From the start, Deangelo had a bit of a bias against Jim (John Krasinski) and Pam Halpert (Jenna Fischer). During his first interaction with them, Pam told a joke about their daughter, Ceci, which went over well with Deangelo, who said he had four kids of his own.
This led the couple to believe they could share more things about their daughter, but Deangelo later said "enough about your baby" in a curt way to both parents.
In a later episode, Season 7, Episode 24 ("Inner Circle"), Jim gently broached the topic of sexism with Deangelo after Angela Martin (Angela Kinsey) and Pam had pointed out that Deangelo's entire Inner Circle was composed of men. The conversation didn't go well, cementing Jim's low standing with the new boss.