Is it okay to ask personal questions to a potential employer during the interview, like how they came to be in their role?
The purpose of every interview is for you to convince the potential employer that you are the best person for the job – and for you to walk away with that same confidence, as well. Part of feeling like you are the best person for a position is understanding how your background, skills and work ethic would fit into their company’s culture, which is where asking more “personal” questions, like an interviewer’s career trajectory, could be helpful.
That being said, wait to ask any “getting to know you” questions until the end of your interview. Remember, you should be thoroughly researched and prepped on the company prior to the interview, and you want the focus to be on YOU and your qualifications for the majority of the interview. But, when/if you get the opportunity to flip the interview, (we all know the “Do you have any questions for us?” standard interview question,) feel free to ask more “nontraditional, personal” questions, so long as you keep it professional, and always find a way to tie their response back to yourself.
For example, you could ask your interviewer what drew them to the company initially, then follow up with why that also drew you to the company, or why that is also important to you. You could also ask them what they love most about their role, how they feel about the professional development opportunities at the company or what their favorite thing about the company is. The questions you ask say as much about you as your answers to their questions do, and give you another opportunity to show your genuine interest in the role and the company.