Questions for a Career Development conversation


  • How would you define your career aspirations?

  • What roles would you be interested in having in 10 years? 5 years? 3 years? Next year?

  • Why is it so important for you?

  • What is the meaning for you once you accomplish your career goal?

  • When you achieve your goal, what will you see, hear, feel?

  • What is the definition of a successful career for you?

  • What experiences/knowledge do you need to have? By when?

  • What competencies do you need to have? By when?

  • What would make your work more meaningful to you?


Section I - Experience & Strengths

  • How would you describe your progress in your career thus far?

  • What are the most important skills you’ve learned so far? Why?

  • What have been the most impactful experiences you’ve had so far? Why?

  • What are your unique experiences or capabilities?

  • What do you do really well?

  • What are you recognized or rewarded for most often?

  • Which of your accomplishments are you proudest of?

  • For what do most people come to you for help?

Section II: Interests & Personnel Drives

  • What is your favorite part of your current role? Your least favorite?

  • What have you always loved doing? What job opportunities are you passionate about?

  • What is the one task or type of project you would like to do more frequently in future roles? Less frequently? • What do you value most in terms of your career (e.g., autonomy, work­life balance, management, collaboration, independence, recognition, prestige, diverse nature of work, influence, compensation, interpersonal relationships)?

  • What drives you (are you more creative or concrete in your mindset, outcomes­ or process ­focused, compensation­ or altruistic­ focused, etc.)?

  • What sort of lifestyle would you like to have?

  • What non­work goals and priorities may influence your career decisions? In what ways?​

Section III: Environment / Organization Opportunity

  • Which parts of our business, organization, or industry do you find most interesting? Why?

  • If you weren’t in this role, what other role do you think would be a good fit for you? Why?

  • Who is a key person to helping you achieve your career goals? How will they help you?

  • What are the potential obstacles to achieving your goal?

Section IV: Gap defined

  • What experiences or capabilities do you lack that people on a similar career path have?

  • What do others perceive as your greatest weaknesses?

  • What development gaps do you need to address before you can pursue your career goals?

  • What other experiences do you need to have in order to accomplish your career goals (e.g., experiences in different functions, geographies, industries)?

  • What sort of additional education or certifications do you need in order to reach your career goals?

  • How well do your career goals align with your current development opportunities?


  • What kinds of options exist to address these Career goals?

  • What activities would help you get closer to the achieving these goals?

  • What performance changes will you see in the next six months? Next 1 year?

  • What else could you do? What haven’t you tried yet?

  • Imagine there were no obstacles, constraints or limitations, what could you do to try to move closer to your career goal?

  • Are any of those options feasible to implement?

  • For the options we have identified, what are some of the advantages and disadvantages of each? What are the short­term and long­term implications of each option?

  • I could think of some more ideas on this topic. Do you want to hear them?

  • Will these activities really help achieve the goal we discussed earlier?


  • What do you do now to best position yourself for the next role?

  • What will you do now? Which options will you chose?

  • What is your action plan?

  • Will you achieve your aim with this option?

  • What is your first step?

  • When will you do it (when will you begin)?

  • Which obstacles may you meet on your way?

  • How will you overcome these obstacles?

  • Who should know about it?

  • What help do you need?

  • Where and how will you get this support?

  • Please rate on a scale from 1 to ­10 if you will stick to it.

  • How sure are you that you will really implement this option to achieve the goal?

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