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Recently I had a job interview, it worked out well and the company is just waiting for me to sign the contract.
It's a startup and they want to hire me as a kind of trailblazer. They have no other employees in my "department" yet, but want to build it up step by step.
During the interview I was very excited about the job, there are many things I really like about it. But after some time thinking about it I got more and more questions and concerns appearing in my mind, about their long term plans, their technology stack, their management plans and so on; things which will affect my work more or less. (I asked some questions about this already, but I didn't cover everything and in depth.)

Is it a bad sign for an employer if I'll raise so many questions and concerns afterwards? Will this let me look irresolute?

Update: I took Lazors advice to heart and arranged a call. It was definitely the right decision. I asked my open questions and in the end it turned out, that my concerns weren't far-fetched and my expectations and vision differed slightly too much from theirs. So I decided to decline the offer and to accept one from another company.
Thanks for your answers!

  • @JoeStrazzere Thanks. In the end I learned my lesson. You are right, next time it's way better to clarify all these questions beforehand, I think I wasn't prepared enough for the interview and that caused all the 'trouble'. – Artery Apr 27 '17 at 6:29
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Your questions are perfectly fine and this is the time to ask them. You might even want to consider meeting with them again to discuss everything in more detail. You can apologize for taking more time to ensure that this is right fit, but you are considering a large role in their organization and they will appreciate that you are taking it seriously. I would want to make sure all of your questions are answered before making such an important decision.

  • I think that an appropriate sentence to push the interview would be nice still. Something in the idea but way more professional : "You're asking me for a big role, can we meet again so we can refine the scope of my role and what will you do to help me assuming it ?" – Walfrat Apr 19 '17 at 7:18
  • Good point about proper phrasing on how you approach this. The goal is to use a collaborative approach to building a vision that everyone agrees with, defining expectations of what everyone will be doing, and generally lay the foundation for success. – Lazor Apr 21 '17 at 22:50
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I wouldn't say it's a bad sign per se, but if you've got a lot of concerns about a workplace than you need to ask yourself whether it's the right role for you or not. An employer might sense that you have some doubts about the role and that make them think that you're hesitant about the role, or they might just think you're super keen and want to do a lot of research.

It's down to the employers opinions and personality. They might think it's a bad thing and you're reserved (which you are, hence the question) or they might not think about it. I would say this though, if you're that worried or concerned about the company, it wouldn't be a bad thing to decline the offer.

It's business, you're there to work and earn a living. You won't be hurting their feelings turning down the job offer by any means.

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    There is a difference between doubts and clearing up expectations/getting more detailed information. I wouldn't take a job simply because the company seemed nice. I'd want to have a good idea what I'd be working on, with whom I'm expected to interact, management structure, etc. I can certainly see both sides being distracted by the initial "are you qualified" for this job and "is this a good cultural fit". But if you're a serious candidate, particularly for a strong leadership position, frankly I'd be concerned if a candidate did not follow up with questions like this. – iheanyi Apr 18 '17 at 18:44
  • The OP mentioned concerns so having lots of questions may be a red flag, having lots of general questions is a different story altogether. Being concerned or hesitant is very different to curiosity which the OP didn't seem to imply from their question. – user66194 Apr 18 '17 at 18:50
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    I'm not sure how that's an issue. Concerns about long time viability is an issue for anyone taking a job at a startup. That's typically assuaged with salary and equity, but that doesn't necessarily cut it for everyone. It's one thing to be concerned with IBM's long term plans. Quite another with a startup where you're being asked to trailblaze something - the trailblazing of which will be directly impacted by what else the startup is doing. His concerns could be a red flag for two reasons - he may not be a good fit or the company is embarking on something not well thought out. – iheanyi Apr 18 '17 at 19:02
  • I can't see how it hurts him to bring it up. If he's not a good fit, then they go their separate ways. If the plan needs revising, then they do so and he hits the ground running trailblazing something that works better for the company. Or he's a good fit, they discuss his concerns, and things move along. If the company isn't willing to discuss an employee's concerns and expect him to just 100% get with the program - perhaps it's not a good fit and so he should move on. Regardless, it seems bringing things up resolves all ambiguity and addresses any open issues of correct fit between the two. – iheanyi Apr 18 '17 at 19:04
  • Unless he has some requirement where he must be employed now and can't afford to continue job hunting, I don't see a meaningful downside from his perspective. – iheanyi Apr 18 '17 at 19:05
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Is raising many questions and concerns after an interview a bad sign for an employer?

