11 Career Development coaching questions to get comfy with

11 Career Development coaching questions to get comfy with

Effective workplace coaching is focused on asking empowering questions and active listening.

We will explore a few different types of coaching scenarios a leader may encounter in the workplace over the next few HOG blog posts. Today, we'll look at Career Development Coaching, which happens to be my specific area of expertise and one of my favorite topics to coach folks through.  

Why you should care: Providing your team with career development tools is a powerful way to keep them engaged, motivated, and energized.

What follows are 11 core questions every manager* should know when working with a direct report on career development. If you are new to coaching in the workplace, I highly recommend you get familiar with these questions.

*If you are not a manager, but interested in moving into leadership, it's helpful to start using these questions as a self-reflection (or self-coaching) tool, and then transition into using them with direct reports when applicable.

Career Development Coaching Questions to Get You Started

1. "What would you love to get out of this career development session?" 

2. "What is your best-case scenario for your career?"

3. "Why would you like to achieve this?"

4. "What are your biggest challenges or obstacles in achieving this?"

5. "Have you taken any steps toward your career goals on your own yet? Why or why not?"

6. "What have you accomplished in your career so far?"

7. "Out of all your accomplishments, which have you most enjoyed or felt most fulfilled carrying out?"

8. "Is there a way to do more of [this type of work] in your current role?"

9. "How committed are you to working toward your career goals and growth?"

10. "What is working well for you right now at work? What isn't working so well?"

11. "When you think about the version of you who has already achieved your best-case career scenario, how do they think? What do they believe about themselves? What types of action do they take?"

As you move through these questions, give the other person plenty of time to think and respond. Refrain from offering ideas or chiming in; your job is to spend the majority of your time listening.

You may not have time to ask all 11 questions in one session. The goal of workplace coaching isn't to cram as much into a single session as possible, but to help your direct reports reflect, question their stories, explore other perspectives, and take responsibility for their growth and development. It's okay (and normal) for this process to take time. 

Other Career Development Coaching Guidelines
  • While regular 1:1s can certainly touch on career growth and development, there are benefits to scheduling 2-4 sessions per year dedicated solely to Career Development with each direct report
  • Set aside 45-60 minutes for each Career Development session
  • To conclude the session, establish 1-3 small action steps that align with long-term career objective(s)
  • Request your direct report send you a recap of their takeaways & action steps
  • Take your own notes and follow up about the specifics discussed in a timely manner
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