10 Questions to Help You Build a Better Newsletter

When it comes to newsletters, there’s no one-size-fits-all strategy. What may work best for one newsletter may not work for another, even if they operate in a similar space, have a similar business model, or have a similarly-sized team. What that means is that it usually takes a lot of questions to figure out what each newsletter needs to do to build the right strategy for them.

If we sat down together to improve your strategy, I’d have a lot of questions for you about growth, monetization, and content strategy. I’d ask you about email design and automations. I’d like to dig into your goals for your newsletter.

I wish I had the time to help every newsletter operator personally, but there just aren’t enough hours in the day! Instead, I’ve put together something that I think can really help: An ebook walking through the questions I ask — and the answers I give — my clients to help them improve their newsletter strategy.

The ebook is called “53 Questions To Help You Build A Better Newsletter.” It’s a guide to making your newsletter work better for you, and you can buy it here.

I’m suggesting a price for this ebook: $39, which I think is a great value. I understand that price is an issue for some. If you want to pay as little as $5 for access to this resource, you can. I’ve set things up in Stripe so you can pay whatever you want.

I hope you’ll buy the ebook and use it to improve your newsletter. To get things started, I’ve excerpted 10 of the questions from the book below. Let’s dive in.

1.) Can you describe your newsletter in a sentence?

Imagine, for a moment, that you and I are at a cocktail party. It turns out we both work in the email space. You ask me what I’m working on. I tell you: “I’ve got a newsletter!”

“What’s it about?” you ask.

“Every week, I share some stories I’ve read recently,” I say.

What’s the chance you’re going to subscribe? Zero? Less than zero? Have I given you any reason to believe that this newsletter will be relevant or valuable to you?

Let’s try this again. I tell you I’ve got a newsletter. But the pitch is better this time: “Every week, I make a newsletter just for people in the email marketing space, where I talk about the stories I read that week.”

That’s a little better. I’ve identified the audience I’m talking to. However, there are a lot of newsletters about newsletters, and I still haven’t given you a good reason why you should subscribe.

Let’s try it one more time: “I’ve got a weekly newsletter for email marketers. Every week, in 10 minutes or less, I examine a successful newsletter and walk through three tactics that have helped them make more money.”

I’d bet anything that right there, at that dinner party, you’d pull out your phone and subscribe.

What makes that third pitch so much better? I’ve identified a clear audience and I’ve identified the value for that audience: Actionable strategies they can apply to their newsletter. They’re going to be able to read, learn, and act.

If you know who your audience is and what the newsletter does for that reader, you’re going to have the chance to build something great.

But there’s one more key piece: The pitch needs to be concise.

You’ve got the pitch clearly identified when you can explain your newsletter in a single sentence. Try it now, and fill in the blanks: “I write the (name of your newsletter) and it (what it does) for readers.”

You’ve only got a few seconds to grab someone’s attention. Keep working on your newsletter pitch until you can explain it in a single sentence.

2.) What subject line format works best for your newsletter?

ubject lines should be a little like fingerprints: Unique to you and the emails you’re creating. Some newsletters like to use shorter subject lines, while others go longer. Some start every subject line with their newsletter name or an emoji, but many don’t. There’s no right way to write one — it’s up to you to figure out what your subject line style should be.

But there are a few rules everyone should keep in mind as you craft your subject line:

Rule #1: Set the tone for your email — Your subject line is your first chance to introduce whatever’s in that day’s email, so make sure it matches the tone of the message. It’s jarring for a reader, for instance, to see a fun, playful subject line and then to open the email to see content inside that’s serious or somber. From the subject line alone, a reader should have a sense of what they’re about to get into.

Rule #2: Deliver on your promise — If you’re promising “Our best deals of the year!” in the subject line and then offering the same 10% off coupon code a user would get on your site, you should rethink your subject line. Don’t overpromise and underdeliver — your readers deserve better than that.

