Dear Annie: Is there any way to figure out, in a job interview, what a company is really like to work for? I’m job hunting right now, and it’s important to me to find a place where I’d be a good cultural fit, because where I work now is driving me crazy.

When I came here a couple of years ago, interviewers told me the culture was “innovative” and “entrepreneurial,” but it’s really the opposite—a huge bureaucracy where new ideas are seen as suspect, decision-making is slow, and every little thing has to get approval from so many different people that no individual is ever responsible for anything. Most of my coworkers seem perfectly content, but I can’t wait to get out of here. How can I make sure I get the “fit” right this time? —Square Peg in a Round Hole

Dear Square Peg: Great question, and one that Jason Hanold spends lots of time pondering. As CEO of boutique headhunters Hanold Associates, he has recruited top talent for Nike, eBay, Amazon, McKinsey, Xerox, and many others. Hanold regards the right fit as so essential to success (not to mention happiness) that “we do sometimes tell people, ‘No, you’re not right for XYZ Corp.’ or vice versa,” he says. No matter how lucrative the offer, “if there’s no appetite there for what you’re best at, it’s the wrong culture.”

The trouble, of course, is that corporate culture is complicated, encompassing everything from office décor and dress code, to history and tradition, to a whole range of unwritten (and mostly unspoken) rules that add up to how work gets done day to day.

Then there’s employer branding, which is the image a company hopes to project to the marketplace of potential employees, and what Hanold calls “aspirational” culture, which is the culture a company wishes it had or is striving toward, rather than the one it has. Those managers who interviewed you probably weren’t trying to mislead you, Hanold says, but buzzwords like “entrepreneurial” and “innovative” can sometimes mean that the person speaking “has got the employer brand, or the aspirational culture, confused with the real thing.”

So how can you be sure you don’t make the same mistake? Over the years, Hanold has come up with a list of five questions he asks client companies to make sure the candidates he brings them aren’t cultural misfits. You can, and should, ask these questions too.

1. How would you describe your organizational culture? “You want to see how quickly they respond. Do they struggle with the question?” says Hanold. “If so, that might mean the company doesn’t have a strong culture, or that different groups are running in different directions.”

Let’s say the answer you get is “entrepreneurial.” Ask for an example or two. “If that’s really true, the interviewer should instantly be able to tell you, not just one, but many anecdotes about speed, flexibility, the autonomy of different individuals and teams, and so on.” If not, well, that says a lot.

2. When you think about the stars here, the most distinctive talents at all levels of the company, are there three or four traits that most of them share? A big chunk of culture is “what a company values and rewards most in its employees,” Hanold notes. “Those traits will tell you the skills and behaviors the organization wants more of.” If an interviewer describes stars as great at collaborating with a team to come up with new ideas, for instance, and you’re better at working on projects alone, the fit may not be a good one.

3. Has anyone with those characteristics ever failed here anyway? If so, why? One of Hanold’s clients told him about a star manager who had all the traits needed for success—he was “fast-moving, results-oriented, and a great problem-solver—but had flamed out anyway, because he was “so arrogant and controlling that no one liked working for him,” Hanold says. “That was an important indication of what kind of personality works in that culture.”

4. If you could change one thing about the culture here, what would it be? “Often, a hiring manager will personalize this and refer to his or her own situation,” Hanold notes. “If he or she says, ‘I wish I had more autonomy to make decisions’ or ‘I wish I didn’t have to operate on such a tight budget,’ that implies a great deal about what it’s like to work there.”

Hanold recommends posing all of these questions to each manager you meet during the interviewing process to see whether the answers you get are consistent—“versus the views of one or two eloquent people who sound good, but who may not be describing a common perspective.”

5. Could I meet some of the people I’d be working with? You’ll most likely be introduced to a few prospective peers during two or three rounds of interviews, but if not, ask if you can get together with some of them for lunch or a cup of coffee. Candidates sometimes hesitate to make this request, Hanold says, but most employers welcome it, because “it shows that you’re doing due diligence, and you’re being selective about your next job. Never forget, you’re interviewing the company every bit as much as they are interviewing you.”

The only situation in which an employer might balk at this idea, he adds, is if you’re interviewing for a job that’s currently held by someone who doesn’t yet know that he’ll be leaving. “Then, of course, there are concerns about keeping you confidential,” Hanold says. “But that’s only the case in about 25% of the searches we do.”

It’s also smart to check out career sites like and to see what you can glean about the culture from the comments there. “The employer brand and how that same company is actually perceived from within might be quite different, or it might be the same,” says Hanold. “But if you see a big gap between the two, and especially if there is a pattern of a lot of negative comments about one particular aspect of the culture, you can certainly ask interviewers about it.”

If this seems like a lot of questions, it is. But, says Hanold, “interviewers like candidates who ask a lot of honest questions. It’s a sign that you’ve put some thought into it.” Good luck.

Talkback: What aspects of a company’s culture are most important to you? Have you ever taken a job that turned out to be a bad cultural fit? Leave a comment below.

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