Unlike in school when we get grades on every assignment and in every course, we get less frequent feedback in professional life, usually once or twice per year, which is also when compensation and level adjustment happens.

The infrequent feedback might be frustrating, since it introduces artificial delays in recognizing and acting on improvement opportunities. Careers management is not so different from product management—fast iterations of small improvements are the proven route towards success.

One-on-one meetings allow a much smaller feedback cycle. You should schedule regular one-on-ones with your direct manager, if not your skip manager as well. However, it is not trivial to run effective one-on-ones. Sometimes they become status updates or are simply skipped over (Pro tip: don’t cancel but reschedule instead). Just like you own your career, you also own the one-on-ones.

Here are some good questions to ask your manager or share your answers with your manager.

What to talk about

In this context, you means the manager and I represents the individual contributor.

Career and Performance

How am I meeting your expectation?

Could you help me understand what the expectations of me are at my current level? What does “Exceeds Expectation” rating mean in the context of our team? From what you have seen in calibration and performance review, what are the set of projects and impacts I should aim for to reach such a rating?

What is my next career goal? Could you help me identify the specific gaps between where I am and my goal? What are the and action items to bridge the gap?

• To grow into a senior/staff engineer or an engineering manager requires different skills and experience. You want your manager to know your aspiration and together devise a plan to achieve it. How can the manager be helpful without knowing what you want?
• Whose job do I want in the future? Do I know what their functions are?

Team and Satisfaction

Am I happy with the projects I am working on?

• Is it too much operation than development? Am I learning new skills? Can I accomplish my tasks?
  • An ideal job/project should mandate a level of expertise of which I satisfy 60%. Anything more will be trivial to solve and not enough growth for me, but anything less will be overwhelming and set me up for failure.
• Are these projects meaningful or impactful?
• I am very excited about the XYZ project that Jane Doe is working on. She would be a great mentor for me and XYZ is a top priority of our team. How can I contribute? Would you be supportive of me to involve in that project for my career development?

Am I happy on this team?

Are my peers capable of delivering results? Do they have a strong personality that makes it hard to work with them sometimes? Do they write awesome reviews on my pull requests, or am I tired of their nit-picking?

Am I happy with my manager?

Do I get the support I need? Does my manager maintain a healthy cross-functional relationship? Do I wish my manager to lean more toward technical leadership or people management?

Am I happy at this company?

Are there certain policies I like or dislike? Do I enjoy the culture? Do I trust senior leadership?

Projects and Processes

• Instead of providing status updates, ask: Do you feel we have a strong tracking process to keep you updated on the project status?
• Are we setting realistic goals? Do you like our quarterly/sprint planning process?