Having Effective Mentoring Sessions
The difference between good and great mentoring sessions comes down to preparation, engagement, and follow-through. Learn how to maximize the value from every conversation with your mentor.
Set Clear Session Goals
Every mentoring session should have a purpose. Without clear goals, sessions can meander and leave you wondering what you gained.
Types of Session Goals
Problem-Solving Sessions
"I'm stuck on X and need help finding a solution or approach."
Example: "I'm struggling to negotiate salary at my current company. Help me develop a strategy and practice the conversation."
Learning & Skill Development
"I want to understand X better or develop skill Y."
Example: "Teach me the fundamentals of system design and walk through how you'd approach designing a URL shortener."
Feedback & Review Sessions
"Review my work and provide constructive feedback."
Example: "Review my product portfolio and provide feedback on how to make it more compelling for PM roles at FAANG companies."
Strategic Planning Sessions
"Help me think through a decision or plan for the future."
Example: "I have two job offers. Help me evaluate them and make the right decision for my long-term career goals."
Pro Tip: The One-Goal Rule
For a 60-minute session, focus on ONE primary goal. You can have 2-3 related questions, but if you try to cover too much, you'll get surface-level answers to everything instead of deep insights on what matters most.
Preparation is Everything
The mentees who get the most value are those who prepare thoroughly. Here's your pre-session checklist:
Review Your Last Session Notes
Look back at action items from your previous session. What did you accomplish? What challenges did you face? This creates continuity.
Write Down Specific Questions
Don't come with vague questions. Be specific about what you want to know.
Gather Relevant Materials
If you want feedback on your resume, portfolio, code, or designs, have them ready to share. Send materials to your mentor 24 hours before if possible.
Set Your Environment
Find a quiet space, test your tech (camera, mic, internet), close distracting tabs, and have notebook + pen ready.
Share Your Agenda
Message your mentor before the session with what you want to cover. This lets them prepare and come with relevant stories, resources, or examples.
During the Session: Best Practices
Start Strong
The first few minutes set the tone. Here's how to kick off productively:
- • Quick update: Share relevant progress or context since your last session (2 minutes)
- • State your goal: "Today I'd like to focus on X because Y"
- • Confirm time: "We have 60 minutes - does that still work for you?"
Practice Active Engagement
Listen More Than You Speak
You're paying for their expertise. Aim for 60/40 mentor/mentee talk time. Resist the urge to over-explain or justify.
Ask Clarifying Questions
If you don't understand something, ask immediately. "Can you give me an example of that?" or "How would that work in practice?"
Go Deeper on What Matters
When you hear something valuable, dig deeper. "That's really interesting - can you tell me more about how you approached that?"
Be Vulnerable and Honest
The more honest you are about challenges and uncertainties, the better advice you'll get. Your mentor has faced similar struggles.
Watch the Clock (Kindly)
At the 45-minute mark in a 60-minute session, check: "We have 15 minutes left - is there anything critical we should cover before we wrap up?"
Ask Better Questions
The quality of your questions determines the quality of the session. Here are question frameworks that work:
"How would you approach..."
Gets their process and thinking, not just the answer.
"What would you do differently if..."
Explores trade-offs and alternative perspectives.
"When you were at my stage, how did you..."
Gets relevant, personal stories and lessons.
"What's the one thing I should focus on to..."
Forces prioritization and actionable advice.
"What am I not asking that I should be?"
Uncovers blind spots and things you don't know you don't know.
Warning: Common Pitfalls to Avoid
- • Showing up unprepared and expecting the mentor to lead
- • Spending too much time on context and backstory
- • Arguing with or dismissing advice you asked for
- • Jumping topics without going deep on anything
- • Not taking notes (you'll forget 80% within 24 hours)
Take Notes That Actually Help
Don't try to transcribe everything. Capture what matters:
What to Capture
- ✓ Specific actionable advice
- ✓ Resources, tools, or people mentioned
- ✓ Key insights or "aha" moments
- ✓ Questions to explore further
- ✓ Frameworks or mental models shared
Simple Note Template
• [Insight 1]
• [Insight 2]
□ [Action 1]
□ [Action 2]
• [Book/Article/Tool mentioned]
[What to focus on next]
Pro Tip: The 24-Hour Review
Within 24 hours of your session, review and expand your notes while they're fresh. This simple practice increases retention from 20% to 80%+ and surfaces questions for your next session.
End with Clarity and Next Steps
The last 5-10 minutes are crucial. Use them to solidify what you learned:
Recap Key Takeaways
Summarize the main insights in your own words:
"So if I'm understanding correctly, the three key things I should focus on are: 1) [X], 2) [Y], and 3) [Z]. Does that sound right?"
Commit to Action Items
State what you'll do before next session:
"Before we meet next, I'll [specific action 1] and [specific action 2]. I'll send you an update on my progress."
Express Gratitude
Thank your mentor specifically for what was valuable. "Thank you especially for the insight about [X] - that really shifted my perspective."
Schedule Next Session (If Applicable)
If you're continuing the mentorship, schedule the next session while you're together to ensure continuity.
The Follow-Through That Matters
The real value of mentorship happens between sessions, not during them.
1 Take Action Within 48 Hours
Do at least ONE thing you discussed within 48 hours. This creates momentum and shows your mentor you're serious.
2 Share Progress Updates
Send a brief message when you complete action items or hit milestones. This keeps the relationship alive between sessions and shows respect for their time.
3 Reflect and Adjust
After implementing advice, reflect on what worked and what didn't. This gives you valuable material for your next session.
Example update: "Quick update - I implemented the state management approach you suggested using Zustand. It cleaned up my code significantly, but I'm running into an issue with [X]. Can we discuss in our next session?"
The Compound Effect of Good Mentorship
Mentees who prepare well, engage actively, and follow through consistently see 10x more growth than those who show up unprepared and forget to implement advice. The difference isn't the mentor - it's the mentee's approach.
Related Guides
Booking Your First Session
Find and book the perfect mentor for your needs
Getting Started as a Mentee
Complete guide to starting your mentorship journey
Communicating with Your Mentor
Best practices for messaging and ongoing communication
Providing Feedback & Reviews
Help the community with thoughtful mentor reviews
Want to Get More From Your Sessions?
Our team can help you prepare for sessions, connect you with the right mentors, and provide resources to maximize your mentorship experience.
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