Rule #3: If you’re not sure what to write, just be direct — Email is for action, so if you’re stuck between a few options, choose the one that gives readers the action you want them to take once they open the newsletter. When trying to win back a disengaged reader, I’ve found that the best-performing subject line is, “Do you still want emails from us?” The user knows exactly what they need to do when they see this — they need to open the email and confirm whether or not they’re interested in receiving additional newsletters. Don’t hide the action — spell it out in the subject line.

Rule #4: Be consistent with your subject lines — Imagine for a moment that you’re the kind of person who wakes up every morning and turns on the local news to start your day. (If you’re already this kind of person, then feel free to be yourself for this hypothetical!) Every day, the broadcast begins with the news station’s theme music. But then, one day, you turn on the news, and instead of that theme music, you’re greeted by the theme from “Benny Hill.” You wouldn’t feel entertained — you’d be confused. And that’s what happens if your subject lines change too much from day to day. You don’t want to startle your readers. Be consistent with your subject lines, and you’ll be able to build a consistent reading habit with your audience. 

Rule #5: Don’t worry about spammy words — Including a word like “discount” or “urgent” in your subject line isn’t going to land your email in the spam folder. Write the subject line you want — even if it does include one of those so-called spammy words.

Rule #6: Know where your subject line gets cut off — Every inbox displays different character lengths for subject lines. On the Gmail app, for instance, you’ll only get about 45 characters, but on the desktop version of Gmail, you’ll get up to 85 characters. Make sure to run a test of each newsletter so you can see what will actually get displayed in the inbox.

3.) What are you doing that doesn’t scale? 

The success of my business can be tied back to two days: The day I launched my newsletter, and the day I invited readers to set up free, 1-to-1 calls with me.

In the weeks that followed that invitation, I scheduled more than 75 calls with readers. Most conversations only lasted 45 minutes, but the learnings I gained from that time were invaluable. Those conversations shaped the work I still do today, and the only way I could have gotten those insights was by making time for my readers.

Many of the people on those calls became clients. Nearly all became loyal readers who enthusiastically shared my newsletter with their friends and colleagues.

Every newsletter should make time for a few things that don’t scale — those are the things that bring you closer to your audience. So reply to every reader. Direct message your contacts and ask them for feedback. Get coffee when you’re in a reader’s hometown. Send readers a personal thank you after they take a survey.

Those things don’t scale, but they can have a huge impact on your newsletter.

4.) Do you ask for something specific in your welcome email?

Here’s something worth trying with your welcome email: Asking a question.

Ask your readers to reply and tell you something. Maybe you want to know:

• Who they are.
• What they want to learn from you.
• What they’re struggling with or need help with.
• For a recommendation.

In my newsletter, I ask every reader, “What is the biggest challenge you’re facing with your newsletter?” (One in five readers reply.) I’ve also worked with local newsletters that ask questions like, “We’re always on the lookout for new restaurants to try in the area. What’s one place you’ve eaten at recently that I definitely need to try?”

This is crucial: The more specific the question, the more likely readers are to reply! (In my experience, you’ll hear nothing back from readers if you say, “Hit reply if you have any feedback.”)

Getting those replies is one of the best ways to start engaging with readers — and early engagement almost always helps keep your emails out of the spam folder in the long run, too.

5.) Are you asking readers for testimonials?

The next time you run a survey of your audience, add one question to the mix: “If you like my newsletter, would you mind describing why in a single sentence?”

Testimonials from readers can be hugely useful. You can deploy them on your sign-up page or on ads for your newsletter. You can use them to update the marketing strategy for your newsletter. You can use them to identify the content you should be focusing on in your newsletter.

Ask — and see what readers tell you they like.

6.) Do you make it easy for readers to share your newsletter?

Every reader on your email list has a friend who might also like your newsletter. They’ll happily share it with them — if you make it easy for them to do so.

Here’s the (not-so-secret) hack to getting readers to share: You’re going to pre-write the email they’ll share with their friends.

When you add a link to a newsletter, you can add what’s known as a “mailto:” link. When you click on one of those, instead of taking you to a website, it opens a new email for you to send.

And you can pre-fill that email with a subject line, body copy, and a link back to your newsletter sign-up page.

