Usually means: Anticipating needs and taking initiative.
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We found 4 dictionaries that define the word proactiveness:

General (3 matching dictionaries)
  1. proactiveness: Wiktionary
  2. proactiveness: Dictionary.com
  3. proactiveness: TheFreeDictionary.com

Computing (1 matching dictionary)
  1. proactiveness: Encyclopedia

Definitions from Wiktionary (proactiveness)

noun:  The state or condition of being proactive.

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