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Advice / Job Search / Interviewing

5 Clutch Questions to Ask When a Job Interview Starts Heading South

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A year ago, I went on a job interview that quickly seemed to be veering into “nightmare” territory. The person I ended up speaking with got called in to talk to me at the last minute and hadn’t really prepared much. He only spent five minutes asking me about my professional qualifications and then answered my questions about the company and his role in a matter of 15-second, one-sentence responses.

Thankfully, I’d brought my “when all else fails” questions. They’re perfect to use if everything you planned to ask at the end was answered in the first five minutes, if you’re not clicking with the hiring manager, or if you’re struggling to get quality answers about the company you potentially want to work for.

In this case, my WAEF strategy turned a 10-minute in-and-out conversation into a 50-minute discussion. And even better: I got the job.

So, what did I ask to turn this around?


1. “Can You Take Me Through Your Day Yesterday and Explain What You Worked On?”

If you ask someone “What’s a typical day like?”, he or she will almost always say, “No day is a typical day!”—and then your conversation is dead in the water. It’s too abstract.

Instead, give your interviewer something concrete: “What did you do yesterday?” People will go through and break down when they woke up and arrived in the office, what meetings they took, what projects they were working on, and so on.

It also makes room for easy follow-ups like, “What makes you excited about that project in particular?” or more technical questions regarding your field.


2. “If Resources Weren’t an Issue, What Would Be Your Dream Project to Work On?”

Not only does this question allow an interviewer to dive into his or her own ambitions, but as a job seeker, you can learn a lot about a company from how big its employees are dreaming and what they consider to be an out-of-this-world project. Not to mention, it’ll give you some quick insight into your potential department’s budget as well as resources you won’t likely have access to.

Keep an ear out for answers that involve standard tools and projects for your industry. It’s OK to join an organization that runs on a tight budget—but you don’t want to join one that can’t provide you with the basics that you’d need to get your job done well.


3. “Can You Tell Me About a Moment When You Thought, ‘Wow, This is a Total [Company] Experience?’”

An interviewer once told me all about how his company had this amazing kickball league and how their championship game made him realize how much he loved his co-workers and the energy they brought to any task. He ended his answer by saying, “It was one of the most quintessential [Company] experiences ever.”

As someone who loves the idea of low-key team sports and company spirit, it made me really excited to know that was the standard for this organization. Now if he’d said, “It’s a company mandate that we always watch every football game together on Sundays at the bar down the street,” that would’ve made me pause.


4. “What Was a Recent Challenge Your Team Faced, and How Did You Solve It?”

It’s easy for interviewers to talk about how great their companies are ad nauseam, but you can tell what a company’s culture is really like when you ask someone about the tougher moments.

I once asked this question and noticed the hiring manager repeatedly used passive-aggressive language to describe the situation and her feelings toward her co-workers. And while she probably wasn’t even aware of it, she subconsciously threw her boss the evil eye at least three times. That alone immediately made me reconsider what I’d previously heard about that company’s emphasis on clear communication and emotional intelligence in the office.


5. “What Skills Does Any Person Working Here Need to Possess, Regardless of Department?”

This one opens up great conversations about specific instances in which all team members showed similar qualities. The answer will instantly tell you about the company culture and what they value in their employees. Is it ambition? Kindness? The ability to work quickly? Independence? There’s no right or wrong answer here (unless, of course, the person says something like “greed” or “ability to backstab shamelessly”).

Keep an eye out for how specific or vague the responses are. It illustrates not only how teams work together, but also how (or even if) they interact with other departments. Not to mention, it’ll show you pretty quickly how clear the company’s messaging about core values is across departments—or, if it doesn’t exist at all.



If an interview isn’t going well, you don’t need to press the big red panic button just yet. Despite the fact that you’re the one being interviewed, remember that you have lots of control over your situation based on what you ask. So, come prepared with your WAEF questions ready and prepare to nail it.