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How to guide people in mentorship conversations

We kept seeing the same thing happen. Brilliant experts, execs, and people with incredible wisdom and renowned careers step into a mentorship or advisory conversation… and default to: “Hey, what can I help you with?”

They mean well, but the conversation then drifts across different topics. Advice comes too quickly, without the right context. And when both people hang up the call, they’re left unsure- did any real growth happen, or did they just listen to a few war stories?

Mentoring isn’t the same as being experienced. It’s a skill.

You see it in advisory calls with managers and their new hires. You see it in mentoring programs where seasoned execs aren’t sure what to say. You see it when someone is asked to mentor because they’re a strong performer - but they’re not sure how to guide someone else..

So we created the First-Time Mentorship Guide: Mentor Edition. It’s a practical 10-page resource designed to help new mentors build confidence, structure conversations, and create meaningful impact.

Inside, you’ll learn:

  1. How to prepare before your first meeting (clarifying purpose, expectations, and boundaries)

  2. The right way to use your first conversation to build trust and alignment

  3. Powerful prompts to define goals, accountability, and success

  4. How to set logistics that maintain momentum and trust

  5. How to share your experience without dominating the conversation

  6. What to do (and not do) as a mentor

  7. How to balance holding space for emotion with thoughtful problem-solving

  8. How to encourage independence instead of dependency

  9. How to normalize uncertainty and nonlinear growth

  10. The mindset shift from “advice giver” to “growth facilitator”

  11. Why your aim doesn’t need to be “changing someone’s life.”


If you’re mentoring or advising or supporting first-time mentors inside your organization, I think this resource will help a lot. 

Happy Mentoring!

Ashley