Job Interviews: 5 Stupid Questions
“A job interview is a conversation between two liars.” Claudio Fernández-Aráoz
There are stupid questions. Make a list of 25 common job interview questions. Don’t ask any of them.
5 Stupid Questions for a Job Interview
#1. “What’s your biggest weakness?”
People spin this into a strength like, “I work too hard.” Anyone who says this is hiding something.
#2. “Where do you see yourself in five years?”
Unless you’re a fortune teller, it’s guesswork that invites flattery. If you ask this stupid question, follow up with, “What will you do your first 30-days to move in that direction?”
#3. “Why should we hire you?”
Ask this if you want a sales pitch that obscures reality.
#4. “Why do you want to work here?”
After asking, go for coffee while they answer.
#5. “If you were an animal, what would you be?”
Gimmicks reveal creativity at best. Another stupid question is, “What color best describes your personality?”
The danger of gimmicks is they’re distracting.
Bonus:
“How many golf balls fit in a school bus?”
This is theater unless you sell golf balls. If you want to assess problem solving, ask how they’d handle a backstabber on the team.
2 Smart Questions
#1. “What have you learned from failure?”
Don’t ask about weaknesses. Listen for a growth mindset.
Follow up, “How are you using those lessons?”
#2. What kind of challenges energize you?
Explore what people love to do. Love is energy. When they answer, ask, “What’s energizing about that?”
Power Tips:
#1. Always ask the second question. “So you love helping people, how do you do that? Who have you helped? What was the result for them?”
#2. Go to the store for a jar of pickles. Talk while you shop.
What are your favorite job interview questions?
10 Dynamic Job Interview Questions
Brian Cook recently purchased, The Vagrant. He left this comment.
“I read the Vagrant this weekend. Starts like every other book and then goes in a completely different direction. It’s a great book. I highly recommend.”
Thank you, Brian!






Good morning, Dan, These are great points for both sides of the interview. One of my favorite questions to ask when hiring is, “Tell me about a time when you pulled out all the stops to get a project done on time…” followed up with, “What did you learn about yourself?”… and “What would you do differently next time?”
Thanks, Lisa. In general, real-world questions give better insights than hypothetical.
Amen!
Excellent as always, and timely. Two final candidates for a high-level position coming on site next week, and as a direct report of the role, I’m a tour guide with some one-on-one time.
I wish you success, Thomas. A leader of one of the largest companies in America told me if you get hiring decisions right 50% of the time you’re doing well.
I’ll flip it around. What to ask when you are the applicant.
You’re being considered for a top leadership position—big title, impressive compensation, and plenty of visibility. Proper due diligence means going beyond the polished job description. You need to understand the company’s culture, power dynamics, and the realities that will shape your success.
During the interview process, consider asking these questions:
1. What happened to the last person who held this position?
2. How would you describe the company culture?
3. What rituals are most supported by the company leaders?
4. What’s one tough call I will have to make in my first 60 days?
5. Who are the top stakeholders I must win over early?
6. What’s broken, but no one has dared to fix?
7. Who has the most influence on the senior team?
8. When was the last time someone said no to the CEO—and what happened?
9. How will success in this role be measured?
The answers you hear (and the silences in between) will reveal more about the organization than any formal briefing or glossy report ever could.
Thanks for this Paul. I received an email asking how to stand out during an interview. My first thought was to say, ignore what your mother taught you, “Don’t answer a question with a question.” If you want to stand out, be curious.
I like situational questions. I often use – “Tell me about a conflict that you experienced at work and how you resolved it”
Powerful question, Anthony. Thanks for adding it.
My two favorites are 1. “If your coworkers were asked what it’s like to work with you, what do you think they’d say? And 2. What would your boss say is an area that can use improvement?
Thanks Katie. The second one feels like an opportunity to notice self-awareness and vulnerability.
Use behavioral interviewing and the STAR method. Phrase questions that evoke conversation: “Tell me about a time when…” then listen for Situation, Task, Activity, Result. This method forces a focus on active listening and naturally prompts the interviewer to dig in for clearer answers (ex: “You mentioned doing “x”; what was the outcome of that action?”).
Note that these questions can be tough on candidates. I always start with reassuring them there are no trick questions and that we are assessing them for a proper fit with our organization – and I hope they are assessing us as a good fit for them as well.
With early-in-their-career candidates for foot-in-the-door positions, some of those situational questions styme the conversation. Contrary to the notes above, I’ve found a quirky question helpful during interviews. It lets me know if I’m dealing with a creative person who can think on the fly. Call it a micro-case study – a peak into their problem-solving technique. I’ve selected some of my most impactful employees using quirky questions.
Thank you, Joe. You bring up an important point. Asking how many ping pong balls fit in a school bus can reveal important aspects of a person’s approach and creativity.
One reason I enjoy blogging is the immediate feedback.
I’m glad you expanded the conversation.