Tag Archives: ask series

Ask 6: Still more questions to ask in interviews

This is the sixth in a series of thoughts I’ve had for unique and penetrating questions to ask during an interview. These days, the expectation is that you will ask questions and there are many articles out there on “stock” questions to ask. I submit these – as an on-going series – in an effort to provide questions that will be revealing in that they’re not going to be the same-old, same-old questions interviewers hear all the time – thus, not only gaining you useful information, but differentiating you in their eyes. The prior ones in the series are Ask, Ask 2, Ask 3, Ask 4, and Ask 5.

Tell me about the last time you went head-to-head in a disagreement with a subordinate. What was it about and how was it resolved? (This can also be reworded to be asked to potential co-workers.)

Hey, if employers can ask behavioral questions, so can you. The positive of this question is that, assuming they answer the question, you will gain insight into how they handle disagreements in the group. The negative, obviously, is the implicit (even if incorrect) message that you are a troublemaker who wants to know how they’ll handle when you don’t toe the line. But, in and of itself, that too would be a useful piece of information about what it would be like to work there. And asking a reworded version to co-workers can reveal if the boss is a “My way or the highway” person, or is open to alternatives and constructive disagreements from the team.


Am I the first candidate you’ve interviewed for this position?

Best to ask this early on, and casually. But this can be a critical datum point. Very often in the interview process interviewers learn from their conversations with candidates details and tidbits of what they want that they hadn’t realized they wanted – and those get added to their mental lists. Thus, you don’t want to be first. Then again, they may have already decided by the time you get there and are just going through the motions. Now, there’s nothing you can really do about it, but… consider a follow-on question if they say they’ve spoken to several other people:

I’m curious: Have you refined what you want in a candidate based on those prior conversations?

This should indicate to a hiring manager that you’re really interested in what their needs are. In my experience, there is always something that they’ve identified from talking with the first candidate or two. See if you can get it out of them, and then address those points. Those newly-discovered, but undocumented, wants and needs can make or break you.

Have you seen a lot of resumes for this position?

This is especially pertinent for companies that use ATS portals, and is probably best asked of HR. It’s an imperfect metric, but the number of resumes the HR person has seen can be an indication of how much competition there is, how fine their ATS screen is, and – if they’ve not seen many and you’re talking with them – this is an excuse to then chime in sympathetically about how hard it is to find qualified people and that you’re glad you’ve met the bar to be them in person. Thus, this can be a psychological trick to get them to put you on the short list since they’ve seen so few resumes come through.

What is the last book or magazine you’ve read?

This is a reversal – hey, they can ask, why not you? – of the third question from here. Just as the person who asks this wants to understand your intellectual base, I think it’s fair to understand the hiring manager’s intellectual base too.

When’s the last time you changed your mind about something “big”, what was it, and what changed your mind?

How open-minded is your potential boss? Are they ossified in their cognitive template, or can they assimilate new information even if it disrupts their world view? Note that this has a danger in that it can tread upon peoples’ deep-held beliefs, and threatens to open up the Three Dread Topics: Sex, Religion, and Politics. So I’d recommend this one only if you are having a good, friendly conversation where there seems to be a good rapport.

Who is the last person who left the group, and do you know why?

This is best aimed at potential co-workers, and can be phrased any number of ways to investigate a little. What are you hoping to find? That people leave the group because they are promoted. If people leave because they’re shown the door, or spew bile about the place as they walk out the door, that’s not a good sign. A related question to ask, if someone left to go elsewhere, is:

How did the boss take it when so-and-so left the company?

When someone finds a better career move, it’s sad for the company they’re leaving but good for them. I read about one company – don’t recall which – that as a person exits on their last day, people line up to applaud and congratulate them. (WOW!) If a boss doesn’t even spring for a goodbye lunch, that can be an indicator of vindictiveness. And a parallel question to ask HR:

What would you say the turnover rate at this company is like?

