First impressions are critical in job applications. Requesting special role privileges, including a remote work setup, right out of the gate can make you look selfish, said Jim Detert, a professor at UVA’s Darden School of Business. “When you’re early in the hiring process, you’re still a pretty indistinguishable applicant,” Detert said. “But the more you interact with a potential employer, the warmer their perception of you will become, and the more open they’ll be to your requests.”