Two Great Questions

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Whether you’re about to interview someone for a job or heading out to a networking dinner…

Here are two questions about business that will either take someone completely off guard or engage you – head on – in a deep and fascinating conversation. Personally, I’m not involved in the HR function at Twist Image. I have always struggled with the interview process. Being an entrepreneur, I have always struggled with the minutia of details that come with negotiating an employment package. Also, I’m often let down by how unprepared so many candidates are when they come in for an interview… and don’t even get me started on things like writing skills, punctuation, grammar and general social skills.

Two great business questions:

  1. What is the coolest thing that you have seen in the past little while? It actually surprised me to see that Marissa Mayer (Vice President of Location and Local Services) from Google asks a very similar questions during her interviews for Googlers (more on that here: Marissa Mayer, Google’s “De Niro,” Reveals What She Asks Job Candidates). This question really demonstrates both how closely someone pays attention to what’s going on around them, but it can also frame what their true passions are. If you’re interviewing someone for a job at a marketing agency and suddenly they’re talking about the recent reboot of DC Comics or the new Amazon Price Check app, you are looking at two very different candidates. It’s also a great conversation starter at dinner parties. I’ve actually seen people whip out their smartphones and start taking intense notes as the conversation takes hold.
  2. What do you read to keep up to date on the industry? Education is everything. Reading is everything. I don’t expect everyone to write, but you have to – at the very least – be following what’s going on in your industry to really understand both your own place in it, and where everything is heading. This is also a leading question because if someone responds with, "I don’t really have time to read…" or "I read a lot of newspapers" (without being more specific about which ones or which journalists), it is a major red flag. It’s also a great questions because it can take you down a fascinating road of discovery that twists with the types of media they prefer to read (magazines, newspapers, books, websites, Blogs) and turns at how they prefer to read (e-reader, smartphones, paper, etc…) then twists again when asking about who their favorite content creators are (authors, journalists, Bloggers, etc…). It’s another one of those questions that will have you looking for something to take notes on.

The truth.

I heard from a recruiter that over seventy percent of resumes and/or the people who go for interviews either embellish or lie. Even if you have decided on a candidate and ask them for some references, who do you think they’re going to come back with? Someone who is going to say something negative about them? I prefer the questions above because you can’t run and you can’t hide from the answers. You also can’t really prep for them. You have to be both sharp and ready for a conversation. Plus, if you can’t answer them, what does it say about you and your abilities… not the abilities to do the work, but your own, personal development, abilities?

What are some of the best business questions you love to ask… or ones that you have heard?


  1. The second one is my favorite question to ask. It tells a TON about what kind of writer, communicator, and thinker a person is. In businesses like ours, those three things are VERY important.

  2. It all readers are leaders but all leaders are readers. Love that quote. I think it applies here. U want people to be able to lead themselves and that starts with reading.

  3. I have two indicators I’ve asked for as well in a former job:
    Q: “What do you think about the (insert much talked about cutting-edge breaking news story) from the other day?”
    I usually asked that to check and see what their responses were — even if they’re right/wrong/balanced/outlandish, it shows that they’re engaged by current events, which — however you slice it — does impinge critically upon the day-to-day.
    Q: “Where’s the last trip you’ve taken?”
    Await response…
    Then follow up with:
    Q: “Oh, really? What do you think about X, Y, Z phenomenon over there?”
    Naturally, the interviewer will need to be rather well-traveled as well, but the point is still made. If they don’t know, they didn’t really investigate. As a marketer, I’d expect deeply curious, highly-didactic, highly-investigative types.
    This reminds me of my old McGill days when we used to bring fellow students in for interviews for things, and they had “Spanish and French spoken well” prominently displayed on their resumes, and one of us who spoke either of those languages would just flip into either of those languages, whereupon the person would lean back dumbfounded.
    It was in-your-face, but it was necessary, because we were looking for bilingual candidates…

  4. Because I work in Marketing and Communications I often ask questions directed at creativity: “Where do you look for inspiration? In your opinion, who is doing “marketing” right? And why?”
    And there’s always the “what campaign, ad, message, product launch, or overall brand strategy do you look at and say ‘wish I’d done that!'”
    Their answers are very telling about the person’s general awareness, their quality standards and their aspirations… and they always lead to an interesting conversation.

