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Struggling to nail your brand tone? Sit down with your 404 error page.

A day spent with your overlooked 404 error page might just unlock the brand tone and messaging answers you're looking for.
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Why is it so hard to define the tone & core messaging for a brand?

Companies often struggle defining the perfect tone, both written and visual, because it’s really rather difficult to not take one’s self too seriously when one knows that one is receiving important guests.

As founders, we’re so busy pitching, selling, and promoting the quality of our product and credentials (to our customers, would-be investors, our parents), that we can often end up overcomplicating things.

So, where to start?

Before highlighting your 404 error page as a really useful playground, let’s make sure we’ve got the basics covered. No rocket science here, just some straight-forward fundamentals:

Define thy audience

Your audience isn’t the world, an entire market, or even an entire market restricted by geography. Especially when in startup or early growth mode, you’re selling initially to a very distinct individual. We like to call them:

The Day Dot Evangelist

Your Day Dot Evangelist (DDE) is the individual who is most likely to appreciate what you’ve got to offer, and most likely to sing about it. You’re going to need them now, and into the future because you’re going to need a small, excited crowd who will refer and provide testimonials (social rule 101 for startups – promote thy customer).

Know thy Evangelist

Crack the perfect persona by brainstorming a day in the life of (including where your product doesn’t play a part – there’s gold there), or run a ‘Job to Be Done’ modelling exercise. However you get there, however formal or informal, you’d better have an idea of what they want and how they interact – essential in unlocking the foundation of your tone and how/where you’re going to approach them with your starter marketing too.

Know the problem you solve

Like, really know it. Get specific. If you’re in start-up mode, and you solve problems X, Y and Z, chances are you should only be focused on building out X anyways. If you deliver on that promise, your evangelist will wait for everything else.

Start shaping your lead messaging

OK so now you know the one thing you do, why you do it, and that specific pool of folk who want it. Great!

This is where most of us would jump straight into a homepage design, or a sales deck, or something of that sort. But that can often put far too much pressure on things. Starting with the all-important hook-line-sinker combo that’s going to sit as a masthead up at the top of your homepage for a year or more can be a daunting starting point.

I’ve seen brands struggle for days, if not weeks at this; only to remain forever indecisive because they’re trying to wrap too many objectives too soon – the brand, the tone, the sell, the promise. Also, the homepage mast isn’t the best ‘template’ from which to build other lead messages for eyeballs on landing pages, starter social posts, and other launch comms.

Enter, the humble 404 error page!

Your 404 – that pesky page that returns when someone tries to visit a page on your website that doesn’t exist. Maybe you moved it (and in which case, you really should set up a re-direct), or maybe your visitor just typed in something a little bit out there.

But how can the 404 help define the brand tone and core messaging?

Traditionally all a bit bland and often an overly-apologetic afterthought, if you’re having a little trouble establishing the tone of your brand, we’ve found that a discussion over your 404 can really help you find your tone and start crafting lead messages like a pro.

Sitting around your 404 takes the pressure off. It’s just a page that a small few users are going to arrive at, accidentally. It’s not your homepage masthead, crafted to sell your brand at hello. It’s not all that important.

Until it is.

Because everything you do starts or stops a user journey, you’re going to need to be engaging, empathic, informative and assistive (all things a brand should be) on your 404 in order to keep your visitor on site, and on side.

  • Are you going to be apologetic (is that really your brand)?
  • Is there room for humour?
  • How clever can you be to engage and signpost them to stop the immediate churn?

The 404 error page has enough of the core challenges you need to solve for your wider tone of approach, in a much less challenging way than anywhere else – and so, in many ways, it’s the perfect place to start.

Fourteen 404 error page examples

1. wawawi

404 error page design - key brand messaging tools - wawawi

Of course we’re starting here! Very quickly, we wanted to do do three things. We (a) didn’t want to apologise – 404s are just a thing, but we provide CX and some other technical services and our target market might not understand that, so we also wanted to (b) inform them what they’re seeing, while also (c) establishing a tone that doesn’t alienate or patronise.

So, no apology, just an informal yet informative blurb, with a link to this very article.

Key takeaway: Nobody is perfect. Cracking how your brand counters a perceived ‘mistake’ or error can define everything else you do.

2. Headspace

Less the shameless self-promo above, I’m starting with Headspace as a great illustration of a 404 error page that nails the tone of the brand. There’s nothing clunky here. Lots of space, a gentle animation, and brand copy that’s 100% on point. Their brand strap line is simply “Be kind to your mind”, and the “…enjoy a deep breath on us” on their error page is in tune with the rest of their website copy.

Key takeaway: How many words is too many words?

3. Medium

A favourite for being clever, this 404 error page is also totally on brand, carefully articulating what medium does for its customer in a tone you’ll find in all of their communications. The 404 error page cleverly links to member ‘stories about finding what you didn’t know you were looking for’. Pair this with the Medium evangelist and their thirst for surfacing interesting content and you get a classic example of a brand in action.

Key takeaway: Your customer wants to be informed and/or engaged. Focus on striking the balance.

4. Basecamp

It might not be the most visually appealing, but everything the folk at Basecamp is unashamedly focused on customer evangelists who love the way Basecamp operate, as much as the products they build. I couldn’t think of a brand more focused on the Evangelist, even to this day. Their copy is straight-forward, informative, and absolutely on the peer-level.