First, HR better know it. If they hem and haw, it means it’s high. And a high turnover rate can mean several things: 1) that they fire lots of people, 2) that lots of people leave, which can indicate lots of problems, whether low pay, high stress, abusive managers, etc. (In parallel, if you have time and access to industry groups in the area related to the company’s business, see if you can dig a little into what the company’s “ people churn rate” is.)

© 2015, David Hunt PE

Ask 5: Some more penetrating questions to ask at interviews

This is the fifth in a series of questions I’ve come up with for candidates to ask in job interviews. The prior ones are Ask, Ask 2, Ask 3, and Ask 4.

Based on our conversation thus far, what do you think I will like most about this job?

This is inspired by a question I saw from Lavie Margolin. It’s a test of how well the hiring manager has “read” you. And by using the word will it’s also a subtle way to prompt the hiring manager to envision you in the position. An optional flip of this is:

And what do you think I will like least about this job?

No job is 100% fantastic all the time, and this is a good way to probe how the boss – and possibly co-workers – views the lesser aspects of the job, in particular in light of their understanding of you. Forewarned is forearmed. The advantage to this question is the opportunity to glean a clue about how they see you and the job, and the possible mismatches in their vision of how you might fit. The danger in asking this is that it brings dislike and your candidacy to mind in the same time frame, something to avoid and which I discussed here (thanks to Neil Patrick of 40pluscareerguru for republishing that essay).

In one sentence, can you tell me the top thing you’d want me to accomplish in the first six months?

This is a different take on the standard question “What would you expect me to accomplish in six months?”. It requires the hiring manager to focus on and articulate what is truly important to them. If you can squeeze this into the conversation early on, it will tell you how to target your conversation focus in a SPARTACUS approach (again, thanks Neil).

What were the characteristics of the best hire you’ve ever made?

Another way to “get inside” the head of the hiring manager to understand what they value in a person. If asked early in a conversation, you can use this to subtly highlight things that will draw an analogy between you and that “best hire”. Note, however, you should not ask the reverse one – once you bring negative traits to mind in the context of hiring, you run a strong risk of the hiring manager starting to try to pin those on you (even just unconsciously).

What do you like most about managing this group? (And the obvious reverse, what do you like least about managing this group?)

This can give some good insights into the group’s dynamics, and how the boss views their role as supervisor, coordinator, and leader.

What’s the most fun you’ve had at work in the last month?

This is for both hiring managers and co-workers. Work is not always fun – that’s why it’s called work. But if a person has to really, really stop and think about the last time they enjoyed their job, that’s a warning sign. And if the hiring manager also has to really scrape through their memory for the last time they enjoyed their job, that’s a huge red flag that they’re not happy – and you know what rolls downhill.

© 2015, David Hunt, PE

Ask 4

This seems to be developing into an on-going series of ideas for “penetrating questions” to ask in an interview setting.  Here are some more (prior ones in the series are Ask, Ask 2, and Ask 3).

How would your subordinates describe you?

I just saw this as a question to ask candidates – “How would people you have worked with describe you?”  So flip it.  See if the potential hiring manager can articulate the sentiments and impressions he gives to those who work for him.  Among other things it’s an awareness test, and a measure of how often the boss interacts with the team – not in an instructional mode, but in real exchanges.

How would you describe your boss?

The corollary to the above question.  Ask this of a potential co-worker.  In combination, you can get two points of information.  First, a “skinny” on how people perceive the boss – though obviously filtered for political correctness (let alone survival).  Second, compare and contrast with the answer from the above question.  What agreement is there?  And more importantly, what dissonances exist?  This can also be a good pair of questions for the hiring manager and their boss if you get to meet them.

Why are you the best company for me to work for?

