The first few months of mentoring are exciting - you're building rapport, sharing insights, and making progress. But around 6-9 months in, many relationships hit a plateau. Conversations feel routine. You're not sure what to talk about anymore. Meetings start to slip.

This is normal, and it's actually an opportunity to take your mentoring to the next level.

This 30-minute session is designed for mentors and mentees who are past the "getting to know you" phase and ready to deepen their impact.

What you'll learn:

✅ What separates good mentoring from great – deeper trust, powerful questions, and structured agendas that drive real progress

✅ How to expand your mentoring portfolio – building multiple mentoring relationships and experimenting with reverse, peer, and group mentoring

✅ How to sustain excellence over time – adjusting cadence, managing natural ebbs and flows, and evolving or closing with grace

Great mentoring doesn't happen by accident. It happens when you intentionally evolve the relationship as you grow.

Unlocking the next level of mentoring: From good to great

Examples of Level 3 questions 

Identity and purpose:

• "What's becoming clearer to you about the kind of leader you want to be?"
• "When you look back on this chapter of your career five years from now, what would make you feel like it mattered?"
• "If you stripped away all the external markers of success—titles, salary, recognition—what would you still want to be doing?"
• "What do you want to be known for in your field?"
• "Who are you becoming through this work, and is that who you want to be?"

Challenging assumptions:

• "What assumption are you ready to challenge about yourself or your career?"
• "What would you do if you knew you couldn't fail?"
• "What's the story you're telling yourself about this situation, and what if that story isn't true?"
• "What belief is holding you back right now that used to serve you but doesn't anymore?"
• "If you weren't afraid of judgment, what would you try?"

Deeper self-awareness:

• "What are you avoiding by staying busy?"
• "When do you feel most like yourself at work—and what does that tell you?"
• "What feedback do you keep getting that you're not ready to hear yet?"
• "What's the gap between how you see yourself and how others experience you?"
• "What do you need to stop doing to make room for what really matters?"

Future vision and growth:

• "If your future self could give you one piece of advice right now, what would they say?"
• "What would need to be true for you to feel genuinely fulfilled in your career?"
• "What's the next version of you trying to emerge, and what's in the way?"
• "What would you do if you had permission to disappoint people?"
• "What conversation are you not having that you need to have?

How to use Level 3 questions

For Mentors:

• Ask one per meeting 
• Give space for silence after asking
• Let your mentee sit with discomfort
• Circle back to it in future meetings

For Mentees:

• If a question makes you uncomfortable, that's often the one to sit with
• Journal on it after the meeting
• Bring your answer back to your next session
• It's okay to say "I don't know" and think about it