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Comment by HarryHirsch | Hacker News Reader

Did I ever mention that interview with a whizzo East Coast startup where the interviewer couldn't answer where the company was planning to be in five years time? It's one of those questions where they will squirm like eels, but you have to know, because you are committing your time and future earnings to them. Squirming is fine, but being struck dumb is not acceptable. The experience was epic, it ended with a greybeard apologizing for the HR lady.

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I always ask "Do you enjoy working here?" Their instant response is usually telling.

Wow! I all ask this on my next interview.

Never thought of this! Great question, I'm gonna keep that in mind.

That's pretty direct, I like it. I try to ask "what is the worst thing about X right now?" where X is the project/product/thing being worked on.

Caginess and dodginess in this answer is a flag. Of course, different interviewers will be more or less forthcoming and straight with you, but if the entire slate of interviewers hem and haw around the question, I take it as a bad sign.

An organization where people are afraid to be frank and call a spade a spade is hiding a lot of systemic problems.

I always ask this. Doesn't even require an honest answer, the length of pause is sufficient.

(although now it's been on HN interviewers will probably be better prepared)

At a guess, I'd put the chance that the person interviewing you has seen this at about 0.1%

I don't think I could have answered that question at any startup I've ever worked at. And, certainly if I had, I would have been wrong in every case.

Right vs. wrong isn't what he's concerned about, I think.

Every company/organization/person should have a long term strategy. That way you can weigh potential actions to see if they are moving you toward or away from your goal. If you don't have that goal, or it isn't well communicated, everyone scrambles to optimize for different things, which frequently leads to people pulling against each other.

It's totally acceptable to update the long term goal as you go along, but it's very helpful to always keep one in focus.

Sure, but long term strategy at a 6 month old company is a year out. 2 years at best. 5 years is multiple lifetimes for most startups.

I think that's becoming an increasingly popular opinion, but I really don't buy into it. If you have one year of runway, certainly you should have a one year plan, but I like to see something longer term as well.

A plan can fail or go right. Parent asked for where were they planning to be, a plan is important.

How did you spend your time at work when nobody knew what the company was trying to do? And where are those companies now?

Knowing where you'll be in 5 years != knowing where you'll be in 3-6 months. For most earlier startups, that is near the optimum lookahead algorithm.

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