Again, this is inspired by reading articles recommending “innovative” questions to ask candidates, specifically, the question “Why are you the best person for this position?”.  It is similar to others I’ve proposed before (e.g., Ask 2) – in this case, it differs from the previous version in that this is a little more challenging (and could – be forewarned! – be perceived as a little aggressive) .  Remember, just as they are interviewing you, with you having to sell yourself to them, they should likewise be reminded that – even with the job market the way it is – they need to market to you.  After all, you’re a skilled professional, right?  And if they look at you as though you’ve turned purple with orange polka dots and get very defensive, that’s a potential indication that they know their power over you… and are surprised at your out-of-the-gate challenge to it.

What intrinsic personality characteristics do you see as fundamental to a “good hire”?

This is a key insight into the culture (and a bit of a trick question too).  If they’re looking for “hard workers” or “rock stars” or “people who want to go places” and so on, they’re only looking at the superficial.  Remember… skills and knowledge can be learned, corporate cultures can be adapted to (to some degree), ambition can cycle up and down, dedication and drive can be inspired by good leadership, but integrity/ethics and intelligence are foundational elements of a person’s makeup.  As a parallel, ask to see their mission statement.  Is it available?  Is it posted?  And does it discuss ethics and integrity?

Describe a difficult ethical situation you had to deal with in this company, and how was it resolved.

This sort-of goes in parallel with the above.  (Hey, if they can use behavioral interview questions, why can’t you?)  There is no business that does not have situations where, depending on one’s ethics, a decision point could go in different directions.  Understanding a situation or two of such events, and how they were handled, can give you insight as to whether you are interviewing with a place with high ethical standards… or without them.

Tell me about a time you had to give bad news to the boss.

Again, a behavioral question to be asked of someone on the team – not the boss.  How did they handle the bad news?  If they’ve never told the boss bad news, well, there’s always bad news at some point in a project.  There’s small bad news which a person can handle, but sometimes it’s big, and needs to be passed up the food chain.  And IMHO how an organization reacts to that can be very revealing.

Can you describe the company culture in five stand-alone words?

Yes, this could be a very difficult question to answer – but that’s one of the reasons you’re in an interview, isn’t it?  Not only to present yourself as a candidate, but to vet them as a potential employer?  Asking this of several people, at different levels, will give you insights into how those different levels perceive the company… what words (or synonyms) are said by multiple people?  Conversely, what outliers are there?  Those outliers can highlight potential dissonances in perception, which can be useful in evaluating how unified the workforce is in culture and vision.  Some differences are expected, both from level and by individual characters, but if there’s a huge difference that could be a warning sign of any number of things.

How have your career goals changed since you joined the company?

This is similar, but not identical, to a question in Ask; that was a very general question while this is one aimed specifically at how the company handles peoples’ career development from the perspective of an employee (so ask this of a potential coworker only).  Lead into this with “So… how long have you been with ?”  If longer than ten years, follow up with this.  Many – but not all – people have ambitions to move up the ladder, or at least not do the same thing their entire career.  Most people want some kind of growth.  How that growth actually happened compared with what they thought would happen can indicate how the company takes into account what you want to do in your career vs. where they put you.  Does this mean, of course, that the company has dictated where a person’s career went without their input?  No; on top of that, people can change as well.  However, it should give you some idea of how people’s aspirations and plans are handled and factored in to their development.

© 2014, David Hunt, PE

Ask 3: Still More “Penetrating Questions”

In my columns Ask and Ask 2 I proposed some “penetrating questions” for candidates to ask interviewers.  Here are five more.

Why shouldn’t I work here?

Yes, you read that right.  It’s a twist on “Why should I want to work here?” that I proposed in Ask 2.  I actually read that as a recommended question for candidates – i.e., “Why shouldn’t we hire you?” – intended to put people outside their comfort zones; IMHO, those types of questions are deliberately intended to shake candidates up – because people who are rattled tend to make more mistakes.  This one will definitely put your interviewer outside their comfort zone, opening them up for some follow-on questions.  (Hey, if they can ask questions to rattle you, turnabout is fair play – but I only recommend this if they are already asking “rattle the candidate” questions.)  Among many other possibilities, you might learn that while they’re willing to dish out such questions, they’re not used to “uppity” candidates asking equivalent questions in turn.  (Body language will tell much here.)

