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This is an example for something I have always troubling arguing with in technical discussions: Sometimes a solution only works if you apply it partially, "in good measure".

I can imagine the discussions on the issue above with the outcome being either no icons, or icons on every item, but nothing in between.

How go about convincing a group of people about this?

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When it comes to quantities, point to https://en.wikipedia.org/wiki/Subitizing. Simply put: "1, 2, 3, 4, many". Designers should be conscious when quantities might cross this (approx) subitizing threshold, and consider increasing the dimensionality with nesting or other techniques, rather than allow the size of simple visual sets to become overwhelming to users.

Whether intentional or not, the Windows example has exactly 4 icons in that column, and the rest are blank space. This makes it easy to visually navigate to, and identify, those emphasized options.

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