Discussing Stupid: A byte-sized podcast on stupid UX

Headless vs traditional CMS: Which one fits your organization?

High Monkey Season 2 Episode 16

In this episode of Discussing Stupid, Virgil sits down with High Monkey’s Senior Developer, Chad Heinle, to break down one of the most debated choices in modern digital strategy: headless vs traditional CMS.

While flashy features and buzzwords like “omnichannel” dominate vendor pitches, the real decision comes down to your organization’s resources, structure, and long-term goals. Chad and Virgil dive into the practical realities of each approach, helping you cut through the hype and avoid the biggest mistakes teams make when choosing a CMS.

They also explore:
• Why your internal team structure matters more than the CMS features
• The rise (and reality) of content hubs and static site generators
• What “freedom” really means in a headless setup
• How traditional and headless CMSs are merging in unexpected ways
• Why reuse and omnichannel content sound good—but rarely happen

Whether you’re in IT, marketing, or somewhere in between, this episode will help you make smarter, more grounded tech decisions.

For more conversations about digital strategy, UX, accessibility, and all the ways we get it wrong (and how to get it right), visit www.discussingstupid.com and subscribe on your favorite podcast platform.

(0:00) - Intro
(2:10) - It's not about the CMS, it's about your team
(4:44) - Headless gives you freedom - if you're ready for it
(6:36) - Traditional & headless are starting to look alike
(9:56) - Don't choose a CMS based on buzzwords
(12:00) - There's no perfect CMS - just the right one for you
(15:00) - Outro

Learn more about High Monkey
https://www.highmonkey.com/

Subscribe for Email Updates on Our Website:
https://www.discussingstupid.com/

Watch Us on YouTube:
https://www.youtube.com/@discussingstupid

Listen on Apple Podcasts, Spotify, or Soundcloud:
https://podcasts.apple.com/us/podcast/discussing-stupid-a-byte-sized-podcast-on-stupid-ux/id1428145024
https://open.spotify.com/show/0c47grVFmXk1cco63QioHp?si=87dbb37a4ca441c0
https://soundcloud.com/discussing-stupid

Check Us Out on Socials:
https://www.linkedin.com/company/discussing-stupid
https://www.instagram.com/discussingstupid/
https://www.facebook.com/discussingstupid
https://x.com/DiscussStupid


>> Virgil:

You're never going to find that technology that's going to do everything you want in the world. And so you kind of have to figure out what are those must haves versus those like to haves versus those. Well, would be nice to have from there as well. You're listening to Discussing Stupid, a podcast sponsored by High Monkey. Join your host Virgil Carroll and others as our podcast helps you transform bad digital experiences into teachable moments you can use. This is one of those episodes that, you know, honestly I wish we didn't have to do because when vendors talk about their products, product stacks and everything, they just made a lot of sense. But the reality is I've been doing this way too long to think that anybody's going to do it well. And so probably one of the most frequent things we get when we're talking with existing customers or new potential customers or just people in the community is really trying to understand what really is to the core the differences between a headless and a traditional cms. And every company out there has a different opinion about this. but today Chad and I are going to kind of talk and we're going to kind of break it down to some of the things that we think are the big differences that you should consider and the reason that you might go, traditional versus headless, it's not an end all beat all answer. I mean it always depends on your individual, organizational situation and kind of what kind of support you have inside there. But overall it's really important to understand that fundamentally where everything has a lot of bells and whistles, fundamentally there's a couple of core differences that you really want to kind of take into consideration and hopefully we're talking to this, about this from a business perspective, to kind of help you really understand some of those differences. So if you are looking or you're trying to just generally understand it in the world, we'll give you a little heads up. So if you were to share from your kind of thoughts, you know, what do you see as the big difference between a headless CMS and a regular CMS?

>> Chad:

Sure, ah, honestly I'd say the biggest difference is not even in the products, but the resources that you have as a company, it's, you know, there's some blurring of the lines between those, those two things. But if you are a smaller operation and you've got limited resources, then a traditional CMS is going to be easier to implement. it's easier to set up. You can take a WordPress for example, you can apply a theme and you can just do it all on your own. It may not look the greatest, maybe it'll look great, but you know, you can do it on your own. and then on the other spectrum, Headless, you need developers. that's the whole point. It's developer freedom. It's clean, code, what's the word I'm looking for here?

>> Virgil:

It's, you know, it's the ability for them to do it the way they want it.

