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Content debt

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The debt crisis: AI edition

What happens when you feed years of messy content into AI? In this episode, Bill Swallow and Alan Pringle dig into the content debt crisis, including increased system costs, neglected localization, and the fallout of “just use AI” mandates. They share practical insights to help organizations get back on track.

Alan Pringle: Is your content updated? Does it reflect the latest information? Is it created for all the different locales that your company serves? Is it in different languages? That is another pile of debt that when you start looking at AI, all the problems will be very brutally magnified, and you’re going to have to address them to really have a large language model that works at all.

Bill Swallow
July 13, 2026
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Make the move successful: Replatforming content ops

Replatforming your content operations isn’t just about swapping systems. In this episode, Alan Pringle and Bill Swallow share what organizations must consider to successfully replatform. From navigating technical debt, system integration, and the people caught in the middle, they discuss change management, technical debt, and why your exit strategy should be part of the plan from day one.

Software isn’t forever. Systems come, systems go, they get improved. Your requirements are ever changing with the content that you need to manage. Not thinking about your next jump is really to your detriment.

— Bill Swallow

Alan Pringle
April 27, 2026
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The five stages of content debt

Your organization’s content debt costs more than you think. In this podcast, host Sarah O’Keefe and guest Dipo Ajose-Coker unpack the five stages of content debt from denial to action. Sarah and Dipo share how to navigate each stage to position your content—and your AI—for accuracy, scalability, and global growth.

The blame stage: “It’s the tools. It’s the process. It’s the people.” Technical writers hear, “We’re going to put you into this department, and we’ll get this person to manage you with this new agile process,” or, “We’ll make you do things this way.” The finger-pointing begins. Tech teams blame the authors. Authors blame the CMS. Leadership questions the ROI of the entire content operations team. This is often where organizations say, “We’ve got to start making a change.” They’re either going to double down and continue building content debt, or they start looking for a scalable solution.

— Dipo Ajose-Coker

Sarah O'Keefe
November 3, 2025
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Cutting technical debt with replatforming (podcast)

When organizations replatform from one content management system to another, unchecked technical debt can weigh down the new system. In contrast, strategic replatforming can be a tool for reducing technical debt. In episode 172 of The Content Strategy Experts podcast, Sarah O’Keefe and Bill Swallow share how to set your replatforming project up for success.

Here’s the real question I think you have to ask before replatforming—is the platform actually the problem? Is it legitimately broken? As Bill said, has it evolved away from the business requirements to a point where it no longer meet your needs? Or there are some other questions to ask, such as, what are your processes around that platform? Do you have weird, annoying, and inefficient processes?

— Sarah O’Keefe

Sarah O'Keefe
August 19, 2024
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Renovation revelations: Managing technical debt (podcast)

Just like discovering faulty wiring during a home renovation, technical debt in content operations leads to unexpected complications and costs. In episode 171 of The Content Strategy Experts podcast, Sarah O’Keefe and Alan Pringle explore the concept of technical debt, strategies for navigating it, and more.

In many cases, you can get away with the easy button, the quick-and-dirty approach when you have a relatively smaller volume of content. Then as you expand, bad, bad things happen, right? It just balloons to a point where you can’t keep up.

— Sarah O’Keefe

Alan Pringle
August 12, 2024
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Technical debt in content operations

Technical debt, hereafter called “content debt,” is “the implied cost of future reworking required when choosing an easy but limited solution instead of a better approach that could take more time,” Wikipedia, “Technical debt.”. Like financial debt, content debt isn’t always a bad thing. You can use a loan to buy a house right away (at least in the U.S.) and then pay off the debt over time while living in the house. Content debt allows you to create something quickly instead of doing it exactly right and taking much longer. 

Too much content debt, though, will hamstring your work. The trick is to find the Goldilocks solution.

Sarah O'Keefe
July 29, 2024
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Content ops forecast: mostly sunny with a chance of chaos (webinar)

In this episode of our Let’s Talk ContentOps! webinar series, Scriptorium principals Sarah O’Keefe (CEO), Alan Pringle (COO), and Bill Swallow (Director of Operations) provide practical insights on the future of content operations. They’ll deliver sunny predictions, warn of upcoming storms, and equip you to weather unprecedented fronts in the content industry.

Sarah O'Keefe
July 22, 2024
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