I have hired hundreds of people throughout my career - both for startups hiring employee number 2 and also for big corporates. Also, I am normally hiring in Europe. Some of the stuff I mention below may be totally illegal in the U.S.

The questions you ask differ a bit depending on where you are in the company life cycle. As you mentioned interviewing for start ups above, let's focus on that. When hiring employee number 2 to 10 I tend to focus on personality and cultural fit. Instead of the typical job interview, I tend to take long lunches, dinners and walks with the people to find out if we would get along. After all, in a startup you tend to spend more time with your co-workers than with your spouse. So hiring at this stage is more like dating. Of course I ask about their past but some common questions I am interest in are:

- why do you want to join a startup? What is your main goal? This is to find out if they have hopes for lots of stock options and to make it big or if they have been frustrated in their old job for not being able to make decisions. Money focus usually is fine but they need at least one more key motivation as most startups will hit a rough patch where money becomes tight. If they join because they want to have big influence, only hire them if you are willing to give up control.

- are you willing to work very long hours and give up weekends if needed? How does your family life fit into this and how will you make sure that your family life does not suffer and in return impact your work performance.

- I tend to throw in a random question to test their problem solving skills like "how many bakeries are in New York". Even though I find these kind of questions pretty common, they throw of most people. If they answer too fast, you know they have faced this kind of question before and you can ignore the answer. If they stall and look at you like you are crazy, then the answer is important. I tend to give them one or two hints and then just watch how they attempt to solve the problem.

- lastly, depending on the role I hire for, I give them some real life examples and ask them to provide answers. For a coder this will be a coding test for a sales guy I will describe a difficult sales situation etc.

hope this helps :)

What is the most creative answer you've gotten from the bakery question?

Someone figuring out how many customers a bakery needs to survive and then guessing the number of people who live in New York and deducting the number of bakeries from that. Not bad :)

Thanks so much for the in-depth response! One of my best interviews was over coffee with 2 startup founders, so I agree that can be more effective than a typical job interview.

Have you ever hired someone who was great in the interview and on paper but didn't work out? Any idea why?

Two thoughts. First, if your startup requires people to give up nights and weekends and you need to ask potential candidates how they will mitigate that situation with their family life, then you need to rethink how your business and software development run. Work life balance is exceptionally important and should not be ruined for the sake of building a business. I realize you didn't bring up the question about giving up nights and weekends. But since the poster above you did, I thought it important that I bring up that requirements like that are absolutely absurd. If you regularly take away peoples personal time for your business, rethink how you run a business.

Second, on to your question. I have hired quite a lot of people and occasionally they are amazing in interviews and on paper and don't work out in real world situations. Over time you get better at spotting these people but it is a risk you take. As with many things, interviewing is a skill and some people are quite good at it. Often times it is not a technical or job skill mismatch, it is a personality or a team fit match. That can take weeks or months to uncover. The best thing to do is to have a clear exit strategy for each person you bring in if they don't seem to work out.

Yes, I had it happen that people are great on paper and in the interview and did not work out. In each case it was a sales hire. The people in question were excellent sales reps. They knew how to sell themselves as well. However, one of the reasons I hired them for (a big and super relevant rolodex of C-Level contacts in our industry) turned out to be the main reason they totally failed. These guys valued their contacts overall. They would never hard sell any of their contact if they had even the slightest doubt that the product would work 100% as expected. Well, we all know how startup products get build and how they often fail before they excel. So these top notch sales guys would keep on setting up all these great meetings with big names but never close. First they tell you that closing a deal with a blue chip company takes forever (true, they often do take forever). So they could ride along for quite some time without getting caught. Then when pushed, they would make up fair excuses, why their contact would not buy our stuff. This happened to me in my early days as a GM and it took me about a year and a half to see through this.

Now I never hire a sales person based on his rolodex anymore. I find out if the sales person is truly passionate about the product.

Also, on that note, stay away from the sales guy who tells you that he will sell anything to anyone. My best sales hires in the past years have always been people who think that they are not sales people at all :)

In her interview, just over a year ago, my girlfriend was asked: "How many coffees are sold in London each week?".

I can't remember her derivation, but I remember her saying the interviewer was taken aback by her answer. Later that day, when she reiterated the question to me, I didn’t even know where to start. Predictably, I’d interpreted the question literally. It was demonstrating your reasoning and decomposition of the problem that was most important.

[She got the job.]

Which questions would be illegal in the US?

