email depends primarily on Stelter’s exceptional insight into the media industry, but the brand isn’t entirely dependent on Stelter the individual. Here are some annotated notes about a recent Reliable Sources send.

  1. Including the byline increases trustworthiness of the email and some newsletters encourage that readers respond directly to the author from their inboxes.
  2. The executive summary at the top of the newsletter provides keywords that may catch the reader as they are scanning their inbox. While this may reduce the likelihood of a user scrolling the email, it could also decrease the likelihood of an unsubscription, as the executive summary reduces the cognitive overhead of having to process a newsletter you only read in-depth occasionally.
  3. The ‘Just Wondering’ block provides a dose of informality, breaking the 4th wall in the same way as Stelter does during his show.

Developing an indispensable email means hooking the reader on your insights. The tactics highlighted above will help you develop a newsletter product that fits into readers habits. Successful newsletters can become part of an individual’s ritual in a way less common to a post-Google Reader generation. Having permission is a wonderful thing.

Here are some more examples of user interfaces that develop trust with the audience.

The Philadelphia Inquirer includes a colloquial intro that tends to end on a positive or reflective note and tee up the biggest or most discussed story of the day.

Inquirer email screenshot

WTFJHT also puts the day’s update into context. Note the use of emoji to summarize “current mood”, standing features like this are a good way to deliver familiarity and new information at the same time.

WTFJHT screenshot

Billy Penn includes an editor’s note in the email that makes use of the “sawdust”, or the byproduct of the reporting process – what’s to be covered, staff happenings, events, or other tidbits that don’t have a proper place elsewhere.

Billy Penn Daily screenshot

While many newsletters go wide on a topic, a few newsletters use the space to go deep on a single issue. Here’s an issue of Tedium (“The Dull Side of the Internet”).

Quartz’s Daily Brief is well known, but their Obsession email (and not to mention Index and Quartzy) takes a different spin. Obsession also goes deep on a single topic, and I think they have one of the best signup pages in the business.

If ultimately you don’t have the editorial resources to put towards an original email product, there is still plenty of upside to be had through automated or assisted mailings. Healthcare Dive (as well as the other Industry Dive publication) includes personalized modules as well as a dedicated & CMS-driven links section.

Healthcare Dive Screenshot

There are even email-first versions of this, like Jason Calcianis’ LAUNCH Ticker, which bills itself as need-to-know tech news in ten minutes or less each day.

LAUNCH Ticker screenshot

Newsletters may not support interactivity, but that doesn’t mean they should be static or artless. On the contrary, the Lily (a Washington Post jawn) makes original illustration a key part of its editorial strategy, even adding illustration to original photography in support of the story.

The Lily screenshot

And regarding interactivity – well, some rules are meant to be broken. See here how Quartz has experimented with makeshift polls in its Obsession product.

For more on interactive emails, check out this Litmus blog post.

Ultimately the newsletter will be a set of tradeoffs, as with all products we launch. The decision of how frequent to send, when to send, and what to send – each decision depends on newsroom goals, monetization plans, and audience characteristics.

Testing and experimentation will be required to maximize the newsletter-audience fit and this may entail some tough conversations about sending time (early mornings? late nights?) as well as the additional editorial obligation.

Despite the additional effort required, if present conditions are a halfway decent indication of the near future, we should expect that membership revenues and newsletter/curated information services should grow hand-in-hand in the decade ahead.

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