As I have previously mentioned, I had been in the job market for months. Had a number of pretty solid offers but I did not feel the cultural fit was there for me to be happy. In the interest of sharing my experiences, here are the questions I wrote down to ask every time I went on a first or second interview. This is not a complete list but a mix of important questions plus the (odd) ones most important to me. I am also adding notes for my reasoning behind them for the purposes of this entry. I would suggest, after looking at the list, you simply disregard the things that do not apply to you– or more importantly– the things you do not care about.

• At will? Contract? 1099? W2? Corp-to-corp?
  Consider the tax implications of a 1099 or corp-to-corp. Seriously, big difference. Remember that if an at-will employee can leave any time– two weeks notice is a good idea because everyone can always use more references– it also means they can let you go for absolutely no reason at all.
• What benefits are offered? Are they fully paid for by the company? How much do I have to contribute if not 100%? How long will it take to kick in?
  Will a lapse of insurance be a problem for me due to an existing condition?
• Insurance offered by the company? Can it cover other people? Worried about in-network? HMO, EPO, ect?
  If you are getting married it may be a great idea to be able to offer such a thing to your spouse. That way they do not have to worry about it and do can whatever (maybe even take care of the rest of the familiy if needed instead of the cost of a day care).
• Do they offer a retirement plan (401k, ect)? Do they do any matching? If so how much?
  If you start this at 18 you are sitting pretty. Starting later is not nearly as good but still well worth the tiny amount it costs you now. Trust me on this, you will not be sorry. If a potential employer does not offer it you can always hire a company to do it for you and it is still very, very much worth it.
• What is the dress code?
  I just hate folding and ironing things with a pasaion. Feel free to ignore my insanity.
• Flexible hours? If I put in 16+ hour days is there any compensation time? Can I work from home at least one day a week assuming I am not required in the office?
  This was very important to me. Even more so if there was no overtime. Your time is the most valuable thing you have because it allows you to do everything else. Do not kill yourself so someone else can get rich and you get shit. There are lots of things worth more than money and, if you are willing, a company may be willing to make non-standard accommodations if you just ask so everyone is happy.
• How do meetings with the other departments go? How often (on average, not with the last big, once-in-a-life-time project)?
  I, personally, used this as a metric to see how big a company was and how much red tape I would have to deal with. Not really a great measure of anything but an indication.
• Tandem projects? How many things will I be working on at once?
  This may not pertain to you or maybe you like it. I just wanted to make sure no one expects the impossible out of me.
• Amount of time spent working vs meetings? Would they say my department makes the decisions it has the skills to make or other departments?
  I was worried that some big-wig boss man would be making decisions based on nothing but cost. Penny wise, pound foolish kind of thing and I wanted no part of that.
• Can they walk me through what most of my days would look like?
  Just because they say they are filling one role does not mean I think they know what they want. Make sure you are clear on what you are committing yourself to. Use your own judgment but do not be afraid to say “no” if the job is too huge and there is little relative up side for you. Again, do not kill yourself so someone else can get rich and you get fired because they sold the company that you have no real stake in.
• Is there a Do Not Compete clause? If so does it apply to post-employment and for how long?
  Wwhen you leave you want to make sure you can still do what it is you do. A DNC that is too broad will fuck you. Do not be afraid to request changes if you feel the spirit of the law is there but the wording is not. I have done this with every DNC I have ever signed and never once has anyone become upset because of it.
• Are any personal projects you generate outside of company time and company equipment property of the company?
  Are things you do on your own time on your own equipment property of the company? For someone who loves what they do this would be a really, really bad thing. I was very, very afraid of this.
• What is the salary they can offer?
  Is it a job you really want? Is it worth it to accept a little less for a better chance at the gig? Perhaps it is cheaper for them to put that difference into benefits when it would have cost you a lot more if you were to do it on your own. Make suggestions if you want something.
• Provide equipment?
  Are they expecting you to spend your own money to do your job? Will you be reimbursted? Is there a limit?
• Bring own equipment?
  Some companies do not like the idea of you using your own equipment (especially things with long-term storage, like laptops, ect). Make sure, if you need something and they will not let you use yours, that they are willing to spend the money required to get the job done right. If they think you suck because you produce crap it may just be because they were too cheap and not because of you. Still, it reflects badly on you and that is not something they will hear very well.
• What time do you start your day? Flexibility?
  I hate mornings. Like, a lot. This may not matter to you. I also want to be able to stay 16 hours one day and four the next so that was important to ask (but be careful about how it comes off).

Check out the recruiters! There are people out there that have just as much stock in you getting a good job and you do not have to pay them. Generally they only get paid if you get the job, get paid relative to however much you are offered, and none of that comes out of your pocket. It is win-win for you. I am more familiar with the IT-related resume-posting sites such as Dice but there is also Monster so use those to get in front of a lot of eyes (recruiters included). I, personally, did not do any of the heavy lifting myself (craigslist, for example) and let the recruiters find the jobs but there is no rule you can not be doing both. Hell, there is no rule you can not be doing five interviews all at the same time (except for the drain on your energy, that is). This is not a marriage and you do not owe anyone anything until you sign those papers: Be a whore.

This whole process can be intimidating so I offer this advice: Do not act like it– seriously, most people hate me for this very reason– but think of yourself as the best; Fuck everyone else, they suck. The truth of the matter is 95% of the population are just doing what they need to do to get by and keeping their heads down. Always put your best foot forward but remember that doing 50% of your best will be worlds better than most of your competition. Also show off what you did in the past because you wanted to and why you loved doing it. Try something new. Tell them about your failures, why you failed, but how it was still worth doing. Do not be afraid of what you will do, not do, or say in an interview. This is as much about you getting what you need and want as much as it is for your interviewer.

Hope this helps anyone who might be looking for a job. It is the accumulation of me adding to and modifying this list over the course of a few months of non-stop, ~five-interviews-a-day job hunting. If you were happy being suck in a cubical you could easily do that but there is also no chance of you finding that awesome place you do not want to leave at the end of the day. Chief Technology Officer (CTO) was a great title I had at my last company, had a nice office over looking Rockefeller Plaza, and the pay was great… but I was dying inside. The more time that past doing something I did not want to be doing the more I could feel myself growing resentful of a place that did not deserve that. Remember that if you are so unhappy your hair is changing color the job is not worth any amount of money. You can find a cheaper place to live but destroying your relationships because you brought home that stress is no longer only effecting you.