5 Interview questions that are designed to challenge the interviewer

I designed these 5 interview questions to challenge the interviewer, and give you a deeper understanding of the role, company, and culture.

An interview is such a strange formality. Some people equate an interview with going on a first date where it’s a series of impressing, courting, and balancing to try and affirm your new relationship with this stranger. This is the first mistake that many people make.

An interview is meant to measure and equip an interviewer and interviewee with the knowledge to make a decision on their ability to fit into a company, execute their role, and their aptitude for that role + beyond.

I’ve interviewed a lot over the years and I find that it’s not enough to ask the simple questions like “What benefits are available at this company?” though you definitely should ask and understand your potential benefits. In order for you, the interviewee, to be equipped with how you will fit into this role or company beyond a list of job requirements means asking questions that will challenge your interviewer and bring forth honest conversation around the pros AND cons of the company and role.

I’ll be providing you with the top 5 challenging questions I ask in an interview when applying for a role. additionally I’ll go over:

  • Why I ask this question
  • What you are looking for in an answer
  • What is considered a red flag



How would you describe your management style and in what ways has it proven to be successful or challenging with the team since you’ve been a manager?

Leading a team is a big responsibility and picking your next manager or boss is the biggest choice you’ll make when choosing a role, more so than the duties of the job or the pay for your work. A bad boss is one of the top reasons people leave their job, as such you should understand, on more than just a surface level, who you’ll lead by. As such, the reason I ask this question is it gets the interviewer to think critically about how they lead. A great leader will know that a team can’t be lead with a single management style, it takes tailoring management to what works best for the team, the individual, and the task at hand and changes constantly.

The second part of the question is designed extract an attitude from them about their own comfort in the role, their team, and place in the company. How do they consider the health of their team? has leading been a challenge? is this person still learning how to be a better leader? How is the team dynamic? there are lots ways to answer this question but your #1 goal is to see if they are self aware enough as a leader to know that it’s their responsibility to lead the team, not just delegate tasks and lead meetings.

A red flag around this question is if they can’t think of a single example of a challenge they’ve had with their team. Even the most perfect teams are going to have challenges, and if the person interviewing you can’t think of, or worse disclose, a challenging moment then you should understand that is a reflection of their abilities, the company culture, and awareness of their team.

Take note of which route they take here, do they go high and talk about accomplishments or do they speak to the difficulties, use that knowledge to guide whether to go positive or critical in each of the following questions.



Can you please share with me what the turnover rate of the team is and what, if any, are some of the reasons for these shifts?

Let’s be blunt, unless this a brand new role, someone had this position before you and they are no longer there. Before you make the same mistake they did it’s in your best interest to understand what is happening at this company, why, and if leadership is actively making changes to prevent this from happening again.

There are lots of reasons for hiring, but unless the company is early stage, going up market, or pivoting their services chances are you are going to be “The New Janet” hell.. her coffee mug might have even been left behind for you. Some reasons for a high turn over rate could be: The company went through layoffs during the pandemic and are now hiring again, the pervious person left for a role in a different industry, the company has a mandatory non-remote policy and that created a post-pandemic exodus, a current member of the team is a few months out from maternity leave and they are using the opportunity to slowly build the team before their departure, and for a smooth return. The reason isn’t really all that important, again it’s about giving you a better picture of what is happening beyond the “fast paced work environment” in the job description.

A red flag is not “We can’t disclose that”, because you might get that as an answer for this question, and that’s okay. if so, then pivot this question more towards culture. The red flag I look for is if the reasons are all negative and they don’t have any internal reasons, or ownership, for any of those departure(s). No job is perfect, and there are really only two options either you retire, or you depart the role. Finding out the reasons for high turn over will help you decide if that’s a good place for you to be involved in and if the company is capable of change to keep good employees.




What are some of the challenges your team is experiencing and what do you think is causing those challenges?

