Best Questions to Ask the Interviewer, and When to Ask Them

From May 2010

Interviews are, in most cases, the only shot you have at gathering the information you are going to need in order to decide if you want a job that is offered. In some situations, a lunch or subsequent meeting can be scheduled to give you an additional opportunity to speak to a potential employer in a more relaxed atmosphere, but typically those meetings only happen when a candidate needs a bit more reinforcement to decide on a job that has been offered. Some interviews may run a bit long and the time you are afforded to ask questions can be short, so be sure to make the most of your window of opportunity.

In many respects, the interview is probably a lot like a blind date. You want to find out as much as you can about your date, but first you have to set the tone and start things off on the right foot. We surely would want to find out if our blind date is, say, a serial killer – but leading off with the ‘Are you a serial killer?’ question would seem rude, and we probably wouldn’t get an honest answer if we asked it as our lead-off.

Your first questions are to get off on the right track and create a positive energy. If you are in an interview situation where you have three or four sessions scheduled with individuals or small groups, you can use these questions as ‘ice breakers’ in each session. Once we set that mood and relax our interviewer, we can start digging a bit deeper to get the answers we really need to make our decisions.

Setting the mood (AKA cocktails and light conversation)…

Question: “What is your background and how did you come to work for COMPANY?”
Reason to ask it: People like to talk about themselves, so give them a chance to do so. Toss in a ‘oh, that sounds interesting’ and perhaps a follow-up question if appropriate.

Question: “What do you like best about working for COMPANY?”
Reason to ask it: This question serves two purposes. First, it gives the employee the opportunity to speak well of the company which again will give an initial positive vibe to your dialogue. Secondly, what the employee chooses to say they like best can be quite telling. If their answer is ‘environment’ or ‘the people’, that is a positive. If the response is ‘the money’, you may want to think twice unless you are a mercenary.

The second set of questions are designed to discover whether or not you would like working at COMPANY and perhaps what COMPANY is all about. ( AKA light interrogation of your date during dinner )

Question: What are the biggest challenges facing COMPANY?
Reason to ask it: The answer here will start to create an image of what this company is going through today and what the landscape is for tomorrow. At a start-up, you may hear answers about financial challenges, which may mean payroll could be an issue. You may hear answers about management re-orgs,

Question: What would the typical day be like for me at COMPANY?
Reason to ask it: You may get an answer that gives you insight into work/life balance (‘typical day ends just in time to catch the 11 o’clock news’), how much of your day may be spent coding or doing other duties, how many meetings you may be pulled into, etc.

Question: What has your career path been like here and what is a typical career path for my role at COMPANY?
Reason to ask it: Find out if they promote from within and if they have separate technical and non-technical/pure management tracks.

Question: How would you describe the environment?
Reason to ask it: You should be able to ascertain if it is cut-throat or cooperative, how much support is given to technologists, and whether you will be expected to work with teams or as a solo entity.

Question: Management styles? Development processes in place?
Reason to ask it: Some of you may prefer some micro-management to avoid mistakes while others prefer autonomy. Asking about the development process is a big one, as a shop without process is the worst nightmare for many of you based on my conversations. Be sure to drill down to get the best understanding of how well organized they are.

Question: Tech stack?
Reason to ask it: If their answer is a list of products and technologies that are severely dated, it could mean the company doesn’t invest in or even investigate the latest and greatest. This also gives you an opportunity to discuss your experience with the tools they are using.

Question: Is this position open due to growth, backfilling due to turnover, promotion, or another reason?
Reason to ask it: You may get an answer that people don’t tend to stay in this job long, and that could be either a positive or a negative. Perhaps this position is a launching board into higher level positions, or maybe it is a dead-end that will burn you out. Growth obviously shows that the company is adding headcount.

Closing the deal (AKA last call and the drive home)…
Question: What qualities/background do you think would be key to making someone successful in this position?
Reason to ask it: Gets things back on the positive side before the end, as well as giving you more info on whether you would be hitting the ground running or may require some learning curve. (NOTE: This one could also be used as an ice breaker)

Question: What type of projects are just getting ramped up or are on the horizon?
Reason to ask it: Interviewers will like discussing projects that they find most interesting and which they think you will find most interesting as well. If they talk about fixing bugs, chances are that is what you will be doing in this job for the foreseeable future.

Question: Where do you see yourself in five years here at COMPANY?
Reason to ask it: Again, it lets the interviewer talk about himself/herself again in a positive fashion, and if the interviewer has a sense of humor expect an attempt to use it on this question.

The Conclusion (AKA the kiss goodnight?)
Thank the interviewer for taking the time to speak with you, and if you think it went well you can ask something simple about how soon you should expect to hear an answer. Provide your contact info and let them know that you are happy to answer any other questions that may come up once the interview is over. Don’t get desperate at this point, chances are you won’t get an offer while you are walking out the door. Good luck!

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