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"Radical Candor" is a great book that is 80% summarized by the following 2x2:

              Care
            Personally
               ^
    Ruinous    |   Radical
    Empathy    |   Candor
  --------------------------> Challenge Directly
  Manipulative |  Obnoxious
  Insincerity  |  Agression

Managers don't want to end up in the bottom right, because no one wants to be an asshole. Everyone remembers the negative impact of assholes, and it's very hard to challenge directly without being a dick. A common management failure (and definitely a personal challenge for me) is avoiding directness instead of building empathy. But I've seen a lot more aggregate damage done by large numbers of managers being stuck in the two left quadrants (ESPECIALLY ruinous empathy) and causing a lack of progress from excess entropy.


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