Content Debt

How putting content on the back burner impacts the user experience.

Think about a library book you want to borrow. How easy it is to look up the book, find it on the shelf, and take it home.

How easy it is to return it.

Now imagine this was the most disorganized library in the world. The online catalogue can’t tell you if the book is in the library or if it’s checked out. There are cookbooks in the horror section and sci-fi novels in the self-help area. The authors are not in alphabetical order, and the Dewey Decimal system seems to never have been invented.

Unfortunately, when it comes to how most companies manage their content, it looks a lot more like the books at your local garage sale than your local library.

Debt, debt and more debt

Technical debt owes its origins to software developers who realized pretty fast that creating things quickly can be scrappy and yield great proofs of concepts — but also leads to a lot of disorganization, confusion, and general trouble down the road.

The same thing happens with content debt.

The thing with content, technical, or plain old money debt is that after a while, it really slows you down and crushes your ability to reach your fullest potential. Because it often accumulates slowly –– then all of a sudden very quickly –– it’s easy to put it on the back burner, unprioritized until it becomes a very big problem.

Every organization has some amount of content debt. For us at Square Risk, here’s how content debt has affected us, and what we’re doing to tackle it.

Inability to grow

It’s no secret that Square is expanding globally. But a global expansion takes a lot of energy, planning, and effort. Someone has to do a cost-benefit analysis, competitive market research, asset acquisition mapping (one of these is definitely made up) and a lot of other business words that people are paid well to understand.

However, what almost always comes last is the realization that the existing content in our hands needs to expand, too. Except, does anyone actually know where all that content is? Sometimes the answer is “kinda, but not really.”

Unfortunately, when it comes to how most companies manage their content, it looks a lot more like the books at your local garage sale than your local library.

The process of organizing, sorting, and archiving content is intrinsic to growth. However, it’s often abandoned in favor of creating and curating new content (new content is always cooler).

The problem that is easy to run into is that the people who create new content may not know exactly what is needed to organize content for localization.

What does this look like for a globally expanding team? Well, it’s a complete mess.

The user experience for any new region in which the expansion occurs will be spotty. In the case of a global expansion, trying to find all your content is a pain, and you’re never really sure you have it all. This can look like customers getting the wrong message, getting accidentally offensive messaging, getting important messaging in the incorrect language, or just not getting the message altogether.

And from a UX perspective, it’s a bonafide nightmare. While we can spend all day discussing what an experience can and should be, nothing can make your customer feel more like a complete afterthought than communicating with them in the wrong language. The last thing you want is someone thinking you’re creating their experiences without them in mind.

What we’re doing to fix it: We are taking steps to start being more mindful in designing our content and being more strategic with it. We’re hiring more UX practitioners to help us unpack and unblock seller pathways with more in-depth research and deeper understanding of user pain points. Lastly, we’re documenting our processes more as they’re done so we can continuously iterate and improve our methods.

Mixed messaging

In order to work correctly, messaging needs to be owned by someone. Not by 204 different functions, but by one. And that function, if at all possible, should be one that has some level of content design involved.

Similar to the inability to scale, mixed messaging happens when content is disorganized. It’s how you end up with 17 different emails from the same company at the same time, which is an incredibly frustrating experience for users.

The thing is, many companies may not know that it’s happening.

The consequences of content debt are ugly. They’re predictable, trackable, quantifiable and fixable. Content debt needs to go.

With so many ways to communicate — email, notifications, text messages, banners — teams, even those within the same company, may not realize how adding a new form of communication interacts with an existing one.

To you, the need to create a notification that automatically goes out when X happens is imperative. The fact that perhaps another team has something similar that can be reused, or that you can expand an existing notification to encompass the new scenario, is often ignored in the urgency to create a brand new piece of content.

What we’re doing to fix it: We’re committed to taking a more holistic approach to our work. With remote teams, different organizations, and time zones that span the globe, it’s easy to get messaging mixed up. We’re working to understand the nuances of the intersections of our content. What someone might be doing on one team may have an impact on a completely different team. Whenever we see these nodes and junctions, we’ll talk to each other, reach out, and ask for help so we can avoid…

Confused and unhappy customers

Obviously, getting a ton of mixed messages in the middle of your user experience can be frustrating. Which of course leads to confused and unhappy customers. The ultimate failure –– er…learning experience –– for a UX practitioner.

Nothing can make your customer feel like more of a complete afterthought than communicating with them in the wrong language.

And if your job involves things like helping people run their business and handle their money, then the situation is even worse.

Chipping away at content debt by setting ground rules about how, why, and when you create copy helps you keep your customers happy. But even more importantly, being organized helps you get ahead of very bad user experiences (or at least clean up after a bad one).

What we’re doing to fix it: Building and maintaining trust. Two of the areas affected most by content debt at Square are our Risk and Compliance departments. Anyone going through a chargeback, experiencing fraud, or unknowingly violating one of our Terms of Service is going to have an experience with one of these two teams. And unfortunately, that experience is admittedly not the best. That’s why Square Risk and Square Compliance have banded together to create the Seller Health team, which will be responsible for helping teams find these shared adverse experiences and work through them to create better ones.

Lost time and doubled up effort

Disorganized content is expensive. Very expensive. People are being paid to create things that already exist and redo things that have already been tried, failed, and tried again. Employees have to learn new workflows and dig through a content management system (CMS) that someone else has already dug through, which may or may not be on the way to a deprecation.

All this costs money. So much money.

The cost of employee labor, bad customer experiences, redundant content management systems, and hours of manual work — it’s clear that bad content management is expensive.

But the part that is the most expensive by any metric? The permanent loss of your customers’ trust.

What we’re doing to fix it: Eliminating content debt and bloat. We’re planning on spending a lot more effort on organizing and maintaining our content, and reducing the amount of content (and length of content) we create.


“We’ll get to that later” is a phrase commonly heard when it comes to creating, editing, auditing, and maintaining content. There are always, it seems, much more pressing issues than figuring out what to do with existing content, where it goes, and who owns it. Engineering needs resourcing, we need to hire more designers, we have to train a new project manager.

But the consequences of content debt are ugly. They’re predictable, trackable, quantifiable, and fixable. Content debt needs to go.

And the faster we can get control of it, the faster we can move our organizations forward.