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12 Unconventional Interview Questions Entrepreneurs Should Ask

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Where potential employees are concerned, obviously skills are important. Yet weve all seen
fabulously talented individuals become a team that was far less than the sum of its parts.
While expertise is important, cultural fit can be just as if not more important. It's
something we obsess over at my company, result in what we call our Culture Code (that
describes how we think about talent and culture at HubSpot).

As a result your interviews should focus on more than just skills and qualifications. You also
need to ask questions to probe whether candidates will fit into your organization: Are they
likely to play well in your particular sandbox? Will their work style and personality
complement your team?
Will they not just survive but thrive in a fast-paced, often-chaotic startup environment?
Do your homework before the interview and you should already have a good sense of
whether the candidate has the right blend of skills and experiences to be able to do the job
well. So definitely dive deeper into an exploration of talent and expertise, but also ask
questions to determine whether the candidate can do the job well in your organization
because hiring even one employee who doesnt fit your culture creates a culture debt you
may never pay off.
Keep in mind how the candidate answers is important, but the conversations that follow
since a great interview is a conversation, not an interrogation can reveal even more:
1. What concerns do you have about our company?

Strange question? Not really. No company and no job is perfect for any employee (even
its founders.) Every company and every job has its challenges and potential downsides.
The candidates you want to hire dont think your company is perfect; theyve done sufficient
research to know that while yours is not the perfect company and the job is not the perfect
job, yours is a company they want to work for because they can thrive, make a difference,
develop and learn and grow and achieve and be a key part of taking your company to
even greater heights.
And as a result theyre willing to honestly share their concerns because they trust you run
a company that values openness, honesty, and transparency.
2. What is the toughest decision you had to make in the last few months?
Everyone makes tough decisions. (Well, at least everyone you want to hire does.)
Good candidates made a decision based on analysis or reasoning. Great candidates made a
decision based on data and on interpersonal considerations because every important or
meaningful decision, no matter how smart it looks on paper, eventually has an effect on and
must be carried out by people.
A company at its core is made up of people. Great employees weigh both sides of an issue,
considering the business aspects as well as the human impact.
3. Tell me about a time when you had to slog your way through a ton of work.
How did you get through it?
We all are required to at least occasionally place our noses on the grindstone. Most people
can slog through the drudgery because they have to.
The candidates you want to hire can take on a boring task, find the meaning in that task,
and turn it into something they want to do.
Great employees turn the outer-directed into the self-directed and in the process, perform
at a much higher level. And gain a greater sense of fulfillment.
On the flip side
4. What were you doing the last time you looked at a clock and realized you had
lost all track of time?
We do our best when a task doesnt feel like work but feels like what we are meant to do.

I have never met an exceptional candidate that didn't at one point have this feeling where
time didn't matter. Call it being in the zone or flow or whatever you want all great
people experience it.
This ability to commit passionately to a project/task is particularly important for highgrowth businesses. These moments of high-creativity and high-productivity are often when
the best ideas come.
Explore what candidates feel they were meant to do. A lack of experience is less important
when a candidate has hunger and drive. And, if someone isn't passionate enough
aboutsomething (whether it's related to their job or not) you should worry as to whether
there's anything at your company that is going to get them fired up.
Why? You can teach skills but you cant teach love.
5. Describe a time you felt you were right but you still had to follow directions or
guidelines.
Surprisingly, this question can be a great way to evaluate a candidates ability to
follow and to lead.
Poor candidates find a way to get around the rules because they know they were right. Or
they follow directions but allow their performance to suffer because they dont believe in
what theyre doing. (Youd be surprised by how many interviewees will admit they didnt
work hard because they felt angry or stifled and expect you to feel their pain.)
Good candidates did what needed to be done, especially if time was of the essence, and
later found the right moment to bring up the issue try to improve the status quo.
Great candidates did what needed to be done, stayed motivated and helped others stay
motivated and get things done, too. In a peer environment, an employee who is able to say,
Im not sure what were doing makes perfect sense, but it might, so lets knock it out! is
invaluable.
In a leadership environment, good leaders are able to debate and argue behind closed doors
and then fully support a decision in public, even if they (privately) disagree with that
decision.
No employee agrees with every decision, every process, every best practice what
matters is how they react and perform when they dont agree.
6. What book do you think everyone on the team should read?

