User Experience and Plain Language – Again

In relation to my previous posts about Apple’s iCloud and syncing capabilites, I came across an article on Poor Copywriting.
How surprised I was to find this picture:

When I think about all of the syncing anxiety I’ve had with Apple’s failed MobileMe product across devices and channeled through the cloud – I realize that it’s not only that, it’s also when syncing a device to iTunes. I actually did mention this in a previous post.
The Poor Copywriting post got me thinking that maybe it’s not simply the unreliability of the Apple’s cloud that is making me so anxious about losing data/media, transferring data/media, adding new data/media, and replacing copies of data/media. Could it simply be that my expectations are not being set correctly via the message copy? I’ve lost songs, been confused and frustrated about why some songs would transfer when others wouldn’t and when some would just disappear, but then show up on other devices…
 
The problem with message in the image above is that it forces users to make their own assumptions.

• If you press ‘Cancel’ – nothing happens and you win nothing.
• If you press ‘Continue’ it’s a house of mirrors. Your stuff is there, then not there. You thought you saw it but you didn’t – or did you? If you did, where did it go?

 
Here are some somewhat better scenarios based solely on this message (and my assumptions):

• There are items on your iPhone that do not exist in your iTunes library. Please transfer these items before updating or syncing your phone. For instructions ‘click here’ (Upon ‘clicking here’, a Help web page opens in your browser to help and inform the user before proceeding).
• There are items on your iPhone that do not exist in your iTunes library. By clicking ‘Continue’ you are taking a 50/50 chance that your data will be inconsistent (still ambiguous, but closer to the truth…)
• There are items on your iPhone that do not exist in your iTunes library. If you have ‘autosyncing’ turned on in your preferences, your data is most likely in the process of getting a bit messy at this moment. Please check your devices when the autosync is complete. You may have to repurchase missing data.
• iPhone and iTunes do not understand the current set of media licensing on your devices and who you are at the same time. Does not compute. Cannot sync at this time. Please view the ‘manual’ on how to address this issue. (when clicking ‘manual’ a pdf opens in the browser and skips to the relevant chapter view…)

 
As a user – what would you prefer to know?

• The harsh truth? (in plain language)
• Wordsmithing?
• Lies (in plain language)

So… straight out of Apple’s Human Interface Guidelines:

How can we understand and measure the effectiveness of said ‘intuition’? User testing!!!!!

1. Write it in plain language
2. Use user-centered language
3. Test it with actual users
4. Get it right