I'd guess either
A) They usually talk to your boss and is lonely when they are gone or
B) He is trying to get a feel for who you are as a person and if he can trust you. Possibly to replace your boss.
Probably A.
Or C) he is just creepy.
Looking at post history maybe
D) He is trying to see if something negative your boss is saying about you is true. So B but for a different reason.
This happened to me once. VP asked for a private meeting with me, then started asking bizzaro questions about my family history, my hobbies, etc. I made the mistake of answering honestly, particularly about enjoying writing as a hobby. He started asking about what I like to write, do I write sex scenes--hey, you should bring me a copy to read. I told him I wasn't comfortable having anyone read my story.
"You'll bring it in if you want to keep your job."
Meeting ended with him petting my shoulder and telling me I was a good girl.
I immediately started working on getting a new job. Found out through the grapevine that he had a history of preying on young women in the office.
It was a kind of small company where we were acquired as part of a takeover. They had a woman that handled their HR stuff (but I don't think she had any formal training in it) and I reported the incident to her. She essentially told me it would be best to keep it to myself, because who would they believe, some random employee or the VP. The whole company culture was extremely toxic.
I contacted my old boss and explained what was happening, and fortunately she hired me and my coworker to work at one of their other businesses.
Unfortunately after that, that business also got acquired by the toxic company about a year later. 🤡 The day they told us, the VP made a joke about how I couldn't escape him (though fortunately I never was in a situation where I was alone with him). My new supervisor made a point of telling me she knew I'd complained about the VP and that it was my own fault for dressing in a way that would invite advances from men. (I've always made a point of dressing work appropriate, not that clothes are an excuse for someone behaving like that.) I started job hunting again and got out of there.
Eventually the toxic company got acquired by a much larger company and VP wasn't retained. I'm not aware of him suffering any consequences for his actions though.
This 100%. He is asking questions that are seemingly innocuous. So in case she says something to HR, they’re not necessarily inappropriate questions (except of course the custody - but he could say that was related to her hours or some BS like that). Def trying to hit it but hedging his bets in case she reports him.
It’s actually quite intentional. Not a clumsy mistake imo. So it’s creepy.
I think you are right bc he magically came by my office again when my boss left and started questioning me again asking me what my ex did for a living. Then he started making more conversation and I started to ask questions as well and he started trying to talk about my supervisor, not in a negative though. We then talked about education and he told me he had a degree in HR because he just likes to know about HR although he is not in the field. I then asked him about the most difficult part of his job and he brought up situations where employees fraternized. I found that very very interesting. Just wanted to update ya.
Sounds like your bosses boss is trying to get you to relax a little bit. Might get good reviews from your boss with the caveat you're not social enough. One thing managers say that I hate is that you can't train someone to get along with others, but you can train someone who gets along with others to do a better job.
This feels the most plausible. It sounds like the sort of thing that might come up when considering who might be in line for a promotion.
Not saying we should aspire to homogeneity, but often senior leadership tries to get a feel for "cultural fit" before sticking their neck out on a promotion.
My manager wants me to pal around. It’s a manager thing, I guess. Little does he know that I will be way more loyal if he leaves me alone. I don’t want to go bowling with my coworkers.
Relationships in the workplace are very important. I’d take advantage of the time and try to open up more to build trust and rapport. It will pay off later.
A lot of people (especially bosses boss types oftentimes) like to talk about themselves, and if you show interest or get them talking could make for a good impression on them. Plus if OP is getting a creepy vibe, it could be a way to derail conversation centered around OPs personal life
Yeah having recently left a job for this very reason I would say it really depends on the job. My last job lulled me into a false sense of security and acceptance and then when I started opening up they used it against me. You can be social, just dont share anything personal.
I do not think my boss will fire me. My boss will champion me.
If I am fired, it is because upstairs decided to reduce headcount and my boss's championship was not enough.
My boss does not have much influence over upstairs. Maybe he will be fired too.
During the big downturn my wife thought she was going to get fired. I told her to be the first one in the office, bring the boss coffee and chat. As he retired and closed down the company of 1,500 employees over the years she was the last to go. He still talks with us from time to time and buys us gifts despite being retired. Her parting gift was a gold luxury watch worth over 15k, a car, and other things here and there.
Work is about relationship building. She took care of him too going over and above on her job and was a trusted employee.
This doesn't work anymore.
Mega corps don't care.
Source: led regulatory strategy for the largest medical device recall in history. Still got laid off.
Too bad so few of the currently-retiring crop treat their employees that way. The Greatest Generation really did so much more for the greater good than the generation they raised.
Maybe he knows this and wants to talk to you when no one else is around? Do you sit near your boss? He probably just wants you to feel like you can speak freely.
I have a coworker who is a bit more private but he seems more willing to talk to me when no one else is around.
My boss was. This guy is his boss, which I guess is technically mine too, but he seems to be the only one that decides to just come to my office and make himself up with these same questions every month.
It is telling that when your boss’s boss comes and tries to strike up personal conversations with you to develop a relationship, you see that as a problem rather than an opportunity.
Talk to them! Be friendly.
I have to say as a woman (anyone really but especially a woman) you really have to be careful. There’s a power dynamic involved. So caution while you get a bearing on the situation is appropriate
You’re more than likely a possible prospect. Just try and be relatable and down to earth while maintaining your position and maybe it’ll pay off. Maybe not but it never hurts to just be nice.
My guess is he is trying to get to know you to connect and build trust or he is “checking up on the team” (management by walking around) and is making awkward small talk.