  5. Mitch, I really liked the first question, in that, for a good ten seconds I was stumped! A blank slate SEARCHING my minds eye! I was also hyper-aware that those 10 seconds would have felt like 60 seconds of *GASP* complete silence under the watchful eye of an interviewer. My pregnant pause made me think two things: a) am I so out of the loop that I have not seen anything cool in awhile or b) For me to say something is ‘cool’, like “WAYYY COOL” I have to be blown out of the water, and how many times a year does that happen? It’s a great question because its passive not active; what have you seen as opposed to what have you experienced.
    I also like Linda Johannessons qualifier about asking ‘who do you think is doing it right? Tell me about a campaign that has been effective?’ For me I would answer the Swiffer commercials; catchy tune that everyone loves, witty & funny, always a different ‘dirt’ specimen/character to change it up…and the clincher; the whoosh into the swiffer pad. Never gets old!

  6. I’m not trying to catch someone in a lie… but I see where you’re going with this. I like questions that will spark a conversation and get the person to think. I always enjoy a line of questioning that falls outside of the standard questions. Why? More often than not, the candidate is well-rehearsed. I don’t like well-rehearsed… I like someone who, intuitively, knows their stuff.

  7. I agree with you Linda, my only challenge back is that people in that space may be expecting (and have rehearsed) those questions. I think our questions are along the same lines, but I’m looking for a more immediate response and conversation than hearing what the other potential employers heard too.

  8. It can be simple… and cool. The first thing that came to my mind was my wallet… it’s a Mighty Wallet… check them out online. Your comment made me realize that a critical error many candidates make is to over-think a question.

  9. When I was going to job interviews right after graduation (or when seeking summer jobs), I like when the interviewer was seeking to see whether or not I was a creative individual. One question that I always think is really smart to ask is : “what was your favorite project or research you have done for class and how does your work stand out from the rest of the class”. Project tend to be team-based work and research is more individual work. You can also see how passionate an individual can be when describing its work – this is also an indication whether the candidate studied in the field that he or she love.

  10. Hmm, the Mighty Wallet seems like something one would sell at Urban Oufitters or on a site like Trend Hunter and not something I would deem noteworthy & not something I can picture an esteemed CEO like yourself carrying?
    I definitely am guilty of the ‘over-think’ but if someone is original enough to ask an outofthebox interview/HR question, I want my answer to reflect that same courtesy!

  11. Terrific stuff. Great questions and I’m anxious to try a few. One that I’ve had some recent fun with is.. If you had unlimited budget to do something with your business, what would it be? If I’m talking in terms of marketing, it fits, if it’s tactics, it fits, the answers have at times been insightful and often times lead to the real issue.

  12. This is a great article for me to read since for the last 13 years I have been in mommy limbo. I have not had a job interview in about 20 years so besides feeling a bit like a dinosaur I’m very grateful to my husband for giving me your book “Six Pixels of Separation”! Also very glad I found your site.
    When my husband handed me his Christmas present to me this year I joked that it must be a diamond necklace, he laughed and said, “read the book and next year it will be”. Thanks for a great post, I look forward to visiting your site again.

  13. Not only a fantastic post but also great ideas in the comments as well. I think it works in any industry, really, if you’re looking for someone who cares about the field they’re trying to get a job in. And with the information at our fingertips, it exposes some ignorance of people who value time on their gaming systems more than time spent educating themselves professionally. Again, bravo. This really got me thinking…

  14. I have three that I like to ask:
    1) If money was not an issue and you could have any job in the world, what would you do?
    2) If money was not an issue and work was an option, where would you live?
    3) If I told you I have a lot of money in my pocket, how much money is that? or an alternate What does the word expensive look like to you?
    The first one tells me what truly motivates someone. How can I keep them engaged in a job or in a conversation. What can I say that will engage this person in deeper conversation.
    The second one lets me know do they like hustle and bustle of a big city, fast paced, deadline driven, interaction with people, the overwhelming surroundings. Or are they more of a small town, close relationship, slower paced sort of person. I have them go into detail as to why. Sometimes its just the climate, which is fine too. I know when they are going to be most motivated to work.
    The third one allows me to find out if they are capable of giving someone a price for something without pantomiming sticker shock. I run into this a great deal in retail and in advertising. I have to remind employees that they are not paying for it with their paycheck, let the customer determine what is expensive to them.
    Great post Mitch.

