Eight great job interview questions for applicants

It’s been a while since I wrote an essay about “penetrating questions” for job seekers to ask on interviews.  For reference, the prior ones in the series are Ask, Ask 2, Ask 3, Ask 4, Ask 5, Ask 6, and Ask 7.  (Ask and Ask 3 were actually republished here on Neil Patrick’s site; this one was written exclusively for him!)

As an aside, one of the questions from Ask 7 was about inviting five dinner guests from history.  I decided to answer it, publicly, myself in an essay.  I’d thought it was a worthy intellectual exercise.

I often get ideas for these questions from other peoples’ essays.  The essay The Interview Secret HR Doesn't Want You To Know... by J.T. O’Donnell, founder of WorkItDaily, sparked a thought for another question… or two or three.  I hope these prove useful to you in your interviews.

What on my resume caught your eye?

This is a question, to be asked of the hiring manager only, that gets to the heart of why you’re in their office.  It forces them to identify something overwhelmingly-positive about you, and puts you in a good frame in their mind (on the flip side of things, if they have no clue, that’s not a good sign!).  And whatever they name gives you specific things to focus on, because that gives you an opening to:

And that, , applies to which problem you have… ?

You’re making them do the work for you.  They’ve just – presumably – named one of the key strengths that they saw in your background.  Now you’ve opened the door to their explicitly naming one of the challenges they have and how your background meshes with it.  Not only can you now address that problem specifically, by getting them to tie your strength to their problem, you help get them to see you in the position.

What last made you laugh at work?

This is a culture question.  Nobody expects work to be a comedy or social club, but it is a place where you spend a significant portion of your waking hours.  The answer doesn’t need to be detailed or elicit a specific joke they remember hearing, but if they really have to think hard about the last time they laughed as a result of something – e.g., “Well, the other day my co-worker and I were ribbing each other about…” – then that’s a potential warning sign that there’s no real joy on the part of people working there.  Even worse if they flat-out can’t think of a single instance.

Am I the first person you’ve brought in for this position?

Very often hiring managers don’t really know, precisely, what they want when they first write the job description; they have a vision, but visions don’t always comport with what’s actually available.  And it’s very typical that as interviews go along tweaks to that vision they have are made.  Gleaning some idea of where you are in the sequence can help you understand the possibility that the real wants and needs have deviated from the published ones.

Can you describe the last time you had to help a subordinate get through a roadblock?  And can you describe, generally, what the issue was?

It is inevitable that projects will run into roadblocks.  Some of these can be gotten through with persistence on the part of the individual person.  Others can require managerial “pull” to get something loose.  A good manager will be willing to help a subordinate get through these – after, of course, the individual has tried without success.  And if an issue happened once, generally, it’s likely to happen again if it involves a different group or function, so forewarned is forearmed about a potential difficulty you might face.

Could you walk me through your day yesterday?

This should be aimed at a potential coworker.  It gives you, at least in a one-day snapshop, what a day might be like.  Also, watch facial expressions – positive or negative?  And do they attempt to gloss over the question?  People who are enthusiastic about the work and the environment will happy to talk about things at length.  People who are not, won’t.

(An example: I asked a similar question, “What’s your typical day like?” to a potential coworker during an interview.  Their answer was revealing: “Oh, I usually get here about 7 AM, …, and I leave about 7 PM… and sometimes I come in on the weekends to catch up!”  My unvoiced thought was “You’re pushing 60 a week at work, and you need to catch up on the weekends?  And this is OK with you?”  

Later, talking to a recruiter, I learned that this company has such a reputation for squeezing workers for immense hours of casual OT that people would tell this recruiter NO THANK YOU when she named the company whose job she was pitching!  One actually said “I’d rather be homeless than work for this company”.  The recruiter ended up not accepting any more contracts from the company.)

What is a typical day like for one of the group?

This is a compare-and-contrast question to the above, to be asked of the hiring manager.  What happens versus what do they think happens?  It’s also an awareness question, i.e., how connected to the group is the manager?  Are they aloof?  Connected?  A “helicopter boss”?  The answer can give some clues.

I hope these, and my former thoughts in Ask 1 – 7, help you not only land a good job by asking great questions, but gain insights into places that, when you hear the answers, you decide you will pass on working there.

© 2017, David Hunt, PE
David Hunt is a Mechanical Engineer looking for a full time position north of Boston, MA in the USA.  He is seeking a job, ideally in the medical device or defense industries, as a:
  •          Design Engineer (with a strength in plastics, but that’s not all he can do)
  •          New Product Introduction Engineer (e.g., DFMA)
  •          Cost Reduction Engineer
  •          Manufacturing / Process Engineer
And do check out his portfolio.


  1. Thanks so much Neil! (And I notice that my "Elephants" post often makes an appearance in your popular list.)

  2. My pleasure David. I gather elephants are the new cats. Look out for funny elephant videos on this blog soon. (Not) ;-)