1. Share a recent success story

Why this matters: Talking about a success story helps demonstrate a person's strengths and skills (while sometimes revealing some weaknesses). This can be a jumping off point for discussions around growth areas. "It sounds like you have strong leadership skills, but that you need support with time management. Let's talk about how to work on that…"

2. Tell me about a time you failed spectacularly—and what you learned from the experience

Why this matters: First, failure is a part of life. What we learn from the experience and how we evolve is what matters. Second, this sort of discussion can help build trust between the mentor and mentee. Trust is an essential ingredient to a successful mentoring relationship.

3. Share a current challenge

Why this matters: Digging deep into challenges can provide a solid agenda for what you hope to accomplish in your mentoring relationship. "My biggest challenges include public speaking, team management, and knowing which battles to fight with upper management. I'd like to tackle these areas over the next nine months and get your thoughts on how you've navigated similar situations."

4. Tell me about a business book you recently read and the effect it had on you

Why this matters: The most successful people in business and in life are curious, and one way they satisfy their curiosity is by reading—a lot. If the mentee is not a big reader, then the mentor can provide the mentee with a reading list. If the mentee is a reader, then an occasional book discussion/book swap can be a good agenda item for a future meeting.

5. Tell me where you'd like to be professionally in three years—and how you plan to get there

Why this matters: Just as mentoring activity #1 can provide structure to your mentoring relationship, the answer to this question can also provide a roadmap on the areas the mentoree needs to address and work on.

Source: https://www.management-mentors.com

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