How do you determine your salary ranges?

I just read an article, here, with a question “Why are you asking for that salary?”  Too many companies these days are salary-obsessed, not value-obsessed.  In the case of this question, candidates are asked to justify their salary request.  Turn it around – after they bring up salary, of course (e.g., “Well, I’m looking for a salary range from X to Y… if I might ask, how do you determine your salary ranges?”).  And if they talk about doing market surveys, competitive analysis, and so on, ask where they fall in that range.  If the answer is something like “We try to be competitive” what they’re really saying is that they try to be enough above average to brag about… while expecting to hire the cream of the crop.

How do you check people out on social media websites?  What do you consider important things to look for?  And how do you know, absent a picture, whether a “hit” on google is the right person?

This is generally intended for HR, but could be aimed at a hiring manager as well.  Social media checking is the latest thing for vetting candidates – and by asking “how” you subtly convey that you expect them to do it, after all it’s not IF they will look for you, it’s WHERE – and what they do with the information.  By explicitly addressing this question you find out what they do.  And if you’ve found some information related to someone else, or information from a while ago when you were hot-headed and posted something you now regret, this is a chance to head it off proactively.  See here, here, here, here, and here for a lot more of my thoughts – shameless self-promotion here – about this topic.

Where do people typically eat lunch?

This is not an inquiry about the local restaurant scene; it is an inquiry into the culture.  The cultures are very different as indicated by whether people have (or take) the time to go to the cafeteria to eat and socialize, vs. bolting lunch down at their desk trying to get more work done.  As a follow-up question, to the hiring manager, is “What’s your favorite local restaurant?” or, possibly, “When’s the last time you ate out for lunch?”  If you really want to be sneaky, and not sound like you’re food-obsessed, ask the favorite restaurant question only (ideally, as you lean back into a relaxed pose).  If the hiring manager has a dumb look on their face, and can’t answer after a moment’s thought, it means they don’t go out to lunch, ever.  Which means, likely, that nobody else does… and likely everyone eats at their desk to squeeze more work out.

How do plan your peoples’ development?

Lots of companies talk about professional development.  Many tout tuition programs.  But for the most part, companies these days leave a person’s career development up to the person.  This is an error.  Now I’m not saying that a person should be pushed through to career positions that they truly don’t want.  Companies as an organization, however, have a vested interest in identifying “high potential” people internally, and helping them develop – both educationally as well as with assignments that broaden their perspectives and time horizons of their decisions – and I don’t mean individual managers picking their own “Golden Children” to nurture… I mean by a systematic, formal process.  The best companies proactively help people along in their careers without having to have people, themselves, do all the planning work and identification of training / developmental assignments.

© 2014, David Hunt, PE

Ask 2 (More Penetrating Questions)

In my essay Ask, I proposed some “penetrating questions” to ask interviewers, in particular the hiring manager.  Many of these questions had hidden layers of insight that could come out during the answer, whether by the words or by the physical reaction / body language of the person when hit with the question.

I’ve come up with some more.

What three people you admire most; and why are these persons the ones?

Companies these days are desperate to add dimensions to the evaluation process, in order to build a more three-dimensional picture of candidates.  They are trolling through social contacts to see who you know; it’s a fair application of the adage Birds of a feather, flock together.  (The one caveat that I’d add is that this should not consider people, e.g., twitter followers, over whom I don’t think you have any control – can you actually force someone to unfollow you?)  And this is a legitimate, albeit somewhat “stalker-like”, tactic.  But what’s good for the goose is good for the gander, and I’ll add another layer: Tell me who you admire and why, and I understand who you are.

What are the challenges the company will face in the next few years?

I have seen this in other venues, so it’s not truly original, but the hidden benefits come from asking people in different levels in the hierarchy.  This gives you insights into the degree of perspective people at different levels have.  It also hints at the communication between levels, how important news is disseminated downward, and how the “lower ranks” understand the strategic direction.

