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Ask Susy: My Boss Blames Me for Overbooking the Work Calendar

Ask Susy

Hi Susy!

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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  1. What to do about the overpowering co-worker / Office Bully
    The request: set up a series of meetings in outlook using a team calendar through the next 18 months. This team meets twice per day for 3 hrs each day 4 days per week across 2 campuses. So naturally Video Conference rooms are in order. One more request, Sheila…if it’s possible to use the same teleconference numbers and meeting rooms for each of the team’s meetings, that would be awesome! So each week, everyone can come to the same room and /or dial into the same conference bridge line.
    From her perspective, she is my customer and the request is simple.
    From my perspective as the Admin, Not so much… let’s break this down mathematically
    4 meetings per week x 77 weeks = 308 meetings This is 1,849 hours of meetings over 77 weeks
    This will take approx 5 minutes each meeting to set up, provided there are meeting rooms available for an extended amount of time.
    I recognize a trap when I see one – what do you do when they won’t take no for an answer.
    Hi there,
    I can schedule these meeting for you through the next month or two but I simply don’t have the capacity to produce an entire year’s worth of meetings. I would suggest you work with facilities on getting your own dedicated rooms. Here is the link to the Project Team Space Request page
    Also you can reach out to Voice Communications for your own dedicated conference bridge line. Here is the link for that request.
    I wish you much luck and success on the project! Thanks very much
    Thanks, Sheila. Getting a dedicated bridge line and conference rooms would be great! Can you please help and initiate those requests? Also, just to be clear, the meetings are already scheduled. I’m just needing conference rooms and bridge lines assigned to them. While some of them need to be done immediately, they don’t all have to be done at once. I’m hoping this will help you with your capacity issue.
    But there are no meeting rooms available for this large block of time. That’s not OK. You need to figure this out. Finally after twisting arms and calling in favors I found a room for her but it was only available for 2 hours and 45 mins and not the whole 3 hours. This means you have to shorten your meeting by 15 minutes or let go of the room. That’s not OK. These are your options, either shorten your meeting by 15 minutes or let go of the room. This is your responsibility. Why are you refusing the task? Sorry if I’m missing something? Do you not have time for this?
    So here is me the lowly admin trying to take the high road Hi there, I got the ball rolling and started the requests for project space and conf bridge lines.
    But Suzy, guess what… That costs money that she does not have in her budget. So, no that’s not OK. That is an Error on my part.
    Why are you contacting facilities? Who told you you should do that>>>??? Ummm…. you did
    So she goes back to my boss, tells him I’m unhelpful, I’m giving her attitude, I’m being hostile in not taking her calls, i’m refusing her requests. So my boss comes back to me and says what’s going on.? Why are you giving so & so attitude, she says you are being hostile.
    Rather than going into too much detail I just ate it. I’m not going to engage her any more. I am done – stick a fork in me. So I tell my boss that I’m sorry on all levels. I’m sorry to you for having to talk to me on this level and I’m sorry to her for not meeting her needs. I’m just sorry . OK? Are we done? Can I go back to my desk now?

    Suzy, I need an intervention here. Got any tips?

  2. Another tip you can try is to proactively problem solve “hairy” looking days that are stacked. You can ask your executive if there is anything they would like to reschedule to another day, reduce meeting duration, or whether their presence is absolutely mandatory. Looking ahead helps the both of you anticipate what’s to come and shows that you are being thoughtful about how they are managing their time. Also, you may want to consider asking the people that are requesting the meeting whether it really does require the full hour? More often than not when I ask this question, a lot of people say that it will only take 45-minutes to 30-minutes. I agree 100% with the above comments that working in buffer times or travel times to get from A-B are absolutely crucial. Err on the side of extra time when possible.

    1. Well said, Crystal. Looking ahead to catch a problem before it even arises is such a Ninja thing to do!

  3. Love the 15 minute block after meetings, I might steal that one, Sarah.

    To the letter writer, when your boss asks you to book the next meeting, you could also ask them for direction on how best to fit it into the diary. eg ‘We’ve been struggling to fit things in, and I know we haven’t always been able to get meetings scheduled during the time period you wanted, for this meeting and to give me context going forward, where in the diary would you schedule this?’

    Sometimes asking them to do a bit of diary management, and to look at it more than one day at a time, can give them perspective (this has worked for me with a previous boss). Also knowing what can be moved in the diary helps – if you can take the lead on moving non-essential meetings to free up space for those immediate meetings, it’s easier to manage without checking in all the time.

    The other thing I always do is ask my boss for a time frame. So he’ll let me know if that’s a ‘today’ request, a ‘some time this week’ request, or a ‘whenever I have a spare spot and I’m likely to move it 3 times’ request. That way we’re both on the same page. You can’t always predict what priorities they are focussed on. I always ask.

    1. SUPER advice here, Jenn! Thanks for adding on to Susy’s thoughts. Requesting a time frame in terms of priority is excellent, we can see that you’re a pro when it comes to handling schedules ;)

  4. When I first came on to my job, I noticed that his calendar was filled. In fact he was quite often double booked. So, I build in desk time for my director on his calendar as “Hold–Do Not Schedule” I do this 3 times every day. For 1 hour first thing in the morning, so he can catch up on e-mail and make phone calls, etc. Over the noon hour, or else he wouldn’t be able to get a lunch and then lastly at the very end of the day, once again for any e-mails or phone calls. Since outlook allows you to assign colors to recurring appointments I also marked these in red so this acts as a big red stop sign to keep people out.

    1. Genius, Sheila! Adding a big signal like a red bookmark or your other suggestion of “HOLD” helps both the exec and other people see that time slot isn’t up for grabs ;)

  5. I’m Executive Assistant to the CEO and VP of an extremely busy non-profit. Our life is constantly overscheduled, with meetings, events, and other requests clamoring for a piece of their time. Neither of them had any time to actually sit at their desk and get things done. They were working evenings and weekends just trying to catch up. So I asked what they would change if they could. Both said they wanted more time at their desk, and that I shouldn’t feel afraid to push back if they were asking me to overbook them.

    So I built in at least 2 hours every week, with some weeks up to 4 or 6 hours that both could be at their desks, in a very scary looking calendar appointment that says DO NOT SCHEDULE. Staff members see this and know they can’t just randomly stop in at that time, I see it and know I can’t grab 30 minutes of that time for someone who wants to chat, and both the CEO and VP can close their office doors during that time and focus. It wasn’t perfect at first, because it felt too easy to ignore or book over, but now it’s become the moment in a hectic week that they both look forward to.

    I have also started building in at least 15 additional minutes between every scheduled meeting. No meeting ever runs on time, so that 15 minute window is either a buffer before the next meeting, or some time to reply to a couple of emails if the first meeting does actually end when it’s supposed to. When there’s travel time, I schedule the travel time plus 30 minutes.

    I also hold a weekly meeting with my bosses to connect, talk about scheduling challenges coming up, and debrief on what worked and what didn’t this week. It’s helped us get in sync with each other and has been a great touchpoint to get their feedback about their priorities and how they want to use their time.

    1. Whoa Sarah, spoken like a true Ninja. Excellent advice here, especially the 15-minute block after meetings!

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