Reminds me of an old micromanaging supervisor of mine. He tried to get me to schedule out my tasks in detail so that they knew what I was doing every minute.

So I broke it down in sub-5 minute intervals all day long until the last 2 hours of the day. The last 2 hours: Filling out the calendar for tomorrow. The directive lasted a week.

I also might have set the notification default to 5 minutes before each event and picked an especially annoying notification tone.