10 questions to ask your boss


Not this kind of boss

Building a rapport with the big cheese is an integral part of success–it never hurts to have friends in high places, and leadership is in the best position to provide performance appraisals and suggest options for career development. Here are ten questions to help on both fronts:


  1. What are two or three important things for me to focus on learning or improving in the next 3 months?
  2. How do you define success for this position?
  3. What can I do to make your job easier?
  4. (If the boss held your position in the past) What did you think was the best part of this position? What was the hardest part?
  5. Do other companies have this position? How do they implement it?
  6. Why do you like working here?
  7. What’s the hardest part about your job?
  8. What is something you know now that you wish you’d known at my age?
  9. What do you do when you want to get completely away from work?
  10. Is there any additional training I can take, or particular topics I could educate myself on?

Demonstrating commitment to the job and a personal interest in your team is a great way to get a leg up, and these questions are an easy start.



2 responses to “10 questions to ask your boss

  1. I love these questions, they are also really helpful to kick off your own development conversations.

    It’s also great to bring some personal thoughts to a development meeting as to your 3 core strengths and opportunity areas and asking for specific advise on how to work through your development plan.

    One of the watch outs I find with people who are starting out and feedback is that they often ask for too much, too often. It’s great to frame up your position with your boss and leadership with questions like this and then set up meeting every other month or quarterly to check in with your manager based on what’s working and what’s not. When you have the chance to connect with senior leadership on an ongoing basis. It’s great to come with some personal development questions and other times use the time to pick their brain about strategy, business questions or larger business context.

  2. Pingback: Reasons you’re not getting promoted | Get a Leg Up

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