When you write this, make sure you give your best two-to-five-sentence pitch for why your newsletter is great. Write it in the first person — it’s a personal email, so it should sound like one.

Let’s say I’ve got a newsletter all about cooking food on the grill. For that newsletter, I might write something like this:

Subject line: I think you’d like this newsletter about grilling!

Body of the email: This guy named Dan writes a newsletter all about grilling, and I think you’d really like it! I always find a new recipe or two to try in each email. It’s free to read — you can sign up at this link —> danBBQnewsletter.com

Readers can always edit the message if they’d like, but if you pre-write this email, you’ve made it as easy as possible for readers to share it with friends. All they need to do is type in their friend’s email address and hit send.

7.) What do you say “no” to?

Saying “no” is the only way to protect your time, your skills, and your team.

Saying “no” is your way to make sure you’re focused on the things to matter most for your newsletter.

Saying “no” is how you’ll be able to say “yes” when the right opportunity presents itself in the future.

I’ll confess I hate to say “no.” Saying “yes” is my default setting. I like saying “yes” to new projects, new A/B tests, new revenue opportunities, and new ideas. But I know I can’t say “yes” to everything.

If I’m not sure if I should say “yes” or “no” to an opportunity, I give myself some space to think about the idea. I won’t make a decision right away. Instead, I put a note on my calendar to revisit the idea in a month.

And then I do nothing — at least for 30 days.

Often, a month later, I look at the opportunity and wonder: Why was I so excited about this? That’s not a bad thing — I’ve just saved myself a bunch of time and effort on an idea I wasn’t all that excited about! And that’s when I finally say “no.”

But if I’m still excited about the idea a month later, that’s how I know it’s worth the investment, and that’s when it’s actually worth the “yes.”

8.) What new content formats do you want to try?

If your newsletter is in a rut, it may be a good time to introduce a new format. Sometimes, readers tire of seeing the same structure in every newsletter.

For an independent writer, for instance, there are a number of content formats that work:

• Advice columns — Readers ask questions, and you answer them in an upcoming edition of the newsletter.
• Essays — Share thoughts or analysis on a specific topic.
• Event calendars — Share a list of upcoming events in your community.
• Q&As — Have a conversation with an expert or influential member of your community, and then share the highlights of the interview with readers.
• Lists — Put together a list based on a theme, like the best books to read this month.

Look through what other newsletters are trying and see if you can find a format or two that you can use as a template for an upcoming newsletter.

9.) Have you tried a poll?

An in-newsletter poll is a great way to collect feedback from readers. With a poll, you could:

• Ask readers how they felt about that day’s newsletter.
• Ask them what types of stories they want to read about next.
• Ask them to vote on how they feel about a certain topic.
• Ask them about themselves (where they live, what kind of work they do).
• Ask them a trivia question (and then answer it in the next newsletter).

A poll could be a great way to start a conversation with your readers.

It could help you understand how you’re doing or what you could do better with your newsletter.

It could be a way to drive some sort of engagement. With Apple’s Mail Privacy Protection, it can be tough to tell if a reader is actually opening a newsletter. A click on a poll is a way to tell that a reader is actually there.

It could also be a way to collect data about your users — what they like and what they want more of — and then use that data to create better segments of your audience.

Sometimes, simple tactics are also the most powerful.

10.) What’s on your “someday” list?

Here’s a future-looking task: Try putting together a list of “Somedays.” 

These are things you’d like to do, not today or tomorrow, but — as you’ve surely already guessed — someday.

With your Someday list, dream big. Someday, I’d love to launch a recruiting agency to match newsletters with talented writers and editors. Someday, I’d love to sell my own page-a-day desktop calendar, where every day, you get a new idea to try in your newsletter. Someday, I’d love to launch a year-long cohort learning program where newsletter operators learn together as they grow their lists.

Will I ever do any of these? There’s a reason they’re on my Someday list. They’re things I’m interested in but not ready to take on yet.

But Somedays do happen. Several years ago, I added one to my list: “Write an ebook.” You never know when something from a Someday list will become a priority — and a reality.