Yes, you're being hired to create a department, obviously since it's just starting their will be multiple things to sort out, many of which they're probably relying on you to solve. Asking so much before you even have the job seems like you don't have a clue what to do unless your hand is held. In which case you're probably the wrong person for the job.

They need someone confident, who can create procedures utilising what they have, make recommendations for essential tools and processes and basically take ownership of building them a robust department.

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    "a kind of trailblazer" is not the same thing as "department head." It might possibly turn into that, but there's nothing wrong with asking questions before you sign onto a project. And from the company's perspective, it's far, far better to answer some more questions now and get an employee who feels comfortable than to hire someone now who ends up leaving in three months. – Caleb Apr 13 '17 at 22:13
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    With full respect to the OP, an experienced expert likely wouldn't be asking whether follow up questions look bad to an employer. – Caleb Apr 13 '17 at 22:20
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    @Kilisi hiring confidence men who can't actually do the job is why sites like these are filled with question about dealing with poor supervisors/management. It sounds like his skills are suited to the job and he needs to narrow down expectations. – iheanyi Apr 18 '17 at 18:48
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    @Kilisi He's being brought in to lead an effort. Questions like his are not only normal, as a hirer if he didn't have them they'd scare me away from him. You're bringing someone in to start a log term effort- you want to not only be sure of their skills, but make sure goals and philosophies align. Or equally importantly, he may be seeing problems that we haven't seen yet. There is absolutely no problem with him bringing them up, in fact he's likely to gain points by doing so. – Gabe Sechan Apr 19 '17 at 6:26
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    Nothing prevent the employer to answer "we will sort it out", "it will be a part of your job to sort it out". At least it helps to understand the full scope of what he will have to do. – Walfrat Apr 19 '17 at 7:13
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An important question here is: do any of the question you want to ask have a non-negligible probability of changing your decision to accept?

It sounds like they might, but if not then the decision that is facing you is whether to accept, renegotiate, or reject the offer. If you feel you have enough information to decide to accept, then you should do so; the remaining question can wait for the "orientation". Obviously, if the answers to the questions have a good chance of swaying your decision in this regard, then you should ask before accepting. You should omit questions that don't contribute to an accept/reject decision.

As you've tagged the question with "professionalism", professionalism isn't about projecting false confidence. A professional will ask for more information/clarification when needed without apology. Even if you "should have" thought to ask the questions in the interview, being a professional isn't about not making mistakes, but it is about rectifying them as they become apparent. Now asking these questions "later" may make you look less experienced and that might negatively impact their decision to hire you, but it won't make you look less professional unless you do it poorly (e.g. by asking questions that they have answered or asking questions in a manner that requires more of their time than necessary). You probably care about getting a job more than some abstract notion of "professionalism", but I'd argue that an experienced professional can find themselves in the situation you're in, and that they'd act as above. Based on your comments, it also sounds like they have some reasonable understanding about your level of experience, so that also suggests that this wouldn't factor negatively for you.

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Is raising many questions and concerns after an interview a bad sign for an employer?

Yes 100%. Ask too many questions, outside the interview is a sign of immaturity. They have given you a contact, and expect you to sign it. Your job now is fulfil the contract agreements and simply do whatever the company wants you to do.

People are busy. They don't have time to respond to your "many" questions. Stop being dubious, work out the solutions and do it.

Successful brands like Apple has a culture like this:

This is just part of our culture as a group. We do it more as a team

Are you sure you embrace teamwork? Don't question your teammates, work with them.

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    It's not a sign of immaturity to have second thoughts after having had more time to think about any topics that were raised during the interview. What would be unprofessional would be OP keeping all their doubts quiet, pretending everything was fine, then quitting at the first opportunity. – Llewellyn Apr 14 '17 at 10:53
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    The OP isn't their teammate yet and asking questions to see if they should become their teammate is absolutely the right thing to do, especially for a small company. Until you actually sign the contract (and they countersign it!), you have no obligation to "fulfill the contract agreements", and you're completely free to ask more questions and possibly ask for a different contract. They are completely free to ignore you and move on to another candidate if this seems to make you not worth it for them. – Derek Elkins Apr 17 '17 at 4:02

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