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Content pitfalls

AI Content pitfalls Podcasts Structured content

Futureproof your content ops for the coming knowledge collapse

What happens when AI accelerates faster than your content can keep up? In this podcast, host Sarah O’Keefe and guest Michael Iantosca break down the current state of AI in content operations and what it means for documentation teams and executives. Together, they offer a forward-thinking look at how professionals can respond, adapt, and lead in a rapidly shifting landscape.

Sarah O’Keefe: How do you talk to executives about this? How do you find that balance between the promise of what these new tool sets can do for us, what automation looks like, and the risk that is introduced by the limitations of the technology? What’s the roadmap for somebody that’s trying to navigate this with people that are all-in on just getting the AI to do it?

Michael Iantosca: We need to remind them that the current state of AI still carries with it a probabilistic nature. And no matter what we do, unless we add more deterministic structural methods to guardrail it, things are going to be wrong even when all the input is right.

Sarah O'Keefe
November 17, 2025
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AI Content debt Podcasts

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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CCMS CMS Content management Content pitfalls Headless CMS Learning content LMS Podcasts

Tool or trap? Find the problem, then the platform

Tempted to jump straight to a new tool to solve your content problems? In this episode, Alan Pringle and Bill Swallow share real-world stories that show how premature solutioning without proper analysis can lead to costly misalignment, poor adoption, and missed opportunities for company-wide operational improvement.

Bill Swallow: On paper, it looked like a perfect solution. But everyone, including the people who greenlit the project, hated it. Absolutely hated it. Why? It was difficult to use, very slow, and very buggy. Sometimes it would crash and leave processes running, so you couldn’t relaunch it. There was no easy way to use it. So everyone bypassed using it at every opportunity.

Alan Pringle: It sounds to me like there was a bit of a fixation. This product checked all the boxes without actually doing any in-depth analysis of what was needed, much less actually thinking about what users needed and how that product could fill those needs.

Bill Swallow
June 2, 2025
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Content pitfalls Content silos Industry insights Podcasts

Do enterprise content operations exist?

Is it really possible to configure enterprise content—technical, support, learning & training, marketing, and more—to create a seamless experience for your end users? In episode 177 of the Content Strategy Experts podcast, Sarah O’Keefe and Bill Swallow discuss the reality of enterprise content operations: do they truly exist in the current content landscape? What obstacles hold the industry back? How can organizations move forward?

Sarah: You’ve got to get your terminology and your taxonomy in alignment. Most of the industry I am confident in saying have gone with option D, which is give up. “We have silos. Our silos are great. We’re going to be in our silos, and I don’t like those people over in learning content anyway. I don’t like those people in techcomm anyway. They’re weird. They’re focused on the wrong things,” says everybody, and so they’re just not doing it. I think that does a great disservice to the end users, but that’s the reality of where most people are right now.

Bill: Right, because the end user is left holding the bag trying to find information using terminology from one set of content and not finding it in another and just having a completely different experience.

Sarah O'Keefe
October 21, 2024
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CCMS CMS Content debt Content pitfalls DITA Localization Podcasts Replatforming Structured content Translation

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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Content debt Content pitfalls Podcasts

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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Content debt Content pitfalls DITA Localization Structured content

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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CCMS CMS Content debt Content pitfalls DITA Webinar

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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Change management Content management Content pitfalls Content reuse Content silos Industry insights Podcasts Structured content

The challenges of content operations across the enterprise (podcast)

In episode 167 of The Content Strategy Experts Podcast, Sarah O’Keefe, Alan Pringle, and Bill Swallow discuss the difficulties organizations encounter when they try to create a unified content experience for their end users.

AP: Technical content, your tech content or product content, wants to convey knowledge so the user or reader can do whatever thing that they need to do. Learning content is about improving performance. And with your knowledge base content, it’s when, “I need to solve this very specific problem.” So those are the distinctions that I see among those three types.

SO: Okay, and from a customer point of view, what does this mean?

AP: Well, in reality, I don’t think the customers care. They want the information available, and they want it in the formats they want it in. And also, they want the right information so they can either get that thing done, improve their performance, or solve a specific problem.

Sarah O'Keefe
June 3, 2024
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Change management Content pitfalls Podcasts Structured content

Ask Alan Anything: Resolving pain in content operations (podcast, part 2)

In episode 156 of The Content Strategy Experts Podcast, Alan Pringle and Christine Cuellar are back discussing more pain points that Scriptorium has resolved. Discover the impact of office politics on content operations, what to do when your non-technical team is moving to structured content, and more.

“Here’s the thing. Skepticism is healthy. If people are trying to poke holes in this new process, sometimes they can actually uncover things that are not being addressed. That is real, that is useful. So don’t confuse that with people who were being a-holes and just being contrary for the sake of being contrary. Those are two different things, and you’ve got to be sure you understand those two things.”

— Alan Pringle

Christine Cuellar
November 27, 2023
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CCMS Content management Content pitfalls DITA Podcasts

Ask Alan Anything: Resolving pain in content operations (podcast, part 1)

In episode 155 of The Content Strategy Experts Podcast, Alan Pringle and Christine Cuellar dig into pain points that Scriptorium has helped organizations resolve since 1997.

“The amount of time content creators spend on formatting and for little payoff, it’s just… the numbers don’t add up. Especially in the 21st century now that we have so many automated ways to publish things to multiple channels, if you are futzing and tinkering with formatting trying to deliver to multiple channels, I can say with a great degree of certainty, you are absolutely doing it wrong.”

— Alan Pringle

Christine Cuellar
November 13, 2023
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Brand credibility Business case/ROI Content pitfalls Scalability Structured content

Quick fixes in your content equal long-term problems

Even when you put an excellent plan for content strategy and solid content operations in place, you can be sure that there will be surprises. Your authors will come up with weird outlier content that your current formatting and your current information architecture can’t accommodate. Faced with a deadline, a quick and dirty solution is appealing.

But those quick fixes have hidden costs that add up over time, especially if the workaround gets popular.

ScriptoriumTech
February 28, 2022
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