The toughest question you never asked about your website

Avoid these common writing traps and deliver better websites

Max Sheridan
Copy Cat
4 min readDec 12, 2022

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Thou Shalt Not Fill Containers by Tug Wells. Photo: Charlton Heston as Moses

“Instead of throwing a big carousel on the page and being done with it, thinking about making a website like an essay encourages us to focus on the tough questions. We need an introduction, we need to provide evidence for our statements, we need a conclusion, etc. This way we don’t have to get so caught up in the same old patterns that we’ve tried again and again in our work.”

— Robbie Rendle, CSS Tricks

I don’t know what I like more about CSS Tricks. The fact that they’re hardcore CSS nerds who write page-turning newsletters, or that they advocate for good writing in web design.

Even if you’re not a CSS nut like I am, I do recommend checking out their blog. Sure, there’s plenty of code that’s way over most of us writers’ heads, but it’s always well contextualized. How can I actually use this on a website to take my content further?

The CSS Tricks newsletter, in particular, can teach us writers a thing or two about crafting accessible, engaging content, thanks to CSS Tricks founder, Chris Coyier, who sets the tone.

Ok, pitch over.

Today, I really just wanted to carve a minute out of my day to give a little headspace to CSS Tricks’ Robbie Rendle, whose words of wisdom you can find at the top of this article, if you haven’t already.

Because, really, they’re spot on.

Tough questions, old patterns

We’ve always framed websites as narratives around here, i.e. as stories with hooks, problems and solutions. But even when writing a typical website story arc, it’s super easy to fall into the trap of ignoring Rendle’s “tough questions” and “getting caught up in the same old patterns.”

From a writing perspective, those questions really don’t change much from website to website. They’re essentially: who am I writing this website for and what do they need to read to start really caring about its products or services?

The “patterns” are a little more difficult to pin down because patterns in web design and writing are partly dictated by trends. Tired writing is always tired writing, but 2020’s mediocre copy will be distinguishable from 2000’s.

For the sake of argument, let’s say, like Rendle, that public enemy number one for copywriters is websites crammed with claims but without any persuasive evidence to back those claims up.

Telling, not showing, if you’ve ever taken a fiction writing class. Pushing products rather than proving value, for websites.

Basic storytelling (and essay writing) principles, yes, but devilishly easy to overlook when actually writing a website — with pretty dire results.

Here’s what I mean.

Show, don’t tell

Just close your eyes and think back to the last website you visited with a scroll-activated 2,914 coffees drunk, 1,055 projects undertaken animation.

Cheesy? A little, sure. But in storytelling terms, that’s telling, not showing, which is dangerous for a few reasons.

One, the amount of caffeine flowing through your veins and the number of jobs you take is a loud statement, not proof of anything. It doesn’t tell me anything about the quality of your work or how you can help me, and hence doesn’t advance your argument (hire me!) an iota. Your “evidence” has no real weight.

Two, that particular information serves no purpose other than to fill containers.

And if that isn’t setting off any alarms, consider this. If Moses had delivered 10 website writing commandments, thou shalt not write copy just to fill containers would have been at the very top of the list.

Always write for the user

Now for those difficult questions.

Do you remember the last website you visited that reeled off its services, i.e. what they did, instead of speaking to your pain points, i.e. what you got?

Figuring out what your clients do as a business is obviously hugely important for any website you’re writing. But this is more important: figuring out how to make their visitors feel like they’ve discovered something that can change their lives for the better when they’re interacting with it.

If you don’t, you’re not taking the time to think about and address the tough questions for your clients. Which, let me say, are incredibly challenging to answer head-on and take a ton of creative thinking that goes way beyond words or copywriting.

Or maybe this will frame it better. Do you remember the last website you visited that really tackled the toughest question of all — why you should click and become a subscriber, follower, user? — and got it right?

That’s the website you should be writing like. (Here’s one of our favorites.)

Never dumb down (the first draft)

Personally, thinking out of the copywriting box is always liberating. It lets me escape the burden of template thinking, which always says, “This website does things right. I’m going to follow their lead.”

And lets me start asking: “What would I want to read here if I was looking for a [insert your product or service here] and the sky was the limit?”

Actually, as a writer, the sky is the limit (at least for the first draft), so pushing clients in the right direction — challenging them to answer those tough questions — is always good. (Read: noble, if sometimes fruitless.)

Because, as Robbie Rendle puts it so well, dumbing down texts to satisfy the dumbed down tastes you project onto your visitors is a self-fulfilling prophecy. Put them to sleep and they will yawn.

The collateral damage of this approach?

The brands you’re writing about.

If you do want to see some examples of leads to follow, here’s Robbie Rendle’s original article on CSS Tricks. It has a few good ones.

But that list is obviously just a starting point. If you’ve stumbled across a website that got it right, share it with us please. We’re always looking for new ways to phrase the tough questions.

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Max Sheridan
Copy Cat

Copywriter by day. Author of Dillo and God's Speedboat. Name a bad Nic Cage movie I haven’t seen and I owe you lunch.