Key takeaway: Map the persona of your ideal, day dot evangelist up front. It’ll save hours of copy editing (and many other branding and messaging woes) later.

Bonus material: Basecamp founder Jason Fried’s blog – a must sub for anyone who works with brand, marketing, product, customers, staff, or anything else.

5. dashthis

Again, focusing on a brand who has nailed the customer fit, the 404 error page over at dashthis talks to a ‘technical marketer’ audience. It’s often no harm making your bullseye feel they’re in on the joke. Who cares if the rest of ‘us’ don’t get it!?

Key takeaway: Be brave enough to gun for the attention of someone who’ll actually buy from you at the risk of alienating those who won’t.

6. Drift

The Drift 404 error page is here as an example of great brand language. Everything else they write has the same approachable tone. Favouring sentences such as “not to worry” (vs. “sorry”), and “head over to our homepage” rather than just a ‘homepage’ CTA are subtle, but make all the difference.

Key takeaway: Find somewhere (like, say a 404 page) where there’s less detail to sweat when building out your brand’s core messaging framework.

7. Overflow

From the team who’ve nailed user-flow stories, overflow articulate the product proposition (mapping/working all user flows in a digital product) on their 404 error page, simply, and in tune with the rest of their site. “Back to home” might be letting things down a little (see drift, above), but otherwise a good clean example of a brand that knows who they are.

Key takeaway: Know the problem you’re trying to solve, and keep it front-of mind. At. All. Times.

8. Iterable

I’m loving the brand, proposition and language of Iterable. They’ve the confidence to use a creative, customer-truth-based headline (“Connect With Customers Like You Actually Know Them”), followed by a functional/descriptive strap line (“Iterable activates your customer data to help deliver joy”) on their homepage, and their 404 follows the same approach playing with the notion of an “epic fail” in a fun yet apologetic tone, without actually apologising.

Key takeaway: Your customer truth is both macro (day to day) and micro (specific, addressable pain point). Understand both.

9. Mighty Networks

Mighty Networks enable anyone to build a community online, and so their brand tone is informal, and extremely approachable. For similar reasons to including ‘drift’, the crowd at Mighty Networks (check them out, honestly), use language expertly. “Jump back to our homepage” is simple, but there are a thousand ways to say it.

Key takeaway: If your customer doesn’t wear a suit and tie, your brand shouldn’t either.

10. Loom

Probably one for the ‘creative use of a 404 page’ list, but we can all respect that the popular video recording service makingthink of using video yourself on their 404 page just makes sense. There’s likely a hell of a bit of kit under the hood at Loom, but the brand site, like any SaaS organisation should be, is about benefit and ease. This nails it.

Key takeaway: Never miss an opportunity to give your core services a nod (also see example 1, and example 14).

11. Tripadvisor

I’d probably get shot if I didn’t include Tripadvisor or Patagonia in this post, so here’s the former. Succinct and with a level of humour that pushes the brand a little, but doesn’t step outside of the positioning.

Key takeaway: Be as playful as possible, then strip it back 10 degrees (be ‘slay’ not ‘cringe’, according to my 11 year old duaghter).

12. Supermetrics

There are a lot or ‘risky’ 404 error pages out there. Supermetrics isn’t quite one of them, but is brave enough to run a play on words that will likely get at least a nod from its target audience. The majority of their web content is largely business and results based – it’s what a no-nonsense CTO/CMO type prospect wants. On their 404, Supermetrics have allowed themselves to play a little, and in doing so defined how far they can go with brand humour.

In contrast, a brand like Monday.com, who have a different role with their target segments, can go further when using a similar play as per their ‘holy sheets’ promo (I did take a look at their 404 too… unfortunately, it isn’t up to much. Yet).

Key takeaway: Your brand personality has rules, but it’s multi-dimensional too. Know when to dress down.

13. Solodev

Talking of knowing thy customer, and with shades of ‘dashthis’ and ‘Supermetrics’, Solodev are talking to their key customer segment on their 404 page. Solodev enables organisations to “build the perfect cloud stack”, and they’re darn good at it too. Brand tone is geared towards a technical audience, and so in reverse to ‘Iterable’ (above), they rightfully lead with a functional “Build the perfect stack” headline, followed by a more creative strap line featuring “assemble a best of breed stack” on their homepage. While their 404 leads with a more playful headline, it’s all in the same wheelhouse.

Key takeaway: Craft an experience for your actual customer (your customer likely isn’t your investor or your spouse – unless you’re crafting a pitch deck, or a Valentine’s card).

14. doddl

OK, we started with ours, so we’ll finish with one of our web client 404 error pages. All backed by a killer bit of custom SaaS, the team at doddl provide expert, no-nonsense advice to homebuyers and mortgage switchers. Accordingly, the brand essence is both authoritative and approachable, a tone carried into the 404 error page that also works to get the visitor back into key journeys.

Key takeaway: Be clear, concise, and creative. Your customers will appreciate it (especially in that Valentine’s card).


There are many great examples of creative 404 error pages. Check out this list by Hubspot, or the now famous most awkward 404 page on the internet.

But, as a tone building exercise, and to put together some of the early components of how you’re going to build out lead messaging and other content elsewhere, trust me – it’s worthwhile spending a day on your 404 error page before you go near anything else.

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