12/17/2014 10:18 am ET Updated Feb 16, 2015

The 1 Question You Must Ask About Your New Job

The first days of my first job were littered with questions. Queries of all kinds swarmed my mind, including but not limited to: Can I wear jeans to work if I dress them up? Will I get a company phone number/email address/computer/phone? and, of course, Will there be a water cooler, and, if yes, will people stand around it and chat?

I went out and bought a dress that is just a notch below a skirt-suit (because who wears those, other than Hillary?). I bought pop-and-lock containers in which to bring my lunch. I joined, now that I faced the prospect of having income to monitor.

Yet, the biggest favor I could have done myself would have been to consider that, not only was I clueless about my exciting new job, but my employers were novices, too. Because I am the first person ever in my position. Because my workplace is an NGO. Because we're breaking boundaries and conventions everywhere, but none of us have any idea how to do it.

Nearly a year later, we're still figuring it out. This autonomy, which has become dual parts freedom and frustration, is the one thing I wish I could have foreseen. Viewing the job as an official position at an organization, I figured that the line of command would be simple: my boss would tell me what to do and I would do it to a better standard than she'd requested. That's how things had always been: teachers gave strict parameters for assignments, and I did them. In school, I sometimes broke the rules (I needed to let my creative genius shine through), but, before I broke the rules, the rules themselves were clear.

Yet, here's what no one in the "real-world" tells you: There are no rules. Or there are no rules in non-profits where your position was created for you and no one agrees on who your boss is, at least. Does this mean that I'm unlucky, or that I've found myself in a bad situation? Hardly; the reality is just the opposite. But I'm also realizing how very well I do with preset, clear expectations. Is the act of creating professional standards and creating a personal goal outline something you learn after a certain amount of time in the workforce? Is it something some people are born with but others can never achieve? Is it yet another skill that Millennials disdainfully lack?

I now know that there is no water cooler at my job (but there is free coffee, soda, hot chocolate, and trail mix. Win.). I got the workstation/email/password. I haven't worn jeans to work yet. But I see now that all of those things will work themselves out in any job. In fact, I didn't really need to ask these questions as I was preparing to start, because I ended up figuring those all out soon enough. Instead, the important questions are these: How much responsibility are you being given? Are you given the proper support to fulfill these responsibilities? And, most importantly, can you handle more autonomy than you bargained for if you find yourself in an environment where the rules are, largely, up to you?