Mentorship, like most two-way relationships, is tougher than it looks. Limited meeting time, often limited acquaintance, and limited understanding of each other can put a squeeze on your interactions. For the mentor, it’s not often acknowledged how many risks there are in mentoring. Sure, a feeling failure is one. But also a rein on the mentor’s time, resources and relationships. For the mentee, opportunity costs and highly personal subject matter (their own improvement) make the relationship stressful, too. While there’s a fair amount of material available on how mentees should ask for mentorship and set expectations, what are best practices for great mentors?

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 menthe’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 on FemaleEntrepreneurs on Facebook or Twitter.