In today’s (frankly weird) job market, hiring the right talent is more important than ever. That said, hiring good people is going to take more than “Walk me through your resume.” or “What’s your biggest weakness?”

Asking powerful and deep interview questions can bring out the best or worst in a potential hire. Here are 50 of our favorites (and no ChatGPT didn’t write these!).

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1/Why did you leave your last role and how did it prepare you for this opportunity?

2/What would your previous colleagues say about you?

3/Is there anything you liked/didn’t like about the interview process to this point?

4/Did anything in the job description scare you? Why?

5/What is the company value that you most align with?

6/ Share an instance where you had to handle a project with evolving requirements. How did you adapt your strategy to accommodate changes?

7/ Describe a project where you were required to work with limited resources or tight deadlines. How did you manage the constraints while delivering results?

8/ Have you ever had to convince your manager that your way of solving a problem was the best way? How did you go about convincing them that you were right?

9/ Have you ever foreseen a problem before it happened? What did you do to prevent this from happening?

10/ How would you go about putting together a 1,000-piece jigsaw puzzle?

11/ Tell me about a time when effective communication made the difference between failure and success. Explain the situation and the reasons that effective communication was so critical.

12/ Have you ever received bad instructions from a manager? How did you communicate that you needed better direction?

13/ How do you incorporate feedback from your colleagues and superiors into your communication style and work approach?

14/ Can you share an instance when active listening helped you resolve a misunderstanding or conflict at work?

15/ Tell me about a time where you failed to communicate. What did you learn?

16/ Tell me about the last brainstorming session you had. What did it accomplish?

17/ What has been your favorite new product/tool/invention of this year? Why?

18/ What is your process for coming up with new ideas?

19/ Where do you pull inspiration and creativity from?

20/ What do you think is our companies’ most creative/innovative product/solution/service/etc.? Why?

21/ What is something you say to yourself internally when things get difficult?

22/ Would you rather work in an environment with constant pressure or no pressure at all?

23/ Think of someone you know that overcame hardship. What do you admire about them?

24/ Do you prefer slow and steady change or quick and explosive change? Why?

25/ Would your previous co-workers define you as resilient? Why?

26/ Do you prefer working with others virtually or in-person? Why?

27/ How do you like to celebrate team successes?

28/ How do you bounce back from team losses/failures?

29/ Who was your favorite coach or leader (non-work related)? Why?

30/ What size team do you like to work on? Why?

31/ Who is your favorite (non-work) leader of all time? What did you learn from them?

32/ How would you describe your leadership style in 3 words?

33/ How would you describe how you like to be managed in three words?

34/ Think of a historical leader, fictional or real, who inspires you. What qualities or characteristics from their leadership style do you try to embody in your own leadership?

35/ Do you have any leadership books/seminars/podcasts/etc. you’d recommend? Why?

36/ Have you ever had to let someone go? Why, and what was that process like?

37/ Do you use a framework for managing conflict? If so, walk me through it.

38/ How do you think about mental toughness and grit at work?

39/ How would you settle a fight amongst your friends? Would you take a similar approach at work?

40/ When you are frustrated are there any physical spaces you like to retreat to to gain perspective and problem solve?

41/ Are you a risk-taker or do you like to play it safe? How do you think that mindset will fit within our company?

42/ If you could choose a mascot for our company what would it be and why?

43/ What is your all-time favorite workplace memory? Why?

44/ How do you like to be rewarded at work?

45/ If your work isn’t meeting standards, how do you like to be informed?

46/ Can you share an example of a skill or competency you actively sought to develop in your current or previous role? How do you plan to keep developing that skill here.

47/ If you were to describe your career journey as a book or a movie, what would the title be, and what genre would it fall under?

48/ Do you prefer a hands-on or relaxed approach to career growth and professional development? Why?

49/ If you had unlimited resources and opportunities, what educational or experiential investments would you make to accelerate your career growth and achieve your long-term goals?

50/ Share an example of a time when you took a calculated risk in your career. What was the risk, and how did it impact your growth and development?


Happy interviewing :)

- The TCK Team

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