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Advanced Psychological Interview Questions

Samuel Dunlap · September 2026


Most interview questions test whether a person can describe their experience. These questions test whether a person can see themselves clearly, hold discomfort, and tell the truth when it's hard.

1.

Imagine that you have $10 million in your bank account, you have your dream partner, you’re famous, have lots of great friends, and you can do anything you want. What would you do with your life?

Assessing the alignment of deep desire over surface motivations with the role.

2.

Imagine that I hire you and we work together for some time. What will have made that time a success for you, what will we have created together, and how will you know when it’s time to leave?

Assessing the quality of vision they bring to the role.

3.

What about this job will cause you to fail? And what are the skills that you don’t currently have that you’ll need to be effective at this role?

Assessing skill gaps and the groundedness of their self-assessment.

4.

What about this job will cause you to lose motivation and engagement with this work?

Assessing tenacity and alignment of interest.

5.

What was the hardest thing you’ve ever had to do?

Assessing tenacity and character.

6.

What is the hardest problem that you solved?

Assessing ingenuity and imagination.

7.

What is the most complex thing that you’ve created using AI and how did you make it?

Assessing technical skills.

8.

Describe the most intimate or connected moment that you’ve experienced with a collaborator.

Assessing relational capacity and maturity.

9.

What’s the worst way that you betray people in your life?

Assessing character and integrity — and their relationship to the question itself.

10.

What’s the worst way that you lie to people in your life?

Assessing character and integrity — and their relationship to the question itself.

Questions I Ask Myself Across All Questions in the Conversation

  1. Do I like this person and are they easy to talk to?
  2. Is this person sincere and authentic?
  3. Does this person hold kindness strongly?
  4. Does this person have humility?
  5. Does this person have demonstrated capability distinct from AI capability?
  6. Do they ask high-quality questions?