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Questions for Mentees to Ask Mentors

  • Writer: Jeremy Gibbs
    Jeremy Gibbs
  • Aug 4
  • 4 min read
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In last month’s post, we explored some of the best questions for mentors to ask their mentees for productive mentoring sessions. This week, we’ll swap sides and look at questions for mentees to ask their mentors.


We’ve all heard that “experience is the best teacher.” It’s a well known saying, and there’s a lot of truth in it.


However, some of the most valuable lessons I have learned through the years are the ones I didn’t have to experience for myself. Instead, I have been able to glean from the wisdom of others who have gone before me.


Isn’t it so much better to learn from others’ experience on the front end than to learn from your mistakes after you make them? Working with mentors can help you to avoid common pitfalls to make you a better educator and leader.


Education is a helping profession, and as you grow in your career, you’ll likely find yourself on both sides of the mentoring table.


Who is Your Mentor?


As you grow in your profession, you’ll want to keep up with the latest trends and find resources that help you develop. You already know that personal development takes work. However, instead of scouring the internet and poring over articles, you can gain a lot from spending time with the right people.


The higher you rise in your organization, the harder it becomes to find someone who has time and experience to share in formal, recurring mentoring sessions. Instead of looking for just one mentor, learn as much as you can from others who are on the same career path as you. Some may be just a few steps ahead of you, and some may be nearing the end of their careers.


Educators are busy, and agreeing to recurring mentoring sessions may not be feasible. Offer to take them out to lunch and pick their brains. Sometimes just a quick five minute conversation in a hallway can give you a wealth of insights.


You should always have a growth mindset and try to learn new things. Truly, you can learn from anyone if you are willing to put in the time and effort. I get feedback from students all the time. If you’re already established in what you’re doing, there may be someone a few steps behind you that you can still learn something from–a new strategy, a new way of thinking. There may even be someone in another field who can help you navigate your own path in education.


Questions for an Informal Mentoring Session


If you are able to gain an audience with someone you don’t see regularly, get the most out of your time together by asking targeted questions. Have follow up questions ready if you’re really interested in a topic.


Here are a few questions you may want to use in an informal mentoring session to get the ball rolling.


  1. How did you get to where you are?

  2. Where do you find inspiration?

  3. What are some of the biggest challenges you’ve faced, and how did you overcome them?

  4. What gets priority in your own work?

  5. What advice would you give for someone just starting out?



When they reply, be sure to listen carefully. Take note of the important points that will be helpful to you. Don’t talk–you’re not trying to impress your mentor; you’re trying to learn. You’ll find that the time flies by when you’re learning from others, so make every minute count.


Questions for a Formal Mentoring Session


In some situations, you may be lucky enough to have a formal mentorship set up by you or your leader. To get the most out of formal mentoring sessions, be sure to ask the following questions.


1. Can you provide feedback on my progress?


Assuming this is not your first time meeting with your mentor, you’ll want to make sure that all of your sessions together are connected. First, make sure to take action on the steps you talked about in the last mentoring session. Be detailed when you describe what you’ve done.


Next, listen attentively. There’s always a next step, so even if you think you’ve knocked it out of the park, there may be room for improvement. Ask for that next step if your mentor doesn’t offer one.


2. What are some areas that you think I need to work on?


We all typically have a general sense of what our areas of improvement are, but sometimes it takes an outside perspective to point us toward which ones need the most work right now. Getting your mentor to point these out gives a great starting point. What we prioritize may not be the most crucial area of need.


If you feel strong emotion when you receive suggestions for improvement, that means there’s truth in the feedback.

For example, your mentor could say that you need to work on building relationships with others before implementing a new initiative. If you want to automatically disagree and respond that you spend plenty of time with your people–that’s when you need to lean in and pay attention.


3. Can you provide any guidance or resources on navigating a difficult situation?


Very few decisions in education are black and white. The toughest decisions aren’t between what’s right and what’s wrong. The hardest choices come when there are several paths forward and you must decide which path benefits the students, staff, and stakeholders.


Getting an outsider’s perspective, especially from someone who has faced similar situations, can be just what you need to make the best choice for your organization.

As you gain more experience, you’ll have more insight into what principles to prioritize. If you haven’t had experience making decisions in certain situations, a mentor can provide examples and coach you up.


What about you? What are some things you’d like to learn from others who have gone before you?


Let me know in the comments below!



 
 
 

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