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