how can I help my boss manage his time better?

A reader asks:

How do you put order and structure to a boss’s calendar that is out of control with constant meetings and no time to get any work done? Due to downsizing, my manager oversees three departments now instead of just one. My boss has meetings on top of meetings on top of meetings, many of which he requests. I manage his schedule and I block off “Office Time” on his calendar, but those times only get bumped for more meetings. I simply must help him take control of his work days, but can’t figure out where to start. Help!

First and foremost, you and your boss need to get on the same page about how he wants to use his time. You both need clarity about what trade-offs to make in his schedule. For example, it’s possible that those meetings that are bumping his work blocks truly are more important than the work that he’d previously scheduled for those periods. Or the work that’s getting bumped might matter more than those meetings; if he’s like many people in this situation, he might be letting meeting invites trump more pressing work without really thinking through what he’s doing. Regardless of which it is, the key for you both is to get clear on the facts that (a) there isn’t enough time in his day to do everything, so (b) that means that he needs to make strategic decisions about what he’s not going to spend time on, and (c) those decisions then need to be protected in his calendar.

Keep in mind that at its core, good time management is about clarity about what the person is there to accomplish and what matters must. And people with lots of demands on their time need to pick and choose what they will and won’t do. When people refuse to make those decisions, often because they aren’t being honest with themselves about the fact they can’t do it all, they stillend up not doing it all — but since they’re not making deliberate decisions about what not to do, they instead end up letting those undone items get picked by default. Point out to your boss that if some things aren’t going to get done, it’s far better to choose those things strategically, not just wait to see what’s undone at the end of the week.

From there, be rigorous about discussing trade-offs with your boss when meetings and other items threaten to bump other important work off his calendar. Be ready to say to him, “If you attend this meeting, you won’t have time left this week to work on X, and you wanted that completed by Friday.” However, it’s key that you not say this in a judgmental or scolding tone. Your boss is should make whatever decisions about his calendar he chooses; look at your role as simply keeping him informed of the trade-offs and consequences on the rest of his schedule.

Also, if you see that your boss is having real trouble carving out time for work that must happen, bring that up proactively. For example: “I know you’re having trouble finding time for the X project and the deadline is looming. Would you like me to cancel the Y meeting and push back the Z project to clear some time tomorrow for you?”

But ultimately, your boss may need to do some soul-searching about where his time will have the most impact. You can nudge him in that direction, but that final step may need to come from him.

{ 16 comments… read them below }

  1. CollegeAdmin*

    My supervisor is like this (although yours sounds like he might be less grumpy about it, so that’s good!).

    Here’s a few things that I do:
    1. Select one day per week for no meetings, and stick to that as much as possible. For example, I will not schedule any meetings for Supervisor on Fridays, unless they’re with her boss. This gives her time to get her stuff done, and allows for worst-case “the college is burning down we need a meeting ASAP” meetings a place to happen. I straight-up tell people that she’s not available on Fridays.

    2. Keep a running list of meetings to be scheduled and periodically review them; see if any can be combined or eliminated. My supervisor recently asked for a meeting with Wakeen from ABC University, but she’ll see him at a conference next week, so I checked in with her and she’ll just grab coffee with him while they’re both there.

    3. When you’re adding “Office Time,” try to instead label it with a project. If he sees, “Percival Project Review” on his calendar, that’s firmer and more likely to stick than a vague title.

    I’ll add to this if I think of a few others.

    1. TNTT*

      Point 3 is a great one, and one that my assistant uses to manage my schedule. You’re absolutely right that general “catch-up” or “drafting” blocks will get bumped, but I’m much less likely to bump a block labeled “Draft Teapot Ltd NDA” because yeah, I really need to get that done.

  2. AnonEMoose*

    Are there any meetings he could delegate to someone else? Maybe someone in one or more of the departments he oversees would be able to step in and represent that department if there some meetings that are regular check-ins or similar items. Or someone who could attend, take notes, and provide them to your boss if the meeting is more about receiving information than actually needing input from your boss.