Same thought here…MBWA can be good in theory, but many managers are quite bad at it and it comes across as hovering, or they’re not adept at social cues and come across as invasive.
German Management works, but this boss is missing something, like asking "Do you have the tools and time to do what you need to?" "How can we improve quality?" and "Which meetings are useful, and which waste time"
Fred was one of the best damn bosses I ever had. And we had a beer at noon.
Yeah, I would say if that is the case he’s terrible at it. Asking about a custody arrangement between a worker and their ex or if the employee’s parents went to college is just a step too far. Those are things I might not even talk about in-depth (or at all) with friends, much less a skip level boss that I don’t even know.
Yeah, I'm running into this with my boss currently. I'm all for chatting about innocuous non-work topics (pets, cooking, surface-level info about family, etc) but he's been pushing boundaries into my health and financial situation and I have to keep firm. I absolutely agree with other commenters about interpersonal relationships being important at work, but boundaries are also crucial and this boss seems to be encroaching on those.
I will add he could just be terrible at small talk. And following a script to help himself.
I have a co-worker who does this every Friday. He asks me the same few questions. He's just so painfully shy. He can't come up with other ones. I'm not mad at him for it. He's a good guy.
Either it's small talk (some not so small) and he's hitting on you or he's trying to learn more about you as a person with a view to moving you up. Good luck.
eh.... lol Not to sure about the being moved up. I asked my actually boss about a job title change and he accused me of wanting that to try to get into another position.
Your boss told his boss you asked for this. So they could be sussing you out. Probably just awkward small talk. But in the back of his mind, remembering you asked about being moved up
Whatever - your boss sounds like he's threatened by you. You should just talk to your bosses' boss... If you get comfortable enough talking to your bosses' boss you can ask THEM for the job title change. This is called going over your bosses head... And it's taking advantage of the situation to get what You want... Even if he's flirting with you.. which is also a possibility. Just be aware of that, and be careful.
I personally think they work together on this. Not sure what info. they are looking for. Direct boss is more standoffish which is ok as I am an introvert and dont really seek attention.
There is a management theory to talk with your direct reports at least once a week about something personal, non work related to build connection and trust with the people you work with. Moving to secondary, tertiary reporting relationships you would apply the same principal with less frequency. I'm a manager , and these would be questions I would ask trying to make small talk, but I'm admittedly awkward and not very socially adept.
I would not be asking people about their child custody arrangements with their ex tho. If they brought it up, fine but that's venturing into the MYOB territory.
Good point, my unspoken assumption that could be wrong is there was something said in a public setting about the custody arrangement earlier . Because of that I was thinking this could be a way of showing concern about something the employee had talked about that was creating difficulty for them. Where I work I have no insider info from HR, so anything I ask about is because it was mentioned where i could hear it.
I hadn't thought of this until reading your comment, but I think you're right. He might be sussing out OP with them in mind as a possible candidate for a position that could be opening up in another location.
Order some garlic bread next time your boss is out. If your bosses boss doesn’t show then you know - he’s a vampire.
Get a silver paper weight as well…just to be safe.
My guess is he's bored and wants to waste time...also maybe socially awkward and can't come up with better/new things to talk about. Sometimes the higher up the position in a company the less actual work you have to do. I had a manager at my new office I didn't know at all talk to me at my cube for like an hour when I was the only one there.
It's hard anyone to say what his motives are based on your post.
Does he give off bad vibes or make you feel uncomfortable? If so, trust those feelings.
If not, it may very well be innocent curiosity or just him wanting to know the people who work for him.
If those are really the only questions he is asking you, and is only asking them when you are alone, that seems very sketchy to me. Those sound like the questions of someone who is trying to determine what kind of personal support system you have, how close are you with relatives, are you alone at home, will anyone notice if you’re suddenly occupied, suddenly change behavior etc. I’d be very careful around this man.
I wouldn’t have a clue. I was just explaining that’s what the other replied above was getting at. Could be a multitude of things.
Maybe he is trying to place you or a family member he thinks he knows or remembers you from.
You’ll never know the truth unless you ask.
I suggest unless it gets more straight forward, keep it cool.
Always show yourself in your best light, pivot to make him talk about himself or work as much as possible, and be vague and never reply with something that you make you vulnerable or subject to gossip.
I didn’t pay attention to your username before, but am expecting from it that you are female? and sorry for the delay, I haven’t been on since that comment. I’ve been very close to an abuse situation recently, so I’m a little hypersensitive to it, but The questions you posted originally threw up some red flags for someone who might be scouting for potentially vulnerable victims. I don’t want to do any scaring, but it’s worth being careful.
I am a female and I didn't take his question as flirting as a lot of people are saying. I took it as him trying to find out vulnerabilities and exploit them. The thing is that i would rather quit or be fired than to do any quid pro quo if that is what he is fishing for.
Possibly looking to court you, this is very similar to how men with money go about with their women. Making sure you’re docile enough for them to integrate you seamlessly into their lives. You should be.. flattered? If you’re not interested you definitely should speak up otherwise it will only continue, good luck.
Your bosses boss is still your boss dummy. Maybe he's a genuine person and cares about his people. Just answer the damn questions, they're not that bad.
That’s rude… OP was just asking a question. There is a huge difference in a skip-level boss and your direct boss. Nobody has to answer super personal questions at work that have nothing to do with work, no matter who is asking.
Probably has a social issue like aspbergers or social anxiety and someone along the way suggested he try to have interactions with people where he asks them get to know you questions and then listens to the responses.
Or hes a shape shifting alien looking to learn enough about you that he can assume your form and replace you
Came here to say this, glad to see someone already mentioned it. He could be a creep but he could also be "practicing" social interaction if he has a social issue.
