Questions to ask if you are on the path to be a super boss:

  1. Do you have a specific vision for your work that energizes you, and that you use to energize and inspire your team?
  2. How often do people leave your team to accept a bigger offer elsewhere? What’s that like when it happens?
  3. Do you push your reports to meet only the formal goals set for the team, or are there other goals that employees sometimes also strive to achieve?
  4. How do you go about questioning your own assumptions about the business? How do you get your team to do the same about their own assumptions?
  5. How do you balance the need to delegate responsibilities to team members with the need to provide hands-on coaching to them? How much time do you usually spend coaching employees?
  6. When promoting employees, do you ever put them into challenging jobs where they potentially might fail? If so, how do you manage the potential risk? And what happens if they do fail?
  7. How much affection or connection do members of your team feel with one another? Do people tend to spend time out of the office socializing? What is the balance of competition and collaboration on the team?
  8. Do you continue to stay in touch with employees who have left to work elsewhere?
  9. Have any former employees of yours gone on to have particularly noteworthy careers, either here or elsewhere? If so, how many? Any examples?
  10. What is the culture like in your team with respect to how much energy you devote to nurturing or developing individuals versus getting the job done?

More questions to Ponder:

  1. Have you answered the “why do we exist” question for your team? Could all of your team members share this answer with me right now?
  2. Do you have people on your team who have followed nontraditional paths to their jobs, or do you find yourself attracted to cookie-cutter backgrounds?
  3. Are people on your team energized to come to work in the morning? How would you even know?
  4. Do you have deep knowledge of the projects each of your subordinates is working on this month? Are you thinking about how you can effectively delegate to team members at the same time as you’re actively coaching them?
  5. What percentage of your time do you spend in formal meetings or working alone in your office? How does that compare to the percentage of time spent in the trenches, working with team members informally?
  6. How often do people leave your team to take a job in another part of your company or in another company? Are they leaving for “good” reasons (i.e., they’re ready to move on to bigger responsibilities) or “bad” reasons (i.e., they’re just not that good or they’re plagued with an inept boss)?
  7. Do you get angry or feel wounded when your people leave?
  8. How often do potential employees reach out to you directly to see if you’re hiring?
  9. Are you inspiring people to believe that they can achieve great things?
  10. Are you removing the bureaucratic barriers and hierarchy that get in the way of meaningful interaction and getting the job done?
  11. How often do you actively teach people how to do something, as opposed to just telling people what to do?
  12. Are you doing all you can to continue helping former employees in their careers? Are you capitalizing on the power of your network, or have you let it become a nonentity?

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