How aggressive should you be at ensuring that your software gets updated at a regular clip?

Perhaps the best way to consider this is in terms of the fairy tale Goldilocks and the Three Bears. This may sound a little nerdy or cheesy, but a good software update is kinda like porridge.

At the enterprise level, a good operating system upgrade shouldn’t be too hot, or too new—because then, you won’t get the benefits of trying it knowing it’s been road-tested first. But nor should it be too cold, or too out of date—because then it will no longer get the updates at all, leaving you open to security issues that eventually emerge with age. You need to strike a balance and find upgrades that hit at just the right time.

Recently, there was a to-do in Hollywood in which a number of MacOS machines regularly used for professional video editing suddenly stopped working. Initially, the belief was that an application called Avid Media Composer had done something to the editors’ systems. In reality, it was a glitch caused by an errant Google Chrome update that was able to access an area of the operating system it shouldn’t have because a key security feature, called System Integrity Protection, was turned off. Either this feature had been actively turned off by users for technical reasons, or the machines may have been using an operating system so old that it did not offer this feature at all. Either way, it’s a pretty good example of the “too cold” approach to software updates.

But at the same time, too new can be a big problem. Windows users are well-attuned to this issue: Microsoft has a track record of not-so-great updates to Windows 10 in recent years. Some of these problems are a result of Microsoft’s overly aggressive update approach, which has led to problems with features as basic as functioning printers, file management, and the Start Menu. “As we recently observed, Microsoft is having a complete nightmare here—a potentially very costly one in terms of its reputation—and the fact that another fix has seemingly caused yet another bug just pours more fuel on the fire,” TechRadar’s Darren Allen wrote last month.

Sometimes you can run into problems because “too hot” and “too cold” mix. Users who have upgraded to the latest MacOS version have encountered this, finding that some of their old apps (most notably old versions of Photoshop and Microsoft Office) no longer work correctly because Apple disabled legacy features in its latest desktop operating system. If you need those apps, you may have to stick to an older operating system—though in the long run, you might just have to bite the bullet and upgrade.

And other times, you may need to throw the “just right” strategy in the microwave, due to a security problem so serious that immediate action is needed. You might run into this, for example, on your various server setups—say, if there’s a security issue involving the latest version of WordPress or one of its plug-ins.

These are all big frustrations, but a way to mitigate them is to have someone to determine when an update is “just right.” That might be your IT department, which can do the testing to make sure that one piece of software isn’t going to ruin everyone else’s day. They might have ideas for keeping that software alive through methods such as virtual machines. And if something is mission-critical even if it’s old, they may have solutions to keep that software working. It might even start a broader conversation about a bigger change—in no small part because of who outdated tech tools could be scaring away.

On top of that, an IT pro for your association—whether a consultant or someone on staff—can see the bigger picture. This person or team will know what needs to work and how upgrades on your machine might cause problems for those you need to collaborate with, such as your members.

Now, there are cases where you might want to go newer rather than older—for example, in the case of iPadOS, which had an upgrade so significant that you’d be missing out on some major improvements if you wait. Likewise, web browsers and security tools are generally considered safe to keep up to date for security reasons. And there are platforms, like Chrome OS, that are designed to always be on the latest version. To a degree, some of these problems are mitigated by the use of web-based interfaces.

Still, though, if you get a notification on your laptop letting you know that a major operating system upgrade is needed, don’t just blindly hit OK. Know what you’re getting into, and make sure that your organization’s needs are covered, too.

You want to get this just right—because there’s nothing worse than porridge that you can’t eat.

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