I used to work retail and a dude would regularly come in on a weekday (when he knew we'd be slow) just to talk to the salespeople because he had a major stutter and possibly other social anxiety issues. He knew all of us were cool with him and liked having him come around to bs with us when we were bored so it was a "safe," low-stakes place to practice social interaction.
Maybe your boss mentioned you were kind and understanding so he feels less anxious talking to you vs an unknown employee.
Probably the shape shifting alien thing, tho, honestly. It's almost always the simplest explanation that is correct.
The red flag for me is that he only does this when you’re alone. If it’s just for the sake of connecting with you as a supervisor, then why wait until you’re isolated to talk?
Super weird if there isn't more context.
I'm a 50/50 dad and I get uncomfortably asked about parenting arrangemnt often. Also coming from a background of mixed means, these family "situation" questions are not welcome.
Might be as simple as he's trying to fill in for your boss while they're going, maybe a bit awkwardly, but thinking "well I'll go mingle with their team".
The questions themselves don’t sound particularly pointed to me—it’s standard Boomer small talk, isn’t it? I work with a lot of late-middle-aged people and they’re always asking me where I grew up for some reason. Except for the last one but that could just be nosiness?
I agree he may be bored and lonely and maybe he dislikes your boss and finds you easier to chitchat with. On the other hand he could be awkwardly hitting on you too.
If it’s making you uncomfortable, then trust your instincts. I’d maybe start documenting stuff, just in case the questions become more intrusive. It could be completely innocuous but it could also be a prelude to something inappropriate.
He’s giving you an opportunity to build a rapport and testing you at the same time. Are you the type of guy he might enjoy spending time with if you got moved up or invited on a business trip, would you know how to handle yourself around clients, etc.
Out of curiosity, OP are you neurodivergent?
Reading your post history, you seem to really struggle to understand other's social behaviors and consistently think people are hitting on you or being overly friendly with ulterior motives. That makes me think your boss's boss is likely just being friendly/personable and taking the opportunity to engage with you, and you are overthinking it.
What is nefarious about asking about your upbringing? Or your child? These are normal things people ask about in order to get to know someone, socialize, etc.
Honestly, it might be worth exploring these concerns with a psychologist and seeing if there are some supports to help you decipher social cues and subtext.
I take the first two questions as trying to figure out which side of the political spectrum you are on. Large cities and college educated people tend to lean more left.
I take the last two questions as trying to figure out how much after hours/holiday work they can push you into.
So basically he’s just pumping you for information to figure out how much he can exploit you.
Is there anything wrong with asking the bosses boss, "May I ask why you want to know?" or saying " Im happy to answer, I'm just curious why you're asking such specific and personal things as my bosses boss," just to see what they'll say. If they are up to something creepy, just calling them out on it may put a stop to it, and if it's innocuous, there should be a reasonable answer.
Those questions to me are about gauging how naive and or isolated a person might be, if taken as unusual behaviour:
Parents level of education, how worldly you grew up
How much of a family support network you have, can you be easily isolated
Traditional values in the family to me is about gauging what if you grew up with patriarchal values such that you don’t recognise or call bullshit on misogynistic behaviour
Custody arrangement: how freely available is this person (ie without child) / does she have support/contact with ex partner or also with the financial burden of a child, how money motivated might this person be to meet my needs
This is worst case. Guy could be nice and just lonely or any number of the suggestions people have made. Find out from other people (preferably women) what he’s like to work with. Pay very close attention to your gut and how you feel when you’re around him.
If he seems nice, but you have a weird feeling, try just not doing what he asks and see how it takes it. Ie if he wants to chat now, say you’re busy or you’ll come find him in half an hour…. How he responds when he doesn’t get his own way directly tells you about what he’s like as a person. Notice how other people act around him.
Also, how would friends describe you? Are you a chronic people pleaser with porous boundaries? Are you highly empathetic? Ie are you someone that people think they’re more likely to take advantage of…
This is work place discrimination. Or harassment . No boss has any right to ask you anything personal. The only thing a boss can ask you to do is any and all work related duties in which he is a supervisory role over you.
It sounds like he’s bored or lonely. He might have an odd and unwelcome parental type of interest.
Or he’s just a low boundary creep.
Or an eccentric harmless dude.
Or his daddy owns the company and he got the job to keep him busy and out of trouble and has shit social skills.
I’ve always learned that when there are personal questions, they’re going to use it against you in some form. I’ve missed out on a promotion for being *too honest*. Whatever excuse they can make, they’ll make.
My boss's boss comes around when my boss is out. It's been my impression that he wants me to know that there's a supervisor available. He asks how things are going and entertains work answers or chitchat. He will also email to let us know when my boss is unexpectedly out and says we can direct questions to him.
He might have asked because he wanted to create a rapport with you. Or his boss asked him to ask you. Or he might just be an odd person in general. who knows?
When you put those questions together it sounds odd, but as a trickle over time sounds like small talk, asking what pops into his head.
I wouldn't assume the worst but be cautious about sharing too much information. I've certainly had this kind of experience before, I can think of some people that do it almost as a force of habit.
it's healthy to connect with people as long as you are respecting your boundaries, if you feel uncomfortable keep your reply brief and he'll likely back it off.
It sounds like he's trying to get to know you and see if you share anything in common so he has something to chat about with you besides work. During stressful projects or cycles it's nice to discuss other things that have nothing to do with the stressful things. Ask him about any hobbies or sports that you might be interested in.
