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Are you sure you want to answer this question?

Solutons:


Yes. There is a very simple, effective heuristic that adjusts to the preference of each user.

Place a check box in the warning message dialog that says:

Don’t show this message again

Which can be improved further by stating where that dialog can be reenabled.

These are Confirmation messages – Windows have a fairly detailed page on their guidelines. The whole of that page is pretty useful but here’s some excerpts (emphasis mine):

Confirmations are most useful when the action requires the user to make a relevant and distinct choice that can’t be made later. That choice often involves some element of risk that isn’t obvious to the user, but risk isn’t essential to confirmations. These elements are necessary to justify the interruption of responding to a modal dialog.

(No further emphasis from me for the below):

Is this the right user interface?

To decide, consider these questions:

  • Is the user being asked a question to proceed with an action that has two or more responses? If not, the message isn’t a confirmation.
  • Is the UI presenting an error or problem that has occurred? If so, use an error message instead.
  • Does proceeding with the action require the user to make a choice that doesn’t have a suitable default? If so, a confirmation may be appropriate.
  • Is there an alternative design that eliminates the need for the confirmation? The need for a confirmation sometimes indicates a design flaw. Often there is a better design alternative that doesn’t need a confirmation.
  • Is the user about to perform a risky action? If so, a confirmation is appropriate if the action has significant consequences or cannot be easily undone.
  • Is the user about to abandon a task? If so, don’t confirm. Assume users understand the consequences of not completing a task.
  • Does the action have consequences that users might not be aware of? If so, a confirmation may be appropriate.
  • Given the current context, are users likely to be performing an action in error? If so, a confirmation may be appropriate.
  • Do users perform the action frequently? If so, consider an alternative design. Frequent confirmations are annoying and have little value because users learn to respond without thinking.
  • Does the action have security implications? If so, a confirmation may be required even if the previous tests indicate otherwise.

Consider the design alternatives

Here are some design alternatives that eliminate the need for routine confirmations:

  • Prevent errors. Design tasks so that significant mistakes are difficult to do accidentally. For example, physically separate destructive commands from other commands, and require multiple actions to complete.
  • Provide undo. Provide the ability to revert actions. For example, deleting a file in Microsoft Windows usually doesn’t require a confirmation because deleted files can be recovered from the Recycle Bin. Note that if an action is very easy to perform, just having users redo the action may be sufficient.
  • Provide feedback. Make undesirable outcomes obvious. Providing undo alone isn’t sufficient if users don’t realize when they make a mistake. For example, the effect of direct manipulation (such as a drag-and-drop operation) should always be obvious.
  • Assume the probable outcome, but make it easy to change. If you aren’t sure what users want but there is a likely, safe, and secure choice, assume that choice, make it clear what happened, and make it easy to change using a context menu. For example, Microsoft Word assumes that users want to spell words correctly. If it recognizes a misspelled word and it knows the likely correct spelling, Word automatically makes the correction but allows users to revert.
  • Eliminate the choice completely. If the choice isn’t important, users just won’t care. Better to simplify your program and eliminate the choice.

Edit:

Further than this, which I think is also worth mentioning from a separate page on UI principles taken from various books talks about novice users:

10. The principle of safety

Novice users need to be assured that they will be protected from their own lack of skill. A program with no safety net will make this type of user feel uncomfortable or frustrated to the point that they may cease using the program. The “Are you sure?” dialog box and multi-level undo features are vital for this type of user.

Apple Guidelines don’t seem to have any guidelines on when, just “don’t over use”:

When it’s possible that users are unaware that their action might have negative consequences, it can be appropriate to phrase the alert message as a question. For example, a question such as “Are you sure you want to clear history?” pinpoints the action users took and prompts them to consider the results. However, don’t overuse this type of alert; users tire quickly of being asked if they’re sure they want to do something.

Google material design suggests that you should only use them for high risk situations and use a clear question rather than ‘are you sure?’ (that is obviously what you should write, rather than when):

Alerts with title bars

Use title bar alerts only for high-risk situations, such as the potential loss of connectivity. Users should be able to understand the choices based on the title and button text alone.

If a title is required:

  • Use a clear question or statement with an explanation in the content area, such as “Erase USB storage?”.
  • Avoid apologies, ambiguity, or questions, such as “Warning!” or “Are you sure?”

Google design screenshot

I’m surprised nobody brought up the Mac OS X shut down dialog. It presents you with an “Are you sure?” window, but has a timer so that if the user walks away, expecting the computer to have shut down, it will while still allowing the user time to cancel.

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