Out of the many questions we could ask in an interview, three keep coming back to me.
What is the biggest accomplishment of your life? How do you learn, and how do you teach? What is the good, the bad, and the ugly about you?
I am interested in them because they can open a conversation about the person behind the resume.
What is your biggest accomplishment?
I rarely hear leaders ask this in such an open way. It leaves room for the candidate to explain what they value, what was difficult, and why a result matters to them.
The follow-up is where it gets interesting: what did you contribute, what did you learn, and what would you do differently?
I would keep the conversation relevant and let the person choose what they are comfortable sharing. The point is curiosity, not an invitation to demand private information.
How do you learn, and how do you teach?
Learning tells me something about how a person handles unfamiliar work. Teaching adds another dimension: can they turn what they know into something another person can use?
I want examples rather than a label. What do you do when you get stuck? How do you check that you understand? What changes when the person you are helping learns differently from you?
Those questions can reveal a working style that a list of skills misses.
What is the good, the bad, and the ugly?
This is the unusual one. I like it because it asks for a fuller picture than a rehearsed strength and a carefully disguised weakness.
It only works if the interviewer makes honesty useful. If every admission becomes a trap, the conversation will immediately return to polished answers.
I would ask for a work-related example, what the person does to manage that pattern, and what support helps them do their best work.
Leave room for the follow-up
These questions do not replace role-specific evaluation or evidence that someone can do the job. They are a way to make the conversation more revealing and human.
The value is in listening to the answer and following it somewhere useful.
Which question has taught you the most about a person in an interview?