Your boss may well be concerned that managing employees who come in nine-to-five is so much more simple than managing individual work arrangements and that your flexible plan may well mean more work for him. That’s why some of the biggest flextime skeptics are the middle managers, who will have to handle a lot of it, and who would often prefer the easy way out. Bruce Tulgan says that there’s no question managers might need some reeducation. “Managers still like to pay a lot of attention to where people are because that is easiest to measure,” explains Tulgan. “It’s visible. Otherwise, you have to be really good at managing results, and that is harder. But the upside is it’s better for business.”
Remember to outline how easy you will make this for him, and that a shift toward focusing on results may ultimately make him look brilliant.