"He brings an intellectual curiosity for why things didn't work out."
We must ask lots of questions about our failures to determine why they didn't work and what we might do differently to reach our goals.
"He brings an intellectual curiosity for why things didn't work out."
Asking whether people are giving their best gives them the opportunity to push themselves beyond their previous limits.

Liberators are more than just good listeners. They are ferocious listeners. They listen to feed their hunger for knowledge. They listen to learn what other people know and add it to their reservoir of knowledge.
They (liberators) appear to hold two ostensibly opposing positions with equal fervor. They create both comfort and pressure in the environment,. In the eyes of the Liberator, it is a just exchange: I give you space; you give me back your best work.-Liz Wiseman in Multipliers

Tyrants create a tense environment-one that is full of stress and anxiety. Liberators like Robert create an intense environment that requires concentration, diligence, and energy. It is an environment where people are encouraged to think for themselves but also where people experience a deep obligation to do their best work.