Ask HN: what do you like to see in interviews with entrepreneurs? | Hacker News Reader

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

20 pointsohashi18 comments

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 potential readers) like?

So when you read or watch Jessica's interviews, Andrew Warner's interviews and any others....

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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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.

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.

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

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

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

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.

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?

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.

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?

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 ?)

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

Their experience of a time with lowest morale or finances or hope as a founder ? How did they overcome it ?

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!"

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

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.

what do you mean by being in your own way?

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.

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

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