Essay that deepens the opinions of scholars, managers, workers of innovative companies, obtained from a research carried out in 2022, aimed at focusing on problems related to the impact of digitalization and AI on work, questioning whether these innovations make work smarter. There is resistance to change, but the bridge between fear and intrigue depends on "how" transitions are made. A cultural approach is needed to design "the new" and evaluate what it generates. Curiosity and rigor, the distinctive words to surf easily in the transformation. Will digitalization make work smarter? Yes, if humans will be able to rethink the evaluation criteria, using the organizational wisdom developed so far, but learning from the "new digital colleagues", the algorithms.