New employee monitors boss's schedule, asking for confidential information and requesting to join meetings with higher-ups, boss left baffled: ‘It's not something I’m willing to discuss’

Author image for Bar Mor Hazut
Bar Mor Hazut • Senior Editor
Oct 5, 2025 7:00 AM EDT

Does it ever baffle you that your work calendar can be viewed by everyone in the office?

It might not be the most technologically advanced feature out there, but we always found it quite bizarre that our schedules are open for everyone to see. We will never get used to talking with our boss and asking for a meeting, only for them to reply: "Just take a look at my calendar and set a meeting whenever I'm free." What do you mean, look at your calendar, boss? Isn't it… Well… incredibly private?

If you think we are overreacting, then maybe you would not find the actions of the employee in the story below as over-the-top. After all, they're just looking at their boss's calendar, which is technically public information. The problem is, they won't stop looking, inquiring about it, and even asking to join meetings they have no business joining. All of which is making the boss extremely uncomfortable.

Is it too much, or is it normal employee behavior? Keep scrolling to read the full story and decide for yourselves.

Advertisement
  • 01
    Office Manager Checking Schedule
    via DragonImages

    Image is representative only and does not depict the actual subjects of the story.

  • 02

    Employee closely monitoring my calendar

    I have a new employee in a team of 12 who likes to closely check my calendar and ask questions about the meetings I have.
    via Terrible-Hurry-3416
  • 03
    For example I had a meeting with the CEO last week and they called me over to ask what it was about and if they could join.
    via Terrible-Hurry-3416
  • 04
    They will also come to find me after meetings just to ask how a meeting was.
    via Terrible-Hurry-3416
  • 05
    I'm fairly senior and some of my meetings are marked as private- they also ask why they can't see the details of the meeting.
    via Terrible-Hurry-3416
  • 06
    It's not something I've come across in 10+ years of management and although I appreciate the enthusiasm, it makes me feel a little uncomfortable and makes me wonder why this person doesn't have more pressing things. to get on with.
    via Terrible-Hurry-3416
  • 07
    I also wouldn't dream of questioning a senior on their schedule when I was a junior but perhaps different times.
    via Terrible-Hurry-3416
  • 08
    Schedule Planner And Date Calendar
    via AndreyPopov

    Image is representative only and does not depict the actual subjects of the story.

  • 09
    I have kept it quite brief when questioned on any meetings to try to convey its not something I'm willing to discuss, but the questions keep coming and I'm not sure how to approach this.
    via Terrible-Hurry-3416
  • 10
    What would you do?
    via Terrible-Hurry-3416
  • 11
    Upbeat Training5660 I'd just explain honestly how you view this situation. They should be able to understand your point of view and adjust their behavior accordingly. If they can't, then that's another situation to deal with. Either way you learn something useful about them. If I had to guess this is reinforced behavior and was rewarded in some manner in their previous employment or relationship.
    via Upbeat_Training5660
  • 12
    Ok_Error_3167 Assuming you can't based on your org rules make your calendar details private and just show when you HAVE meetings and not what the meetings are called: "Hey, I wanted to bring to your attention that the frequent checking my calendar and questioning me about the details isn't appropriate here. Different companies do it differently and at [company name] we have our calendars open so people can more easily check schedules for meeting invites, not to keep tabs on each other."
    via Ok_Error_3167
  • 13
    DirectBat5828 I'd try not to assume anything about their motives. I'd just ask, "I've noticed you seem interested in my schedule, which is unusual to me. Can you say more about that?"
    via DirectBat5828
  • 14
    SnooRecipes9891 Address that if there was something they needs to know about you'll let them know. Anything other than that is not part of their job description.
    via SnooRecipes9891
  • 15
    troy2000me "It seems like you're interested in the wider goals and direction of the company, I think that's great. However I don't have the bandwidth to loop you in on my daily activities. Let's see if we can put you on a few projects to help you grow." And then either start marking all of your calendar items as private or just have IT block them from seeing it.
    via troy2000me
  • 16
    JehPea To be blunt, it's none of their business? Why are you treating it so delicately? "No" is a complete sentence.
    via JehPea
  • 17
    Wonderlandian This is absolutely wild. I've always kept pretty close tabs on my leaders calendars (and have learned some pretty interesting stuff by doing that for things that probably should have been marked as private) but I would never in a thousand years do anything to indicate to my bosses that I ever look at their calendars for anything other than a basic conflict check. This is wild.
    via Wonderlandian
  • 18
    FamousStore 150 I am not sure I would categorize this behavior as "enthusiasm", and it seems to be more in line with FOMO (i.e., paranoia about job security, etc). I would schedule a 1:1 with this person, and convey that your role requires you to be in meetings that he or she doesn't need to attend. You could also convey that you will share any information that pertains to the broader team, or to this specific person, as needed. Gently explain that the questions regarding your attendance at cert
    via FamousStore150
  • 19
    soulfulsummer Their desire to climb the ladder is clouding their judgement on what's appropriate. I'd say two options be direct and tell them to stop, or occupy them with other tasks to keep them busy and make them feel like they're progressing. I think a lot of people in the workforce now don't understand that often, you don't need to forcefully "network" to climb up, you just need to do your job better than anyone else on the team and put your name forward for additional projects.
    via soulfulsummer
  • 20
    Past-Reference 1260 Okay so this definitely crosses the line. First I would diagnose what's going on... do they have low EQ/professional immaturity? Do they have too much idle time? Are they trying to gain visibility by being in these leadership meetings? I don't think you're being overly guarded by protecting professional norms here. The reason you've never seen this before is because most people intuitively understand this boundary. I would set a very clear boundary: "I appreciate your enthusi
    via Past-Reference1260

Want More? Follow Us and Add Us as a Preferred Source on Google.

Tags

management schedule boss workplace-stories employee calendar manager job tales-from-the-workplace new hire reddit story ceo workplace Reddit company
Scroll Down For The Next Article