>> Chad:

Yeah, performance, all that kind of stuff. It's a lot more finite control. but you need the expertise to manage that

>> Virgil:

Well and I think, you know, when I think of when, when headless first started coming out, I mean one of the things that kind of these, or these headless organizations kind of pushed us, it's freedom. So it's, but it's also central. I mean this is the whole concept that you're keeping the content and the, the page structure and everything completely separate from actually what gets presented. And the thought was, is, you know, not necessarily does your digital content just exist on a website, but it could exist in a mobile app, it could zip in a third party thing, you know, it could come into your, to your print documents and all that kind of stuff. And if you just had this content repository and then you said I wanted to pull over here and then you wrote the code and did the development separate in that. Which is funny because actually a lot of CMSs today are starting to bring in this concept of a content hub or something inside of it. And how many times did you and I, you know, did we architect up a regular CMS to basically be like a content hub and service a bunch of different sites with the same content in that. Which, which is a great goal. but overall I think you really hit the nail on the head. If you were to look at this. It's just the most simplistic terms. Do you want to be developer dependent and do you have the developer resources to do that? And there's some great advantages of that, or do you need to have this more in the business side? And I think that still today is very much the lesson we learn with this, is that headless is just not as business centric as typical CMSs are.

>> Chad:

Yeah, and it's a spectrum too. We talk about these two things like they're the only two options. But even traditional CMSs have, like you said, we've used them and they're getting to be more like this where you can, you can utilize them as a, as a headless. You can use APIs to call the content, and serve it up. I think the marketing word that you wanted earlier maybe was omnichannel. Everybody loved that.

>> Virgil:

Omnichannel, yes. Omnichannel, yes.

>> Chad:

but you know, even when you, when you, as soon as you get away from the simpler CMSs, I use simpler, sorry, like WordPress, where you can really do the work yourself if you want to. even if you want a new theme, you're going to need a, developer. If you want, some customizations, you're going to need a developer. And then you start moving towards some larger CMSs. you're going to need a developer anyways. but that, that headless idea with developers, I think was a good thought, especially for those that already had, languages that they were comfortable with. Because the whole idea was, the whole idea is that you can use what you know already,

>> Virgil:

Right, mhm

>> Chad:

instead of having to bring on new skill sets or anything like that.

>> Virgil:

well, I think another big advantage to it, and especially is kind of when headless really came out to be, is that traditional CMSs tend to have so much overhead, and that they have a lot of their core things that have to be loaded up. And now that's changed somewhat now that you have models where in traditional CMS, the website is much more separate from not really running on top of the CMS, but instead calling data from it. But I think the other part was, is this whole concept of a static website, you know, which is so funny because back when I first started, I mean, that's how websites were back in the late 90s is, you know, static. You were, you were building an HTML page, you were using software like Microsoft Front Page or Dreamweaver or something like that to build out a site, in there. And then a lot of organizations needed dynamics. So that's really where CMSs came, is that they wanted people to work under standards, you know, so that everybody was doing things the same way. And then also you could pull content dynamically. So if I added another blog post, I didn't have to go and add it to 27 pages. And now we're kind of at this other side where performance is so important, not only just, you know, for your site usability, but also from an SEO standpoint and everything else that we kind of got this static site. And so there were a lot of static site builders out there that would kind of take the stuff from the headless and make it into a site that is just raw HTML so that it's served up much faster. But this never really caught on. I mean, it's never really taken the big leap that I think everybody thought it would be. in the majority of the instances where I see people using Headless, they're using it exactly like a Traditional and they're pulling the content dynamically. And so I think, you know, where you're comfortable is probably where it is. And even more ironically now, where probably one of the biggest deficits in headless used to be about page layout, now a lot of the systems are starting to build page layout into it. So I think there's getting to be a merger where there's probably a lot less differences and eventually it's going to be seen as well. Do you have a CMS here or a CMS here? But overall they're kind of the same.

>> Chad:

Yeah, I think. You know, I agree with you that when we first started seeing Headless, it was billed as the ultimate freedom, but it also meant the most amount of work that you had to do. because it didn't have those core CMS services, forms, page builder, that kind of stuff. even if, even if you really did want to decouple those things, those were, those were, those are such, you know, real important pieces of a content management system that businesses didn't want to get away from. even if it meant, their developers could, write in whatever language they wanted to. so it's, it's, yeah, it's, I think you're right in that the Traditional is swaying in the way of, towards Headless. And I think we'll end up with one product in the end that can act as both.

