29 questions you must ask in 2021 job interviews

It’s time for my twice-a-year update on the best questions for you to ask in an interview. I started this biannual tradition ten years ago; ultimately, it turned into our Amazon bestseller Ladders Interviews Guide

As I mentioned in my last update to these great interview questions, the coronavirus marked a sudden, catastrophic change in the employment landscape.

Fortunately, we’ve recovered quite a bit, and we’re seeing very strong hiring demand at Ladders.

So here are my easy-to-ask, revealing-to-answer questions that will uncover the most important information for your career search, and make you look like the most prepared candidate for your 2021 interviews:

1. How has COVID impacted your team and your company? Compared to other teams, was yours more or less impacted by the COVID changes?

2. What’s one thing that’s key to this company’s success that somebody from outside the company wouldn’t know about?

3. What’s your (or my future boss’) leadership style?  

4. What are the three things I can contribute in the first 100 days to make you feel great about hiring me?

5. About which competitor are you most worried?

6. How does sales / operations / technology / marketing / finance work around here? (I.e., groups other than the one you’re interviewing for.)

7. What type of people are successful here? What type of people are not?

8. 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?

9. How did you get your start in this industry? Why do you stay? You’ve been at his company a while, what is it about this job that keeps you fired up?

10. What are your group’s best and worst working relationships with other groups in the company? What are the pain points you have to deal with day-to-day?

11. What keeps you up at night? What’s your biggest worry about the days ahead?

12. 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)?

13. What’s the timeline for making a decision on this position? When should I get back in touch with you?

14. COVID has been a big hit to the economy, and every position is precious right now when it comes to the budget. Why did you decide to hire somebody for this position instead of the many other roles / jobs you could have hired for? What about this position made you prioritize it over others?

15. If I get the job, how do I earn a “gold star” on my performance review? What are the key accomplishments you’d like to see in this role over the next year? (And, remember, for this one you want the vibe to be a cool & relaxed Channing Tatum, not a cringing Jonah Hill.)

16. What is your reward system? Is it a star system / team-oriented / equity-based / bonus-based / nice-gif-in-the-chat-channel-based? Why is that your reward system? What do you hope to get out of it, and what actually happens when you put it into practice? What are the positives and the negatives of your reward system? If you could change any one thing, what would it be?

17. What does success for this group / team / company look like in 1 year?  In 5 years?

18. What information is shared with the employees (revenues, costs, operating metrics)? Is this an “open book” shop, or do you play it closer to the vest? How is information shared? How do I get access to the information I need to be successful in this job?

19. 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? How does this position help achieve those goals? How does COVID impact those goals? (This question helps show your ability to look beyond today’s duties to the future more than a year away. It’s really a surprisingly easy way to come across as somebody who is always looking ahead.)

20. How does the company / my future boss do performance reviews? How do I make the most of the performance review process to ensure that I’m doing the best I can for the company?

21. 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?

22. What type of industry / functional / skills-based experience and background are you looking for in the person who will fill this position? What would the “perfect” candidate look like? How do you assess my experience in comparison? What gaps do you see? 

23. What are the plans for “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.)

24. 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? 

25. What is your (or my future boss’) hiring philosophy? Is it “hire the attitude / teach the skills” or are you primarily looking to add people with domain expertise first and foremost?

26. 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 you hope change?

27. When we are working together six months from now, what will be my biggest surprise?

28. 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?

29. Who are the heroes at your company? What characteristics do the people who are most celebrated have in common with each other? Conversely, what are the characteristics that are common to the promising people you hired, but who then flamed out and failed or left? As I’m considering whether or not I’d be successful here, how should I think about the experiences of the heroes and of the flame-outs?

I hope you find these interview questions useful in your interviews, Readers! If you’re looking for a 90-minute read on mastering interviews, please check out Ladders Interviews Guide, available at Amazon.

A final note.  Previously, another commenter, “Lenore”, asked:

Hi Marc.  Awesome interview questions!

My question for you is…..how do you ask great questions when you are meeting with more than one interviewer.  I met with 3 to 4 interviewers, one at a time.  I didn’t want to come off generic by asking each of them the same questions.  I guess you can go by their role to determine what questions you are going to ask.  Sometimes they are all top executives. I’m guessing there are enough questions to divide amongst them all.  I had asked so many questions in an interview once, that I didn’t want to seem redundant. Do you think this is ok?

To which I replied:

Great question Lenore.

Three options:

1) Change the wording a little bit each time so you’re not asking the same question in the same way.

2) Mention that “You know, I already asked your colleague about this, and I’d love to hear your thoughts…”

3) Divide the list and ask different people different questions, as you suggested.

Hope that helps!