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I found a job I am interested in and I have some deal-breaker questions I want to ask before applying (example: if they offer relocation, remote work, visas). I tried to find the answers on their site/internet without success.

My goal is to save time (to both parties), considering this company has a policy of only notifying shortlisted candidates.

Because the job listing doesn't have a person responsible, I contacted one of the HRs of the company, Jane, via LinkedIn. I told her about my interest in the position and if she could point me to the person responsible as I had some questions before applying.

On the same day, Jane came back to me saying that Joe is the one responsible but she'd be happy to answer my questions.

My gut tells me I should ask the important questions to Joe, considering they may be an opener to create a connection that could help me land the position, but Joe may not be as responsive/eager as Jane before even applying.

I though about asking Jane one of the questions and send the others to Joe to have a fallback in case Joe doesn't answer.

What's the proper etiquette for handling this situation?

In case it is relevant: Joe and Jane have the same role and seniority stated in their LinkedIn.


Update: I followed the accepted answer's advice, but now I've been waiting 3 working days for Jane's answer, see the follow-up.

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    Why do you think talking to Joe directly would help your job chances if he has the same role as Jane? – Peter Feb 4 at 13:26
  • @Peter honestly, I was hopping this could be a chance to send my covert letter and CV directly to the person responsible for the role, bypassing the automatic screening/ATS (assuming the answers to my questions are positive and they don't mind the bypass) – unperson Feb 4 at 15:09
  • How large is the company? The compartmentalisation and rigidity of process will vary between companies, but I find it much stricter for larger companies. – Lio Elbammalf Feb 5 at 22:47
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Jane should be able to answer your questions since:

  • Jane & Joe have the same role as well as seniority
  • Your questions are rather general ones than specific to the position
  • Jane agreed to communicate and is keen on answering your questions

..so you should go with that.

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  • The deal-breaker questions are indeed not specific to the position, but I also have some position-specific ones (2) that would make this job the nº 1 on my application list. I realize these two questions are more appropriate for the interview but, if I already made a connection it could make sense to ask them early. – unperson Feb 4 at 15:17
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    If the deal breaker questions fail then you won't be asking them, no point going to extra effort for anyone until the first hurdle is passed. – Kilisi Feb 5 at 2:19
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    @unperson You don't specify what industry, but almost all openings are having more applicants than ever these days. (There is a pandemic, you see...) I would highly recommend that you just apply as soon as you're sure a position is on your reasonable list, without worrying too hard about where it is on that list. If you do get multiple offers, you can worry about which one is number one at that point. – user3067860 Feb 5 at 21:43
  • Though the other answers have additional important points, I am accepting this answer since it is the most direct, on point and concise. Thank you, @Kilisi and @iLuvLogix! – unperson Feb 8 at 18:28
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First rule: don't insult HR.

Jane is offering to help. She's fully able to answer all of the questions you need answered now. You've already admitted that any questions she might not be able to answer would be reasonable to ask at the interview, and the answers she's able to give are sufficient to tell you if it's worth taking the interview or not.

So... under those circumstances trying to go around her to get to Joe starts to be rude, perhaps insulting. You may not intend it that way, but it would even imply a bit of sexism on your part. This is especially bad because of how open and helpful Jane is trying to be for you.

It is reasonably likely that if you try to evade Jane in order to get to Joe, Jane will get at least somewhat offended. She'd have reason to. If she has a good working relationship with Joe (probable), that's going to do far more damage to your prospects than any sort of vague attempts to "build a connection" with Joe might gain you. If you don't treat HR as people deserving of respect, it will damage your ability to get a job. Jane is offering to help you out. Treat her with respect. Ask your general questions. If you have position-specific questions, acknowledge that she may not be able to answer, but include them too. You don't know what information she has access to. Be appreciative and polite. This is your opportunity to "build a connection" with Jane. Even if she's not directly involved, that's still a valuable thing for getting your resume where you want it to be.

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    The names Jane and Joe are made-up names, in fact "Jane" and "Joe" are both female, but I get your point. Thanks for answering. – unperson Feb 4 at 16:50
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    I mentally replaced that headline with "Don't trust HR" and got really confused for a minute ^^ – Kaz Feb 5 at 9:57
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    @Kaz I think that this stack has internalized that message a bit too hard, and ignores this one a bit too much. HR, more than anything else, is made of people. Often they are overworked, and poorly treated, in a thankless job. Often, especially during the interview process, they have more power over your life than they do over their own. Treating them in a respectful and appreciative manner, and trying to make their life easier where you can, can pay serious dividends. – Ben Barden Feb 5 at 15:14
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    @BenBarden - indeed, always be nice to the receptionist, office admins, and the custodian. A little friendliness and goes a long long way. – Jon Custer Feb 5 at 15:42
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Just ask Jane all the questions.

