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Letter to Leaders & Swenson Insights

Even More Questions To Ask Your Boss

But communication goes both ways. A manager can’t inherently know what an employee wants. Good managers ask – and good employees proactively manage up by asking what their boss wants.

In April 2008, we wrote about great questions to ask your boss, and it remains the most visited article in the history of this blog.

Here are some more questions, courtesy of Caroline Ceniza-Levine via

  1. How will we gauge my success in three, six or 12 months?

  2. How do you prefer to communicate and how often?

  3. What does my career path look like at this company?

  4. What areas do I need to develop to advance my career?

  5. What’s our top priority?

  6. Let me see if I understand this correctly … am I missing anything?

  7. What are my strengths?

  8. What can I do to help you?

  9. I’m working on X, Y and Z — do you think I can handle this task?

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