

Ask HN: what do you like to see in interviews with entrepreneurs? - ohashi

I have been interviewing entrepreneurs for a couple months as a job and it dawned on me that as it stands, I am just writing based off what piques my personal curiosity and what type of stuff I like to hear about.  I also balance it so it matches the overall feel of the site.  But I never really went out and asked what you (the <i>potential</i> readers) like?<p>So when you read or watch Jessica's interviews, Andrew Warner's interviews and any others....<p>What kind of questions do you like to be answered?  What are you trying to get out of reading each interview?
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jyothi
Their experience of a time with lowest morale or finances or hope as a founder
? How did they overcome it ?

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scottyallen
As someone who's doing a lot of failing right now, I really like hearing about
the failures of successful entrepeneurs. What were their failures before and
during their big successes? What did they learn from them? How did they cope
with the mental and emotional burden of failing, and yet continue to keep
going?

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cubicle67
Two of the best interviewers I've seen are Michael Parkinson and Andrew
Denton. I've spent some time watching them trying to find what makes them so
good, and I think I've figured some of it out

The both have two abilities

1\. They get out of the way. Both understand, which so many interviewers
don't, that we're interested in the story the interviewee has to tell, not the
interviewer. Their job is simply to bring out the best in the person opposite.

2\. They have an instinct for a potentially interesting story, and are skilled
at detecting and then drawing this out of the interviewee.

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al_
I like to know about the time when their business didn't have any traction
yet. What was their business like during the first days/weeks. And if the
company became successful, what elements made them gain traction ( who did you
meet ? How did you approach the first customers ? Who did the first sale ? how
?)

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ohashi
Thanks, I will definitely try to incorporate this type of question where
appropriate (and it hasn't been answered to death in other places).

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drtse4
If i was you i'll follow the Andrew's approach. He asks basically 2 types of
questions:

(1) Questions aimed to understand the reasons behind a success and identify a
sequence of actions/decisions that, with some variations, could make that
success repeatable. Basically: How it started-environment description/key
events-turning points/main problems-solutions/what's next.

(2) Questions related to the solution of uncommon problems(but that could
easily happen to someone else) and uncommon solutions to common problems.

