When I was younger, I used to have a very different approach toward job interviews. I used to see them as one-sided events where you had to prove your worthiness as a potential employee rather than as a two-way street.

As I’ve developed professionally, though, I came to realize that the point of interviewing shouldn’t just mean rote memorization, giving correct answers, and asking the right
questions. Interviews are also a rare opportunity to have a dialogue with an insider, one that should be taken advantage of to really understand whether the company you’re interviewing with is “right” for you.

Business school will teach you that you should always have questions for your interviewer in order to appear interested and enthusiastic about the company, and there are even lists of typical questions you can ask. Those are fine, but they’ll seldom get you to the crux of the matter, things like whether the company and group you’re interviewing with has good prospects, good leadership, and whether you’d enjoy working there.

I’ve found the best way to get to the heart of the matter is by asking the right probing and, yes, even atypical, daring questions. But the key to all this is that you must also have some answers to these same questions about the company that you’ve concluded yourself so that you have something to compare their responses to.

Having gone through interviews recently, here’s a list of things I did to prepare my questions and the type of questions I asked almost all my interviewers in one form or another. I happen to focus on questions related to “finance’s role in the company” because that’s my area, but you could easily customize it to whatever functional area you’re interested in:

What is finance’s role in the company? I always ask this open-ended, broad question to almost everyone I interview with. With it, I’m looking for a number of things. The first is direction. If someone you’re interviewing with (presumably your manager or his manager) can’t articulate the group’s role and purpose succinctly, what does that tell you about future opportunities? Second, if you do get a succint response, how does that fit into your own image of the role that the group should play? Third, ask this question to interviewers at various levels. Is there consistency in their responses? Nothing’s worse than hearing a good response at one level and a contradictory response at a senior level! For example, I ask this question in search of companies where finance is seen as a business partner, not just a number-crunching organization. Finance should also be the ones to bring a little realism (and, occasionally, pessimism) to analyses and forecasts when necessary. I look for hints of this when asking interviewers this question, and if I don’t hear it consistently, I probe a little more and ask about how finance is perceived and why it hasn’t played a more influencing role.

How is the group laid out? What does the reporting structure look like? The main thing I look for here is whether the group’s layout would be one I’d enjoy working in. I like small companies and small groups where I can make a difference. I don’t like hierarchy or structure, or really places where titles separate people from each other and you aren’t allow to talk to a VP because you’re not a director. But, some people may enjoy that, so if you do, and you hear responses that are vague or have several dotted-line reporting, that might indicate the company’s culture might not be the best match for you. You might also hear about lots of recent group restructurings. To me, this is a big warning sign, even though it seems inevitable these days. If I hear about restructurings, I ask point blank about when these will be completed, and why they haven’t been effective so far.

To whom will you be reporting? How does that person prefer to communicate? Email? Phone? One-on-one meetings? Does this fit with your own style? In some situations, you won’t know to whom you’ll be reporting until after an offer is made. But if at all possible, getting to know your immediate manager and how he or she works is always good knowledge to have beforehand. Is she structured? Does he do regular reviews? Or is it on an ad hoc basis? And, as always, how comfortable are you with this sort of work dynamic?

What are the biggest challenges facing the company or group, especially ones that might affect your role? Here’s another biggie question. I’m looking for candidness, how intune people are to their own employer and industry, and, most of all, honesty. I’m always impressed when I hear people give an honest opinion about their workplace. I’ve stopped a job search process before after hearing feedback about a place that I thought wouldn’t fit well with my own vision (and felt I’d made the right choice later after the person in question also left, for the same reasons).

Another thing I ask but not as often is for the interviewer to list a few things he likes best about a company, and what he likes the least. It seems few interviewees dare to ask the latter question (which is almost always the more interesting part), but I don’t do this to be sassy or annoying. If you get serious about a company and really want to make sure you haven’t missed something, an insider’s perspective can be of immense help.

What happens when the growth stops? This is a critical question to ask high-growth companies. You’d be surprised how many of them are in denial about the future, which is another big warning sign for me, personally. If they think the growth will last much longer, do you believe their answers (do they perhaps know something you don’t), or if not, can you do something to change their thinking? Or will the axe fall on you, too, if growth suddenly hits the wall? If you get the impression that they think this is an inappropriate question, what does that say about how direct people are in a company? Does that sit well with you?

Of course, some of the questions above only work if you yourself have assessed the company and its prospects. Otherwise, how would you know if the interviewer was right or not? As such, the first thing I always do in preparation for interviews is to read a company’s Annual Report or 10-K. If you’re not comfortable with that, I’ve written a how-to tutorial on reading 10-Ks. If you don’t go through the whole thing, at least cover the MD&A section. In addition to recent press releases and SEC filings, 10-Ks are the best way to learn about the industry and the company.

Remember, learning about a company from an interviewee’s standpoint isn’t that different from evaluating it as an investor. For example, ask yourself if you would invest in this company. Why or why not? What are the revenue drivers? Does this company have a good business plan? Any warning or danger signs down the road? You’ll find that your answers to these questions are the foundation to building the right questions for your interviewers.

As you develop your career, questions like how well your visions for the company align with those of the company’s leadership becoming increasingly important. I ask all of the questions above as a means to learn more about a company first hand, from employees who are working there. You don’t often get such an opportunity, so why not take full advantage of it? Of course, these questions work best when you also know yourself well. Compensation is certainly important in a job, but all too often it’s put center and forefront above other intangibles that really matter more when it comes to job satisfaction.

The more you know about kinds of places and environments you enjoy working under, the types of people you enjoy working with and working for, the better chance you have of finding a place where you’ll be happy long-term.

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