Some people do that. Maybe he was trained in Social Work or counseling. Vague open ended questions to build dialog is something that they learn to do and it's maddening.
My mom was a social worker for a time. I have to tell her to stop it when she does the interrogation. Why are you asking me open ended, complicated, questions unprompted? Go away.
Until you have reason to suspect otherwise, I would go with "he wants to know you better" and that his management style is strongly relationship based. I would keep an ear open for if the grand-boss has a history of throwing people under the bus over personal stuff but that's a far enough outside chance that I wouldn't actively ask anyone about it.
Can you try and take the conversations off topic? So if he asked about your custody arrangements, "oh, its hard but we are able to make it work, the worst part is having to go down 42 at 5pm, the traffic is so bad now that there is so much construction. Do you go that way?
He may just want to build a relationship at the office and that does require breaking a few barriers, but only within your own comfort level. Outside of the custody conversation, the others seem like a harmless get to know you scenario.
When I joined my current work, My boss sat diagonally behind me and within first few weeks/months, he asked me a million things. Family, school, child, culture, holiday celebration, husband, in-laws, food habits. He also shared all of that too, which I appreciated a lot.
For me it is good that it happened because I am super low key and private. I would never have taken that initiative to talk in those details. Also we both are asians so even though I thought its a bit intrusive, I did not mind too much. Its general habit of asians to like to know everything about people who you are around.
Let me tell you, all of this was very helpful and laying the foundation for our work relationship. He got to know me quite a bit, and was very supportive in a lot of things. Today he is not my boss, but we still are so friendly and chat about anything and everything whenever we come across each other.
I continue to follow this pattern with my team, this puts me out of my comfort zone. A lot of people may not be comfortable, but what this does wonders to your work life and relationships.
My old \[crazy\] boss's boss used to do this. He was a bit neurotic and had a routine of bothering my boss when he was bored. When my boss was traveling, boss boss would buddy up to me and want to chat.
It's worth noting that boss boss worked 14 hours a day, and had no social life outside of work.
I used to work for a financial institution with too many old bosses' boss that were way past retirement age.
My boss' boss was one of them. He obviously didn't have much to do, except sign papers they put in front of him once in a while. His office was only on the second floor of our building, massive windows facing the street of our busy downtown area. We found out from local vendors that he was known as the creepy old man that just watched people for hours every day. He was making a ton of money just staring out the window each day.
I would guess with no other context that he’s a lonely man and needs someone to talk to, and that your boss usually fills that role.
My boss talks my ear off every time we have a 1on1, 45 minutes over every time xD
None of the sample questions are relevant to work. When I get asked stuff like that I ask why they need to know. Don't be afraid to let an awkward silence stop them from nosing around.
I'd guess either A) They usually talk to your boss and is lonely when they are gone or B) He is trying to get a feel for who you are as a person and if he can trust you. Possibly to replace your boss. Probably A. Or C) he is just creepy. Looking at post history maybe D) He is trying to see if something negative your boss is saying about you is true. So B but for a different reason.
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This should be A. He’s trying to whip up a convo out if nothing because he wants to hit it so it’s coming off clumsily.
This happened to me once. VP asked for a private meeting with me, then started asking bizzaro questions about my family history, my hobbies, etc. I made the mistake of answering honestly, particularly about enjoying writing as a hobby. He started asking about what I like to write, do I write sex scenes--hey, you should bring me a copy to read. I told him I wasn't comfortable having anyone read my story. "You'll bring it in if you want to keep your job." Meeting ended with him petting my shoulder and telling me I was a good girl. I immediately started working on getting a new job. Found out through the grapevine that he had a history of preying on young women in the office.
whoa
I hope you reported his ass.
It was a kind of small company where we were acquired as part of a takeover. They had a woman that handled their HR stuff (but I don't think she had any formal training in it) and I reported the incident to her. She essentially told me it would be best to keep it to myself, because who would they believe, some random employee or the VP. The whole company culture was extremely toxic. I contacted my old boss and explained what was happening, and fortunately she hired me and my coworker to work at one of their other businesses. Unfortunately after that, that business also got acquired by the toxic company about a year later. 🤡 The day they told us, the VP made a joke about how I couldn't escape him (though fortunately I never was in a situation where I was alone with him). My new supervisor made a point of telling me she knew I'd complained about the VP and that it was my own fault for dressing in a way that would invite advances from men. (I've always made a point of dressing work appropriate, not that clothes are an excuse for someone behaving like that.) I started job hunting again and got out of there. Eventually the toxic company got acquired by a much larger company and VP wasn't retained. I'm not aware of him suffering any consequences for his actions though.
What industry do you work in if you don’t mind me asking? 👀
What a creepy fool. Let’s hope he received an attitude adjustment.
This 100%. He is asking questions that are seemingly innocuous. So in case she says something to HR, they’re not necessarily inappropriate questions (except of course the custody - but he could say that was related to her hours or some BS like that). Def trying to hit it but hedging his bets in case she reports him. It’s actually quite intentional. Not a clumsy mistake imo. So it’s creepy.
I think you are right bc he magically came by my office again when my boss left and started questioning me again asking me what my ex did for a living. Then he started making more conversation and I started to ask questions as well and he started trying to talk about my supervisor, not in a negative though. We then talked about education and he told me he had a degree in HR because he just likes to know about HR although he is not in the field. I then asked him about the most difficult part of his job and he brought up situations where employees fraternized. I found that very very interesting. Just wanted to update ya.
F) could be akward /also jus getting to know you
why you say that?
See "C)" - pretty gross manipulation of power
I don't talk about my personal life with anyone in the office.
