Being strict with IT can be pretty difficult.
Bosses "need" particular things e.g. out-dated software, confidential documents on personal devices, confidential samples for potential clients etc. and a lot of this is against the rules but "has" to happen.
The only way to really fight this is to have a guy at the very top who agrees that IT should be strict, and backs IT up every time they have a problem imposing this.
However I've seen some outfits where tech-aware bosses are allowed to break the rules if they know exactly what they're breaking, and what the potential consequences are.
That said, with MDM and BYOD abilities in common devices (e.g. "bring your own phone and we'll automatically wipe the work stuff when you leave") getting better and better over time, this is slowly becoming less of an issue. Personal iPads are much less of a worry than some personal crappy laptop.
Win 10 in particular will be interesting, as it will be manageable via MDM instead of solely via Group Policy.
