I haven't listened to Dwarkesh, but I take the complaint to mean that he doesn't probe his guests in interesting ways, not so much that he doesn't criticize his guests. If you aren't guiding the conversation into interesting corners then that seems like a problem.
He does a lot of research before his interviews, so comes with a lot of good questions, but then mostly let's the guests talk. He does have some impromptu follow-ups, but mostly tries to come back to his prepared questions.