    I also second the advice to, whenever possible, put a specific project or item on his calendar rather than just “office time.” It’s a psychological thing, but maybe if he sees specific things he needs to get done, rather than just “office time,” he’ll be less likely to want to bump it for another meeting.

    1. Lindrine*

      I love this for managing my own time too! I use it to put in time to work on stuff with a deadline or put in calendar reminders for “Deadline: Organic Chocolate Teapots United Trade Show Booth” and color code it.

  3. Hooptie*

    My VP is super-busy and has about a 50% travel schedule right now. While this took some time to click, once we developed the habit of doing this every week whether he was travelling or not it became a piece of cake, and reduced both our stress levels significantly. When I first brought it up to him, I said, “Can we try something? If it doesn’t work I’ll never ask again but it will only take 10 minutes.”

    Find 10 minutes to review his calendar for the next two weeks. Look at the calendar together and have him accept or decline accordingly (this can be done very quickly). See if there is any prep work you can do for him (presentations, handouts, research, etc.) . Are there any meetings that you can sit in and take notes for him? Are there meetings where he can just read the notes?

    If you’re in charge of his calendar, can you speak up for him? If I see someone trying to double book him, I call them and find out the reason why. So many times they aren’t even bothering to pull up attendees’ calendars, instead just picking a time when they as the meeting organizer are open. Ask for agendas if they aren’t being provided. This will help your boss decide if they really need to be there or if the notes or a delegate will be sufficient.

    When you are the meeting organizer, pad your meetings if you can. I add in an extra 20-30 minutes whenever possible. If the meeting runs over, fine. If not, I just gained my boss some extra time that no one knows he has.

    Mine is a very direct approach and may not work for everyone, but if I think of anything else I’ll add it in.

    1. Jillociraptor*

      Super smart. This was the first thing that really worked with my manager too: we (her assistant and I, her chief of staff) start by sharing what we know about her priorities for the following week, then ask her about what else she’s thinking about. Then we go through her calendar, note anything we think might not be a priority (giving her plenty of room to sign off) and identify everything that needs to happen to reach those objectives. We often assign specific tasks to specific workblocks, but not always.

  4. jennie*

    Yikes I’m getting video ads in the sidebar that auto-play with sound. (On PC, in Chrome). Never had that issue before.

      1. Monodon monoceros*

        I’ve had this happen a lot lately also on PC using Chrome. The ads are usually local to me (in Norwegian). I’ll try to get the URLs.

    1. Mike C.*

      Make sure it’s not a Chrome add on that’s injecting ads into the page. I’ve heard recently that this can be an issue.

      1. Monodon monoceros*

        AAM is the only site it is happening on for me, though. I would think if it’s a problem with Chrome it would happen on other sites, too.

  5. Melanie*

    1. Definitely develop an understanding of current projects and business priorities.
    2. Who is requesting these meetings, your boss, his higher-ups or his subordinates? Obviously meeting that he or his higher-ups request must be prioritised in his schedulebut his requests coming from his employees for meeting should come with an objective i.e. what the agenda will be and what they hope to achieve.
    3. No meetings just for the sake of a meeting. What can be better covered a report or briefing? Can some of these meetings be delegated?
    4. Have you ever noticed that meetings expand to fill the time allotted to them?Consider making the default period for meetings 45 minutes rather than 1 hour. Most meetings will actually be able to cover what they need to in that period of time if attendees are focused. Keep the ‘extra’ 15 mins up your sleeve as a buffer (e.g. Bathroom break, meeting runs over time, brief email catch up, etc).

  6. Vicki*

    I haven’t seen anyone else say this but: Who is adding all of these meetings to the calendar?

    If both the admin and the manager “control” the calendar, you’re going to run into problems. Someone needs to own the calendar.

    If the admin thinks the calendar is her job and the manager just changes everything all the time, then it’s not the admin’s job and that’s the first conversation they need to have.

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