Need good interview questions for startup founders | Hacker News Reader

Need good interview questions for startup founders

15 pointsy200227 comments

I'm interviewing a lot of startup ceo/founders in the next few weeks for my website. What are some great/insightful/funny startup questions you wish people would ask you?

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If someone paid you $1 billion right now, with the condition that you could never work a day in your life again, and never start a company, would you do it?

Edit: rms is right. How about "If someone paid you $1 billion with the condition that you could never do anything productive ever again, and basically had to live a playboy's life forever, would you do it?"

I think that's an easy question, as long as a non-profit doesn't count as work or a company.

Edit: Revised question is really interesting. I don't know what my answer would be.

My answer would be a resounding no. Some things just cannot be bought. Everyone knows what things they would never do regardless of the money involved. If I could not do anything productive ever again, I'd be depressed.

Also, I think there is such thing as too much money. In terms of happiness, money provides diminishing returns. I believe that having enough to not worry about having to generate income is a good goal for most people. Beyond that, it can create a feeling of alienation with regards to the rest of the population, as you would be too far to the right on the wealth distribution curve and would have few peers. What do you get in return? Fame (if you want it) and access to extravagant toys. The real problems in life remain the same whether you have 10M or 1B: you will get old, you may have family or health problems, accidents happen, etc.

Alienation + productivity ban = sad life. No thanks.

Ditto. "Productive" is such a loose term. The question basically boils down to "would you take a billion dollars along with an interdiction from trying hard at anything that you think you might enjoy doing?"

Definitely no.

The thing is that technology is only a means, so ask a real question such as:

What "can" you design under $1 that solves a major problem in the world?

Example answer: packets of salt and sugar is all it takes to prevent/solve dehydration in many sub-saharan countries. Can it save the world? Yes. Is it executable? Yes. Is the UI simple? Yes, ziplock sugar packets. Marketing costs? evangelize.

Point is that the technical skills can be evaluated to a great accuracy more or less, it is the real-time thinking skill that matters; i.e. it is extremely ok to ask a question that demands considerable attention and problem-solving. An ideal interviewee knows that a good answer is not a matter of complete polarization, but careful articulation.

How do salt/sugar solve dehydration?

OMG. Did you never heard about one spon of sugar, one spon of salt and one liter of water? It's the best for dehydration.

"How do salt/sugar solve dehydration?"

http://en.wikipedia.org/wiki/Oral_rehydration_therapy

"The thing is that technology is only a means, so ask a real question such as:

What "can" you design under $1 that solves a major problem in the world?"

With all due respect I wonder how many successful entrepreneurs (Steve Jobs for e.g) would be able to answer this question?

This sounds like one of those textbook/puzzle questions which sound very clever but don't stand up to any rigorous analysis( imo).

I would be very surprised if answering this question "well" (your salt/sugar answer for example) correlated with any significant measure of entrepreneurial success. Needless to say, I would love to to data or studies that show otherwise.

The question is just an example, the underlying subtle notion is that what can an entrepreneur cook up with limited resources? Of course, you can ask them an intelligent question in any variety of ways - you can ask Jobs what can Apple design that solves audio learning problems in the third world for less than 20$ or so? Can Steve Jobs answer that question? Yes. Can he (or Apple rather) build it? Yes (well, in an interview you would ask a question that requires quite a bit of insight, not puzzles)

"This sounds like one of those textbook/puzzle questions which sound very clever but don't stand up to any rigorous analysis( imo)."

Again, it was an example. One could very well ask someone an on-the-spot question that would arise in a typical startup situation.

Answering the question "well" - if you are basing a hire's success just on the outcome of a question, then you may have some serious issues with measuring success.

Okay. I have a few.

First question: why? You guys are smart/energetic/young/etc -- why do this? Why not join BigCorp or become a priest or something?

Second question: What do you worry about the most? What keeps you up at night?

Third question: If you could only pick one thing to validate your reason for forming a startup, what would it be? In other words, what would be the single biggest indicator to you that you are doing the right thing?

1. What have you learned?

2. How have you changed since you started?

3. What key skill or experience did you lack when you started that has caused you the most problem?

4. What has been the biggest surprise: what was one key assumption you made, perhaps even unconsciously, that has caused the most grief?

5. What development, event, or new understanding since you started has had the most impact on your original plan? How has your plan changed in response?

We have a number of founder interviews up at http://www.skmurphy.com/blog/category/founder-story/

I checked your profile but I can't determine your website, where will the interviews be posted?

What was your biggest failure before starting up?

If you had to choose between succeeding and finding the love of your life, which would you choose and why?

Things I am curious about:

1. What made you first think that starting a company is right for you?

2. Was there anyone/anything who inspired you to manage the company the way you do, and to define the culture the company has?

3. Was it obvious that the company needed to be in place X? If X is not in Silicon Valley, why not? Do you think it was the right decision?

4. Where is the best source of good people for you? What characteristics are important for them to possess (good schools, lots of experience, dedication, etc).

That's it for now. I'll add more if I think of any.

What stage are these founders in? Have they succeeded, are they on their way there, are they just in a the planning stage? Different questions apply to different stages.

These founders all have products at least in beta. They are in various stages of funding: some are self-funded, some have angel investors, others have institutional funding.

Ok then, my questions would be:

How much money do you think you'll make from this (to see how they evaluate their chances and worth), do you want to sell or remain and make a salary (to see what they are building the company for - longevity or a quick flip, not that either are bad), and what do you see your retirement like?

In my opinion, the person should be clear why (s)he wants to do a startup. Does the person aspire to (hopefully) earn a lot of money in a relatively short time, or is it sheer satisfaction of doing your own thing or some other valid reason?

It might be better if your core thinking and goals, match to some extent with your probable co-founder.

Having said that, the 'skill set' of the person should compliment yours, so that as a team you are able to achieve more.

Have you ever done/worked at a startup? I know you already prequalified your interviewees, but I'd still ask that.

How many iterations took it from the initial idea to the current product? How did you get your first customers?

What did you decide not to do in order to focus on your startup?

When did the business model become clear for your business?

Which do you think is most important: the right market, the right product, or the right team?

What will you do if you fail?

Did you consider yourself bipolar before or is this a new experience for you?

If your company tanked tomorrow, would the experience have been worth it?

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