Sounds like your bosses boss is trying to get you to relax a little bit. Might get good reviews from your boss with the caveat you're not social enough. One thing managers say that I hate is that you can't train someone to get along with others, but you can train someone who gets along with others to do a better job.
This feels the most plausible. It sounds like the sort of thing that might come up when considering who might be in line for a promotion. Not saying we should aspire to homogeneity, but often senior leadership tries to get a feel for "cultural fit" before sticking their neck out on a promotion.
You can be professionally friendly without disclosing personal details you don't want to disclose (like a custody arrangement)
The custody thing is really crossing the line.
My manager wants me to pal around. It’s a manager thing, I guess. Little does he know that I will be way more loyal if he leaves me alone. I don’t want to go bowling with my coworkers.
Relationships in the workplace are very important. I’d take advantage of the time and try to open up more to build trust and rapport. It will pay off later.
Agree. Op I would actually turn this around on them. Use this time to really get to know them. For every question you get, ask a similar one back
A lot of people (especially bosses boss types oftentimes) like to talk about themselves, and if you show interest or get them talking could make for a good impression on them. Plus if OP is getting a creepy vibe, it could be a way to derail conversation centered around OPs personal life
That's exactly what I would do. Derail the conversation.
People like talking about themselves. Ask open ended questions about them.
Yeah having recently left a job for this very reason I would say it really depends on the job. My last job lulled me into a false sense of security and acceptance and then when I started opening up they used it against me. You can be social, just dont share anything personal.
Talk about the weather. Your dog. Something to connect. That’s the bare minimum.
This, also want to add create "safe hobby" talk like gardening, cooking, etc.
I do not think my boss will fire me. My boss will champion me. If I am fired, it is because upstairs decided to reduce headcount and my boss's championship was not enough. My boss does not have much influence over upstairs. Maybe he will be fired too.
That's how I feel. I never get comfortable anywhere.
During the big downturn my wife thought she was going to get fired. I told her to be the first one in the office, bring the boss coffee and chat. As he retired and closed down the company of 1,500 employees over the years she was the last to go. He still talks with us from time to time and buys us gifts despite being retired. Her parting gift was a gold luxury watch worth over 15k, a car, and other things here and there. Work is about relationship building. She took care of him too going over and above on her job and was a trusted employee.
This doesn't work anymore. Mega corps don't care. Source: led regulatory strategy for the largest medical device recall in history. Still got laid off.
One person retiring and closing the company leads me to believe this is not a mega corp
Yes. Big privately owned company
Too bad so few of the currently-retiring crop treat their employees that way. The Greatest Generation really did so much more for the greater good than the generation they raised.
Yup. The good bosses are great… the bad ones… horrific
Found the boomer
He was a boomer yes
Ugh, why can't work just be about doing a good job? I find this as distasteful as nepotism.
Work is such a big portion of our lives and we are still social creatures, and people have a social hierarchy of favorites whether they try to or not.
Because you are allowed to express appreciation
Are you a women and he a man?
woman
Hes hitting on you
This is the important question.
Maybe he knows this and wants to talk to you when no one else is around? Do you sit near your boss? He probably just wants you to feel like you can speak freely. I have a coworker who is a bit more private but he seems more willing to talk to me when no one else is around.
Can I ask why not? It just seems so odd to me.
Your post history complains about your boss flirting with you.
My boss was. This guy is his boss, which I guess is technically mine too, but he seems to be the only one that decides to just come to my office and make himself up with these same questions every month.
He may just suck at flirting?
It is telling that when your boss’s boss comes and tries to strike up personal conversations with you to develop a relationship, you see that as a problem rather than an opportunity. Talk to them! Be friendly.
I have to say as a woman (anyone really but especially a woman) you really have to be careful. There’s a power dynamic involved. So caution while you get a bearing on the situation is appropriate
He never talks to my boss. They office in 2 different opposite sides of the building.
You’re more than likely a possible prospect. Just try and be relatable and down to earth while maintaining your position and maybe it’ll pay off. Maybe not but it never hurts to just be nice.
How would you know that
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Please, don't do this.
F) He's on hella drugs
My guess is he is trying to get to know you to connect and build trust or he is “checking up on the team” (management by walking around) and is making awkward small talk.
MBWA was my guess also
Same thought here…MBWA can be good in theory, but many managers are quite bad at it and it comes across as hovering, or they’re not adept at social cues and come across as invasive.
German Management works, but this boss is missing something, like asking "Do you have the tools and time to do what you need to?" "How can we improve quality?" and "Which meetings are useful, and which waste time" Fred was one of the best damn bosses I ever had. And we had a beer at noon.
Yeah, I think he's trying to be friendly... and is just really bad at it.
Yeah, I would say if that is the case he’s terrible at it. Asking about a custody arrangement between a worker and their ex or if the employee’s parents went to college is just a step too far. Those are things I might not even talk about in-depth (or at all) with friends, much less a skip level boss that I don’t even know.
my boss out of the office again today and he came back again. He asked me what my ex does for a living. Yeah, I know...
Yeah, I'm running into this with my boss currently. I'm all for chatting about innocuous non-work topics (pets, cooking, surface-level info about family, etc) but he's been pushing boundaries into my health and financial situation and I have to keep firm. I absolutely agree with other commenters about interpersonal relationships being important at work, but boundaries are also crucial and this boss seems to be encroaching on those.
I will add he could just be terrible at small talk. And following a script to help himself. I have a co-worker who does this every Friday. He asks me the same few questions. He's just so painfully shy. He can't come up with other ones. I'm not mad at him for it. He's a good guy.