So far you’ve really probed your interviewer, and if i’m honest, this far into the interview they might be frustrated with you and might end the interview early, not everyone is comfortable being challenged. Some companies are just trying to hire an executioner of the tasks, not a critical thinker or someone that is going to challenge them. That’s okay, even if it’s not what I’m looking for. This entire process is about learning how we’d work together and if the answer is “We wouldn’t work well together”, then at least I have an answer.

But if you can tell it’s going well and you want to give them an opportunity for a positive light to be shed about them and their role then you can the word “challenges” -> “successes/victories”.

Again the entire point of these questions are to unlock more information about the actual culture and environment you are attempting to step into. If the team’s victories are data driven then you can probably guess your main KPI’s are going to be data driven, If the team’s victories are outcome based then you know that your skillset as a story teller will probably help you in translating your results to your manager, if the team’s challenges are performance based, then it might be a sign that the company is understaffed and that you should be prepared to be doing more than just what’s in the job description.




Can you please share with me a time when you had to take responsibility for a poor decision or a mistake you made?

If you’re wanting to shift more into a positive questioning then you can swap out the words “take responsibility for a poor decision or a mistake you made?” -> “shared in celebration with the team on a victory you all accomplished together?”

With this question I’m trying to measuring their ego and their ability to take/share responsibility and stay humble. A bad leader can quickly ruin your ability to move up in a company because when you’re not in a leadership/exec meeting it’s easy for them to say to the CEO “oh so and so didn’t get me that report, I’ll get it for you before the end of the day” when really you sent them the report a few days ago, they just weren’t on top of their shit. Either way it paints you in a poor light to other members of management or leadership and that could come back to bite you when it comes to promotions, raises, or just being on better projects.

Red flags that I look for are if you feel that the interviewer isn’t being authentic with you. You are asking for vulnerability and about their short comings in their current role, it’s a direct shift in the power dynamic of an interview. The interviewer could either lash out, question your authority, or directly lie to you. It’s important that you are aware that this is not a reflection of you, but a glimpse into what could happen if you “have a different idea” or “morally disagree with” their choices, or directions. It sucks, but it’s better to know how they react when questioned or challenged now than after you’ve spent two years with the company.




What are some of the goals you are prioritizing to address this year or quarter on your team?

After a few tough questions it’s nice to end on a question that refocuses on the goals, why they are hiring, and what they are working towards. In the previous 4 questions we’ve asked them to think critically in either the present or the past, now with the finally question we’re looking to see how they can look forward into the future. What are their goals? Are their goals measured by data, experiences, or a dollars made? Did they focus the goals cross functionally or did they focus the goals to your specific team? 

Red flags here are having goals without plans, if they speak broadly such as “we want to be #1 in our industry” or “we want to disrupt the status quo” then you know that everyday is a probably too chaotic for them to have long term plans or roadmaps. Well organized companies have a road map, goals, and a some what idea of what they need to do to get those goals across the finish line. 

By the time they finish answering this question you should feel that excitement in your belly about the role, the company, the goals, and your place in it all. Thank them for their vulnerability and honesty, it’s not easy to answer these questions, even about the roles and company you love, they are designed to be challenging and to spur critical answers of their systems.

If done right you’ll know the company/team better than probably any other candidate, stand out by demonstrating critical thinking, built some healthy tension and conversation in the interview, and know whether or not this company and role is right for you, your talents, and your time.

If you plan on using any of these questions in a real interview, I highly encourage you to practice the hell out of it, seriously, I didn’t title this “5 interview questions that will leave your interviewer with the warm fuzzies about you” these are questions that will likely have the interviewer ending the Q/A early or ending the interview early if not delivered with empathy, mutual curiosity, and respect. The same can be for you though, it’s perfectly fine to stop an interview and say, “I’m sorry, thank you for your time, but I am no longer interested in the position and wish you the best of luck on your search”. 

Bonus tip, if it’s a virtual interview, is to look directly into your webcam through the entire interview and pretend it’s a phone interview. It makes a world of difference in making them feel heard and that you’re listening.