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I've got a functional-heavy web app for a closed number of users who tend to forget about some features, like shortcuts. I could periodically train them, but that's not a good way.

I'm wondering is it a good idea to show them some hints like "do you know that..." in a pop-up and how effective is it?

I don't want users to just dismiss them without reading the content.

Are there any other ways (other than writing docs, wikis etc.) to teach users the interface in a friendly way, so they would discover some things themeselves?

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I agree with Kevin's statement. Remember Clippy, Microsoft Word's beloved assistant? Everybody hated him because he got in the way. You would be in the middle of trying to do something, and you would have to shift your focus away from your task to see what he wanted and to dismiss him.

It seems that your users are heavily focused on a task. It may be urgent, they don't want to deal with random popups that take their focus away from what they're trying to do. Instead, a small notification or hover tip that will display the information without requiring dismissal and can be easily ignored may be your best bet.

Think about how people currently learn their shortcuts. Usually they start off through the File menu, and next to the action, they see the keyboard shortcut. After repeating the opening of the menu and selecting the action enough times, they decide "this is an action I do frequently, I should learn that shortcut." So in a scenario like that, removing popups altogether and simply "integrating" the tips into the actions may help.

  • Like in cartoons a lightbulb popped up above my head. I found a good place for such hints and I'll do them in a classic way, not a pop up. Also, I realized that I must do some research how do users work on the interface to improve it. Thanks – Tom Feb 13 '14 at 7:59
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I highly recommend a new paper by Cockburn et al. "Supporting Novice to Expert Transitions in User Interfaces" ACM Computing Surveys, Vol. 47, No. 2, Article 31, Publication date: November 2014.

It reviews a lot of research in four areas of novice-expert transition:

"(1) Intramodal improvement concerns the rapidity and magnitude of performance improvement with one particular interactive method (e.g., pointing with the mouse) for one particular function (e.g., selecting the bold function in a word processor).

(2) Intermodal improvement concerns ways to assist users in switching to faster methods for accessing a particular function (e.g., switching from cursor-based interaction to keyboard shortcuts).

(3) Vocabulary extension considers ways to help users broaden their knowledge and their use of the range of functions available in an interface.

(4) Task mapping addresses higher level issues of the strategies that users adopt when seeking to complete their tasks with a UI. It concerns the coordination of functions to complete a task."

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I would recommend to: 1) remove this feature because users don't need it - and forget about its existance 2) make this feature usage necessary for users - so they cannot perform their tasks without this feature

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