Career Coaching: Courageous Conversations or What?

Randy Conley had an excellent post last week titled:  Courageous Career Coaching – Ten Questions Trusted Leaders Aren’t Afraid to Ask.   You’ve likely seen the research on the current state of employee engagement – ugly.  (See my earlier L.L.L. post for more.)  Randy’s firm has identified that “job/career growth is one of the critical factors that create engaged and passionate employees, and it’s important for leaders to know that employees believe it’s the primary responsibility of their direct manager…”  Randy suggests the quickest way to figure out what employees want and need to be engaged and achieve career growth – is to ASK THEM.  And do so regularly – – not only during Annual Review season or when your employee has one foot out the door. 

Yet Randy explains, and he’s right…that many of us are “often afraid to engage in career development discussions because we feel unprepared to respond to the employees’ desires, or even worse, powerless to do anything about it due to organizational constraints. Yet in order to establish a high level of trust with those you lead, it’s critical your employees know you’re genuinely interested in, and committed to, their career growth.”

Randy Conley’s 10 Courageous Career Coaching Questions

  1. Why do you stay?
  2. What might lure you away?
  3. What did you like about your prior job (where you stayed several years)? What kept you there?
  4. Are you being ____ (challenged, recognized, trained, given feedback) enough for now?
  5. What would make your life here easier?
  6. Are things as you expected they would be?
  7. What do you want to be doing 5 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 a day off?

I can’t imagine rattling off these questions before you’ve built a relationship of trust or you’ll be climbing The Wall of Wary.  Yet what’s Plan B?  Do we roll the dice and hope it all somehow works out for the best –  or do we dive into the deep end and have a courageous conversation. (Yes, rhetorical question).   Imagine for a moment that you are on the receiving end of these questions from your current boss.  Your reaction?  He/she cares. 

Next steps?  Let’s go…

Source: Image: Photobucket


  1. Hi David. I’m honored that you would reference my post and continue the discussion about this important topic. You are right when you say that it takes a high level trust to engage in these discussions, but even if the level of trust isn’t at the level you’d like, what’s the alternative? Sometimes you just have to jump into the deep end of the pool and start swimming!


  2. I wish my bosses would have asked me these questions. The only issue I would foresee is that the employee needs to have the security that their answers won’t effect their career. I know that in my past job my bosses were uncomfortable with my answers when a couple of these questions were asked.


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