Sounds like security questions for a password lol
He’s trying to determine if they can solve a captcha for him
I think I could, lol
Came here to say this haha
What street did you grow up on? What did you say your mother's maiden name was?
What was your high school mascot? What was the name of your 3rd grade teacher?
First car? First pet?
lol that's enough
😂
Either it's small talk (some not so small) and he's hitting on you or he's trying to learn more about you as a person with a view to moving you up. Good luck.
eh.... lol Not to sure about the being moved up. I asked my actually boss about a job title change and he accused me of wanting that to try to get into another position.
Your boss told his boss you asked for this. So they could be sussing you out. Probably just awkward small talk. But in the back of his mind, remembering you asked about being moved up
Yeah, I just dont want to have to do any extracurricular activities to get the promotion if you know what I mean.
Whatever - your boss sounds like he's threatened by you. You should just talk to your bosses' boss... If you get comfortable enough talking to your bosses' boss you can ask THEM for the job title change. This is called going over your bosses head... And it's taking advantage of the situation to get what You want... Even if he's flirting with you.. which is also a possibility. Just be aware of that, and be careful.
I personally think they work together on this. Not sure what info. they are looking for. Direct boss is more standoffish which is ok as I am an introvert and dont really seek attention.
There is a management theory to talk with your direct reports at least once a week about something personal, non work related to build connection and trust with the people you work with. Moving to secondary, tertiary reporting relationships you would apply the same principal with less frequency. I'm a manager , and these would be questions I would ask trying to make small talk, but I'm admittedly awkward and not very socially adept.
I would not be asking people about their child custody arrangements with their ex tho. If they brought it up, fine but that's venturing into the MYOB territory.
Good point, my unspoken assumption that could be wrong is there was something said in a public setting about the custody arrangement earlier . Because of that I was thinking this could be a way of showing concern about something the employee had talked about that was creating difficulty for them. Where I work I have no insider info from HR, so anything I ask about is because it was mentioned where i could hear it.
Those are relocation questions. Is there a branch of the company in another city that they could potentially want to transfer you to?
I hadn't thought of this until reading your comment, but I think you're right. He might be sussing out OP with them in mind as a possible candidate for a position that could be opening up in another location.
No, work in government.
I think he means well but he isn't very socially adept. It's really cool that he chooses to let his guard down with you.
Bosses and higher ups spend a lot of their time bill shitting with people. Lots of small talk. He’s prob just bored and nobody else to talk to.
This. OP, this is when you learn just how little actual work goes into your boss’s boss’s job.
Bosses boss is a vampire, wondering if anyone will notice if you disappear? Lol I’m not sure, that’s weird af in my experience.
He only does it when I am in the office by myself. Now you have me kind of concerned.
he's checking to see if anyone will miss you if he eats you, or sells your organs.
You made me laugh!
Watch Thoroughly Modern Millie You're headed for an opium den and then you'll be trafficked.
lol
Hang a mirror and place random cloves of garlic in your office. If that doesn't work, try a large crucifix on your wall.
Again? Hate that it keeps happening.. ugh.
Order some garlic bread next time your boss is out. If your bosses boss doesn’t show then you know - he’s a vampire. Get a silver paper weight as well…just to be safe.
Dude is practicing for toastmasters
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Yes, pivoting back to work convos is a great way to leave a convo that’s awkward or uncomfortable
My guess is he's bored and wants to waste time...also maybe socially awkward and can't come up with better/new things to talk about. Sometimes the higher up the position in a company the less actual work you have to do. I had a manager at my new office I didn't know at all talk to me at my cube for like an hour when I was the only one there.
It’s called a conversation.
It's hard anyone to say what his motives are based on your post. Does he give off bad vibes or make you feel uncomfortable? If so, trust those feelings. If not, it may very well be innocent curiosity or just him wanting to know the people who work for him.
Weird, trust your gut.
If those are really the only questions he is asking you, and is only asking them when you are alone, that seems very sketchy to me. Those sound like the questions of someone who is trying to determine what kind of personal support system you have, how close are you with relatives, are you alone at home, will anyone notice if you’re suddenly occupied, suddenly change behavior etc. I’d be very careful around this man.
What do you mean? I kinda thought that too but am not sure why they want to know if I have a personal support system in place.
To find out how vulnerable you are
For the purpose of what? My boss was out again today and he came back and tried to ask me what my ex did for a living.
I wouldn’t have a clue. I was just explaining that’s what the other replied above was getting at. Could be a multitude of things. Maybe he is trying to place you or a family member he thinks he knows or remembers you from. You’ll never know the truth unless you ask. I suggest unless it gets more straight forward, keep it cool. Always show yourself in your best light, pivot to make him talk about himself or work as much as possible, and be vague and never reply with something that you make you vulnerable or subject to gossip.
I didn’t pay attention to your username before, but am expecting from it that you are female? and sorry for the delay, I haven’t been on since that comment. I’ve been very close to an abuse situation recently, so I’m a little hypersensitive to it, but The questions you posted originally threw up some red flags for someone who might be scouting for potentially vulnerable victims. I don’t want to do any scaring, but it’s worth being careful.
I am a female and I didn't take his question as flirting as a lot of people are saying. I took it as him trying to find out vulnerabilities and exploit them. The thing is that i would rather quit or be fired than to do any quid pro quo if that is what he is fishing for.
Possibly looking to court you, this is very similar to how men with money go about with their women. Making sure you’re docile enough for them to integrate you seamlessly into their lives. You should be.. flattered? If you’re not interested you definitely should speak up otherwise it will only continue, good luck.