Either she can answer them all, in which case great. Or some of them she'll have to defer to Joe, in which case you get your introduction.

Win-Win either way.

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Even though Jane is not the one responsibile for the position, she still works with Joe and her impression of and interaction with you may be relayed to Joe anyway, and may even make you stand out as a candidate by expressing enough interest to reach out.

She's willing to answer the questions you want answered, she seems positive about the interaction, and she's likely equally knowledgeable about the topic since she has the same position and rank as Joe. The worst that can happen is she may not be able to answer the position-specific questions and will either direct you to Joe or simply get the answers from Joe and relay them back to you.

Just for the potential to use this as your foot in the door, and as an oppurtunity to schmooze, I think would be beneficial for you.

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Deal with Jane.

My gut tells me I should ask the important questions to Joe, considering they may be an opener to create a connection that could help me land the position

I'm sorry to break it to you, but your desire to ask someone else simply isn't relevant here.

Here's how I'd characterize what has transpired so far:

  1. You contacted the company and asked who to address your questions to.
  2. They told you who.
  3. You (for vague reasons) don't like their answer. (Or you think it decreases your likelihood of landing the job.)
  4. You came here to ask for permission to ignore their clear and direct answer and contact someone else instead--in spite of their clear and direct instructions.

The grown up and professional thing to do here is very simple: do as they instructed you.

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  • I respectfully don't know from where you got the impression I didn't like Jane's answer. I am not familiar with these situations and I wanted to know what was the proper course of action. On the other hand, maybe I'm wrong, but why talking with the person responsible for handling the candidates for the role I would like to apply could be such a bad idea? – unperson Feb 6 at 23:42
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    Thanks for asking for clarification. The point I was trying to make is that it doesn't matter whether talking with the hiring manager is or is not good for you. The company told you they want you to speak with HR, so that's what you should do. It's that simple. I'm sure you realize that it's disrespectful to ask someone explicitly what their preference is, be told, and then act completely against their wishes. Hope that helps. – ron rothman Feb 7 at 0:56
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I found a job I am interested in and I have some deal-breaker questions I want to ask before applying (example: if they offer relocation, remote work, visas). I tried to find the answers on their site/internet without success.

Frame challenge: maybe they originally weren't planning to offer these, but if you convince them that you're the candidate they really want, you can get these things in the negotiation.

This blog is something anyone should read before going into a negotiation on salary and benefits, and expands my point in much more detail. But the essence is this: if they want you, a lot of policies turn out not to be carved in stone.

I think given that you're already talking to Jane, you might be best off getting information from her. If it's not utterly and completely crushingly negative, apply and talk with Joe. Then, wow Joe with how wonderful you'd be in this job. If he can just help deal with these obstacles blocking you from taking his offer...

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If you really feel that Jane may not be able to really answer the questions, then I would suggest that you send the questions to Jane, but CC Joe.

In this way you'll be able to get the answer you want and mitigate the insult to HR. As long as Jane replies with Joe still on the email, you can be assured that he (she) agrees with the response, otherwise would respond with corrections.

I've never done this with HR and a new position, but I do this commonly with colleagues.

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  • 'mitigate the insult to HR' on you first interaction with a new company imho it is not a good strategy... What about avoid insulting HR altogether? – Paolo Feb 7 at 20:11
  • @Paolo, that's what mitigation is. I'm not sure that it would remove it all together, but there a lot of things that one could do that might unknowingly insult someone. Is there something that could improve the answer, or do you just not like my opinion? – Ben Feb 8 at 16:49
  • definitely I don't like your suggestion, but that's not an issue for me: it is expected to find different point of view on this site. anyway maybe we use different definition for mitigation. mine is: reduce the possible consequences of unavoidable risks or patch what already broke. I read your answer as: 'knowingly insult HR and then try to mitigate the outcome'. I hope now is clear why I find your proposal a solution I would not apply. I agree with you that it is a strategy that sometimes helps among colleagues, but I would never try my chances using it at a new company... – Paolo Feb 12 at 7:54
  • btw, downvote is not mine... – Paolo Feb 12 at 7:55

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