Calendar rules I learned from an EA

The first rule an executive assistant taught Jade Rubick sounds obvious but most people violate it constantly: don't let two meetings overlap on your calendar. When you get a conflicting invite and ignore it, you're creating a surprise for someone later. Maybe you handle it the day of, and everyone who expected you suddenly has to improvise. That's the calendar equivalent of merge conflicts in code. Resolve them immediately or pay compound interest on the chaos.

The revelation came from seeing how the EA color-coded the CPO's calendar. Not randomly, but systematically by meeting type: staff level versus org level versus above your level. Client meetings. Technical versus people matters. Meetings where you're helping others versus delivering your own goals. Once you can see patterns in your calendar, you can budget your time. Stick that budget on your monitor. Color-code the categories. Start saying no to things that exceed your budget. If you spend too much time being helpful to others (a classic engineering manager trap), color-code those meetings and limit them to one or two per week.

The practical stuff matters more than philosophy. Make calendar entries editable by default so people can adjust times without the "propose another time" workflow. Turn on speedy meetings so 30 minute meetings end at 25 and hour-long meetings end at 50 or 55. People need bathroom breaks and water. If you run meetings to the exact end of the hour, you're making the overall meeting load less effective. Start on time. If people are late and the meeting hasn't started, you're encouraging lateness. Schedule and block out lunch. Sync your personal and work calendars so you're not manually copying events. Hide declined events to simplify your view.

The power move is using tools like Reclaim to schedule your actual work on the calendar. Put in todo items, estimate time (2h for two hours), set priorities (p1 p2 p3 p4), add deadlines, and let it tell you if anything won't get done on time. As long as you do what your calendar tells you to do, you're fine. It updates automatically as things shift. The other hack Nic Benders taught Rubick: schedule a day after vacation as reentry time. Don't come back and immediately drown. Give yourself a buffer to catch up, plan your work, and get ready to go.