This is one of my favorite questions. It's partly because I just love books and always looking
for new ideas but partly because most great people always have had a book that they
found to be super-useful and like sharing with others. If the person can't think of a single
book that they'd recommend to others, that's a warning sign. Either they don't enjoy
reading or possibly, they don't think that the kinds of things they need to learn can be
found in books. Both worry me.
Curiosity is a wonderful indicator of intellect and, oddly enough, modesty, because curious
people are willing to admit they dont know and are then willing to work to learn what they
dont know. Curious people also tend not to be cynics (see Skeptics vs. Cynics: Which Are
Toxic?).
Every business needs employees who can set their egos aside and ask questions. Every
business needs employees who are willing to say, I dont know how can you help me?
7. Tell me about a time you felt company leadership was wrong. What did you
do?
I certainly dont have all the answers. And Im definitely not always right. So I want people
to question my perspectives; push back when I come to conclusions; ask, Why? and,
sometimes more critically, Why not?
Power is gained by sharing knowledge, not hoarding it, so we make uncommon amounts of
information available to everyone in my company, HubSpot. We dont want to just win
debates. We want to be right. We want to make smarter decisions and support smarter
behavior.
So we want employees who arent afraid to take that information and run with it and
challenge, in a healthy way, each other and executive leadership. Especially executive
leadership.
8. What does, This parrot is no more! mean to you?
Walk around some companies and youll hear Monty Python (the quote above), or Office
Space, or Spinal Tap, or Seinfeld quotes tossed around all the time. Thats because
recognizable quotes are like verbal shorthand, getting across in one or two sentences what
normally takes much longer to explain. And, speaking of Seinfeld (of which both my cofounder and I are fans), one of the quotes we use all the time is Why don't you just tell me
the movie you want to see (from the classic MoviePhone episode).

The candidate doesnt have to recognize the quote or cultural reference you make. In itself
thats not important but if your team has, say, a quirky sense of humor, its awesome if
the candidate does, too.
And just in case you dont get much of a response to this question, go to
9. What movie, no matter how many times youve seen it, do you have to watch
when its on?
Same thing. A favorite movie can indicate a lot about a candidates personality. I can watch
Moneyball over and over because its an entertaining movie filled with lessons on business
and entrepreneurship.
One candidate may love a story about overcoming the odds. Another may love a comedy.
Doesn't matter. The question really helps you learn more about the person (not their skills).
This question often leads to a fun, engaging conversation.
10. Tell me about the last time a co-worker or customer got angry with you. What
happened?
When your company is focused on getting (stuff) done conflict is inevitable. The candidate
who pushes all the blame and the responsibility for rectifying the situation on another
person is one to avoid. Better is the candidate who focused not on blame but on addressing
and fixing the problem.
Best of all are the people who admit they were partly or completely at fault (because it
always takes two to do the conflict tango), took responsibility, and worked to make a bad
situation better.
Every business needs employees who will admit when they are wrong, take ownership for
fixing the problem, and most importantly learn from the experience.
11. What business would you love to start?
Startups naturally attract entrepreneurs-in-training. Thats awesome: Sure, they may leave
someday to start their own companies, but in the meantime your business benefits from
their entrepreneurial spirit, drive, and attitude.
And theyre much more likely to fit in to your organization, since they immediately embrace
the differences in working for a startup rather than a corporation.

What type of business they would like to start may not matter; what does matter is the fact
they have ideas and hopes and dreams because if they do, they will bring those ideas and
hopes and dreams to your business.
12. What would you most like to learn here that would help you in the future?
This is somewhat of a follow-up to question 11. If they do have a startup in mind that they'd
love to start someday. It's revealing to figure out where they think they need help (finance?
marketing? sales?) The other benefit of this question is that it sends a signal to the
individual that we care about growing people. The saying at HubSpot is We don't want to
just build a great company, we want to build great people.
Now its your turn: Take a look at the qualities and attributes of your top performers.
Think critically about the business culture youre trying to create. What questions should
you ask and what conversations should you try to spark that will help you identify the
qualities and attributes your business needs? Yours may be different than these which
only makes sense since every company and every company culture is different.
And in the comments below, please share unconventional interview questions you
like to ask!
Posted by Dharmesh Shah on Wed, Jun 05, 2013

