The 40 best questions to ask a mentor about career development

When navigating your career, it can be tough to go it alone. So many questions and concerns pop up. Often you don't know what the right decision is. That's where having a mentor can come in handy. Having someone who is a little further along in their career can be the best way to find encouragement, support, and advice when you need it. While there are several types of mentorships, such as peer mentoring, group mentorship, and even flash mentorship, in this article we’ll be focusing on the traditional, one-on-one mentoring relationship and the questions to ask your mentor about career development.

In this article, we’ll also discuss:

• How can a mentorship relationship improve career success?

• What qualities should you look for in a mentor? 

• What do you talk about in a mentor meeting?

• The 40 best questions to ask your mentor

How can a mentorship relationship improve career success?

Mentorships are professional relationships that are most often created in a workplace environment. The point of a mentorship is to help the “mentee” develop their network, enhance skills, and set them up for success. It’s also a great opportunity for a less experienced worker to learn from someone with a few more years under his or her belt and receive the needed support and encouragement for success.

Mentorship also leads to greater employee retention. A study by Randstad showed that their mentoring program meant that employees were 49% less likely to leave the company, which means less job-hopping and potential more upward mobility within a company.

What qualities should you look for in a mentor?

A mentor isn’t someone that you put on a career pedestal or admire from afar. It should be someone who plays an active role in fostering your career, so it’s important to choose wisely. While everyone’s needs are different, as are every mentor, there are a few key commonalities that make up a great mentor.

1. They communicate effectively

It may seem obvious, but working with someone who is a good communicator is key to a successful relationship. A mentor should also be a good listener and be able to answer questions, provide advice and support, and guide their mentees towards having the confidence to make independent decisions and find appropriate solutions to problems.

2. They can “walk the walk”

A mentor may look good on paper, but if they don’t have the knowledge and expertise to provide relevant advice and support, they won’t be of much help. A potential mentor should be a few steps ahead of you, career-wise, or have experience in the field you’re interested in pursuing. Basically, they need to have “been there, done that”.

3. Provide guidance rather than directions

Sometimes, it feels like it would be easier to have someone just tell you what to do. But that’s taking the easy way out and you won’t learn for yourself if you’re not an active partner in your career. Instead, a good mentor points you in the right direction, asks you pertinent questions, and shares their experiences, but lets their mentee take ownership of their decisions.

4. They can be honest and open in their feedback

A good mentor is not there to coddle you. They must be willing to provide frank feedback in a way that is supportive, kind, and constrictive, and give you that "kick in the pants" when you need it. This will help you develop the confidence you need to make good decisions and move forward in your career.

5. They hold themselves accountable

You don’t want to work with someone who thinks they’re above reproach. Good mentors hold themselves accountable when they make mistakes and learn from them and that means apologizing and making things right. They don't ask anything of their mentees that they wouldn't do themselves. They accept responsibility instead of brushing it off onto others.

What do you talk about in a mentor meeting?

First of all, a “mentor meeting” is a scheduled session with your mentor in which you’ll discuss various aspects of your career, set professional development goals, and decide what actionable steps you can take next. You’ll also most likely go over what you discussed in the last meeting and what your outcomes were. Your mentor will provide guidance and advice about any challenges you may have recently faced, and reflect on the progress you have made.

The 40 best questions to ask your mentor about career development

Every mentor is different and will want to talk about different things based on their knowledge and experience. Having a slate of questions prepared for your sessions will help you make the most of your time together. Since your mentor's job is to guide you, rather than tell you what to do, focus more on open-ended questions rather than closed-ended. Closed-ended questions can generally be answered with another one-word answer, like "yes" or "no", while open-ended questions require more detail and prompt more discussion. 

Here are X great questions you can ask your mentor during your meetings:

Informal questions to ask your mentor

1. How are you doing?

2. Is there anything going on that you’re excited about?

3. What’s new with you?

4. How do you keep your motivation up?

5. Do you have any new goals?

6. Is there anything exciting in your personal life that you feel comfortable sharing?

Questions about why they became a mentor

1. What motivated you to become a mentor?

2. What are you hoping to get out of our mentoring relationship?

3. How frequently should we meet?

4. What’s the best way to get in touch with you?

5. How should I prepare for our meetings? 

6. How do you like to structure your meetings?

Questions about your mentor’s career path and advancement

1. How did you decide to become a [name of position or field]?

2. What was your career path?

3. What challenge did you have to overcome in [name of position]?

4. What are the top skills you had to develop?

5. What networking advice do you have? Are there specific organizations I should get involved with?

6. Do you find achieving a work/life balance to be a challenge?

Questions regarding your mentor’s professional experience

1. What do you like best about your job? What do you find most meaningful in your work?

2. What life skills have you developed to support your career? What skills do you advise that I learn?

3. If you could give your younger self one piece of advice, what would it be?

4. What are the biggest obstacles you’ve faced in your career and what did you learn from them? 

5. Did you always want to work in [name of field]?

Questions about specific situations you’re facing

1. How can I best discuss a promotion with my boss?

2. X happened to me recently. Here’s what I did, but how would you have handled this situation?

3. I’ve been offered a new job. Do you think I should accept it?

4. I’m making much less than my peers who have the same level of experience. How do I ask for a raise?

5. I feel like I'm stagnating at work right now and I’d like to learn some additional skills. How do you think I should go about doing this?

6. How can I handle a conflict with a co-worker?

Questions about your professional growth

1. In what areas can I improve?

2. What are the main skills you think I need to develop?

3. Are there any professional development courses I should look into?

4. How do I maintain a positive attitude in my career?

5. Here’s a challenge I faced recently. What could I have done differently to improve the result?

6. Are there any good books or websites you know of that would help me improve [skillset]?

Questions about making a career change

1. I’m wondering if I should change careers. How do you know it’s the right time?

2. How do I land a job that is more suited to my interests and personality?

3. Will making a career change hurt me professionally? 

4. I’m feeling a little lost. How have you found value and purpose in your career?

5. I know I need to be more proactive in my career. What’s the best way to do that?

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Key takeaways

1. Mentorships are professional relationships that are most often created in a workplace environment and help the “mentee” develop their network, learn new skills, and set them up for success. 

2. An effective mentor is a good communicator, takes ownership of their mistakes, offers expert guidance and feedback, and is willing to listen.

3. A “mentor meeting” is a scheduled session (usually once a month) with your mentor in which you’ll discuss various aspects of your career, set professional development goals, and decide what actionable steps you can take next.