Probably need to review these questions every quarter.

The Current Gig

  • What are your strengths? How do you know that?

  • What do you need to work on? How do you know that? How are you working on this area? Is your company helping?

  • How long have you been at the current company?

  • How long have you been in the current role?

  • When was your last promotion of role? How was this communicated to you? What is the one thing you believe you did to earn this promotion?

  • When was your last compensation increase? (Compensation = Base salary, bonus, and/or stock)

  • Do you feel fairly compensated? If not, why? If not, what would you consider fair compensation? What facts do you base that opinion on? Have you told this to your manager?

  • When was the last time you received feedback from your manager?

  • What compliment do you wish you could receive about your work?

  • Are you learning from your manager? What was the last significant thing you learned from them?

  • What was the last thing you built at work that you enjoyed?

  • What was your last major failure at work? What’d you learn?

  • What was the last piece of feedback you received (from anyone) that substantively changed your working style?

  • Who is your mentor? When was the last time you met with them?

  • When was the last 360? What was your biggest lesson? (A 360 is a process where a neutral party gathers feedback from all the humans in your working sphere. Your managers, your peers, and if you’re a manager, your direct reports. I try to do a 360 every three years because the synthesized feedback is always revealing.)

The Next Gig

  • When did you last change jobs? Why?

  • When did you last change companies? Why?

  • What aspect of your current job would you bring with you to a future gig?

  • What is your dream job? (Role, company, etc.)

  • What is a company you admire? What attributes do you admire?

  • Who is a leader that you admire? What are the qualities of that leader that you admire?