When AI Gets Tipsy: 5 Newsletter Blunders to Chuckle At (and Avoid)

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A bit of a light-hearted end-of-the-week email today…

I’ve been waxing lyrical about how much time AI can save you with your writing, and how the output can often be more thorough and better written than you’d come up with yourself.

Obviously there are some downsides too. Ones we’ve bumped into more than a few times.

And if you’re feeling a bit overwhelmed by this whole AI thing they may make you chuckle and reassure you that sometimes our AI friends aren’t quite as clever as they might think they are.

So here, with all the dogmatism of brevity, are my top 5 AI blunders:

1. "When Numbers Go Haywire"

Your AI confidently declares your product has a 1000% satisfaction rate. Impressive. But…

Unless you've cracked the code to parallel universe customer service, something's a bit... off.

It’s not always going to be as obvious as that. It’s more likely to be a quote about a 57% improvement some company saw or £1.2m of savings or another vaguely plausible number that conveniently backs up your point.

Our finding is that AI is very reliable when there’s lots of data available. But when there’s a numbers vacuum it tends to panic and make things up.

Tip: Double-check those stats with good old-fashioned Google. In fact often just asking your AI to double-check its figures will result in it ‘fessing up.

2. "The Case of the Imaginary Expert"

Ever heard of Dr. Fakey McFakeface, the world-renowned expert in... everything? No? That's because your AI might have just invented them to back up a claim. The same goes for referencing.

We wrote a couple of dozen AI-assisted articles with detailed referencing (in APA 7th Edition style no less) and Claude nailed them perfectly. Then all of a sudden, out of nowhere, it got about half of them wrong on the next article.

As with point #1 it was most likely because there were plenty of available references for the first articles but we veered into more obscure territory with our later one.

Tip: Always cross-check at least a sample of your references or expert quotes. Ideally all of them.

3. "The Jekyll and Hyde Newsletter"

Does your newsletter start sounding like a formal academic paper and end like a text from your teenage nephew? You might be experiencing a case of AI personality disorder.

This happens particularly when writing a long article via multiple prompts in a chat. As you fill up your AI’s “context window” (working memory) it seems to forget things from earlier in your chat. We’ve had it lose the writing style, or even forget the main topic of the article and start writing a section completely out of context.

Tip: Repeat the main style parameters you’re looking for in every prompt (e.g. “please use my writing style as you analysed earlier” or “please write in a minimalistic journalistic style at Flesch-Kincaid Grade Level: 9-11”). And use phrases like “Remember to keep it in the context of [umbrella topic]” to avoid your AI disappearing off down a rabbit hole.

4. "The 'Oops, Wrong Audience' Blunder"

Nothing says "we value you as a customer" quite like explaining basic industry terms to your expert audience, or peppering your newsletter with Gen Z slang when writing to retirees. Fr.

Tip: Make sure your AI knows your audience as well as you do. Give it a clear picture of who's reading, and it'll be less likely to make your readers go "Huh?". Our early years articles always include an audience definition along the lines of “You’re writing for an audience of early years professionals and practitioners who work in nurseries and kindergartens and are looking to develop their professional skills and provide the best support to the children in their care”.

5. "The Clickbait Catastrophe"

"You Won't BELIEVE What This Newsletter Says (Number 4 Will SHOCK You!)" If your subject lines are starting to sound like they belong in a late-night infomercial, your AI might be going a bit overboard.

It’s not just headlines. When you ask an AI to write a promotional email or post it has a tendency to go a bit over the top. In our case every interview Kathy has done is apparently game-changing or revolutionary.

Tip: if your AI comes back with something over the top you can tell it to try again and be less clickbaity. For our emails we add prompts like “Avoid hyperbolic phrases like ‘game-changing’ and ‘transformative’”.

So there we are: five AI blunders that might be lurking in your newsletters.

But don't worry – with a bit of oversight and a good sense of humour, you and your AI can create newsletters that inform, engage, and occasionally make your readers smile for all the right reasons.

Until next time, keep it real (even when your writing buddy isn't)!

- Ian

PS: This newsletter was written with the help of an AI. Any unintended blunders are purely the fault of Claude, not me. Obvs.