COMMENTS
Great Questions ! Now that's thinking outside the framework of a typical interview.
Good Job
posted on Wednesday, June 05, 2013 at 9:39 AM by Joe Weidner

How about is there actually a job here or are you going to hire your mate from india
because he's cheaper? quote unquote
posted on Wednesday, June 05, 2013 at 10:01 AM by atwat

Superb. Very nice. I am just conducting interviews this week, sure to use few of the
above.
posted on Wednesday, June 05, 2013 at 10:11 AM by Amit

Great questions to ask and I also found them introspective. From the other side,
when I interview for a job I actually interview them. They need to fit my personality
and drive also. It works both ways. Thanks for the list!
posted on Wednesday, June 05, 2013 at 10:13 AM by Tom

"Tell me a story about a bear." It's pretty revealing to see where someone
will take this story and it's a great way to filter for creative positions (i.e.
marketers).
posted on Wednesday, June 05, 2013 at 10:16 AM by Suresh Srinivasan

Most of the Time Employer use premade interview questions which is saturated
everywhere and candidates also know the answer like nursery theory. But
Dharmesh your Interviee questions making sense, Employer can findout right
employee and candidate will understand where he is gonna work. Excellent point :)
posted on Wednesday, June 05, 2013 at 10:22 AM by Sharanyan

Excellent Questions!
As a startup, attracting and retaining good talent is critical not only to growth but
very survival of the business.
These questions, especially the personality related questions (8 through 10) are
extremely insightful.
Thank you for sharing.
posted on Wednesday, June 05, 2013 at 10:26 AM by Sanjay Verma

Relative experience- employment,...having held key positions of responsibility in


both small (<$10M,) and large (>$100M)companies is important.
In the words of a prominent VC, "I'll put my $$$ in an "A" company with a "B"
product, rarely the reverse.
Re culture;....small emerging technology companies can be an energy charged,
financially rewarding, fun environment,....or a prison.

posted on Wednesday, June 05, 2013 at 10:26 AM by Gary Zatkovich

I love these questions and I wish more people asked them during the initial
interview process. Sometimes it is hard to show your awesome entrepreneurial
qualities through the typical interview but these questions would make us start-up
minded folks shine. I hope to encounter an interview like this soon!
posted on Wednesday, June 05, 2013 at 10:35 AM by Rob Livada

Actually i like to interview the candidates on what they know the best, instead of
asking the algorithmic questions or the stuff that i know. The whole purpose of the
interview is to find the candidate who actually knows what he is doing. Experience
doesn't matter much if you have not learned or changed from it. I have see 15
years old programmers who still program like it's 1990s. If you have to hire for a
startup hire some once who not only knows the stuff but also knows how to sell
himself/herself :).
posted on Wednesday, June 05, 2013 at 11:05 AM by Neelesh Vaikhary

Dharmesh - great questions - all Behavioral based. Excellent.


I'd like to connect with you on LI if possible.
posted on Wednesday, June 05, 2013 at 11:06 AM by Jim Coughlin

Question: "What's a question you were expecting me to ask you but I didn't, and
what's your answer?"
I ask this question because it either gives the candidate an opportunity to talk
about something they really wanted to (highlight personal skill/achievement,
research on the company, etc) or the one thing they were worried you would ask
them about (but you didn't notice), and they'll actually end up revealing to you.
posted on Wednesday, June 05, 2013 at 11:07 AM by Daniel

I always ask, "Tell me what the word, "work" means to you?". Purposefully openended. Best answer ever? "I never use that word. I find projects, whether my own
or others' ideas, that I feel passionate about. when complete, I move on to the next
one. That is why I am interviewing here today. I feel my present employer has run
out of interesting ideas and projects. And I have told them that. What you are
building is intriguing to me."
posted on Wednesday, June 05, 2013 at 11:10 AM by sgleahy

Wonderful questions, and useful for teams to ask of each other and not just in an
interview context (started a discussion for this over on the Team Performance site
on LinkedIn). Another approach to interviewing that I find even more compelling is
to have the interviewee ask the questions. I find I can tell a great deal about a
person and their concerns by the questions they ask (though one has to make
some allowances for different cultural practices).
posted on Wednesday, June 05, 2013 at 11:12 AM by Steven Forth

