Issue #245 All About Email

Hi, {{first_name|friend}}. 👋

Welcome to Issue #245 of All About Email!

Last week, we went back in much more detail to something I mentioned almost in passing in Issue #237, one of about fifteen reasons I listed for why subscribers don't click. I gave it two sentences and moved on.

This week, I have my first guest author of the summer! We will take a look at deliverability as email therapy: uncover the habits behind complaints, poor engagement and filtering, and make the changes that rebuild trust.

Let’s go! 👇

🏝️ It’s the beginning of the annual summer series, bigger than ever before, and I’m beyond excited to introduce my first guest.

Alison will tell you a little bit more about herself later, but if Alison speaks, I listen. I’ve been waiting for this moment for two years, so without further ado, I take it away, Alison Gootee. 👇

A while back, I wrote a LinkedIn post about how Spamhaus listings mirror the stages of grief. Denial ("This must be a mistake"). Anger ("Get us off this list NOW!"). Bargaining ("What if we just sunset unengaged contacts but don't implement confirmed opt-in?"). Eventually, acceptance. Once you see the resemblance, you can't unsee it.

But here's what I've realised after over a decade of doing this work: it doesn't just happen with blocklisting. It's basically the same story every time, which has led me to a somewhat uncomfortable conclusion:

🧠 Deliverability consulting is just email therapy.

Most of the time, senders already know exactly what's wrong; they just don't like the answer.

💡 The devil is always in the (omitted) details. Deliverability conversations rarely start with outright lies. They start with half-truths, and the interesting part is rarely what people tell me, but what they leave out.

🚨 When a sender tells me double opt-in is too risky because they'll lose subscribers, my question is always the same: if those people genuinely wanted your email, why wouldn't they confirm?

(Nobody has ever enjoyed that question!)

🤷‍♀️ Okay! Then why are they generating spam complaints? Why are they going to addresses at yhaoo[dot]com? Do those seem like the behaviours of people who are excited to hear from you?

💡 If a message is truly expected, relevant, and wanted, complaints should be extremely rare. Addresses should be pristine. When they're not, the relationship deserves a closer look.

Great! Then could you explain why, if your targeting is so precise, people reported you as spam?

💡 The segmentation might be "sophisticated" (because it has to be, to obscure bad behaviours). The audience could technically be "highly engaged" (with someone else, somewhere else). The content strategy "mature" (spamming is as old as email).

When I see a campaign going to thousands of disposable Tempmail addresses, I start feeling less like a consultant and more like a therapist asking gently probing follow-up questions:

🧠 Nobody schedules an urgent call because inbox placement is fantastic and revenue is climbing; they call in an expert when something hurts. And when something hurts, people do what people have always done: we look for a solution that doesn't require changing our behaviour.

Maybe there's a secret setting. Or a new IP to rotate in. Maybe Gmail is wrong. Maybe Spamhaus is wrong. Maybe everybody is wrong except us. Maybe they're in cahoots with our biggest competitor!

🤭 (Okay, and maybe you're just a little delusional right now, babe.)

💡 The questions change, but the underlying request is often the same: Can I keep doing the thing that's causing the problem, but with your approval?

Sometimes the answer is a conditional “yes”. Yes, you can keep sending to your engaged users if they actually signed up for what you're sending, and you can prove it.

❎ But often the answer is “no, you need to make some changes”, and that's where the real work begins.

I rarely discover the root cause of a deliverability problem on my own. Most senders tell me what it is within the first fifteen minutes, and my job is to help them accept that it’s the problem.

💡 The most successful senders I've worked with aren't the ones who never have problems; they're the ones who are willing to be brutally honest about them.

🚨 The inbox is refreshingly, if brutally, honest. It tells you the things your subscribers aren't saying out loud. If you're not listening to complaints, poor engagement, and filtering decisions, eventually you'll hear it more directly, in a very awkward but productive meeting with somebody like me.

You can always stop coming to sessions; nobody's forcing you to listen. But if you plan to keep seeking second opinions until somebody tells you to continue doing exactly what you're doing, I have some unfortunate news about both therapy and deliverability.

🤔 So, how does that make you feel?

Not ready to book a session? I post free deliverability advice on LinkedIn every week. No copay.

🎉 A huge thank you to Alison for kicking off this summer’s series. As always, during my time on her couch, I laughed while taking away some excellent advice with a healthy dose of honesty.

💡 If you felt this week’s advice was aimed a bit more towards enterprise, think again, the psychology is the same even if you have a smaller list.

A few things I want to pull out from this one. 👇

💡 And yes, if you've ever sat in a meeting (or a Zoom meeting, or an email thread) quietly knowing the answer but hoping someone would tell you it wasn't, this piece is about you…

It's about all of us, at some point.

See you next week, {{first_name|friend}}. 👋

Every week, as I write this newsletter, I'll share the track of the moment to create an unbelievably eclectic playlist just for your inbox.

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This week's excellent and insightful email news & tips:

If you have any questions about this email or email marketing, please reply, and I will get back to you as soon as possible.

I hope you have a great week! 👋