7 Thought-Provoking Questions to Ask Your Mentee

Are you a new mentor? Congratulations! Not only are you embarking on a relationship that will help someone else grow in her career, but this also represents a huge milestone in your own career, too. After all, someone is seeking out your guidance — which means you’re a person people look up to for support and advice as a successful professional. In other words, you've made it.

While others regard you as a role model, starting off the mentor-mentee relationship can be nerve-wracking. Your mentee should generally be responsible for setting the agenda and asking questions, but that doesn’t mean you shouldn’t take any responsibility for the structure and content of your time together. This more junior professional is looking to you for guidance, after all. To that end, here are seven important questions to ask a mentee to make your sessions more productive.

7 questions to ask a mentee

1. What are your short-term goals?

First things first: You need to know what your mentee hopes to accomplish in the near future. Why did she seek out your support in the first place? What does she hope to do soon — say within the next few months or year? This will help you set the agenda and help you both make the best use of your time together. 

2. What are your long-term goals?

It’s also important to understand where your mentee hopes to be in the next, say, five to 10 years. Your advice will be very different for someone who hopes to move up the ranks at her current place of work than it will be for someone who wants to branch out and start her own business, after all. 

Moreover, many industries are continually evolving and changing. Some goals may no longer be applicable in the next few years, so knowing your mentee’s long-term aspirations can allow you both to work on alternative paths and steps in case her original plan is no longer feasible down the road.

3. What’s working in your career?

This question multifold. You want to know:

• What she’s doing to make strides in her career

• What circumstances are going well for her (say she just got praise for project or received a promotion)

• Her innate and learned skills and talents

This can give you a sense of her current motivation and ambition, as well as her confidence. If your mentee were to say that nothing is going well, for example, you would know that you need to work on developing strategies for boosting her self-esteem and outlook on her career. 

4. What’s not working?

Understanding the challenges your mentee is facing is also important for your work together. Perhaps they’re self-imposed, in which case you’ll need to develop strategies for overcoming them together. Or maybe other people or circumstances are getting in the way of her success. If that’s the case, then part of your guidance should cover methods of getting around roadblocks and dealing with work struggles head-on. 

5. What ideas have you developed to help you overcome challenges and meet your goals?

You’re not there to solve problems for your mentee. Rather, you’re someone who can offer advice and support for overcoming them. That means she needs to put in the work, too. She should have come up with some ideas for dealing with the obstacles standing in her way. If she’s just spinning in circles and hasn’t taken the time to work on solutions, it could be a sign that she’s helpless or lazy — in which case, you have deeper issues that you need to address. 

Of course, if she has already come up with some ideas, you can assess their feasibility and work on a plan together, as well as develop new thoughts. 

6. What areas do you feel comfortable addressing on your own and what areas require more support?

You could very well start off your first mentoring session thinking your mentee wants one thing out of the relationship and find that she already has that under control and really needs help with something else entirely. It’s important to establish which areas require further guidance and which ones she feels comfortable handling independently. After all, time is precious, and you don’t want to waste it on helping her with something she doesn’t need. 

7. How can I help you achieve your goals?

This is really the most important question, and it goes hand in hand with #6. Your mentee’s response will define the entire course of your mentoring relationship. 

It’s okay if your mentee doesn’t have an exact picture of how you’ll help her achieve her goals. Still, she should have some thoughts on it. There should be some key areas she wants to address, and she should have taken the time to consider what you can work on together and how you can do it. Moreover, she must be realistic in her expectations. For example, you can’t get her that raise she’s coveting, but you might be able offer suggestions about negotiating effectively. Is her self-esteem holding her back in her career? You’re not going to heap praise on her (although some words of encouragement will probably help some), but you can give her some strategies on coping with setbacks and being more confident at work. 

The mentoring relationship can be a powerful thing for both the mentee and the mentor, but you both need to work on building it together. Of course, your mentee will need to put in plenty of hard work toward the end goal of, well, achieving her professional goals. But she may very well look to you to set the tone for your meetings.

These questions can help you kick off the relationship on the right foot, giving you both a starting point. You’ll learn about your mentee and what she wants out of both your time together and her career in general and allow you to set a clear agenda. This will ultimately lead to more trust and a stronger bond between you. 

What advice do you have to provoke career-development thinking in your mentee? Share your experience and perspective in the comments to help other Fairygodboss members.