Upgrades are a vehicle that carry new features and innovations from the developer to the user. While developers like to see their latest work being used, users generally don't like upgrades, according Kathy Sierra.

In a recent blog entry, Why they don't upgrade (and what to do about it), she notes that,

People don't upgrade because they don't want to move back into the "Suck Zone."

They worked too damn hard to reach a level of competence and the thought of sinking back down—however briefly—into that awful state they clawed their way out of ... is too unpleasant.

We've trained users to fear upgrades. Raise your hand if you've ever installed an upgrade only to find yourself back in that confused I-have-no-frickin'-clue-where-they-put-that-dialog-box state? Raise your hand if you felt the upgrade just wasn't worth it, even though you knew that the way you did things in the current version was pretty much an inefficient hack. Raise your hand if you felt intimidated and maybe even a bit humiliated that after upgrading you could no longer do some of the simplest things.

Bottom line: nobody likes doing things they suck at. If there's a way to avoid it, we will.

Sierra mentions several things developers should think about in order to ease their users' upgrade pains:

• Make sure the users know it's worth it.
  
  
• Go over the top with documentation.
  
  
• Try not to break things that were previously important to them.
  
  
• Don't tell me what cool things you did to the new version, tell me what cool things I can do with the new version.
  
  
• The pain of an upgrade begins with download and installation.
  
  
• Don't make me pay for your bug fixes.
  
  
• Seed the community early.
  
  
• Set the tone for future upgrades.
  
  
• Try making more frequent, smaller/incremental upgrades.
  
  
• Entice, bribe, or potentially force them to upgrade.
  
  
• New releases can be a source of great enthusiasm and energy. Exploit that.
  
  

While Web-based applications represent an additional twist in the notion of a software "upgrade," users still perceive new Web site features as an upgrade—and, if users don't have a choice to switch back to an older version of a Web application, they might consider it a forced upgrade, according to Sierra.

What are the ways in which you entice your users to upgrade? And what have your biggest challenges been in convincing users to upgrade?