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I have a site with a lot of different functionality and I'm having a hard time with guiding users as to what to do and when, especially because they don't have to do tasks in any specific order.

Having overlays like those in Foundation Joyride or Bootstrap Tour saying "you can do this here" and/or "click here to do this" I feel could be helpful, but I haven't seen it in the real world yet (can't find any sites with it) or know if it's actually helpful or just gets in the way/gimmicky.

Is there another term for these types of help dialogs? Do you know of any sites that use it and does it actually help or is it just gimmicky?

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"Tour" and "Walkthrough" are the common terms for this type of functionality. Zurb's Joyride is one approach to this using modal dialogs. There's a twitter bootstrap alternative called "Bootstrap Tour".

I believe it's a fairly common approach for notifying users of new features to the system. It's helpful to have the system point out what's new for you within the interface when you have a system that already have a lot of stuff in it.

Here are some examples:

Facebook

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Google

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WordPress

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This is much less helpful for walking a new user through for onboarding, since users probably just want to start doing stuff as oppose to reading through all of these little blurbs. See article: Are UI walkthroughs evil. You should always strive to design the UI so new users can get started without a walkthrough. Only if you're dealing with an immersive experience or functionality that's crucial to your system but not readily discoverable should you consider onboarding UI. Even then, there are other approaches to this than modals.

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    Early versions of the Mac Operating System had a similar functionality called 'Balloon Help' en.wikipedia.org/wiki/Balloon_help. You could usefully turn it on or off. – PhillipW Mar 9 '15 at 19:36
  • It seems like Wordpress calls those "Admin Pointers". So I'm not sure if we've came to a standardized term for these yet. – nightning Mar 9 '15 at 19:45
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The term you are looking for is "Onboarding" one of the most recent examples I've seen was when I began using Slack. They have animation hotspots appear on the page for you to discover what each interface element does.

For a higher level exploration of the topic you could look at http://www.useronboard.com/.

And of course a quick search of this site will show a number of interesting questions.

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