To this day, I can still remember my very first meeting with my very first mentor. At the time, as a young associate starting out in Big Accounting, I didn’t even really know what a mentor was, what they represent for anyone’s career, and most importantly, what the heck to discuss with them. We went to a newly Starbucks on Newbury street, ordered espressos and started staring at each other, literally. She was a prominent Senior Manager in the Audit group, I was a young associate right out of college, with zero professional experience, looking to make my mark. Yet when she asked me how she could help me, I nervously took a sip of my double shot White Chocolate Mocha espresso, and said nothing…Needless to say, that was probably the shortest mentoring session ever (and the most embarrassing one at that…)

A great mentor, if you are fortunate enough to have one, is one of the most important relationships in your career. Mentors are not just role models, they can become confidantes, guides, and friends. Some mentors have pushed their mentees to success, guided them towards their path and remained a great presence in their lives and careers. Yet as you start out in a new mentoring relationship, what do you ask your new mentor? How do you even begin to put your career in perspective enough to actually ask smart, outstanding questions to get the most out of these crucial career relationships? Do you start on a personal note, or keep it strictly professional? Do you trust them enough to reveal your career plans, or do you fish for information first?

Fast forward a few years, a few unsuccessful mentoring relationships and lots of double-shot White Chocolate mochas in crowded Starbucks coffee shops, I’ve gathered some of my best (and most humbling) lessons about what to ask your new mentor:

1. Where and how do you spend the most important part of your time?

Get information about your mentor, learn to know who they are, professionally as well as in their personal lives.

2. What professional groups and organizations are you a part of and would you recommend?

Your mentor will be the key to many many networking opportunities. Learn where they network, and you will learn how to increase your influence.

3. What career advice would you give someone like myself?

Pick their brain. Hindsight being 20/20, you would greatly benefit from their perspective on your exact career station at the moment.

4. How did you get to this point in your career?

Chances are your new mentor had a non-conventional career path. Or that they bulldozed through their own path to get to where they are. Ask them how they got here, what they did, and wish they could undo.

5. Who would you recommend I connect with?

Your network is your net worth. Take advantage of your mentor’s vast network to gain insights into who else you should connect with.

6. What were your biggest weaknesses and/or failures, and how did you overcome them?

Failures are the biggest career boosts, learn from others who’ve overcome them and turned theirs into successes.

7. How can I help you?

Last but not least, surprise your new mentor with a question they’re probably not expecting. Ask them what you can do for them!

What other questions would you have for your new mentor?

The Corporate Sis.