My favourite question: "You have 10 units of productive time/energy for a given


timeframe. You have three customers. One requires 4 units of your time/enery; one
requires 5 units of your time/energy; the third requires 3 units of your time/energy.
All projects are due at the end of the given timeframe. How do you handle this?"
The answer tells me a lot about the candidate's business sense, out-of-the-box
creativity, customer sense, personal and group work ethics, etc.
posted on Wednesday, June 05, 2013 at 11:27 AM by Richard Sikes

Great list. Getting people "off script" in an interview is never easy. Your questions
do it in a fun, engaging and non-threatening manner. Well done. My favorite? What
motivates you more, fear of failure or the lure of success, and why?
posted on Wednesday, June 05, 2013 at 11:41 AM by Nate Brochin

Great questions. I have my doubts about the movie questions. Not everyone looks
to movies for a correlation to life. Some people like horrible movies for a complete
distraction.
I've also asked,
"What have I forgotten to ask you?"
"Do you think you're smart? Why?"
"How do you learn new things?"
posted on Wednesday, June 05, 2013 at 12:14 PM by David Geller

Those are great questions, thank you for sharing them. With these kinds of
questions you really see how the though process of that person works. I will start
using many of these questions now in my interview process.
posted on Wednesday, June 05, 2013 at 12:20 PM by Joshua Varney

Thanks Dharmesh. As always, a great perspective on what's usually a very


stereotypical setting. The challenge that I face with these open ended behavioral
questions is when the candidate is not used to or not a natural at story telling. For
most of the technical folks, they feel more comfortable talking data/numbers/specs
etc. vs. giving insights into their personal behaviors. I guess it depends on what
skills you're hiring for, and would need to balance based on the real time feedback
received from the candidate.
posted on Wednesday, June 05, 2013 at 12:30 PM by Vikram Parekh

I always try to see if an employee will take ownership of his or her responsibilities.
It's one thing to get a job; it's quite another to assume a level of responsibility for
simultaneously achieving success for the employer, one's colleagues and one's self.
It's a tall order.
posted on Wednesday, June 05, 2013 at 12:37 PM by Andrew Ellis

Not a question, but a comment. Before you ask a candidate these questions,
answer them yourself. Seriously. Take a legal pad and answer each of these
questions as though your very life depended upon it. The insights you gain about
yourself may be immeasurable. And you'll know exactly how hard it is for a
candidate to come up with the answers.
posted on Wednesday, June 05, 2013 at 1:04 PM by John Elrick

This is an integrity question. The answer to the question doesn't really matter, as
long as the answer is yes !
What was the last thing you stole?
It usually stops people dead in their tracks. I find watching how they answer is
more important than what they say. Happy interviewing !!
posted on Wednesday, June 05, 2013 at 1:07 PM by Arthur Docherty

How about something of substance: "Many people have one driving principle by
which they live, upon which they base their decisions. Is there a driving principle by
which you live? If so, what is it?"
posted on Wednesday, June 05, 2013 at 1:07 PM by Phil Jamieson

I tell them I'm looking for quality people and ask them to define a "quality" person.
Their answers speak volumes.
posted on Wednesday, June 05, 2013 at 2:10 PM by Tom Harvey

Luckily, very few "smart" entities go so low during the interviewing. I understand,
it's very "niche", kind of Entrepreneurs Anonymous...
posted on Wednesday, June 05, 2013 at 2:12 PM by Mario Andretti

If I hear the questions where do you want to be in 5 years and whats your biggest
weakness one more time, I will puke. The first ? I answer with is that depends on
where your company will be in 5 years. The last one shows that you may have an
issue but this is how You are dealing with it, but If I cant stand the interviewer I
just answer pepperoni pizza with lots of garlic.
posted on Wednesday, June 05, 2013 at 2:37 PM by sam

I like to ask about hobbies. A person without any hobbies is a danger for any
workplace, especially a start-up. A hobby, especially if it's not related to
technology can say a lot about a person. A person who takes his hobby
seriously (I call it the "black belt" question), will usually take his work
seriously as well.
posted on Wednesday, June 05, 2013 at 3:05 PM by Guy Brodetzki