  15. My very first job interview straight out of college 20 years ago, which landed me the gig that led me into this career, and, by extension, this post, started with your Question #2 — only shorter and broader: “What do you read?”
    When I started to rattle off authors, the guy who would become my editor and mentor stopped me: “What periodicals do you read?” I’ve stolen this line and used it in every interview I’ve done since.
    A person’s answer to that question reveals more than their grasp of your industry, but about the cultural and intellectual influences that shape them. And it makes me wonder: how prepared are you/we to give a compelling answer? Thanks for this post.

  16. I like these types of questions too because they speak to not only teamwork but how the individual identifies themselves in the team (the leader? a contributor? etc…). It speaks volumes to the person’s self-perception.

  17. What is you Best Professional Accomplishment? (Then Digg Hard for Challenges, Role, resources used, results, plan, areas you improved, problems, conflicts faced, learn about self/others/reports, dislikes, what would you do differently?, recognition/awards, etc.)
    Best, Brian
    PS, I am a biz owner/recruiter

  18. Mashable recently shared questions asked by tech firms. The title is “The 9 Oddest Job Interview Questions Asked at Tech Companies in 2011.” Here is the link.
    Also, the strangest questions I have ever been asked is: What is the significance of your name and do you epitomize it?

  19. I love question #2. It’s something that I ask prospective clients to better understand their base of knowledge. More than once I have not accepted work from a client because I knew from their reading that what they wanted and what we could provide were world appart.
    I like what Bobb Biehl says: “If you ask shallow questions you get shallow answers!”
    Thanks again.

  20. Joel,
    Two great and powerful questions. The first one can be very telling about personality, interests, and passions.
    I like to ask, “Tell me about one of your recent professional accomplishments.”
    (A seemingly innocent question…)
    However, Part II is, “Tell me how you created the idea, planned it, and made it happen.”
    This can be a very telling conversation about the individual’s creativity, organization, and ability to execute.
    It can also be interesting to see if the “recent success” is suddenly unsupported by any details. (Oh… I was just on the team…)

  21. Mitch;
    This is an interesting thread, and I like your questions. Two I have been asking lately:
    1. What does a great day at work look like for you?
    Is it a day when they were super, busy but got lots done? Did they make a breakthrough? What is their favorite/best day? How often are they going to get that day here?
    2. Tell me about the time when your integrity was most challenged, when you felt the most pressure to do something against your conscience.
    The “safe” answer here is never. But I’ll discount that. If you’ve never had your integrity challenged then you must have a pretty low bar.
    Thanks for all your other suggestions.

  22. Cale, can you explain the third question further?
    “3) If I told you I have a lot of money in my pocket, how much money is that? or an alternate What does the word expensive look like to you?”
    If the person answered “$200” or “$5,000” or a more creative answer like “unlimited credit card,” what would these replies indicate as far as their poker face for giving a price and their ability to let the customer determine what is expensive?

  23. I just read that post… I think a lot of them don’t really help in an interview (other than to make someone feel very uncomfortable). The idea for me is a live conversation, not to make someone either feel stupid or think that the process is a joke.

  24. It’s curious you bring this up, because where I work at right now the interviews are also focused more os less on: what are your passions? And you wouldn’t believe how people slip that one up. They overprepare to sell themselves, their CV, their abilities and experience and their views, and can’t even tell what they truly love about life.

  25. Of course, in that case I guess you have a clear case of “it’s not gonna work out”. I believe it’s also all about knowing how to sell yourself, another underdeveloped capacity amongst candidates (and, in a specific matter, on most people my age — I’m 23).

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