The content of the questions varies greatly considering who you are
interviewing. Usually i appreciate an interview when it catches the uniqueness
of a given entrepreneurial experience, i don't care about stuff that i could
read elsewhere with more ease without watching a video.

~~~
ohashi
Thanks for this. It's a nice breakdown into 2 general ideas that are very
fascinating to hear about. I will keep them in my notepad of questions to
think about when I am interviewing people :)

I definitely agree with on the last bit, I don't like asking the same
questions I've seen. I will generally try and see if the person has done some
other interviews or talked about stuff on their blog and either ask about that
stuff (going further) or avoid it and talk about something else. The biggest
problem in my mind (not sure if it is only there or not) is whether everyone
has the same background information... just because it's out there, does that
mean I should ignore it? Odds are in many cases people never heard of the
story of the entrepreneur (unless it's a fairly big name). What do you think?

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drtse4
Generic and well-known info (agreed, can usually be quite common things) can
make sense for the sake of completeness of the interview but not for much
else.

Less known or seemingly trivial background information could instead help to
evaluate some of the answers the interviewee give or understand the reasoning
behind some of his choices. Just to give you an example, does the fact that
the interviewee knew at some point in his life person X or that he previously
did Y lead him to do Z? Knowing that X and Y exist could help to find the
answer.

These kind of questions aim to explain the _why_ and thus interesting only
from a biographic point of view, personally i feel the _how_ to be more useful
so i'd limit the biographic data to a minimum, explain only what is needed to
give context to the interview.

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wcarss
How many false starts did they have? A musician in a successful band might've
tried several band combos before finding one that 'hit it big', and many
entrepreneurs (I suspect) try a lot of ideas or founding groups before finding
one that they stick to and succeeds. I'm curious about how many false starts
most successful entrepreneurs have, and what sort of things caused them to
identify "this won't work" and in contrast, what kept them on their now-
working idea.

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ohashi
So basically addressing the issue of The Dip (to use Seth Godin's words)?

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wcarss
I suppose that's an apt generalization. As I understand the dip, it is
figuring when a difficulty is conquerable and not going to kill you, then
conquering it. If it's not conquerable, then it is more than the dip.

This is related closely for certain - my thesis is that most entrepreneurs
quit several times in a row before seeing a dip for what it is, and my
question is "what changed?" - specifically, did they find a better team, have
a better idea, have a better market position, a better personal financial
position, or just more stubbornness?

edit: reviewing the book's synopsis (it's been a little while since I glanced
at it), I was incorrect - it is exactly the recognition of dip vs cul-de-sac,
etc. I want to hear about people's failures and successes at recognizing
these.

What might be of interesting statistical note is who among them had read
Godin's book :P

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ohashi
:) I just started reading his newest book Linchpin, he is a fantastic writer.
I am always curious what people are reading as well.

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Mz
I'm quite fond of hearing personal reasons behind x, y, or z. For example, as
I understand it, Sam Walton designed Walmart the way he did because his wife
was adamant about raising her kids in a small town and was unwilling to follow
his career dreams to the big city. He lover her enough to accommodate that and
still go after his dreams. It made him ridiculously wealthy. (IIRC, when he
died, five of the relatives that split up his wealth were among the top ten
wealthiest Americans.)

I also like knowing what inherent personality traits or other personal issues
someone has which were problematic for them and they made it work by choosing
a career that fit with something they couldn't change about themselves. For
example, my understanding is that Jim Carey was considered to be an obnoxious
class clown in high school and then, when he became a millionaire for his
sense of humor, suddenly his class mates remembered him as "Yeah, he was
always funny like that!"

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ohashi
Interesting question... do you most/all entrepreneurs have this or is it
something rare?

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Mz
That might just be me. I am usually a "statistical outlier" on ....just about
any topic.

However, at the age of 17, I noted that I was surrounded by very intelligent
people who were quite miserable in most cases. I concluded that I would rather
by wise instead of smart and set about trying to figure out how to get out of
my own damn way. Some studies indicate that very talented, intelligent,
educated people who can't make their career (or lives) work are failing
because they are basically in their own way and just won't quit being in their
own way. (They are obnoxious, rude, arrogant....etc...and sooner or later
employers (and others) conclude that the downside is just not worth whatever
they have to offer.)

Or, to quote a conversation I had with my sister some years ago:

Me: "Some people with high IQ's just seem to go around shooting themselves in
the foot."

Sis: "...and using their high IQ's to improve their aim."

I tend to assume that people like Sam Walton or Madonna or Bill Gates were
fortunate in that they were born and/or raised without the tendency to stay in
their own way all the damn time. I don't seem to have started life with such
good fortune. I've had to work at it. Given the high failure rate of startups,
I tend to assume I am not the only person who could stand to work at it.

Peace and good luck.

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sz
what do you mean by being in your own way?

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Mz
Part of my story is that I gave up a National Merit Scholarship and quit
college to go figure out who I was other than an obnoxious brainiac. I grew up
in a school system that shaped me to have no friends and then lord it over
everyone else that "I'm smarter than you!" as the only ego defense I had
available in the face of tremendous amounts of social rejection and
negativity. I'm satisfied with some of the big pictures outcomes and it is
clear in my mind that my choice to walk away from all that was critical to
being able to get my life to work. I know people who didn't walk away from
something similar, have similar sets of problems to mine, and aren't getting
them resolved the way I am getting mine resolved. So I think I did the right
thing.

I have seen many people who were so invested in "being smart" or "being right"
that they just couldn't let go of an argument and couldn't give up habitually
arguing with people when there was a huge social downside for doing so and no
real upside that I could tell. I used to be more argumentative than I am now.
My life works better now that I am clearer about when to just shut up and walk
away.

I hope that makes some sense to you.

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sz
So I guess the lesson is "keep your perspective". A good philosophy.