How would you move Mount Fuji?

This is, of course, a commonly-discussed question – from google IIRC.  Turn it around.  Ask them, with a great big smile on your face.  Incidentally, I do have an answer which I used the one time I was asked; I’ve never seen my answer listed as one of the answers reportedly given.  (And no, I’m not telling.)

What’s the last disagreement you had with the boss?  What was it about, and how was it resolved?

This is best asked of a potential co-worker.  It can indicate all sorts of insight about how the boss handles disagreements, the dynamics of the group, etc.  And how did he handle a subordinate contradicting him, especially if the subordinate was right?

Aside from the mercenary aspect of a paycheck, what gets you up in the morning to come here?

What motivates people here?  Is there a gestalt mission that’s understood?  Or is this a collection of people there for the paycheck – of course, nobody’s going to admit that, but by asking several people this same question you can get a statistical sampling of the evasions and diversions given to reverse engineer what attitudes really are.

When was the last layoff?  Did the RIF make sense to you?

This gives some indications of the stability / security of the company.  But who got let go, if they are known to the respondent – ask a potential colleague, nobody higher – can indicate how much merit there was to layoffs vs. how political the targeting was.  Ask this towards the end of the time period after, hopefully, you’ve established a rapport… which can lead to their being comfortable venting a little.

Why should I want to work here?

This is a turn-the-tables question based on “Why do you want to work here?”  It has two results.  The first is, obviously, they get put outside their comfort zones, which can open them up to revealing more about themselves and the organization than they intend.  But the second is that it makes them have to justify why they’re good enough for you.  An interview should be a two-way street, not endless groveling by supplicants pleading for mercy from those who have power.  Make them work for the product of your mind.

How long have you worked here?  How has the company changed over that time?

The first is a not-uncommon question to ask.  It’s nice to know that people stay.  But if you get someone who has been there over ten years, ask the second.  A lot can come out unintentionally, especially if they don’t like the changes.

© 2013, David Hunt, PE


“Since before your sun burned hot in space… I have awaited a question.”  – The Guardian of Forever, Star Trek episode City on the Edge of Forever.

Questions are the lifeblood of an interview.  The interviewer asks the candidate questions.  Too often, though, candidates do not ask questions in reply.  This should be a conversation, not a one-way interrogation.  Reading the online literature from job search coaches, they all discuss the need to ask questions as a part of the interviewee’s presentation.  Questions show interest, motivation, and they give the interviewee information to judge the employer, not to mention their potential boss, in turn.

Multiple sites and columns exist with scores upon hundreds of questions for candidates to consider asking in an interview.  If you search with google or bing the phrase “questions to ask on/during an interview” you will find more questions than you can possibly imagine – many are good, and when interviewing I try to ask them if I can get a word in edgewise.  But I’d like to discuss a few of my favorites which I’ve not seen elsewhere.

Who will introduce me to the people outside the department with whom I will need to interact to get my job done?

Not “Will I be introduced”, not even “how”, but “who”.  This puts a spotlight onto both the company’s and hiring manager’s onboarding process, and the role of HR.  It also highlights their commitment to you as a new person to help you get up to speed.  A lack of this basic action as a standard part of the process implies weakness in other aspects of your coming on board – the “Here’s your anvil, now go swimming” mentality is not going to be conducive to your success.  Body language can speak volumes here, especially if they have no such process.  I’ve seen people literally squirm and shift uncomfortably when I ask this.

How are decisions made here?

This is actually a double-whammy question.  The first is that it gives insight into how the group functions.  Are big decisions done by committee, by one person, etc.?  But it’s also an insight into the perspective of the manager… because decisions are not made by teams, but by a person.  Teams can recommend courses of action, they can agree on a consensus or majority path to choose, but ultimately the decision to do X and not Y has to be made by a person, even if that person decides to accept the recommendation of a group.

