Inside the March 2026 roundtable : Automations built in isolation will clash

March's email roundtable was yet another saucy one. We had CEOs and CMOs of good businesses who already have automations running, which led us to ask a lot of honest questions about what those automations were actually doing.

Here are the three main topics we covered:

1. Automations built in isolation will clash

Most businesses build automations to solve one problem at a time: a welcome sequence here, a post-purchase flow there, a call reminder automation somewhere else - but nobody steps back to look at the whole picture.

What ends up happening is that subscribers are getting three emails in one day because one action got them into two different automations plus the regular newsletter cadence. We all cringed collectively at the very thought.

My two cents: the problem isn't the individual automation, or even the emails within each one. It's the fact that nobody mapped how they interact with one another, or what happens when a subscriber takes any action that moves the relationship with your brand from one stage to the next. 

For the first time in one of these roundtables, I showed a complete email customer journey map I recently built for a client so everyone in the room could see what this ecosystem thinking looks like in reality (one more perk for joining one of those live!).

2. Your Email Service Provider (ESP) won't tell you when something breaks

One attendee shared that just days before the roundtable, they discovered that their re-engagement sequence had been switched off by their platform. It had been off for months and nobody had noticed. Then, one day, 60,000 contacts went through it all at once (which can be a huge issue for deliverability and very confusing for many subscribers).

My two cents: your platform won't flag when an automation has stopped running, when it's firing at the wrong moment, or when it's working against the experience and trust you've spent years building. So you can’t set and forget an automation once it’s up and running. (This is one of the many things I check regularly with clients who hire me as their Chief Email Officer.)

3. The ROI of automations isn't always linear

Automations are usually built with a specific goal in mind. But in many cases, they end up achieving other things that are just as valuable, if not more.

Here's an example of a client I worked with last year whose list had gone cold: they hadn't been emailing consistently, and without a strategic re-activation, deliverability would’ve been at serious risk the moment we started sending emails more regularly. So before anything else, we created a re-engagement sequence. The goal was to wake the list up and set the right foundation for everything that was coming next.

We included a survey in that sequence, and we got 30 submissions from people who were interested in what the company had to offer. That opened the door for Sales to reach out and start conversations, gather more data, and fill up their pipeline. From the client's end, those 30 responses were one of the most valuable outcomes of this automation.

My two cents: making or saving time or money, or both, is only the first layer of automation ROI. The second layer is building authority, trust, and relationships that compound over time - and those will never show up in your ESP dashboard. If you're relying only on your ESP stats, you’re seeing a very partial image of what email is doing for your business.

Many businesses think that once their automations are sorted, it's time to shift the focus to growing their lists (so that people would actually go through those!). Which makes sense, but it’s not necessarily the first thing I recommend you’d do.

The email roundtables are hosted monthly, each one addressing a topic that fits where good-doing businesses are at, or what they need to revisit at that stage instead.

If your business for good is sending emails, you don’t want to miss these discussions. 

Seats are limited to only 10 and the only way to grab one is to sign up to my newsletter. 

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