Rights granted through http://morguefile.comThis past week I enjoyed co-facilitating Blanchard’s new Servant Leadership Immersion program (which I co-authored) with Ken & Margie Blanchard in Rancho Bernardo, CA.

Margie, the director of Blanchard’s Office of the Future, is always working on cool projects that increase leader effectiveness. I first reported on Margie’s courageous career questions a year ago in this post. Margie has updated the questions to make the career conversation even more effective.

Connect Before You Communicate

That’s the advice Ken offered Servant Leadership Immersion participants. It is a core mantra of Ken’s: your effectiveness in influencing others is directly proportional to the degree of connectedness created between you, the leader, and your followers. Margie believes that courageous career coaching is a conversation that well-connected leaders have with each direct report annually.

Courageous Career Questions, Version 2.0

The updated questions below can help the leader learn the follower’s motivations, aspirations, and frustrations in the workplace. The leader guides this honest conversation, explaining that he/she wants to learn more about how the direct report is feeling about their career so far. The leader makes no promises to “fix every problem” or “grant every wish” – the conversation is about the leader connecting to their direct reports’ perceptions and goals. The updated questions are:

  1. Why do you stay?
  2. What might lure you away?
  3. What did you like about a prior job (one where you stayed several years)? What kept you there?
  4. Are you being (pick one or two: challenged, recognized, trained, given feedback) enough for now?
  5. What would make your life easier here?
  6. Are things as you had expected they would be?
  7. What do you want to be doing five years from now?
  8. What would we need to do to keep you here?
  9. What is most energizing about your work?
  10. What about your job makes you want to take the day off?

Think about how valuable the information gathered in this discussion is for both the leader and the follower! You learn what the follower wants more of: challenging goals and tasks, more recognition, more feedback more often. You learn your direct report’s expectations. You learn about gaps that you might be able to address quickly and easily.

Great bosses proactively ask about such gaps and do everything they can to address them, quickly. They reduce frustrating procedures and requirements where they are able. They increase the frequency of direct reports’ enjoying the things that are most energizing about their work. Great bosses work hard daily to provide an attractive, inspiring work environment for the talented staff on their team. If the work environment is not inspiring, talent will move on to more gratifying opportunities.

Ken’s Career Questions for Me

Ken and I were sitting in the back of the room while Margie facilitated this activity in our program. I enjoyed fifteen minutes of discussion with our remarkable Chief Spiritual Officer. Ken wanted to learn from me why I’d stayed with Blanchard for over 17 years. It was marvelous to help Ken see that the company that he and Margie created offers me the chance to:

  • Learn from colleagues who are some of the smartest, kindest in the industry
  • Engage with clients who are serious about making their organizations better places to work
  • Develop books, articles, tools, and programs that help share my unique experience with high performance, values aligned cultures

What five courageous career coaching questions would you love your boss to ask YOU? What are the best career coaching questions your mentor(s) have asked you in the past? Join in the conversation in the comments section below.

S. Chris Edmonds

Chris helps leaders create purposeful, positive, productive work cultures. He's a speaker, author, and executive consultant. He blogs, podcasts, and video casts. He is the author of two Amazon bestsellers: Good Comes First (2021) and The Culture Engine (2014).
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