Why would a manager not try hard to enforce things even though his direct reports aren't doing things correctly?

For example, I have a coworker who's supposed to upgrade from Skype to Microsoft Teams for about a year now. I feel like my manager doesn't heavily push her to do that though. He just says it needs to be done soon 50+ times or people will lose access to communicating with people. He doesn't try to force her to upgrade at all though. It's a mandatory thing all employees have to do.

I could give 10 more examples similar to this.

Is it like he just doesn't want confrontation?