University of Wisconsin–Madison

Informal and Formal Career Conversations

Research has proven that career management is the most powerful tool a manager has for driving retention, engagement, productivity, and satisfaction. However, managers continue to back burner this in the workplace due to lack of time and extra administrative work. Please take a few minutes to review some simple yet effective resources you can use immediately with your team.

Something you can consider as you get to know your staff is extending the interview process.  Engage your employees using some of the questions during daily conversations or one on one meetings.

Skills and Strengths

  • What have you always been naturally good at?
  • What can’t you keep yourself from doing?
  • What are you known for?


  • Looking back, what’s always been most important to you in life and in work?
  • What issues or problems do you feel most strongly about?
  • What are your top three values or things you hold most dear?


  • What do you enjoy learning about most?
  • What do you wish you had more time for?
  • How would you spend your time if you didn’t have to work?


  • What kind of work have you typically gravitated away from?
  • What tasks routinely get pushed to the bottom of your to-do lists?
  • What bores you?


  • What aspects of past jobs have you loved most?
  • How do you like to work?
  • What kinds of work settings/ spaces help you do your best work?


  • What lessons do you find yourself learning over and over again?
  • How do your strengths sometimes work against you?
  • What skills do you appreciate in others that you don’t appreciate in yourself?

Download (PDF)

Adapted from the book “Help Them Grow or Watch Them Go, Career Conversations Employees Want” by Beverly Kaye & Julie Winkle Giulioni

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"Trust is not a matter of technique, but of character; we are trusted because of our way of being, not because of our polished exteriors or our expertly crafted communications."

You build and maintain trusting relationships and a culture of trust in your workplace one step at a time through every action you take and every interaction you have with your coworkers and employees. Trust may be fragile, but it has the capacity to grow strong over time.

Marsha Sinetar, corporate psychologist

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