I’ve been a manager of various size teams since being at Microsoft and really appreciated when my team members would start the good discussions about their careers! I love the hard questions and encourage everyone to add some of these to your toolbox for career development and career discussions. If you have any others that you’ve found very helpful, add them in the comments!
Career Focused
- Why haven’t I been promoted already? (or, alternatively, what are my gaps to the next level?)
- What are my strengths? Areas of improvement? Blind spots?
- Is there room on the team for me to grow 2 levels?
- What’s the most important thing for me to accomplish in the next 6 months?
- What data do you take in to calibrations/promotion discussions and can I participate in providing it? (or, alternatively, How does your manager advocate for their team?)
- Why should I get a mentor?
Feedback
- Was I as good as I could have been?
- Did I perform to my potential?
- What are the top 3 things I should keep doing?
- What are the top 3 things I should stop doing?
- If you had to say something negative, what would that be?
- What feedback have you heard about me from others?
Setting Expectations
- How do you measure success?
- What can I do to make your job easier?
- What values are most important to you? To the team?
- What are your manager’s career aspirations? (or, alternatively, what did your manager do to get into their current position?)
- What is your management style? (or, alternatively, how much status & information does your manager want on a daily/weekly basis?)
- Am I giving my manager & team what they need to be successful?
- What’s your top priority? (or, alternatively, what can I do to help you?)
- What’s the most important things for the team to change in the next 6 months?
Work Life Balance
- Is it necessary to be online nights & weekends to be successful on this team?
- Why are you OK with me working late/weekends? (there are lots of negative effects to this)
- What’s your approach to coaching people who work too much? (or, alternatively, how important is it that the team works only business hours)?
Understanding Broader Context
- What is the team’s top priorities?
- How does my discipline align with the other disciplines on the team? (or, alternatively, What’s the primary value of my discipline on our team?)
- What is your vision of our product/service/technology in 6 months? 2 years?
- How do you determine what’s a good use of time for the team (return on investment)?
- Are we making the best use of our resources? (people, assets, time, etc)
- What’s the most important thing to your boss?
If you found these helpful, let me know! 