Courageous Career Coaching – Ten Questions Trusted Leaders Aren’t Afraid to Ask

“What would we need to do to keep you here?” If you’re like most leaders, chances are the last (and only) time you’ve asked that question is when one of your valued employees was about to resign. In a last-ditch effort to keep her from walking out the door, you ask the question that you should have asked long before she even started to contemplate leaving your organization.

Leaders are often afraid to engage in career development discussions because they feel unprepared to respond to the employee’s 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.

Last week the Gallup organization reported that 71% of American workers are “not engaged” or “actively disengaged” in their work, and we know that disengaged employees are more likely to leave for other jobs, or worse, “quit and stay” at their current job. Research by The Ken Blanchard Companies has identified job and career growth as one of the 12 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 and senior leadership to influence and improve the environment for growth.

So how is a leader supposed to know what employees want or need in order to be engaged, committed, and grow in their work and career? Here’s a revolutionary idea: Ask them. Regularly.

Career growth discussions should occur on a regular basis, not just once a year when a performance review is conducted (and even then “career planning” is often just a euphemism for next year’s goal setting). Margie Blanchard advocates that leaders engage in “courageous career coaching” with employees and created 10 key questions to facilitate the process (see below)¹. It takes courage to ask and act upon these questions, but when you do, it sends a clear message to employees that you are committed to helping them grow in their jobs and careers.

Have you asked your staff any of these questions? Are there other questions you would add to this list? Leave a comment to share your thoughts and experiences.

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?

¹Adapted from Love ‘Em or Lose ‘Em by Beverly Kaye and Sharon Jordan-Evans

12 Comments on “Courageous Career Coaching – Ten Questions Trusted Leaders Aren’t Afraid to Ask

  1. Randy,

    I like the way you think! In other words, wow! Those are tough, challenging questions to ask your team. Having them, though, would be extremely productive; all would need to be honest, open, and determined to work through the answers.

    We need to be challenged, as do our teams. Thanks!


    • Hi Jon. Thanks for the comments!

      Those are definitely challenging questions to ask, especially if you work in an organization where there isn’t much traditional vertical job growth available. However, I think going through the process is what’s valuable. It helps employees know that we as leaders are committed to helping them grow. I can’t take credit for the 10 questions – those are Margie Blanchard’s creation.

      Take care,


  2. Wow, this is such a good article. The only thought I can add is that you have to make sure that you set a safe climate for employees to answer truthfully, otherwise the exercise is all but useless. TRUST… it has to come before the exercise; and then ask yourself if you’re mature enough to face the answers you might elicit. Truth is, the ones who dare walk this path probably are, the ones who are not need to hear the answers more, but probably never will.

    • Hi Daryl. You make an excellent point that a climate of trust needs to exist for these discussions to really bear fruit. If leaders aren’t genuinely interested in developing their people, I think people will see through the charade when the leader tries to engage in these conversations.

      Best regards,


  3. Leaders/Managers are often afraid to ask tough, direct questions of their followers/employees. I think one reason for that is because they do not know where to begin. Your post and especially the ten questions gives a good framework within it is possible to assist employees to develop not only their career but also themselves.

    • Thanks for the comments Stephan. Engaging in career development conversations can be difficult because as you said, it’s hard to know where to start. It seems as though it’s one of those things where you just have to decide to do it. It may not be the best or “right” way to do it, but at least get a start…and these 10 questions can definitely help.

      Take care,


  4. Pingback: Career Coaching: Courageous Conversations or What? – Lead.Learn.Live.

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  6. That’s a good idea to have someone help you identify what you like and don’t like about your job. It would be a shame to leave a good job just because you don’t like a few things and don’t notice all the good ones. I’ll have to think about having someone help me decide what to do when it comes to changing jobs and how to get a better one.

  7. Hi Randy, I like the way you think!

    I have personally found that asking similar questions has opened up valuable conversations with my team members, helping me understand their aspirations, concerns, and what they need to thrive. It’s an approach that can make a real difference in employee engagement and retention.

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