5 Questions for Mentors to Ask Mentees
- Jeremy Gibbs
- Jul 7
- 5 min read

Have you paired up your new staff with a solid mentor yet? Get the most out of your mentor/mentee relationships by using the questions provided in this post.
Once, at the beginning of a new school year, my principal handed me a printout and said, “I’m pairing you up with the new teacher down the hall. You’ll be her mentor this year.”
Me?
I’d only been teaching for a few years, and I was relatively new to the school myself. I mumbled that I’d be glad to help, but I had no idea where to even start mentoring a brand new teacher. All I knew to do was to share what I had been doing in my own classroom. So I did–and the sessions became more about me than about my mentee.
I learned quickly that my new mentee and I had two totally different teaching styles. Even though I tried to share some of my valuable experience, my mentee didn’t even know what she didn’t know–she wanted to blaze her own trail and learn from her own mistakes.
I wound up doing a few drop-ins with her during her planning period, but our sessions could have been so much better if I had known the right questions to ask. I would have been better able to provide what she needed to be more successful in her first year.
Has this ever happened to you? If not, it could–whenever you are doing a good job in your role, your leader would likely love for you to rub off on someone a little further behind where you are.
The problem is that while leaders may require mentorships, they often fail to schedule times to meet or to set protocols for discussion. This leaves many mentor/mentee relationships foundering.
When you mentor others, you can be prepared to have better results by having a handful of questions ready to guide you through a mentoring meeting. Ask these five questions to get the most out of your mentoring sessions.
Question 1
What’s one thing that you’re proud of?
Some teachers begin their lessons with a morning meeting or a quick “Tell me something good” to start the class off with a positive spin. You can use this strategy in your mentoring sessions, too. What is something that your mentee is doing right?
It’s a good idea to start off any mentoring session with a discussion of your mentee’s wins. Mentoring sessions usually result in constructive criticism. Criticism is always uncomfortable, even for people who crave feedback.
The timeline is important here. You should be talking about something that has happened in the recent past. Get your mentee to talk about something that’s fresh, and be sure to give plenty of praise. Remember, even small wins are wins.
Question 2
What do you hope to achieve, and what steps are you currently taking to achieve those goals?
The purpose of any mentoring session should be to see systematized improvement over time, and the only way to measure that improvement is to clearly define goals and action steps.
When you ask this question, you could refer to big, overarching goals, or you can drill down into specific strategies the mentee is currently using.
Too often, newer educators (and even experienced ones!) get bogged down in the details. They have deadlines and paperwork, and they never quite get around to setting goals. Ironically, even though they may put in lots of hours, busyness without a clear goal is wasted effort.
If your mentee has trouble articulating exactly what needs to be achieved and which step to take next, help them to set SMART goals. SMART goals are specific, measurable, achievable, relevant, and time-bound. Check out my post about SMART goals here.
Question 3
What challenges are you currently facing?
Everyone, from the most scattered, brand-new educator to the war-hardened veteran, is facing some sort of challenge. Encourage your mentee to open up about what is bothering him or her, and together you can find ways to overcome that challenge.
When you talk about challenges, your mentee is vulnerable. Actively listen when your mentee speaks, and be sensitive to any emotions that are revealed. If you have faced a similar situation, you can offer your story. However, make sure to make it all about meeting your mentee’s needs rather than just telling your old war stories.
A follow up question could be, what are you doing right now to overcome that challenge? Ideally, as a mentor, you will encourage your mentee to come up with his or her own solution to guarantee buy-in. It’s also a good idea to follow up with your mentee in the next session to see how that challenge was resolved, or if it is ongoing.
Question 4
How do you assess student learning, and how do you adjust what you’re doing based on that assessment?
This is the goal of education in a nutshell.
Teachers know all about formative and summative assessment, but inexperienced teachers may not always have those assessments in place, or they may not adjust their instruction based on assessment.
Remind teachers about ways to assess students informally. If they are not currently using them, suggest that they poll the class by using exit tickets, bell ringers, or just a show of hands. The worst thing for new teachers is to administer the test at the end of the unit only to find out everyone failed. Talk to your mentee about beginning with the end in mind when developing lessons.
Asking about assessing student learning is good for school and district leaders, as well. The end result of everyone’s contribution in a school or district should be for students to learn and be prepared for their next step. How do principals, coordinators and directors, and superintendents assess student learning and adjust what they do based on their assessment?
Question 5
What do you need from me?
The more times you ask this question, the more comfortable your mentee will be opening up and asking for help. Make sure that you add value to your mentee each time you meet.
Your mentee may not know what he or she needs, so be prepared to offer something to them that you think would be helpful. You can offer to let them observe you in action, demonstrate a lesson or technique in their classroom, or share a resource that you use.
I like to close sessions with this question, but as your relationship develops, your mentee may ask for your help at other times. Make time to be available for your mentee. The more you develop people, the more your influence grows. The results will be exponential over time.
Remember, as a mentor, your primary goal is to support and guide your mentee towards success. Encourage open and honest communication, active listening, and constructive feedback to ensure that your mentoring sessions are productive and beneficial for both you and your mentee.
Be sure to take good notes in your mentoring sessions so that you can measure progress over time. At the end of the school year, you can review your notes with your mentee and show them how far they’ve come. You’ll both be pleased at the progress.
Serving as a mentor is also a good way to demonstrate leadership and to gain valuable experience working with adults and coaching. It is up to you to ask the right questions and to make sure your mentoring sessions are beneficial to everyone involved.
Remember that you don’t have to wait to be formally asked to serve as a mentor to others. Always seek out opportunities to share what you’ve learned and to add value to people.
What about you? What are some ways that you can really show up as a mentor?
Let me know in the comments below!






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