25 Uncommon Interview Questions That Help To Understand What It's Really Like to Work at the Company

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Anne Matsushita197
May 22, 2024 at 5:9AM UTC

As a Career Coach, many of my clients ask what questions they should ask at the end of an interview to make a good impression. But what if you flipped the script? I would challenge you to reframe the interview as an opportunity for the company to make a good impression on you.  

You can do this by getting clear on your must-haves or nice-to-haves. Think about things you’ve enjoyed in previous roles, or things you didn’t like that you would want the opposite of. Then build questions around these. Outside of pay and benefits (save these until you have an offer, unless they bring it up first), most questions are appropriate to ask so you can show you’re interested in more than perks.

Below are potential questions to help you get started. Notice that many of them are open-ended. If the interviewer struggles to think of a recent situation, that might be a red flag.


Find out if there are opportunities to do group work, or if people operate more in a silo, especially if the job is remote.

  • Can you tell me about a time the team worked together to successfully reach a goal?


See if they have a Town Hall or Slack channel so everyone receives the same information at the same time. Or does it trickle down from the top, which increases the possibility of a miscommunication.

  • How is information disseminated across the company?  

  • What is done to keep employees up to date on what's happening in the market?


If you ask what the company culture is like, they will rattle off positive adjectives. So you want them to show, not tell, through personal stories or concrete examples. 

  • What's a time the company culture made a positive difference for you?  

  • When did the company culture help you through a difficult situation?  

  • How does the company hold people accountable to living the company's values?

  • What makes the company different from its competitors?

  • I noticed a lot of people on Glassdoor recently mentioned that “fill-in-the-blank” is a concern.  Is the company aware of this and how are they responding?


Check if the company is tracking this information, transparent in sharing it, and working towards improving.

  • What are the company's DEI initiatives and how could I get involved?  

  • What groups are underrepresented and what is the company doing to address that?

Flexible Schedule

Rather than asking if they offer flexibility, see if their definition matches yours.

  • How does the company encourage employees to rest and recharge?

  • How does the company support working parents / caregivers?

Growth Opportunities

Get a glimpse into opportunities to move up or laterally in a different department.

  • What does the company do to encourage internal mobility?

  • Where have previous people in this role moved within the company?


If you want your voice heard, find out if it’s accepted or even rewarded to speak up.

  • How does the company empower people to raise ideas?

  • When was the last time someone on the team raised an idea that was implemented?

Learning and Development

Look to see if they will not only give you positive and constructive feedback, but also the tools to help you get to the next level. For instance, perhaps they’ll hook you up with a mentor, or cover conference fees.

  • How is feedback given?

  • What does the performance review process look like?

  • What happens if someone makes a mistake?

  • What kinds of development opportunities does the company provide?

Management Style

Depending on your preference, see if the manager will help set you up to succeed.

  • How much time do you spend with your team and how much time with your stakeholders?  

  • What's a recent accomplishment one of the high performers on your team had?  

  • Can you tell me about a time you had to provide someone with difficult feedback?


Try to get a sense of the environment, like are people smiling or stressed? Are they interacting with each other or sitting alone with headphones on?

  • (If it’s an in-person job) Can I have a tour of the building or department where this role will be sitting?

  • Can I talk with a peer on the team?

You can also check out more questions here: 5 Types of Bosses You Want to Avoid, Looking for an Inclusive Employer?, 3 Better Questions to Ask in Your Next Job Interview, and How to Spot a Toxic Culture in a Job Interview.

A good rule of thumb is to have more questions prepared than not enough, in case the interviewer answers some of your questions during the conversation. Also, feel free to take notes as the interviewer is talking. They will be taking notes on you too! The goal is to get as much information as possible so you can decide if the position checks the boxes for you. Then you can decide if you want to continue moving forward in the interview process, or even accept an offer. An interview is a two-way street - you’re interviewing the company just as much as they’re interviewing you!


This article reflects the views of the author and not necessarily those of Fairygodboss.

After 12+ years of progressive HR experience in the entertainment and education industries, Anne pivoted to a Career Coach opportunity with Randstad RiseSmart. She’s passionate about crafting customized job search strategies for diverse clients and helping them navigate emotional highs and lows. She’s thrilled to see clients land at Dish Network, KCBS, LinkedIn, Mattel, Salesforce, Workday, etc. and negotiate additional double-digit compensation. Feel free to connect with her on LinkedIn.

What’s your no. 1 uncommon question to ask during an interview? Share your answer in the comments to help other Fairygodboss members!

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