How to write a newsletter people reply to
A client sent me this Slack a message last week...
This was the reply they received from said prospect who they hadn't heard from in two years...
That prospect went quiet after an initial conversation and never came back. Until last week.
The fun part? I knew this was coming. Not that specific email, but something like it.
When we started working together a few months prior, I told them one of the signs that your content brand is taking shape is that you'll start getting replies to your newsletter, DMs on LinkedIn, etc.
Not just "great issue!" replies. Real ones. People telling you...
- They're dealing with exactly the same thing.
- They forwarded it to their team.
- "Get out of my head."
Resonance.
Most companies sending newsletters (or creating for any medium) aren't getting those replies. They're not resonating on that level.
They're getting opens. Maybe a click or two. The content goes out, the metrics come back, nobody says anything. It's content into the void.
That's because most newsletters aren't designed to make anyone feel anything.
They're link dumps. Undifferentiated.
When I first got on a call with this client, I didn't need to see their newsletter to know what it looked like. I asked a few questions — how often they sent it, what was in it — and the picture was clear.
- Sent monthly.
- Came from the company, not any one person.
- Curated links (recent blog posts, upcoming webinars, downloadable resources, a few tips, etc.)
No inherent value in the medium itself. You had to click away in order to receive it.
When I suggested scrapping it in favor of a new format, the first question wasn't pushback. It was genuinely curious: "But what do we do with all the other stuff? The links we were sharing?"
I asked what those links were getting them.
About one click per email. Sometimes less.
One of them said it out loud: "So maybe your approach is the better one."
Here's what we changed:
- It comes from a person, not a company. A co-founder's name at the top, his voice throughout. First person. Readers know exactly who they're hearing from.
- No links out. The value lives inside the email. No clicking away to get it.
- One idea per issue. Not a roundup. One focused thought, developed fully, grounded in what their team actually sees with customers every day.
- Content starts from the inside out. Every issue begins with their own experiences, observations, and insights rather than relying on keyword volume or competitor content telling them us what to write about.
- Problems over solutions. Instead of "10 ways to set up your CRM," the newsletter asks: what does it look like when your CRM is set up wrong? The symptoms. The specific signs something is quietly broken that your team has just learned to live with.
One recent issue mapped out eight of those signs. Not generic warnings, but real, expert observations. Written in his words, from his experience with customers.
A prospect who'd gone cold two years earlier read that issue. Two years ago they had implemented the same software. Two years later, they were still feeling it.
He replied, CC'd his Head of Ops, and asked to get back on the calendar.
That's what a content brand does and looks like in practice.
Generic advice or a link to a blog post doesn't do that.
But when someone reads your newsletter and sees their own problem described back to them, in the words of someone who clearly lives in this work every day, they don't just click. They reply.
The format matters. But the format is just the container.
What goes inside it, specific, experience-backed, problem-framing thinking that only you can write, that's what motivates someone to explore not just more of your content, but your product or services, too.
If your newsletter (or blog, or podcast, or social presence...etc., etc.) looks like everyone else's, that outcome isn't possible.