I believe any question that relates to your life outside work such as your marital status, your kids or how your relationship would endure a startup job can get you in trouble in the U.S. - but I am not a U.S. HR pro. However, I learned that it is safest to just focus on job related things in the U.S., while in Germany people will put things like their picture, marital status, religious affiliation, age, etc. on their resume - all of which will send a U.S. HR manager into shock :)

When you're small (startup), hiring is a reflection of founders' values. When you grow big, it's a reflection of your company's values.

First hence, be clear about what your values are. It's not easy to figure those out. You have to interview several candidates and introspect after each interview, to narrow down on what you want. It's a bit unfair to first few candidates, but overall it works out better. Once you arrive at a nugget of values you can cohesively describe, you design your interview process and questions based on what you've arrived at.

Also realize that you cannot design direct questions to probe for values you want. You have to demonstrate that value yourself first and see if they get excited with it. e.g. if one of your values is transparency, you can't ask "are you transparent in your interaction with people"? You have to tell them some things about your company or the role that they are not expecting you to disclose and see if they value that.

If coming up with core values is too hard or too vague for you, then start with these three: Curiosity, Humility and Hard work. You won't go wrong with these. Most high performing people demonstrate these values.

In order to probe for these values, you can ask pretty much any reasonable question, and then pick up on cues. e.g. if it's a programmer interview, you can ask them a difficult coding question/assignment based on their background. Then see, if they ask good questions (curiosity)? Do they test their code (humility)? Do they give up, or continue to push through (hard work)? Don't expect precise answers to your question, but look for these signals.

When picking questions, you should prefer questions that are "peeling the onion" type questions. i.e. start with a simple question, let them answer it and then add constraints. Keep adding constraints/twisting until they are able to answer it. That will give you great insights into how they think and how they value.

Hope this helps.

[About me: Founder of http://InterviewKickstart.com. I've interviewed an obscene number of people in my career. Have been in the valley for a number of years. I have to think about this for a living]

I use a mix of asking about what's on your resume (chronological works nicely, so I understand why you switched jobs and how your skills evolved) and a set of standard technical questions (so I can compare candidates over time). I'll usually dig deeper technically until you give up. Giving up doesn't mean failing, on the contrary.

Do you ever try to assess traits like motivation or curiosity? Do you allow those to just come out in regular conversation? Or do you just stick to the resume walkthroughs and technical questions?

Motivation and curiosity should come through naturually when the candidate discusses their past experience.

Regarding the actual questions, I just like to talk about the actual CV / past. There's got to be something exciting in their previous job. Or outside of job. Or during studies. If there isn't... depends if you look for someone with creative solutions, or you're ok with average coder to type out standard CRUD.

Otherwise, I really like small tasks without limits. For python job it was something like "read csv, write to database". It can be a 3-liner and take 10 minutes. But if you say "no limits, make it production quality code", there's so much you can learn about the candidate.

It can have error reporting. It can have documentation. It can be a proper module. It can handle encoding issues correctly. It can care about SQL injection or not. It can have configurable paths and backends. It can support py2/py3/both.

Do you try to look for specific nontechnical traits, like determination? Or do you just let that stuff come up naturally during conversation?

I was mostly involved in technical interviews. But for the non-technical stuff - yes, it usually comes up during conversations about previous jobs. Why they left / what they achieved / what they wanted to achieve / etc.

> What are your favorite questions?

I like to probe for curiosity.

Q: You've read the position summary, company profile, and met with other members of the team. What questions do you have now? What more would you like to know about us?

On this subject of questions, Andrew Sobel has a good read> http://www.goodreads.com/book/show/13510967-power-questions-...

I haven't interviewed anyone before, but I have been interviewed.

At my current place of employment - during my interview I got asked a series of brain teasers and puzzles and had to work them out on the whiteboard. It was interesting and fun and I didn't expect it at all, but it did make me think a lot.

Same with my current place of employment. Do they also ask any kind of behavioral or fit questions? Was there anything you thought the interview was lacking?

Actually, I took an online personality test of sorts as well. I'm fairly certain their reasoning behind it is to find level headed people (or at least find people that could potentially work well together).

I didn't think it was lacking much - it was enjoyable and I also got surprised with some programming tasks(wasn't sure if that was going to happen or not). For me, it was an OO question on "How would you design an elevator" just talked through it and explained the different functions and functionality.

The puzzles were super laid back and were asked by another developer, so you got to see his personality as well as the other people in the room participated.

Awesome experience thus far.

The questions you got probably come from a book just like the one you want to write.

Ha...it's true. I've just observed a lack of interviewing knowledge at a bunch of startups, and am trying to figure out if it is a trend. In my experience most startups nail the technical questions, but don't know what else to ask. For example, I was recently asked "How do you stay organized?" as one of the only questions that wasn't about my past job experience.

I think a great, brief handbook could go a long way.