Deep questions to ask in a work/professional situation

This may seem a little off subject from my normal posts, but I think relationships are ESSENTIAL to our growth and expansion. While surface level conversations are fine, I always feel like I get the most benefit out of a conversation where I really get to know the truth of who a person is. I often find that the more open and vulnerable I am willing to be, the more that is reciprocated. I try to be as open as I can with my clients about anything I am struggling with, what got me through tough times, and anything else I might be dealing with. I often find that the relationships that are built because of this mutual openness are some of the most fulfilling and supportive relationships I have. I end up learning just as much (or more!) from them as they do from me!

Where this can get tricky are situations that are assumed to be more professional upfront. I do think it is possible to get to know a person on a deeper level in ANY situation but I find that in certain settings, it's important to be more tactful about what we're asking and how.

A good starting point is to ask questions about life outside of work to find some common ground or interests to build upon. Here are some ideas for questions to ask to facilitate getting to know someone in a professional setting:

1. What is the most impactful lesson you have learned in your career thus far?

2. What is your favorite part of what you get to do (and why)?

3. What has been the most trying time in your career and what did you do to get through it?

4. What is the most important people skill or relationship building skill that you value most in the people you deal with in your work?

5. What do you think my biggest strengths are?

6. What do you think my biggest weaknesses are?

7. What are some of your biggest goals? What is your next step?

8. What brings the most fulfillment to your life?

And of course these questions can be modified to facilitate relationship building or deepening in non-professional settings as well. I'd love to hear ideas for further thoughts or probing questions!