Mentoring can be one of the most rewarding parts of your career—or one of those “well, we tried” moments if you show up unprepared. The good news? A little intention and structure go a long way. With just a bit of prep, mentor sessions can become more meaningful, productive, and actually fun for both sides. In this third and final post in our mentorship series, learn how both mentors and mentees can show up authentically and make the most out of every conversation.
If you haven’t already, be sure to read the other two posts in this series, Mentoring 101: Everything You Need to Know to Get Started and 6 Powerful Types of Mentorship to Advance Your Career.
Mentoring is one of the most powerful tools for career development, yet many of us walk into these conversations unprepared, unsure, or overly reliant on “winging it.”
Whether you’re the mentor or the mentee, there’s so much more to it than just showing up. Done well, mentoring is a structured space for reflection, realignment and growth.
Through my Mentor Minutes sessions, I’ve seen firsthand how a little bit of planning goes a long way. So today I’m pulling back the curtain on what makes mentor sessions work – for both sides! Whether you’re mentoring someone new in their role or navigating your own next step, this post is for you.
Let’s get into it!
For Mentees: Show up with Cohesion
Mentoring works best when you do a little prep beforehand. Think of it like going to a personal trainer. You could technically just show up and see what happens, but if you come in knowing what muscle group you want to strengthen, you’ll walk out feeling so much more aligned with your goals.
Here’s how to make the most of your time with your mentor:
- Come with a focus. Is there a challenge you’re stuck on? Perhaps it’s a skill you want to build or a decision you’re trying to make. Give your mentor a compass so they can steer the conversation in a helpful direction. You don’t need to have it all figured out; just give yourself time to identify what’s top of mind.
- Reflect on what’s changed since last time. As the saying goes, growth isn’t always linear, and that’s just fine. You can still track your progress. Before your session, jot down a few things you’ve learned since your last conversation. What worked? What didn’t? What surprised you? This builds momentum and shows your mentor you’re engaged and intentional.
- Be honest about the messy middle. Mentoring is not about impressing someone. It’s about sharing your real struggles so you can create change. Talk about the things that aren’t going well. Be specific. This is where the best learning happens for both the mentee and mentor.
- Take notes and follow up. You don’t have to leave your session with a 10-step plan, but try to walk away with a few next steps or key takeaways. Then, follow through! This creates progress and keeps the relationship active.
For Mentors: Lead with Curiosity
During mentoring, it can be tempting to cut to, “Here’s what I’d do.” This is more aligned with the role of a consultant. After all, your mentee is drawn to your experience. However, the most impactful mentors don’t just give answers. They also ask great questions.
Like coaches, mentors should listen deeply. They hold space for the other person to come to their own conclusions, even when it’s tempting to shortcut the process, because they know holding this space for the mentee to think big will bring the best value.
“The delicate balance of mentoring someone is not creating them in your own image, but giving them the opportunity to create themselves.” — Steven Spielberg
Some tips to elevate your mentoring game:
- Start by asking, “What would feel most useful to focus on today?” This question sets the tone for a collaborative conversation and prevents you from projecting your own assumptions about what a mentee should care about.
- Ask, don’t assume. If a mentee says, “I’m stuck,” resist the urge to jump in with solutions. Ask questions like, “What have you tried so far?” or “What’s the real tension here for you?” The more curious you are, the more empowering the session will be.
- Offer your perspective with humility. When you do share personal advice, frame it as “what’s worked for me” rather than “what you should do.” The difference might seem small, but it demonstrates respect toward your mentee and keeps the conversation grounded.
- Invite accountability without pressure. At the end of a session, ask: “What feels like a good next step for you?” Let them own it. Then, remember to circle back to those actions next time. A gentle follow-up can be powerful encouragement and help mentees feel seen and heard.
How to Structure a Mentor Session
Whether you’re meeting monthly, quarterly, or ad-hoc, a bit of structure helps keep your conversation productive without being rigid.
Here’s a simple, repeatable format you can use to stay on track:
1. Check in (5-10 mins)
Start with a personal check-in. The question, “How are you, really?” builds depth and care in the relationship, showing that you’re genuinely there to listen.
2. Review Progress (10-15 mins)
Look back at what’s happened since the last meeting. Celebrate wins. Talk through lessons learned.
3. Current challenges or goals (20-30 mins)
Dive into one or two focus areas. Be specific, and stay solution-oriented.
4. Identify actions (10-15 mins)
What will you do between now and the next session? What support might you need? Write it down together.
5. Wrap-up (5 mins)
Ask: “What was most helpful from today?” or “What should we carry forward into next time?”
This rhythm helps conversations stay grounded in real-time progress while building toward longer-term growth.
Want a Head Start? Download My Free Agenda and Goal Templates
To make your mentorship journey even easier, download the free templates below to use for your mentor sessions. These worksheets can help you identify what matters, track your progress, and structure the conversation with intention. They’re simple, flexible, and easy to use before or during a session.
Download the Mentoring Agenda and Goal Setting Templates here.
Whether you fill them out or just use them as a guide for prep, these tools can give you a solid place to start and return to over time.
Mentoring is a Two-Way Street
Whatever side of the table you’re on, mentoring is most rewarding when both parties come open-hearted and prepared. Don’t strive for perfection; strive for intentionality. It will help build a relationship rooted in respect, growth, trust and clarity.
If you’re a mentee, give yourself permission to ask for what you need. And if you’re a mentor, remember that you don’t have to have all the answers. Trust that your presence, questions and stories are more than enough.
And of course, if you are interested in Mentor Minutes sessions with me, please get in touch!
With just a little structure and a whole lot of honesty, mentoring can become one of the most transformative parts of your career journey!
I hope these tips, tools, and templates help you walk into your next session with more clarity, confidence, and connection.
Thanks for reading! xx
