Sure, you like the technology you have now. But is it really a fit for what you’re trying to do long term? That’s a tough analysis to undertake, but sometimes it’s necessary, especially when it comes to open-source components.

Recently, I found myself pondering this as I debated which content management system to use for a personal project. The CMS I’ve used since the start of that project has treated me well, but some concerns with the tool’s long-term direction had cropped up in my head, and I was worried that it was diverging from the things I hoped to do with my project. Additionally, while it seemed the right way to go early on, I felt like I was outgrowing it.

This has happened to me a few times in the past, in different ways. Sometimes, I’ve switched my CMS because I was trying to tap into a community and was willing compromise some functionality to reach that larger goal. Other times, I wanted the freedom and creativity earned by going off the beaten path. (In other words, I don’t use WordPress these days.)

Taking a Deep Dive

Now, there’s only one of me, and I can make a decision about a big change without having to go to a board or discuss it with a giant team. But my recent CMS search, low-key as it was, got me thinking about the needs of organizations and why there may be reasons, even outside of technology, that a piece of software can be a bad fit.

A few considerations I had during my process that you might find helpful during your own technology search:

Can you grow with the tool? This is the hardest thing to figure out. A tool’s marketing language often gets in the way of this larger question—which is really an issue of functionality, something that isn’t clear if you’re just reading a list of features. You’re trying to figure out how a tool is going to work for you six months from now, or perhaps even longer. In my case, I bee-lined to a demo of the tool. I was looking for customization, good design, and flexibility.

How hard will it be to move to the new tool? My current CMS exports old content using a format called JSON, but the new CMS I’m considering accepts content imports using only CSV. That meant I had to spend some time figuring out how to convert the two, as there was no plug-in set aside for this purpose. I pulled it off, but the process wasn’t perfect. Still, it wasn’t as hard as it could have been—and the upside seems higher than the ask. However, your organization might be dealing with a lot more data, and that could create a lot of heartache.

Just because something is buzzy doesn’t mean it’s right for you. Over the past couple of years, there has been a major trend in content management systems toward static site generators, which push online an entire site without the use of a database. These tools—particularly Hugo and, to a lesser extent, Hexo and Jekyll—have earned a lot of buzz among developers, particularly as headless CMS tools like Netlify and Contentful have gained attention. But when I tested these out, I felt like there was too much management and not enough content for my need. The tools were command-line-oriented, and I wanted an interface. That’s not to say that they wouldn’t work for your needs; just that they didn’t work for mine. Your tech team should consider options that are getting a lot of attention, but they need to think in terms of whether the products fit your strategy and your workflow. They might, but not because they’re drawing buzz.

Look at the community around a product. In my search, I discovered that some really interesting tools were managed by small groups of people or hadn’t seen updates in two or more years. If you’re paying to use a platform, you may not run into this issue because you have some say over the customization. But for an open-source platform, that can be a nonstarter. Even if a tool looks interesting, you have to factor in where it’s going. If it’s being operated by a startup, how is its marketing and user base shaping up? If it’s an open-source project, how many people are using it, and are there people available to help you in case something goes wrong? If you don’t feel comfortable with the ecosystem, it might not be the tool for you.

What Associations Should Consider

So that’s the calculus I had to deal with. Of course, there are places where this differs for associations.

For one thing, many prominent tools are proprietary, rather than open source, which can be a good thing based on your vendor needs. But it’s not like you can simply test an association management system or an event app platform just by hitting a button on a vendor’s website. The ask, quite often, is simply too big and has too many variables.

For that reason, we’ve seen a rise in sites like ReviewMyAMS and ReviewMyEventApp, which try to offer detailed reviews to association executives looking to spend a lot of money on a difficult problem.

The main takeaway I think you should have about making tough tech decisions is this: Don’t choose based on what’s cool or what everyone else is doing. You’re not buying an album or a hot toy—you’re investing in a product that could make or break your business. And that requires some thoughtful, data-informed decision-making strategies.

Do a deep dive, and ask the tough questions along the way.

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