Three Points in the Upgrade Game

Software vendors are invariably after you to upgrade. Should you? If so, when?

Right now, WordPress — the tool I use to run both my blogs and my Lexician.com site itself — nags me at the top of every screen: “WordPress 2.9.2 is available! Please update now.” [Exclamation point in original.] There’s nothing that tells me why I should update, other than their excitement as conveyed by that exclamation point: “We worked for weeks or days or hours on this version! Ya gotta do it! Now!”  Except…

  1. It’s a minor upgrade to fix a small bug that doesn’t affect me.
  2. The upgrade to the version before my current one had a serious bug that they failed to catch that led to the hijacking, corruption, and loss of the first year of NoCCrit, including about 250 posts and innumerable comments.

This message staring me in the face for a week, coupled with my beta testing of Office 2010 and discussions with a couple of client folks, got me thinking about when to upgrade. There are, I think, three different upgrade approaches vendors use:

The Big-Release Upgrade

Most server and desktop systems from large vendors follow the Big-Release methodology. Every two to four years, these vendors issue a major new release. Microsoft, for example, released Windows 7 last year, and they’re planning to release Office 2010 in a few months (June, according to word on the Web).

Should you upgrade?

Pros:

  • These upgrades are generally safe and competently tested, despite the so-called words of wisdom suggesting you wait until the first service pack.
  • They have new features that are likely to be useful, though you may not “get” them until you’ve worked with them. After all, what can Microsoft add to Word at this point that (a) isn’t already in there and (b) you might actually need? Surprisingly, there’s still a lot of room for growth, from little touches — moving the highly valuable Document Map to where users might actually find it and renaming it Navigation Pane — to new ideas such as the online/web version that competes directly with one of Google Doc’s strengths.

Cons:

  • It costs money. (It’s a different calculus if you’re on an enterprise-wide license.)
  • It takes time and effort, people think. It does take a bit of time while your machine grinds away, but you can do it during lunch. As for effort, Microsoft rolls out new versions to 50,000 people a night internally with virtually no glitches or hassles. If your corporate IT department can’t figure this out, suggest they talk to their Microsoft rep and ask how Microsoft does it. I assure you, there’s no magic, just an IT group that’s got this part of their act together.
  • It will break some existing apps built atop the current version. If that’s the case — and I know it often is — then your IT team isn’t learning from experience. Stop doing this! Build on published APIs, not hacks. And then test with the beta versions. Even Microsoft occasionally gets this wrong internally, but it’s usually because a developer tried to do something extra-special and pushed into unsupported territory. That said, occasionally big companies change the underlying model in an unanticipated way, such as the file-formats change in Office 2007.
  • You believe you know better than the users what they need. ‘Tain’t so.

The Annual Upgrade

Some companies do annual upgrades as an ongoing revenue stream. I use some music-creation software that used to dun me for annual upgrades, at about $300-400 a year in total. It’s an economic model users hate… but it’s a model that keeps the companies in business, instead of selling maintenance contracts or the like.

Software — mostly — isn’t free. If you have a solution you like that is free, great; go for it. WordPress, for me, is such a solution. On the other hand, I couldn’t have written my book Legal Project Management in anything other than Word (I tried Open Office and Google Docs to see if they’d work).

But often you pay in ease of use, or lack of testing, or intrusive (or hidden) advertising, or no support. There ain’t no such thing as a free lunch — TANSTAAFL, as Robert Heinlein put it. It’s a trade-off, one you should make carefully. Sometimes free is the answer; sometimes it isn’t.

If you don’t take an annual upgrade, you’ll likely pay considerably more for your next upgrade, almost as if you were purchasing new again. Sometimes you can find opportunities to join the “welcome back to previous customers” program and minimize those costs; keep your eye out for them.

The Quick-Turnaround Upgrade

The WordPress 2.9.2 upgrade falls into this category; so do many SaaS/hosted solutions, where they push upgrades out whether you want them or not. Many are insufficiently tested. If you can, resist them for at least a few weeks to see what problems other guinea pigs are turning up; check the support boards, Google for answers (can you Bing for them?), and exercise caution.

The other end of this scale is the semi-automatic upgrades pushed out by Microsoft, Adobe, and other large companies for your desktop software. In an ideal world, I’d put many of these off too, but we don’t live in an ideal world. We live in a world with sufficient bad guys who like taking on high-profile targets not just because it’s somehow cool to beat Microsoft’s engineers but because they are actively trying to rip you off if they can get past your computer security. Thus I think there’s little choice but to take upgrades in a timely fashion for popular software such as Windows, QuickTime, and Flash; it’s a matter of security.

These companies have reputations to protect and so they test the heck out of these rapid upgrades. That doesn’t mean they’re foolproof, but it does lower the risk so that taking the upgrade is safer, all told, than not taking it.

Finally, there are the antivirus companies that suck innumerable cycles from your machine with their daily upgrades. Again, the bad guys are truly out there, and so I think you have to accept these daily updates. My main cavil is that not all of these vendors properly throttle down the amount of bandwidth they use to push the updates, so that it can interfere with your use of the computer.

Other

Like any classification scheme, this one isn’t perfect. Where, for example, would you put the every-other-year major service packs for Windows releases? Still, it’s a good framework to think about how and when you want to upgrade, rather than leaving it to chance.

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