Want to be a Great Mentor? Do These 3 Things

The go-to questions that every great mentor should know.

Mentorship is a two-way relationship, taking a lot out of both the mentor and the mentee.  Often times mentors are adjusting their already compounded schedule in order to spend enough time with the mentee, while the mentee opportunity costs, as well as the challenge of discussing personal, subject matter, creates stress.  Like any relationship, it takes time, to understand one another, but as a mentor, there are best practices that can allow you to meet your mentee’s expectations.

Great mentors use questions, not answers

All mentor/mentee relationships have their own vibe. I am lucky to have some terrific mentors who’ve helped me build confidence. I was reflecting on how they’ve shaped our various relationships, and the best of them, those that prompted change, ask questions a lot more than they share advice. In fact, Square co-founder Jim McKelvey is famous for sharing that he is actually skeptical of advice from successful people, because what worked for them then is not necessarily what works for you now. I noticed the great mentors in my life all come back to the same three questions, in their own words.

What’s down the road if you follow this path?

This is a great question because it forces you to articulate your own expectations. The best mentors ask it when you didn’t realize this was the topic–perhaps while discussing a more tactical problem or a frustration. The beauty of this question is that it takes you out of the day-to-day of your career and into a bigger space, the future, where you and your mentor can explore scenarios. Often, the mentor is pretty darn clear on what’s down the road if you follow that path, but the question allows you to play it forward instead of following. You’re learning to lead your own way to deeper insights.

What’s getting in your way?

This question from a respected mentor pushes you, to be honest. A great mentor won’t accept platitudes here like “no time,” or “I just don’t know.” In your answer, there are bound to be issues that are under your control, and those that aren’t. Great mentors use this type of question, or a version of it, to help you make those distinctions. Two good things happen. Ideally, you see more clearly see the issues outside of your control, and stop wasting energy on them. Second, you snap more clearly to the issues that you do leverage some control over.

Who can I introduce you to that might help overcome that?

One of the natural tensions in most mentorship relationships is the relative wealth of social capital on the mentor’s side and the relatively sparse social capital on the mentee’s side, although that’s not always the case. This question is used by great mentors to further empower the mentee while also doing part of the mentor’s expected work of opening up a network.

I’ve learned that mentors who introduce me broadly to their network and mentors who habitually cherry pick the few people they think I need to know are both less powerful than mentors who use this question. Why? It respects my knowledge of their network, it shrinks the pool of people for intros, and it puts the responsibility on me to use the privilege of introduction wisely. The mentor learns a lot about my own understanding of his or her capabilities. As a follow-up, the mentor can always offer a better connection than the one asked for–but by asking, the mentor learns a lot about what the mentee perceives.

Learning from great mentors in your life

Most of us are in mentor and mentee relationships through out our career. When you’re mentoring, think about the questions you’re asking. Are there any other great questions you find great mentors always use? Share them in the comments.


This was originally published Lisa Calhoun’s Inc Column.

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