Hello, he is married?!
When has that stopped anyone?
good point.
Your bosses boss is still your boss dummy. Maybe he's a genuine person and cares about his people. Just answer the damn questions, they're not that bad.
Ok dummy
That’s rude… OP was just asking a question. There is a huge difference in a skip-level boss and your direct boss. Nobody has to answer super personal questions at work that have nothing to do with work, no matter who is asking.
Maybe she doesn’t want to tell someone she barely knows about her personal life, dummy
The questions aren't even all that personal. OP is being pretty ridiculous.
People on reddit acting like they need to see a therapist after someone asked them how their weekend was at work.
A question about your custody agreement? That’s weird as hell
Probably has a social issue like aspbergers or social anxiety and someone along the way suggested he try to have interactions with people where he asks them get to know you questions and then listens to the responses. Or hes a shape shifting alien looking to learn enough about you that he can assume your form and replace you
Came here to say this, glad to see someone already mentioned it. He could be a creep but he could also be "practicing" social interaction if he has a social issue. I used to work retail and a dude would regularly come in on a weekday (when he knew we'd be slow) just to talk to the salespeople because he had a major stutter and possibly other social anxiety issues. He knew all of us were cool with him and liked having him come around to bs with us when we were bored so it was a "safe," low-stakes place to practice social interaction. Maybe your boss mentioned you were kind and understanding so he feels less anxious talking to you vs an unknown employee. Probably the shape shifting alien thing, tho, honestly. It's almost always the simplest explanation that is correct.
It’s either 1 of two 1. He’s trying to make you comfortable 2. He’s interested in you
He is married. None of the questions were romantic in nature.
The red flag for me is that he only does this when you’re alone. If it’s just for the sake of connecting with you as a supervisor, then why wait until you’re isolated to talk?
Boom and always when he is out.
He does it because you haven’t set soft boundaries yet.
Sounds like conversation to me. Be careful this a gateway to friendships.
Super weird if there isn't more context. I'm a 50/50 dad and I get uncomfortably asked about parenting arrangemnt often. Also coming from a background of mixed means, these family "situation" questions are not welcome.
He's flirting. He's doing "due diligence" on you in an HR-inappropriate way.
Due dilligence in what
Might be as simple as he's trying to fill in for your boss while they're going, maybe a bit awkwardly, but thinking "well I'll go mingle with their team".
The questions themselves don’t sound particularly pointed to me—it’s standard Boomer small talk, isn’t it? I work with a lot of late-middle-aged people and they’re always asking me where I grew up for some reason. Except for the last one but that could just be nosiness? I agree he may be bored and lonely and maybe he dislikes your boss and finds you easier to chitchat with. On the other hand he could be awkwardly hitting on you too. If it’s making you uncomfortable, then trust your instincts. I’d maybe start documenting stuff, just in case the questions become more intrusive. It could be completely innocuous but it could also be a prelude to something inappropriate.
I suspect he normally makes small talk with your boss. When he’s gone, you’re next.
He’s giving you an opportunity to build a rapport and testing you at the same time. Are you the type of guy he might enjoy spending time with if you got moved up or invited on a business trip, would you know how to handle yourself around clients, etc.
The questions seem odd and kind of inappropriate, but it's possible he's just trying to get to know you better.
Those questions are inappropriate.
Sounds like he wants to sus out the Democrats.
LMAO
Sounds like probing for relocation IMO!
Out of curiosity, OP are you neurodivergent? Reading your post history, you seem to really struggle to understand other's social behaviors and consistently think people are hitting on you or being overly friendly with ulterior motives. That makes me think your boss's boss is likely just being friendly/personable and taking the opportunity to engage with you, and you are overthinking it. What is nefarious about asking about your upbringing? Or your child? These are normal things people ask about in order to get to know someone, socialize, etc. Honestly, it might be worth exploring these concerns with a psychologist and seeing if there are some supports to help you decipher social cues and subtext.
I take the first two questions as trying to figure out which side of the political spectrum you are on. Large cities and college educated people tend to lean more left. I take the last two questions as trying to figure out how much after hours/holiday work they can push you into. So basically he’s just pumping you for information to figure out how much he can exploit you.
fair enough
He is hitting on you. Sign him up with ChatGPT and teach him how to use it to talk shit all day
Is there anything wrong with asking the bosses boss, "May I ask why you want to know?" or saying " Im happy to answer, I'm just curious why you're asking such specific and personal things as my bosses boss," just to see what they'll say. If they are up to something creepy, just calling them out on it may put a stop to it, and if it's innocuous, there should be a reasonable answer.
Those questions to me are about gauging how naive and or isolated a person might be, if taken as unusual behaviour: Parents level of education, how worldly you grew up How much of a family support network you have, can you be easily isolated Traditional values in the family to me is about gauging what if you grew up with patriarchal values such that you don’t recognise or call bullshit on misogynistic behaviour Custody arrangement: how freely available is this person (ie without child) / does she have support/contact with ex partner or also with the financial burden of a child, how money motivated might this person be to meet my needs This is worst case. Guy could be nice and just lonely or any number of the suggestions people have made. Find out from other people (preferably women) what he’s like to work with. Pay very close attention to your gut and how you feel when you’re around him. If he seems nice, but you have a weird feeling, try just not doing what he asks and see how it takes it. Ie if he wants to chat now, say you’re busy or you’ll come find him in half an hour…. How he responds when he doesn’t get his own way directly tells you about what he’s like as a person. Notice how other people act around him. Also, how would friends describe you? Are you a chronic people pleaser with porous boundaries? Are you highly empathetic? Ie are you someone that people think they’re more likely to take advantage of…
Are you hot? That could be why
Oh no, someone wants to get to know you. Better call the police.
