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We are testing our website navigation and content arrangement before we begin the redesign on our informational website. We want to know if users can easily find what they are looking for and see which content needs to be easier to find. We are going to ask volunteers to find content that we think most users will be looking for on our website (based on web analytics and the purpose of our site).

We conducted practice user tests and there were a couple of things that users just could not find. After looking for a few minutes some testers gave up and some just kept on looking and got frustrated. Our practice testers found most of the things we asked them to find in 30-90 seconds. Some testers spent over four minutes looking for one question before I asked them to move on to the next. Is it okay to mark a question as a fail and move on to the next after a set amount of time has passed (e.g. three minutes)?

The closest question I can find on this topic is: When to end usability test task but it doesn't address ending a question after a certain amount of time has passed.

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From what I have read and learned about website navigation I think that if it takes over 3-4 minutes to find information that it has already been too long. Users don't stay long the link shows that most users won't spend over 1-2 minutes especially if they can't find the information they are looking for immediately. I would base your tests on the grounds that you have very little time to present information to new users and if they can't find the information you are going to lose them. Maximum 2-3 minutes before you mark the question as a fail.

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It may be worth spending the extra time even after it is clear the UI tested failed the specific test case by taking "too long".

You could gain additional insight on what is wrong if you allow the tester to come to some conclusion, because then, he will be able to give much better details on what he thinks "went wrong".
With a test case timeout, a tester would mostly state "took too long" - and not even care enough what the real issue was to remember it.

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Yes. However, if they have not already been narrating out loud and explaining their interpretation of what they see, where they would expect to find that content, etc. I would recommend pausing before moving on to the next task and asking questions to make sure you understand why they failed.

It can also be useful to perform similar tasks on competing websites to get a sense of the average time that task could last. People's interpretation of how long a task should take is partially influenced by previous experiences. If it takes 15 seconds to find something on your site but only 3 seconds on your major competitor's site, that could still be a less-than-ideal design.

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