The 19 best questions to ask during your job interview this year, according to a careers expert on high-paying jobs over $100,000

  • Marc Cenedella is the founder of Ladders, a career advice and job search site for positions with annual salaries of at least $100,000.
  • Despite a tumultuous 2020, he says the employment picture may be fully recovered later this year.
  • In this market, Cenedella recommends asking about WFH culture and COVID’s impact on the company. 
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Twice a year I update my best interview questions for you to ask during your job interview. It’s helpful to have a handy list of queries available whenever an interviewer asks “do you have any more questions for me?”

At last year’s update on the best interview questions, we were all too stunned by the rolling disaster that was 2020 to have gained any perspective on the situation.

Now, with hindsight, we can see that the coronavirus marked a sudden, catastrophic decline in the employment landscape followed by a steady, gradual improvement. Overall, the employment outlook is quite good, and may be fully recovered later this year.

So here are 19 questions for you that are easy to ask, revealing to answer, and will uncover relevant insights about the people and the company with which you’re interviewing:

  1. Who does well here? What type of people are successful? What type of people are not?
  2. How has work-from-home impacted your team’s productivity? During COVID, what’s been the best boost for your team productivity and morale? What have you tried that hasn’t worked?
  3. How did you get your start in this industry? Why do you stay? How long have you been at this company? What keeps you fired up?
  4. In my career, I’ve primarily enjoyed working with big / small / growing / independent / private / public / family-run companies. If that’s the case, how successful will I be at your firm?
  5. How has COVID impacted your team and your company? Compared to other teams internally, was yours more or less impacted by the COVID changes?
  6. What’s one thing that’s key to this company’s success that somebody from outside the company wouldn’t know?
  7. What’s your (or my future boss’) leadership style?  
  8. What is the rhythm to the work around here? Is there a time of year that it’s “all hands on deck” and we’re pulling all-nighters, or is it pretty consistent throughout the year? How about during the week / month? Is it pretty evenly spread throughout the week / month, or are there crunch days?
  9. About which competitor are you most worried?
  10. What keeps you up at night? What’s your biggest worry about the days ahead?
  11. Who are my customers (internal or external) and how do they measure me/ us? Who views me / my team as a customer (internal or external)?
  12. What’s the timeline for making a decision on this position? When should I get back in touch with you?
  13. What information is shared with the employees (revenues, costs, operating metrics)? Are you very open with financial information or is that kept rather confidential?
  14. If we are going to have a very successful year in 2022, what will that look like? What will we have done over the next 10 months to make it successful? (This question is a surprisingly easy way to come across as someone who is always looking ahead.)
  15. How does the company / my future boss do performance reviews? If I ask my future peers about the performance review system, will they say that it does, in fact, help them to improve their performance? How does the company support employees in raising their game from year to year?
  16. What are the plans for post-COVID “back to normal?” What will normal look like? How are you thinking about time in-office vs. flex vs. remote for the workforce? (Please note: nobody knows the answers to these questions yet, so expect a conversation, not a conclusion.)
  17. Were you forced to make staffing cuts or furloughs during the past 12 months? Do you anticipate they’ll be permanent? Will there be more? 
  18. Is this a new position, or an existing position? If new, why was it created and what are the expectations? If an existing position, where did the prior person go? What were the things that person did really well, that you hope to see in the next person? What are the things that you hope change for the better?
  19. When we’re working together six months from now, what will be my biggest surprise? 

For all of these questions, the goal is not to come across as prosecutor, judge and jury. Rather, you want to be someone who is interested — not committed yet, but somewhere between mildly interested and moderately enthusiastic, depending on your style, their mien, and how much you want the job.

The pro tip with these questions is to find three or four that you ask each and every person with whom you interview.  It’s OK to do that, and even better if you let them know you’re asking everyone similar questions. 

By asking the same question multiple times, you can gather insights into how well-aligned a team or company are, the different personality types based on their different answers to similar questions, and, hopefully, a 360-degree view on the questions most important to you.

Good luck, and have a great interview!

Marc Cenedella is the founder of Ladders, a career advice and job search site for positions with annual salaries of at least $100,000.

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