Episode 45 – Creating email newsletters people WAIT for

Episode 45 – Creating email newsletters people WAIT for

About Ann

Ann Handley is a Wall Street Journal bestselling author who speaks worldwide about how businesses can escape marketing mediocrity to ignite tangible results. IBM named her one of the 7 people shaping modern marketing. She is the Chief Content Officer of MarketingProfs; a LinkedIn Influencer; a keynote speaker, mom, dog person, and writer.

Ann’s One Hot Thing…

  • Creating email newsletters people WAIT for

Connect with Ann


My one hot thing is to approach every newsletter that you write, every email newsletter that you send out to your list, as a letter. And I have very specific ways that I do that. I try to keep my voice conversational. I try to think about one person that newsletter is intended to go to that week. I

I don’t think of a list. I don’t think of a segment. I don’t think of a persona. I think of one actual person.

Focus on the letter… not the news

I write that letter every week with a focus on the letter and not on the news. I keep in mind who that human being is that I’m trying to address that week.

It’s easy to say, “Write your email newsletter as a letter,” but it’s a little hard in practice because so many of us when we sit down in front of a screen, have a blinking cursor and our hands on the keyboard – I don’t think that it’s a natural place to start a letter. And I think a lot of us kind of freeze up.

Especially if you have any background in marketing or in business, you almost approach that moment as an opportunity to market yourself. You can talk about what it is that you want to say versus who it is you’re trying to reach.

So the issue that I had to address was how do I actually keep my voice conversational? How do I keep this as a letter and not just as a marketing piece that I want to send out.

Approaching it as a letter, less as marketing, is so important because the inbox is such a special opportunity to speak directly to somebody. My newsletter goes out every Sunday morning, people open up my newsletter while they’re lounging around in bed with a coffee.

Whether you send a more casual letter like mine or a professional email newsletter, it’s really important to recognize that you are in a very sort of sacred space in somebody’s email inbox… people have invited you to that space. The inbox is the only place where people and not algorithms are in control.
So that’s a very special place and so you need to respect it as such and you need to treat it as a special opportunity to connect with someone directly. So how do I do that? How do I keep my voice conversational?

I do it in two ways.

Avoid the keyboard

I don’t start that letter by sitting in front of a laptop with my hands on a keyboard. Instead, I start it internally, as a sort of a conversation by voice in my own head. Usually I’m either out walking the dog and I’m dictating it either on my iPhone or just sort of internally just to myself.

Then when I get back I think about that one person that I’m trying to approach and I’ll write it down or sometimes I’ll use a transcription service at that point, but more often just kind of write it down from my phone directly or just from my own head depending on my process that morning, or I’ll think it through in the shower.

That’s the other spot where I tend to do a lot of my best thinking. So why dog walk and why shower? It’s because that’s the two places where generally I don’t have a bunch of other electronic inputs or I don’t have notifications.

It’s a great thinking time, and that’s where I do my best letter writing.

I start thinking of the letter I want to write to Natalie that weekend or of somebody else who I either met at a conference or who asked me a question online, and I think about that person and then how their question can maybe be applied more broadly.

Invite interaction

I think this applies to any brand who’s sending out an email newsletter and it’s to approach your newsletter not just as a one way communication, not just as a broadcast tool, as a distribution strategy, but rather as a two way opportunity to hear back from people.

I very often invite interaction in my newsletter and I hear back from people a lot.

Very often they ask me questions either through the newsletter or I get questions just through my own website, or on Twitter, for example.

I write down the questions and then when I’m ready to start writing that fortnightly letter, I’ll just flip through them and figure out which one I’m most interested in writing about or most passionate about writing about that particular week. And I’ll start the letter that way.

Very often I have a built in list of questions from either readers or from people I’ve interacted with, to choose from.

Be consistent in your schedule

It’s important to be consistent in a few key ways. But I also think that you should leave some room to mix things up and experiment.

The areas where I think it’s important to be consistent, are number one, on the schedule. If I don’t mail an email newsletter every other Sunday, I get notes, I get letters and that is the highest compliment I can get.

Any kind of content asset that you’re creating, it’s important to have that goal of, will your audience miss you if you don’t show up? Adhering to a schedule and being pretty strict with yourself about it is important.

Keep your tone consistent

Your voice should be consistent every single week. What do I mean by my voice? I mean if you read it out loud, does it sound like it comes from the same person? Does it sound like it comes from you?

And I think about that obsessively, I obsess over voice because it’s that important to me. I want people to know that this is coming directly from me and it could only come from me.

