39 Smart Questions to Ask a Mentor, According to Experts

Mentorship is more than having someone to go to for advice. It also "provides the necessary support system that empowers women to navigate career challenges and seize opportunities,” says Miriam Groom, founder and CEO of the career consultancy Mindful Career.

According to McKinsey & Company's 2023 Women in the Workplace Report, for every 100 men that were promoted from entry level to management, only 87 women were promoted—and that number is even lower for women of color (73, down from 82 in 2022). Mentorship is one way to change that statistic and elevate more women into positions of leadership.

Working with a mentor can be powerful, but you’ll only get out of the relationship what you put into it—and that means preparing for your meetings and coming armed with the right questions. What preparations do you need to make, and what questions do you need to ask, in order to get the most out of your mentor relationships?

How to prepare for a mentor meeting

If you want to lay the foundation for a successful mentor/mentee relationship, it’s important to show up to your first meeting prepared. What exactly does that look like?

Do your research

You don’t want to wing it during your first mentor meeting. You want to show your mentor that you understand their background and experience—and how that background and experience relate to your mentorship relationship.

That means doing some research.

Before your first mentor meeting, make sure to research your mentor. What are their biggest accomplishments? What kind of career path have they followed? How have they made an impact in their industry? What are they passionate about?

Once you have an understanding of your mentor’s professional experience, the next step to prepare for this meeting is “matching your skills and interests with the mentor’s expertise,” Groom says.

For example, let’s say that after doing your research, you learn that your mentor serves on the board of a local charity. In that situation, you might come to the meeting prepared to share about your own volunteer work—and ask questions about how your mentor was able to successfully grow their career while actively giving back to the community—something you’re also passionate about.

Bottom line? Doing your research shows your mentor that a) you’re serious about working with them and b) you understand why and how their specific experience would be beneficial—and that you chose them for a reason.

Set goals

If you want to get the most out of your mentorship experience, you need to know what, exactly, you’re trying to get out of it—and that means setting some goals.

“Come up with some clear, achievable goals you hope to accomplish,” says corporate consultant and coach Kym Medina. That way, you can clearly communicate what you’re hoping to get out of the mentorship—and make sure that you’re both on the same page.

In addition to setting goals, you’ll also want to share any background information that could impact your ability to hit those goals—like strengths, potential areas for growth, and any challenges you’re currently facing. The more information your mentor has about you, the better they’re able to mentor you—and help you develop a plan to make your career goals into a reality.

Prepare thoughtful questions

What you get out of your mentor meeting will, in large part, come down to what questions you ask—so make sure to prepare your questions well before your meeting.

“The best thing you can do to prep for mentor meetings is come up with some interesting questions to ask the mentor,” Medina says.

“Being proactive and preparing questions for mentors is vital,” Groom says. “It signifies commitment and readiness to learn, allowing for a focused and productive exchange that benefits both the mentor and the mentee.”

What questions should you ask? “When conceiving questions, it's always a good idea to frame a good amount of them around your mentor's experiences,” Medina says. For example, instead of asking, “What do you think I should do to get promoted into management?,” ask them a question that directly relates to them and their experience, like, “How did you make the jump from individual contributor to managing a larger team?”

Another best practice is to get specific with your questions.

For example, instead of asking, “How do you balance your work life and your personal life?” which feels very generic and broad, go for something more specific and tailored to a situation you’ve dealt with/are dealing with, like, “Have you ever been in a position where you had to choose between hitting a deadline or dealing with a family issue—and, if so, how did you make the decision?” 

Be ready to act on advice

Preparing the right questions is important, but it’s also important to be ready to not only listen to, but act on, your mentor’s answers. 

While you’re certainly not required to act on every piece of advice your mentor gives you (especially if it doesn’t feel resonant with your goals and direction), one of the main points of mentorship is to get guidance and direction—and if you don’t take any guidance or direction, your mentor could get frustrated.

As such, make sure to “approach the mentorship with an open mind and readiness to act on the advice given,” Groom says.

Should women seek out female mentors?

One question many people have about mentorship is, as a woman, is it better to seek out a female mentor?

The answer is: It can be.

“While mentorship is valuable regardless of the mentor's gender, female mentors can offer unique perspectives and understandings of the challenges faced by women in the workplace,” Groom says—for example, dealing with gender-based discrimination or balancing a career and a growing family.

Working with a female mentor can be helpful, but being female alone isn’t enough. In order to get the most out of mentorship, you need to choose the right mentor—for example, a woman that has conquered similar career goals (and has the time, energy, and desire for mentorship).

Must-ask questions for your mentor

As mentioned, preparing questions before your first mentor meeting is a must, but what should you ask?

Let’s take a look at key questions to ask a mentor:

Questions on the mentor/mentee relationship

• Why did you decide to become a mentor?

• What do you enjoy about being a mentor?

• What is your preferred method of communication? (Text, email, etc.)

• What are your expectations around meeting frequency and length? (Or, in other words, how often are you willing to meet—and for how long?)

• Are there any boundaries that I need to know about in order to maintain a respectful relationship? (For example, no texting on the weekends.)

• How would you like me to prepare for our meetings?

Questions on career growth

• What were some of the most pivotal decisions you’ve made in your career—and how did they impact your career trajectory?

• What are some of the biggest challenges you’ve faced on your career path—and how did you overcome them?

• If you could talk to yourself as you were starting your career path, what would you say to her?

• How did you know when you were ready to grow into a new role—and how did you communicate that to your higher-ups?

• Was there ever a time when you felt “stuck” in your career? If so, how did you overcome it?

Questions on leadership

• What are some strengths or skills that have made you an effective leader?

• What are some challenges you’ve had in learning how to lead effectively?

• What do you do outside of work that allows you to be a better leader at work?

• What do you do in your free time to strengthen your leadership skills?

• What’s your leadership style—and how did you develop it?

• What do you think are the most important elements of being a good leader?

• What do you think are the most effective ways to communicate with direct reports?

• What are your tips for delivering challenging feedback?

• As a leader, how do you make your employees feel seen, heard, and respected?

Questions on working with others

• In your opinion, what’s the best way to deal with a co-worker who has a negative attitude?

• What skills do you think are essential in being able to effectively work and collaborate with others?

• What do you do when someone tries to take credit for your work?

• In your opinion, what’s the best way to deal with a manager who doesn’t recognize your accomplishments?

Questions to ask a female mentor

• As a woman in leadership, how do you handle gender bias or discrimination?

• As a successful woman, what challenges have you faced in the workplace—and how did you overcome them?

• As women, how can we uplift other women in the workplace—and help them get the pay and recognition they deserve?

• What’s the best way to deal with sexist coworkers?

Questions on pay

• In your opinion, what’s the best way to navigate conversations about compensation?

• Have you ever been in a situation where you realized you were being paid less than you deserved? If so, how did you handle the situation?

• In your opinion, what should you do if you’re offered a job you’re really excited about—but the compensation is less than you’d hoped for?

• What are your top tips for negotiating a higher salary/compensation package?

Questions on work-life balance

• What have been your greatest successes in creating a sense of work-life balance?

• What have been some of your greatest challenges?

• How do you prioritize work responsibilities vs. personal responsibilities—and what do you do if/when those responsibilities both need your attention?

• How do you maintain a sense of balance when things are hectic at work?

Questions on skills development

• What skills do you think are critical for advancing in this field?

• How did you develop the skills needed to succeed in your role?

• There’s a role I want to apply for, but I’m missing some of the core skills. How can I show leadership that I have what it takes to learn those skills quickly?