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I want to know if I can get away without numbering a list of items. My hypothesis is that when the # of list items is < X that a user will not need numbering to indicate the order in which that item is in the list. If this is can be true then what is the max X?

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It depends less on the number of items on the list as the nature of the list.

If order matters, then you should use a numbered list regardless of its length. If order doesn't matter, then a bullet list works just fine.

e.g. you have a recipe

The list of ingredients may contain 10 items, but is given as a regular bullet list. But the 3 steps in the recipe should be numbered.

  • The problem is I don't know if "order matters". The use case is logging sets in a workout. They all happened in a set order, chronologically, but it is often more contextually appropriate to refer to the set relatively i.e. 'B happened before C'. To be honest, I did end up using a numbered list, but am still hesitant on my decision. – occur Feb 15 '16 at 19:29
  • @occur ah if most of the time people do think of sets relatively, then yes using a numbered list makes a lot of sense. – nightning Feb 15 '16 at 20:13
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If i understand, you want your user to be able to numerate items "at glance". If your list has no spatial clues the maximum number should be 5. This is just my opinion, not cognitive science.

Otherwise, you can perform some simple test simply asking "how many they are?" and showing a list of items for 1 sec. Starting from 2 or 3 items and adding items each test. You should probably note a decrease of correct answers percentage after 5 or 6 items.

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It does not depend on list length, but on two others factors:

  • if the order matters;
  • if single items' length is really long to refer to them easily.

For example, if you have to refer to an article of a law.

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