30 Questions to Ask a Professional About Their Career

The best career conversations go beyond job titles. Use these questions to understand what a career is really like, how people get in and whether it fits you. Pick five to eight that matter most to you.

What the work is really like

• What does an ordinary week look like for you?
• What part of your job takes more time than people expect?
• What do you enjoy most, and what do you find hardest?
• Who do you work with every day?
• What skills do you use most often?
• How has the job changed since you started?

How you got in

• How did you get your first break?
• What was your first job in this field?
• Which experiences mattered most in getting hired?
• What would you do differently if you were starting today?
• Which training or credentials actually mattered?
• Is there a common path in, or many?

Whether it fits me

• What kind of person does well in this field?
• What kind of person struggles?
• Based on what I have shared, where might I fit?
• Which related roles should I also look at?
• What would make you advise someone not to choose this career?
• How do people balance this work with the rest of their lives?

Getting ready

• What should I learn or build in the next three months?
• What would make my resume or portfolio stand out?
• Which mistakes do beginners usually make?
• How can I get experience before my first role?
• What do interviewers in this field look for?
• Which communities, events or resources are worth my time?

Looking ahead

• Where is this field heading in the next five years?
• Which roles are growing, and which are shrinking?
• How do careers usually grow from here?
• What do you wish more people knew about your work?
• Who else should I talk to?
• What is one thing I should do this week?

Ready to ask these questions? Request a session with a vetted professional, or take the free career direction assessment to find the right kind of conversation.