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I consider this a very valuable question that does not have good write-ups/tutorials yet in Joomla documents (we should create one). I am trying to give here some workable info on this.
Loading Form Fields using Joomla implemented show-on conditions is not for loading dynamically changing checkboxes, list or combo field's values and fields. For loading Form ...
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First of all you may well be able to use the Joomla SQL Form Field for your Job Title field, instead of having to write a custom field.
To make the Technologies dropdown dependent upon the Job Title field you may be able to use the showon attribute as described in Enabling showon to work in list options. In your Technologies custom field you'd have to select ...
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