Do you approach the interview process like an interrogation or a conversation? Or, I’ll put it another way: When sitting across the table from a potential hire, is your style more Peace Corps or Marine Corps?

If you’ve only had challenging interview experiences yourself, you might think they’re all about stumping the candidates or having “gotcha” moments where mistakes are revealed and awkward silences endured.

But it doesn’t have to be this way. In fact, the whole process should feel like an authentic, revealing conversation—not an embarrassing one. One of my most memorable experiences with a candidate included a tangent about apps that we would recommend to friends. This wasn’t just a fun discussion for both of us to have, but it also showed me a lot about her interests and personality.

Over time, I’ve learned how to turn interviews into a revealing, enlightening, and pain-free dialogue for both parties. The secret is all in asking the right questions. Like these:


1. Describe the Best Moment You’ve Had at Work

Instead of asking an applicant to list his strengths, I look for a more personal story about his best moments on the job. Is the candidate talking about an impressive success in the face of adversity, or is he talking about how great he finds his current company’s work-from-home policy (which would suggest he may not be OK working at a desk like he suggested in an earlier question)?

I also listen to see if the candidate’s focusing solely on herself or also mentioning team members that helped lead to the successful moment. Does she mention specific deliverables and measurable results (i.e., our new slogan increased sales by X %), or stick with vague generalities like “I think I’ve helped increase sales”?

Not only will the story of a favorite moment tell you more about the candidate than a memorized answer about his or her strengths, but it will kick off the interview on a positive note. After all, people love sharing their career highlights.

2. What Business Would You Start Tomorrow if You Could?

I always use this question to replace the old “Where do you see yourself in five years?” Too often, people think you want to hear: “I see myself here, supporting you,” which doesn’t tell you anything. It also puts the candidate in an uncomfortable position, because answering truthfully might come off like, “I’ll just be here until I can get something better.”

By asking about the person’s entrepreneurial vision, you’re still learning about his goals and aspirations, but you’re also providing a space for him to discuss his creativity and vision, which should help him to feel engaged and excited about the interview. Who doesn’t like talking about their dream career?

This question also helps give you a feel for if candidates are really passionate about your industry—or just taking whatever job they can get. For example, when CJ Pony Parts, a Mustang parts company in Harrisburg, PA asks this, the right answer includes cars or the auto industry. If it’s left out, it’s safe to assume that he or she might not have the (pardon the pun) “drive” needed for the job.


3. Tell Me Something About You That I Wouldn’t Know From Your Resume

Many interviews start with, “Tell me about yourself.” To which interviewers get a well-rehearsed recap of the highlights of the candidate’s resume.

I prefer to ask for a bit of personal trivia. When you go beyond the polished, professional biography, you may discover something quirky or interesting—as well as something relevant to the position.

For example, someone who has been to 20 foreign countries probably won’t mind the occasional travel the job requires (but she might get itchy chained to a desk). Someone who talks about managing her kids’ theater production is demonstrating leadership, creativity, and a desire for work-life balance.

Use the question to give candidates a breather from regurgitating their resumes, and use the answer to gauge if the candidate would be a good fit for your company culture.


4. Are There Any Questions You’d Like to Revisit?

Many interviewers conclude with, “Do you have anything else to add?” or some variation of that vague question. In my experience, most applicants use this time to repeat their original elevator speech about their education and experience.

However, when you inquire if a candidate would like to go back, you can learn a few valuable personality traits. First, is she able to admit when she’s been less-than-perfect or even wrong? Is he able to admit he’d like clarification or a do-over? These are important employee traits. A person unable to admit mistakes could cost you time and resources.

Bonus: This question goes a long way in making the applicant feel good about the interview. Who hasn’t left an interview thinking about something he or she should have said differently? Most people will be excited that you’re giving them the chance to revisit a question they might’ve bombed earlier.


5. Do You Have Any Questions for Me?

OK, fine, this is a typical interview question. But I recommend that you keep it on your list.

It will tell you if the candidate has prepared only standard (a.k.a., safe and boring) questions, or if he can think quickly and process the information exchanged in the interview. Is she referencing an earlier conversation about expected responsibilities? Has he made an observation about the job in the moment, and does he want to know more?

Additionally, even though some candidates dread having the floor, this question shows that you value their voice. It demonstrates that you’re open to employee questions and feedback. And, if someone has had a nagging question all interview, she’ll be thrilled for the space to ask it.



If you asked someone how much he enjoyed his last interview, it might rank somewhere around doing his taxes or getting an annual physical. But interviews don’t have to be excruciating. The five prompts above will help you get a good sense of the candidates—and will (hopefully) be questions they’re excited to answer.


Photo of interview courtesy of Shutterstock.