Gotcha

“Palms are sweaty, knees weak, arms are heavy. There’s vomit on his sweater already: Mom’s spaghetti…”

If you were a teen in the early 2000s or if you ever made a playlist for some #gymspiration, you know those are the opening words to Lose Yourself, a song Eminem made about a freestyling rapper who chokes during a high octane rap battle. Though not as intense as a rap battle, job interviews can be super stressful and job seekers can choke and lose their cool in exactly the same way.

While your interviewer isn’t likely to be lobbing disses at you, they’ll almost definitely hit you with the dreaded “Gotcha Question.” Gotcha Questions are questions that seem to have no right answers. Questions that ask you to reveal, explain away, or rationalize some sort of personal vulnerability. Questions that cause people to cough, stutter, clear their throat or intentionally spill water on themselves to NOT ANSWER THEM.

But if you knew a Gotcha Question and prepared an answer before it was asked, is it really a Gotcha Question at all? (See our philosophy minor WAS worth it Mom!). We’ve scoured the internet* and compiled a list of the top 50 hardest gotcha questions likely to be asked during interviews so you won’t ever find yourself choking again.

Questions about weaknesses or failures


Cover Photo
Photo Source: talknerdy2me.org


1) What’s your biggest weakness?
2) Have you ever been fired? If so, why?
3) What’s an instance where you failed?
4) What’s an instance where you did something you are ashamed of?
5) Give me an example of a time when you really wanted something, and you failed to achieve it.

Questions about your career history


Cover Photo
Photo Source: pinterest.com


6) How do you explain the gaps in your resume?
7) Why did you leave your last job?
8) Why were you only at your job for less than a year?
9) Why haven’t you been promoted even though you’ve worked at WXY Inc. for 3 years?
10) Who is the worst manager you ever had and why?
11) What’s the worst job you ever had?
12) What’s your current salary and what do you want to make?
13) What constructive feedback did your last boss give you and what have you done to implement that feedback?
14) If you knew that your last company was going to fail, why didn’t you abandon ship sooner?

Questions about your experiences


Cover Photo
Photo Source: mememaker.net


15) What’s the biggest risk you’ve ever taken?
16) Tell me about a time when you had to convince a group to implement one of your ideas.
17) Can you tell me an example of something you’ve taught yourself and why you wanted to learn it?
18) Describe a time when someone you worked with wasn’t doing their fair share of the work. How did you react?
19) Tell me about a time you had to work with someone whom you didn’t get along with.
20) Tell me about the last time you were frustrated and why?
21) Please give an example of the most difficult political situation that you’ve dealt with on a job.
22) Talk to me about one of your proudest achievements.

Questions specific to the position and the company


Cover Photo
Photo Source: diylol.com


23) What’s your favorite thing about this position?
24) What’s your least favorite thing about this position?
25) Where do you see yourself in five years? How can this position help you get there?
26) If you were the CEO of this company what would be the top two things that you’d change?

Questions about what drives you


Cover Photo
Photo Source: quickmeme.com


27) Are you more motivated by money or by mission?
28) What’s your dream job?
29) When were you most satisfied in your job?
30) How do you define success?
31) Where else are you interviewing?
32) How much of your success can be contributed to luck versus initiative?
33) Do you check your email and voicemail while on vacation?

Hypotheticals and behavioral questions


Cover Photo
Photo Source: quickmeme.com


34) How would you react if I told you to do something a certain way and you found a better way to do it?
35) What would you do if you discovered this company was doing something illegal?
36) Do you think a company needs B performers or is it better off only having A performers?
37) Who do you think has a better perspective on a company’s operations: management or ground level employees?
38) What advice would you give your manager?
39) Explain how the internet works to your 8 year old cousin.
40) Is it more important for a manager to be liked or respected?
41) Tell us a story where the title is “The Purple Coat.”
42) In 30 seconds, list as many uses for a shovel as you can.
43) Teach me something.

Questions testing your level of self-awareness


Cover Photo
Photo Source: mememaker.com


44) How would your former supervisor describe you?
45) If your best friend could describe you using 5 adjectives, what words would they use?
46) How would your worst enemy describe you?

Questions about your personality


Cover Photo
Photo Source: memecenter.com


47) So, tell me about yourself.
48) On a scale of 1 to 10, 1 being smart and 10 being hardworking, what number are you?
49) What are some things you’re passionate about?
50) What do you do on weekends?


Gotcha questions look tough, but deep down really aren’t that bad. Look at each one as an opportunity to reveal a mature and positive understanding of yourself and your career goals to your interviewer. We recommend going through this list before the interview and writing your answers down in as much detail as possible. Then if they come up during an interview, you’ve already thought about your answer and the gotcha question won’t have got you after all.

Want to land some startup interviews ASAP? Check out Planted and apply to top startup jobs in seconds.


*Sources: Forbes, Lifehack, Business Insider, Inc, About, Huffington Post, Monster, Glassdoor, Personal Anecdotes