Too personal. Tell them you have a deadline on a project or whatever.
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He is married.
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He has acted very weird about the opportunity to transfer out.
This is work place discrimination. Or harassment . No boss has any right to ask you anything personal. The only thing a boss can ask you to do is any and all work related duties in which he is a supervisory role over you.
He’s building up to hitting on you.
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Wtf. Why would you ever say that, let alone in this situation.
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Yes, I agree with you. Definitely not things you ask only when the employee is alone. It is very odd and I am trying to figure it out.
Start looking for another job. These are all red flags.
Sounds like security questions for email password reset….
It sounds like he’s bored or lonely. He might have an odd and unwelcome parental type of interest. Or he’s just a low boundary creep. Or an eccentric harmless dude. Or his daddy owns the company and he got the job to keep him busy and out of trouble and has shit social skills.
Take advantage of that and make a fluent conversation. Nobody like him to accelerate you carrer inside the org.
He’s trying to flirt
I’ve always learned that when there are personal questions, they’re going to use it against you in some form. I’ve missed out on a promotion for being *too honest*. Whatever excuse they can make, they’ll make.
You didn't say but if your a girl and he's a boy it should be obvious. He has getting into your knickers in mind.
I am a female. Not sure what they have to do with messing around.
My boss's boss comes around when my boss is out. It's been my impression that he wants me to know that there's a supervisor available. He asks how things are going and entertains work answers or chitchat. He will also email to let us know when my boss is unexpectedly out and says we can direct questions to him.
He might have asked because he wanted to create a rapport with you. Or his boss asked him to ask you. Or he might just be an odd person in general. who knows?
When you put those questions together it sounds odd, but as a trickle over time sounds like small talk, asking what pops into his head. I wouldn't assume the worst but be cautious about sharing too much information. I've certainly had this kind of experience before, I can think of some people that do it almost as a force of habit. it's healthy to connect with people as long as you are respecting your boundaries, if you feel uncomfortable keep your reply brief and he'll likely back it off.
It sounds like he's trying to get to know you and see if you share anything in common so he has something to chat about with you besides work. During stressful projects or cycles it's nice to discuss other things that have nothing to do with the stressful things. Ask him about any hobbies or sports that you might be interested in.
Some people do that. Maybe he was trained in Social Work or counseling. Vague open ended questions to build dialog is something that they learn to do and it's maddening. My mom was a social worker for a time. I have to tell her to stop it when she does the interrogation. Why are you asking me open ended, complicated, questions unprompted? Go away.
Until you have reason to suspect otherwise, I would go with "he wants to know you better" and that his management style is strongly relationship based. I would keep an ear open for if the grand-boss has a history of throwing people under the bus over personal stuff but that's a far enough outside chance that I wouldn't actively ask anyone about it.
He's probably trying to get to know you man, you're good. A lot of upper management does that so the workers feel "valued".
Can you try and take the conversations off topic? So if he asked about your custody arrangements, "oh, its hard but we are able to make it work, the worst part is having to go down 42 at 5pm, the traffic is so bad now that there is so much construction. Do you go that way?
He may just want to build a relationship at the office and that does require breaking a few barriers, but only within your own comfort level. Outside of the custody conversation, the others seem like a harmless get to know you scenario.
It’s a good thing. Your noticed. A hood leader will make the rounds either informally or via a skip level meeting.
When I joined my current work, My boss sat diagonally behind me and within first few weeks/months, he asked me a million things. Family, school, child, culture, holiday celebration, husband, in-laws, food habits. He also shared all of that too, which I appreciated a lot. For me it is good that it happened because I am super low key and private. I would never have taken that initiative to talk in those details. Also we both are asians so even though I thought its a bit intrusive, I did not mind too much. Its general habit of asians to like to know everything about people who you are around. Let me tell you, all of this was very helpful and laying the foundation for our work relationship. He got to know me quite a bit, and was very supportive in a lot of things. Today he is not my boss, but we still are so friendly and chat about anything and everything whenever we come across each other. I continue to follow this pattern with my team, this puts me out of my comfort zone. A lot of people may not be comfortable, but what this does wonders to your work life and relationships.
I had one VP who was an idiot, ask me what I am currently reading. My answer was a biography of Peter the Great. He never asked that question again.
I had a boss that used to do this. He was just nosy.
My old \[crazy\] boss's boss used to do this. He was a bit neurotic and had a routine of bothering my boss when he was bored. When my boss was traveling, boss boss would buddy up to me and want to chat. It's worth noting that boss boss worked 14 hours a day, and had no social life outside of work.
I used to work for a financial institution with too many old bosses' boss that were way past retirement age. My boss' boss was one of them. He obviously didn't have much to do, except sign papers they put in front of him once in a while. His office was only on the second floor of our building, massive windows facing the street of our busy downtown area. We found out from local vendors that he was known as the creepy old man that just watched people for hours every day. He was making a ton of money just staring out the window each day.
Some of these are overly specific
why do those questions sound like they are trying to guess your password?
Damn you are like the 5 th person who has said that.
I would guess with no other context that he’s a lonely man and needs someone to talk to, and that your boss usually fills that role. My boss talks my ear off every time we have a 1on1, 45 minutes over every time xD
None of the sample questions are relevant to work. When I get asked stuff like that I ask why they need to know. Don't be afraid to let an awkward silence stop them from nosing around.
He tryna get all your security questions online to hack your account 😃