Consistency when it comes to schedule and tone are key… the rest of it, you can play around with it. I play with around with it all the time. I add sections in, I take sections out. I have a ‘shelfy’ section where I talk about books. I found that people didn’t really click on that. They didn’t really engage very much. So I don’t put it in every week like I used to. Every once in a while I’ll share it but I play around with that.

I play around with length too. Mine is long, but it’s also, I think it’s inherently skimmable. I think it’s probably close to about maybe 1,400 words, which is very long for an email newsletter, but I break it up into sections with headings so people can jump to the parts they’re interested in.

I play around with the number of items that I include in the newsletter too. There’s all kinds of ways that I’m testing it. Every issue I’m usually testing one or two things.

Getting to know your email audience

My audience is pretty varied. One segment of my audience is made up of writers, freelance writers. A lot of them, people who are content creators who work for brands or work for themselves and want to know how to write better, might write more efficiently.

Another part of my audience is marketers. Very often they come from brands, both big and small. So very much in the marketing space, a lot of product marketers and strategists.

My sort of third bucket is people who are just starting out in their careers. So either as marketers or as writers, or in some cases, as early content marketers. They’re just starting to dip their toes into that, because they’ve just graduated or because they’re doing a career shift.

I know who they are because when they sign up, I ask them, what brought you here? What do you hope to learn here? I get a lot of information from them in that way when they respond to me directly, which again goes back to the idea of a two way letter, not just a one way broadcast.

In part, that’s why my newsletter is long, because I want to make sure that I at least serve that audience with something. And what that means is that not every item in the newsletter is going to be applicable to everybody. And that’s okay. That’s why I make it as skimmable as I can. I break it up with subheads, I make it pretty clear what this item is about. So if you’re not into marketing, you can skip that piece, if you’re more interested in writing.

So make it accessible. And by that I mean, skimmable, easy to glance at, easy to digest and fun. And make it an experience, make it feel like it’s something unique and interesting, and that people want.

Make people feel they’re part of a community

I always welcome new subscribers to my list, which has the effect of making people feel like they’re part of a community.

There are other ways to accomplish that with an email newsletter. I’ve seen a lot of companies and marketers do it effectively through some sort of onboarding program. You sign up for an email newsletter and every person who signs up gets a sequence of emails welcoming them to the brand, orienting them. My company MarketingProfs does a series of welcome emails, but I’m not set up for that, it’s just me. At least for now. I may change my mind at some point.

The other way that I try to bring readers in is the very last section, which is the love letters section where I give a shout outs to people who give me shout outs or who have done something awesome that week, or have published something about me, or MarketingProfs, etc.

It’s another way to highlight the community such as it is, even though it’s not really a community in a traditional sense, at least having a feeling that they’re part of something bigger than just this email newsletter.

The magic email subject line

I play it fairly straight and try to let people know instantly what it is that they’re going to get. I also throw in an emoji just because I love emojis. I also think that it makes you stand out in the email inbox
I have toyed with the idea of doing some sort of experiment where I make it a little bit more cryptic, or and I’ve thought about using a pun in the subject line as well but I honestly feel that since I only publish fortnightly, being more direct is better in the subject line.

I’ve also heard the argument that rather than doing title case, so in other words, rather than capitalizing every word in a subject line, that you should write in sentence case, which makes it feel like it’s more from a person to you. Like like someone has dashed off a note to you because that feels more personal and accessible. But I don’t know, I think it’s just a matter of just choose a format and then stick with it.

Promotion versus giving value in a newsletter

You can do both. Giving value to your audience doesn’t mean that you’re sacrificing the marketing of your own business. We’re publishing a newsletter because we need to engage with an audience so that we can ultimately have a successful business and fuel the success of our business. So I don’t think that those two things are in balance. I think they tend to get out of whack. Then we forget that we should lead with value first, and make sure that that’s super clear to the audience.

And I think if you are providing value to the audience on a consistent basis, then you can talk about whatever it is that you have to sell in the context of that.

As long as you approach everything from a value first mentality. So what does that mean? Like for example, if you’re promoting a podcast, if you were going to send out an email newsletter about the conversation that we’re having right now, you could just pull out one or two things that we said and lead with that value first. So… hear Ann’s thoughts on how to keep your voice conversational. She offered three great tips, boom, boom, boom. And then click here to listen to the whole conversation.

That’s value first. Now you’re not sacrificing your business or your listeners. And you’re not shortchanging yourself or your audience.

There may be some people on your list who don’t care what I have to say about that, and that’s totally cool. I think that the point is though to lead with value and so you’re ultimately driving people who are interested in the value of that, to dig deeper and hear more.

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