>> Virgil:

Yep. No, and I agree. And I think that that kind of is it. I mean, you know, and, and I, I know when I was talking with Cole about this and he's kind of like, you know, there's obviously a good conversation, but where's the stupid? Well, there's lots of stupid, but probably the biggest stupid is the reason people choose one versus the other. And, and the reality is is what we're talking about here is probably the real reasons you should choose one. but, the other thing that I think of that a lot of times happens in CMS is, you know, kind of feature buzz. And you know, people get very excited about features. I mean, how many times have we seen organizations purchase because of the digital marketing components, yet nobody implements the digital marketing components and it's just one of those funny things and So I think you really have to break it down from that. but the other part, and since you gave me the correct term to use, because you know how much I love buzzwords Omni Channel, it's a great thought. You know what if you could use the same content for your mobile app and your websites and all that kind of stuff. It's a great thought and it's a great ideal, but the reality is most organizations just don't have the internal ability to be able to one, get there. But two, think like that because when you start talking about content modeling and you start talking about sharing things across multiple systems that, I mean it takes a higher level than most organizations have internally to really kind of think through that process and really do it. Because it takes a lot of discipline and it takes a lot of understanding on how your information is presented on these different mediums in the first place.

>> Chad:

Yeah, I mean we were talking a lot about development, but this is architecture, this is content modeling, this is strategic planning. there's a lot of work that goes into those things, outside of just the development and even, you know, even that omnichannel idea where you can reuse the same content. But are you going to reuse it? We see this now, you know, in the social media age that we're in, where you get content delivered on a, ah, TikTok or Instagram reel or whatever. But it's, it's adapted, it's changed, it's modified. It's not the same content, that you're serving up, elsewhere in an ad. You're not going to have the same content as you're going to have on your page. It's going to be targeted, it's going to be specific. So the idea was, I think the idea was sound but the practice is much more case specific than that allows for, I think.

>> Virgil:

Yeah, I mean, I think there's definitely a benefit to doing that global, but you have to be willing to do what it means to be global, which is typically to have the compromise. Even with our podcast, I mean, you know, obviously we do both the video version and the audio version. So we're, we're on YouTube and, and, and, and then on the audio, we're on Apple, Apple Podcasts and all those places and that. So speaking of that, anybody, that's listening today, we're really appreciated if you make sure you hit the subscribe and the like button and also let your friends know about our podcast because that's how we get our podcast to be more omnichannel. That's not a way to add that in there.

>> Chad:

That's good.

>> Virgil:

But, yeah, I think from that side, when you start looking at this and you really start breaking down the differences between them, the barrier between them is getting to be a lot less as far as the differences in that. But overall, no matter what, getting really sucked into those features and getting excited about it in there, you really have to go through a comprehensive, how do we do things now? What do we really want to do? how is it going to affect it? What system really works? And it's always a joke, you know, whenever we look at software that we say that, like, man, if we could just grab this feature from this one and that one from that one, that one, bring it all together, we'd have our ultimate system. You kind of also have to figure out what you're willing to compromise on, because you are never going to find that technology that's going to do everything you want in the world. And so you kind of have to figure out what are those must haves versus those, like to haves versus those. Well, would be nice to have, from there as well.

>> Chad:

Yep. And just, you know, I think in the end, too, on all ends of it is how are you resourced? What can you do as an organization? Or what do you need help with? And maybe hire a, consultant company.

>> Virgil:

Yeah, right. Yeah. Well, thanks for joining me on this one, Chad I forgot to mention up front that Cole's not with us today. This is our first episode without him, so this is something that's a little bit more in your set than that. So thanks a lot for joining me.

>> Chad:

Ah, happy to be here.

>> Virgil:

Just a reminder, we'll be dropping new episodes every two weeks. If you enjoyed the discussion today, we would appreciate it if you hit the like button and leave us a review or comment below. And to listen to past episodes or be notified when future episodes are released, visit our website at www.discussingstupid.com and sign up for our email updates. Not only will we share when each new episode drops, but also we'll be including a ton of good content to help you in discussing stupid in your own organization. Of course, you can also follow us on YouTube, Apple Podcasts, Spotify or SoundCloud, or really any of the other favorite podcast platforms you might use. Thanks again for joining and we'll see you next time.

People on this episode