Three things to ask before you join a startup

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In the business of software development joining a hot startup company, playing XBox in the break room, eating free food and cashing out your options for big money is the career three-pointer everyone seems to be aiming for. Many are the balls chucked at the hoop, and few are the shots being made. Still, playing the game can be fun, even if you’re not going to get rich (and you’re very likely not going to get rich). Playing on the wrong team can be a lot less fun. A startup can be a great place to work, and it can be a damned miserable place to work. I’ve done three of them in my career, and based on that experience I can suggest a few questions you should ask yourself before taking to the court.

Is it a great idea?

Is it even a good idea? This is a question that you can only answer for yourself. The SVP who is recruiting you thinks it’s a great idea. The CEO is super-excited. Everyone else you meet in the process of interviewing will be similarly positive. They have to be, even if they really aren’t. You can’t expect a frozen smile and secret hand signals under the conference table telling you to run for the door. The ones who believe are bought in, and the ones who don’t are trying to pretend they do, because they wouldn’t still be there if they didn’t need the paycheck. So it’s up to you to decide whether the product will fly, and how much it matters to you. Obviously needing a paycheck is a valid reason to keep a job, assuming the job is legal. But if you’re shooting for the win then whether there is any chance of winning matters.

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