I am so thankful and glad for the chance to get your input on my issue. I’m responsible for managing the calendar for two VPs. Both are heavily involved in committees, boards, teams, travel to conferences and events, etc. I fear that one of these individuals is a little overcommitted, but haven’t had luck convincing them to delegate more. But, they get very upset with me if they feel their calendar is overbooked or if a meeting is delayed too long. Other than time travel or cloning, is there anything I can do to ease up on the calendar madness?
— Overbooked & Overworked from Harrisonburg, VA
Ah yes—the boss who thinks they must do everything and be everywhere all the time. Some categorize these bosses as crazy, but I like to think of them as well-meaning workaholics who just need some perspective. It sounds like your boss is drowning in de Nile—as in, denial about how much can be achieved without being stressed, overworked, and frustrated. And then, with no time in the day to unwind, your boss projects all that negativity onto you because you’ve got the keys to the calendar.
First, say you’d be happy to help destress and manage the workload, but that the packed agenda isn’t because of a mistake you made. As a Ninja, you’re doing all you can to support the VP, which means booking every last thing they tell you to. Consider your relationship when you phrase this. If the team has a defined hierarchy and you don’t feel comfortable being candid, let the boss set the tone when you talk.
Then I think you should book a meeting (I know, another thing to add) to talk about scheduling and the workload. Mention that you feel like things have gotten out of control and suggest ways to streamline commitments. You should prepare these ideas beforehand. Comb through the past few months to look for specific events or times that seem especially busy. Then tackle those first.
If it’s a clear case for delegation, make sure to explain the benefit of siphoning a task off. If you simply present your boss with a list of things that could go to someone else, it won’t be as convincing as if you say, “By letting the Team Lead run that Tuesday meeting, you’ll save two additional hours so you don’t have to write your reports during lunch.” See how enticing that sounds? Everyone loves lunch.
You can also ask your boss if building personal time into the day is a feasible option. Some people live by their calendars. If this is in your boss’ personality, blocking off a few chunks of time could literally interject downtime into the mix. I imagine you’re already doing that—because you’re an excellent Ninja—but maybe it goes unnoticed.
In this case, it could be helpful to point out that three quiet planning sessions in a row were skipped. To keep from feeling like a nag, follow your observation with a question that encourages self-reflection. Try: “I noticed your mornings seem too full to take that 30-minute break at 10:00, would you rather me move it to 2:30 before your afternoon calls?”
Aside from any personal confrontations, this issue will also affect committees, teams, conferences, boards, and everything else your boss attends. And that’s why I think you should stand up for yourself. You’re not responsible for overbooking the calendar, but are merely following through with requests to attend events X and Y between meetings A and B. It’s also not your fault if a meeting runs long—but you can help strategize ways to trim down the cascading effect.
Give that a go, and make sure to let any fellow overworked Ninjas in on new scheduling secrets.
What do you think, Ninjas? Have you handled a similar scheduling conundrum?
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