Powerful Interviewee Questions


I have been in more job interview discussions in my career than I care to count.  The vast majority of them are when I was the one interviewing the candidate.  I always invite the candidate to ask me questions either during the interview (or after by way of email if they wish).  I have also been on the candidate side of the table as well and I am accustomed to being asked if I have any questions.

It occurred to me recently that in nearly every case, the questions that come from candidates are weak by comparison against the questions asked of them during an interview.  Questions posed to candidates come in many flavors and go in many directions – all with the goal of learning as much about the individual as possible.  Makes sense.  The interviewer seeks to learn as much as they can about the person with whom a relationship they are considering investing.  The candidate also must make a decision as to whether the opportunity costs of forging other opportunities are worth the investment in this relationship.[i]  In contrast, questions posed by candidates are often focused on the interviewer’s views and experiences of the organization.  By asking such questions, the candidate does not, in my opinion, learn any real valuable insight about what will likely be a critical success factor for them if they are hired.  The relationship between the prospective employee and the reporting manager is essential to the success of both.  It is no less important for the candidate to learn as much about that person as is learned about them.

For example, common interviewer questions try to uncover how difficult situations have been managed in the past in the hopes of learning behavioral patterns of the candidate. I strongly feel that reciprocation is key to learning if you, as the candidate, will feel that you can be yourself and truly excel without undue stress and anxiety in this new relationship.[ii]  What follows are a few examples of what I believe are powerful and fair questions that can provide the candidate with insight necessary to astutely evaluate whether or not the professional relationship appears to be one that will support them in their pursuit to be optimally contributory.  Before I share my examples, please understand that I do not intend this list to be complete, inclusive or in any way used verbatim in all cases.  My aim is to broaden the candidate’s mindset and provide new thinking in ways that help them assess if the opportunity is really best for them.  I recognize this is indeed delicate – tact is key.  My point is to evoke a desire and willingness to reasonably learn about the person(s) whom the relationship with which, your success and happiness will depend. My advice: synthesis the sentiments below into words you feel comfortable using.

  • How do you handle situations when one of your direct reports has communicated a challenge in meeting a specific expectation? (This question aims to learn how disappointment is managed.)
  • When such challenges arise, how do you prefer the news to be communicated to you?
  • How do you communicate expectations? Do you drive for clarity or do you prefer ambiguity? If ambiguity, how have you managed in the past when deliverables were not completely in alignment with your preconceptions? (This tries to uncover how much autonomy is granted.)
  • Do you consider coaching and/or mentoring as part of your job? (Some candidate’s might not value this. My experience has taught me that managers that do engage in these activities have better overall team performance.)
  • Can you provide examples when you have gone the extra mile to come to the aide of a direct report or the aide of the entire team to help raise the team performance?  (This addresses servant leadership.) 
  • When you give feedback, do you focus the conversation on the person or the issue.  (Honestly, I’d love to ask for copies of past evaluations – sanitized to protect everyone’s anonymity of course – but that might be pushing things.  The point of this question is to assess if feedback is delivered in way that is constructive or is used manipulatively or to assert power.)
  • If you could change one thing about this organization, what would it be? (The interviewer might well hold back on his or her most honest answer. Nonetheless, question seeks to learn just a little more about the the interviewer’s values.)

The first two suggested questions might evoke a response along the lines of “…deadlines are simply not to missed…!” or “… never disappoint the boss…!”  May I politely request we pull our heads from the sand?  Sh…t happens and constituents need to be informed. Success relies not on what happens but rather on what happens next.  I  am merely trying to learn an individual’s preferred style of being informed.

As I mentioned in the beginning of this post, I have been the interviewer far more often than I have been the interviewee.  And I honestly will say I would embrace each and every one of these questions with openness so long as the candidate asked them in an honestly inquisitive manner.  Moreover, I might tend to be somewhat reserved about a candidate who did not demonstrate the interest and self-confidence to learn more about me and my working and management style.

One final note: we cannot ask about family status or situation (or any other personal information over liability concerns about discrimination.)  I understand the logic, yet it is unfortunate to some extent because awareness of common bonds can accelerate the formation of a terrific working relationship.  That level of sharing only happens (if at all) after the candidate has been accepted for the position.

In closing, I share a story that a friend of mine experienced when being interviewed by a large consulting firm. He was dutifully rich with inquiry to learn as much as possible about the relationships into which he would enter if hired.  By his account, the collective response from those who interviewed him were something along the lines of, “..well, if you are asking these questions, you obviously don’t get how much of an honor it is for you that we are considering you as a candidate…”  They saw his inquiry not as wisdom or interest, but as a lack of gratitude for the great opportunity in front of him.  That is woefully egotistical and no other interview experience would convince me more that management, at least the representative group selected for conducting this interview, is quite insecure by their defensive response to thoughtful questions.

The next time you are conducting an interview with a candidate and they ask you insightful questions about your management style, please do not be put off, but rather, embrace the fact that you have in front of you a candidate who truly cares about and appreciates the importance of workplace relationships and is being both diligent and conscientious.

Your thoughts and comments are always welcome.

Thank you for reading, have a Great Day!

Matt G.


[i] Even if the candidate is only presently pursuing or is shortlisted for a single opportunity, there are still unseen future opportunity costs.

[ii] Stress in episodic manageable doses is indeed healthy and good for developing self-confidence. The undue stress I speak of here is that which results from continuous misunderstanding of the intention of others.

About Matt Gorman

Life-long learner. Collaboration enthusiast. Avid cyclist.
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