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When you’re interviewing, you probably have the answers to “Tell me about yourself,” “What’s your greatest weakness?” and “Why do you want to work here?” down pat. (And if not, check out our tips here, here, and here.)

It’s when you get a question that’s a little different from the norm that you have to think on your feet.

Interviewers don’t do this to be mean or throw you off (usually), but to get the real scoop. They know they’ll get a far more genuine answer and learn a lot more about you when you’re speaking off the cuff, rather than reciting something you’ve rehearsed over and over.

Well, here’s a little secret: You can use this exact same technique on your interviewer when it’s time for you to ask questions.

For example, one of the most common questions I get from interviewees is, “What are the best and most challenging parts about working here?” I have a standard response I give in return—something that, while true, is not particularly detailed or revealing.

The other day, though, a candidate posed a different question: “What was the best day and the most challenging day you’ve had in the past three months?”

Instead of reciting my script, I had to think about this. And when I answered, I know I gave him a more honest illustration of the ups and downs he could expect if joining the team.

So, if you want to get the real goods from your interviewer, try doing the same. Start with a list of the questions you want answers to (here are 51 to get you started), then think about how you can ask them in a more detailed, specific, or unusual way. Don’t go too crazy (this is a conversation, not an interrogation), but do think about how you could shift your question in a way that will get the hiring manager off script.

Here are a few ideas.


Instead Of: “What Does a Typical Day Look Like?”

This question often tends to breed the answer, “Well, there’s no real typical day…” which tells you exactly nothing. Instead, ask for a rundown of a real workday in the past (or future), such as, “What did the person who currently holds this role do yesterday?” or “If I was a month into the job, what would my day look like today?”


Instead Of: “What Are the Biggest Challenges Someone in This Position Would Face?”

“Tough clients.” “Resources.” Hiring managers don’t like to scare candidates away, so when they talk about challenges, they tend to couch them in vague terms like these. So, try asking about specific challenges or a specific number of challenges. Think, “Can you tell me about the most difficult client situation you’ve faced in the last six months?” or “What are the two biggest challenges the department is dealing with right now?”


Instead Of: “What’s the Company Culture Like?”

Asking about company culture can get you anything from a list of pretty meaningless adjectives (“innovative,” “collaborative,” “focused”) to a description of the company break room. To get the results that matter to you, think about the parts of culture you most value. Do you want a team that plays as hard as it works? Ask, “Tell me about the last few team bonding events that were held.” Concerned about a competitive environment? Ask, “What motivated employees to reach their goals last quarter?” And if you are looking for more of a broad overview, try, “What’s different about working here than about anywhere else you’ve worked?” which will get you a much more meaningful description.



Good interviewers know how to get honest answers, not canned responses, which helps them figure out who’s really going to be the right fit for the team. So steal their techniques to make sure the company and role is the perfect one for you.