As with the last article in this category, you may want to tread lightly around this unless you have the same weirdly obsessive personality as me. We’re talking about multi-select, and the ways it works and doesn’t work on the desktop and on the web.

If it helps, it’s an interesting time to be thinking about this; there are a few standards on the desktop, but they’re not as standard as you might think. And, as the web squeezes further and further into desktop territory, it’s going to have to decide how to handle multi-select in a much more mature way.

After the jump, let’s see what’s out there.

Multi-select on the desktop: the standard way

I’ve looked at Mac OS and Vista and it looks like there are two ways of offering multi-select on the desktop. The first way is used in both operating systems, and you’ll be familiar with it if you’ve ever right clicked any files; use it on a file you’ve selected, and it will show you a contextual menu; use it on a file you haven’t selected, and it will select it instead and show you a contextual menu. The behaviour is exactly the same whether you have one file selected, or many.

If, like me, you use a mac in column view, you’ll notice that the original file keeps its selected appearance and the active file gets a border. I’m not a fan of this; it’s confusing, and it’s inconsistent with the way things work in all of the other Finder views.

Multi-select on the desktop: the, um, other way

The second way of handling multi-select is slightly different. In this one, instead of replacing your selection, a right-click on an unselected file will add that file to your selection and show you the contextual menu for the whole set. You can find this method in apps like Candybar or Evernote:

Putting aside the fact that these apps behave differently from the OS they’re running in, I think this is quite convincing behaviour. You have some files selected, you right-click another file without first clearing your selection, and the app bets on you wanting to work with all the files you’ve been touching. I’ll buy that.

Multi-select on the web

Multi-select on the web is currently so unimaginative that it makes my brain cry. Think of a service that’s hailed as innovative or fresh or exciting, or as anything that would make you think they’re trying new things with the way people do things. I’ll suggest Google and Facebook. They’re pretty good bets. And here’s how they deal with multi-select:

I wish I could show you a screenshot of Hotmail from 1996, because I bet there’d be some similarity. I don’t like that a mechanism that has users clicking one area, moving over to another and then being able to trigger an action has become the default way of doing things and has stayed unchanged since the internet dark ages.

There are developments in a few places, though. Smugmug has taken things a step further and started to treat the entire object as a checkbox; click once, select an object, click another object, add that to the selection. It’s a behaviour that’s a bit unexpected – especially for an image gallery – and it isn’t reflected in either web or desktop paradigms, so I don’t think this is going to re-define web selection behaviour. But I do like that they’re starting to feel out some new directions. And I like that they’ve added the potential for a contextual menu in the hover/click behaviour.

With the web 2.0 thing, there are of course more desktoppy implementations. Something like Mobile Me uses desktop selection behaviour coupled with the standard web toolbar; for me, that’s the worst of both worlds. Users are unlikely to realise that they can multi-select, and they still have the inconvenience of splitting attention between object and toolbar.

All of this is not to say that someone should make me a goddamn right-click behaviour for the web immediately. Teamroom’s had right-click for years, and I would willingly string up whoever is behind that jewel of user experience. What would be helpful, though, is a bit of thought into how a clear, consistent, and compelling experience of working with multiple objects can be brought to people on the web.

As ever, there are more pictures than you’ll probably want to look at on my multi-select collection.