Career Coaching Questions to Ask Yourself

• Posted on November 11, 2014
• by Lisa Sperow
• in Career Planning
• No Comments.

Are you trying to choose a new career?

In order to make a meaningful change, you can’t just go the “quickie” route and pick a new career out of a hat.

If you’re going to do it, do it right.

If you’d like to have someone help you go through the discovery process of finding the right work for you, career coaching may be an option to think about. Career coaches can ask you questions that will help you thoughtfully consider both your current situation as well as define your “ideal” situation.

But if you’re not ready to visit (pay!) a career coach, see if you can get a friend to help you. We’ll give you a list of 25 top career coaching questions that you can use for some DIY career coaching! In choosing the friend to help you, pick someone who will be patient, who will avoid the urge to “counsel” you, and who can just be there to guide you and let you talk through your answers. There’s value in actually vocalizing your thoughts, so.. don’t try to cheat and do this by yourself in your head! Grab a friend, go somewhere you can talk, and present your friend with this list. Your friend can pick and choose from the list, going in any order.

1. What do you love to do?

2. What comes easily / naturally for you?

3. When are you most proud of yourself?

4. What kinds of activities did you enjoy as a child?

5. As a kid, what did you want to be when you grew up? Why did you change your mind?

6. What dreams have you given up on? How does that make you feel?

7. What are the three accomplishments that you are most proud of in your life?

8. If the issue of money was off the table, what would you like to do?

9. What do other people tell you you’re good at?

10. Who or what do you think is holding you back now?

11. What does your ideal life look like? Think in terms of your friends, your work, and your relationships.

12. Do you have a vision for your ideal life?

13. What’s bugging you now? What can you do about it?

14. If nothing changes in your life, what will that feel like?

15. What would the advantages of changing your life be?

16. What would the disadvantages of changing your life be?

17. What are the advantages of NOT changing?

18. What one thing could you do this week that would move you closer to your goals? Will you commit to doing it? What would stop you from doing it?

19. What would you need to change in order to attain your goals?

20. What obstacles could stand in the way of achieving your goals?

21. Who are your biggest supporters? Who are the people who would help you to achieve your dreams and hold you accountable to them?

22. Who are your biggest nay-sayers? What will they say about your dreams? How will you stand up to them?

23. What do you wish you had accomplished by now?

24. What’s the biggest obstacle you’ve ever had to overcome in your life?

25. If you could change anything in your life, where would you start?

If you take the time to answer these questions – really answer them — your wheels should be spinning with possibilities! Best of luck with your DIY coaching efforts!

LEGEND Talent Management works with mid-career professionals who are looking to make a career change. Our Pathway Planner assessment tool can help identify career options that are a natural fit for your abilities, personality, and interests. This online assessment can be completed from home in 60-90 minutes. Please contact us at info@LEGENDTalentManagement.com for more information.