A Two Step Conversation that Helps Your Boss Help You Get Ahead


unlock your potential by actively seeking feedback

Step one:

Ask your boss to talk about her aspirations for your department or team.

Provide focus. Don’t extend the conversation into the distant future. You might say, “I’m thinking about the big picture for the next year.” 

  1. Listen to understand. Let her speak 80% of the time.
  2. Don’t judge.
  3. Accept.
  4. Restate her ideas to be sure you’re on the same page.

Step two:

Ask your boss to talk about her aspirations for you. The context is within her organizational aspirations.

This approach feels awkward to many bosses. They may fall back on generic answers like, “I want you to enjoy work.”

Practice humble inquiry. 

  1. Thank her for her response.
  2. Explain that everyone benefits from an outside perspective.
  3. Restate the organizational aspirations she explained in step one.
  4. Provide a specific context. “I’m wondering about your aspirations for me as a team leader?”
  5. Press for more. “I’d like to hear what you think. I was wondering if you might have specific aspirations for me.”

Try one of these conversation starters.

  1. “What do you see in me that’s holding me back?” Explore the aspiration behind the concern. Seek feedback. Don’t wait to receive it. 
  2. “How might I make new contributions to our organization?” Listen for specific behaviors.
  3. “What are your aspirations for my leadership?
  4. “What are my greatest opportunities, from your point of view?”


  1. Turn negatives to positives. Your boss might explain something to stop. Look for something to try.
  2. Your boss may need time to think about this.
  3. Let your boss know that her viewpoint matters to you.
  4. Listen openly. Reject defensiveness.
  5. Don’t pressure her to make commitments to you.

Help your boss help you by seeing yourself through her eyes.

How might you help your boss help you?