Excellent
posted on Wednesday, June 05, 2013 at 3:11 PM by Regina Sanchez

Wonder set of questions for any company. Many times the large companies are
broken down to small nimble groups.
My favorite ending question is, If you have to write your eulogy, what would you
say? This tells me what they value in life, and makes sure those values align with
mine.
posted on Wednesday, June 05, 2013 at 4:42 PM by George Tyler

Unconventional questions are not okay for some people and you risk losing out on
candidates who might have fit much better than you thought on your team. In fact,
I would wager more than half of so-called good fits you seek would be lost because
those questions are too hard to answer spontaneously. They require memory over
critical thinking, humor over substance, and personal revelations that nobody
should have to devulge unless the job requires a high security clearance. I think

you have a right maybe to one "gotcha" question like that -- just because you
believe you need to see the person respond to pressure. By the way, if you want
really thoughtful answer to the questions, consider issuing them to applicants in
advance. (Author of Job Interviewers: Get Inside Their Heads.
posted on Wednesday, June 05, 2013 at 7:43 PM by Jack Dermody

Great questions to help the interviewee and the interviewer evaluate the fit. In the
unpredictable world of startup businesses, these are a great way to set the tone.
posted on Wednesday, June 05, 2013 at 9:44 PM by Elizabeth Londo

1. What concerns do you have about our company?


Not enough hot women wearing miniskirts commando
2. What is the toughest decision you had to make in the last few months?
Rather to pay for porn or not to pay for porn
3. Tell me about a time when you had to slog your way through a ton of work.
How did you get through it?
I just slogged away on my dick. This isnt rocket science!
4. What were you doing the
last time you looked at a clock and realized you had lost all track of time?
Masturbating..obviously
5. Describe a time you felt you were right but you still had to follow directions or
guidelines.
When I jazzed in the coffee creamer.. company thought I broke guidelines :-/ ..
idiots
6. What book do you think everyone on the team should read?

how to increase your penis size


7. Tell me about a time you felt company leadership was wrong. What did you
do?
I jazzed in the creamer again
8. What does, This parrot is no more! mean to you?
this penis is no more!
9. What movie, no matter how many times youve seen it, do you
have to watch when its on?
Couch Casting Anal Audition Video
10. Tell me about the last time a co-worker or customer got angry with you. What
happened?
My coworker had coffee and I jazzed in it as creamer
11. What business would you love to start?
REALLY? IS THIS QUESTION REALLY NEEDED? Porn .. DUH!
12. What would you most like to learn here that would help you in the future?
How to jizz more and increase my dick size.. and jizz even more .. JIZZ JIZZ
EVERYWHERE
posted on Wednesday, June 05, 2013 at 10:02 PM by Mr Big Parrot

These are great - I've been using your content marketing guide list of questions
recently and have found that although some of the questions there are quite tough
and unconventional as well, as long as I set the scene appropriately at the
beginning of the interview, and give the candidate plenty of time to think, no one

complains, and in fact they enjoy the interview and enjoy learning about
themselves. I even recently threw the questions at an intern, who would normally
have a much lower barrier to entry, but when she answered the questions even
better than any of the candidates for the highly paid roles, we took her on full-time
immediately!
posted on Thursday, June 06, 2013 at 12:26 AM by Ivan Mazour

Dharmesh and tweeps, 3 thoughts:


- Always thinking about repurposing content... If you note a promising hire's
answers to these Qs, what a cool bio the hiring company could write about the new
employee!
- Remember the article @dmscott wrote a couple months ago about former Eloqua
CEO Joe Payne's hire of Brian Kardon as Eloqua CMO (*before* Brian had made a
paradigm shift to modern internet marketing)? Oh to know how Joe spotted Brian's
talent... maybe piercing Qs like this?! (Article is
at http://www.webinknow.com/2013/04/the-journey-from-a-traditional-marketingexecutive-to-a-modern-cmo.html)
- Dave Geller your additional Qs above are great.
posted on Thursday, June 06, 2013 at 2:02 AM by Rebekah Donaldson

a
posted on Thursday, June 06, 2013 at 3:49 AM by pawitar

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