How long have you worked here, and what is your story of how you ended up here?  How has it measured against your expectations?

This is a chance to learn more about the career history of your potential manager.  This is also a chance to see how the company’s marketing to potential employees, and their self-serving spin (and they all do self-serving spin, just as candidates do), matches the reality.  In particular watch their body language as they describe the correlation between their own expectations vs. reality.

If you could change one thing here, what would it be?  And is that a local phenomenon, or is it global to the whole company (if a large company)?

This is another chance to see what a potential sore point your manager might have about the place.  It’s also a great question to ask a potential colleague who also reports to them.  Ideally, do both.  First, you get to see how peoples’ perceptions of organizational weaknesses align with the different perspectives of position.  It’s also a good segue to learn more about your possible new boss from their subordinate, without specifically asking.

How long ago did you move from being an individual contributor to a manager?  What induced you to make that switch, and do you have any regrets?

Again, this is a chance to learn more about your potential boss’ history and motivation.  But there’s more.  If they’re new to their level of responsibility, they might be nervous about someone gunning for their chair, and scared they’re not up to their new responsibilities.  And if they have regrets, that’s a warning sign they might micromanage and possibly meddle in your day-to-day activities, because they want to keep their hands in the business of their subordinates, as opposed to managing it.

What happened the last time a big project went awry?  What did you learn, and how do you keep these issues from happening again?

A number of things can come from these questions – so ask several people.  The first is that there is no organization that is so fine-tuned that projects don’t go off the rails to some degree.  A company that says it’s never happened either has a really poor collective memory, or people are hiding reality.  The second thing is that it gives an indication of how flexible and adaptable the organization is.  It’s also an opening for one of the people to descend into finger-pointing, which can teach you a lot about how the company handles people who make mistakes.  And last, informal companies fight fires but are unable to prevent them from happening again.  Good companies document and disseminate such information formally.  Where are you interviewing?

Describe the best, most successful project that you’ve seen done here.

The answers to this question can reveal if the company does projects well, if things going right is considered normal or not, and what’s involved in a successful project.

I’m curious; what are the top three things about my background that interested you?

This forces the hiring manager to bring to mind specific things they liked about your background (as opposed to the question about any shortcomings or objections, which forces them to think of negative things).  It also gives you insight about what the company values in general, which can help you color your answers to emphasize the traits that led to the accomplishments they cite.  Lastly, if you know you are an “imperfect fit” for the position, it can indicate what they value enough to bring you in anyway despite those things that are lacking.

Have you ever abandoned a significant project (or cut loose a client, or whatever is suitable to your profession)?  What went into that decision?

Not everything in a business works out.  If they’ve never done this, they’ve either been blessed with extraordinary success, or are so desperate for revenue or cost savings that they don’t dare give up anything, or are too stubborn to cut their losses on something… among many possible reasons.  Regardless of the root cause, this is useful to know.

Stock questions have their uses, and many are good and worth asking.  But just as good candidates have created stock answers to stock questions – and there are a million “best answers to top interview questions” articles and books – so too have veteran interviewers created stock answers to the canned questions from candidates.  Just as interviewers try to ferret out information from candidates, candidates must do the same.

In the sci-fi masterwork novel Dune, which I’ve praised before (don’t bother with the movie IMHO; I suffered through it so that I could recommend you avoid it – instead read it, and then immediately start reading it again), arch-villain Baron Harkonnen is gloating to his nephew Rabban about having suborned his enemy Duke Leto Atreides’ trusted employee, Doctor Huey.  The doctor, a graduate of the Suk medical school (famous in that novel’s universe for the loyalty of their students to their employers), has conditioning and training that supposedly precludes exactly this type of betrayal.  Rabban asks “Does the Emperor know you’ve suborned a Suk doctor?”

The Baron was surprised and paused, thinking “That was a penetrating question.”

Surprise your interviewers.  Ask penetrating questions.

© 2013, David Hunt, PE