14 Best Questions to Ask a Mentor

Don’t shy away from potentially sensitive topics such as leadership and failures.

Written by Lisa Bertagnoli
14 Best Questions to Ask a Mentor
Image: Shutterstock
Brennan Whitfield | Oct 19, 2023

A mentor can provide valuable feedback and advice that you may not be able to get anywhere else. That’s why asking them important questions — even difficult ones about finances, failures and other tender topics — can be critical to your career development.

“The biggest opportunities for growth will usually be the ones that entail the most discomfort,” Greg Aponte, head of data science and investments at real-estate tech company Orchard, told Built In. “Rather than being discouraged by discomfort, view it as a sign that you’re doing it right.”

Top Questions to Ask a Mentor

  • What do you still struggle with?
  • How can I be a leader?
  • How hard was it for you to grow your company and be successful?
  • How and when should I reach out to you?

While you might think asking a mentor sensitive questions is disrespectful, embarrassing or downright cringey, the responses they elicit can be essential to professional growth, making them worth the initial discomfort. 

In this article, several seasoned mentors reveal the questions they’re eager to answer, and explain why more people should be asking them.


Questions About Career Development and Advancement

1. What Soft Skills Should I Develop?

Acquiring and improving soft skills — such as communicating credibly, having productive conflict and holding yourself and others accountable — takes work. Soft skills become more critical as a professional rises through the management ranks, and often do double duty as work and personal life tools, so it’s important to ask mentors about them.

That said, early career professionals might not know to ask mentors about soft skills. Most of Aponte’s mentees, for instance, focus on the hard skills they need to have a successful business, but this can be detrimental to overall career growth.

“[Hard skills are] only part of professional success,” Aponte said. “People would be much better served focusing on the behaviors and attitudes they need to demonstrate in order to be successful.”  


2. How Can I Be a Leader?

Talking about leadership with a mentor can help mentees prepare to take initiative.

“I really wish more mentees would ask me how to become a leader,” Ari Kryzek, co-founder and chief creative officer of Chykalophia, told Built In. Over five years, Krzyzek has mentored almost 50 people, many of them women aged 30 to 45 in the midst of a career change. Not once has she been asked about leadership.

She understands the hesitancy. “When I got my first mentor I wasn’t even thinking about leading,” she said. Her mentor encouraged her to get involved in groups and establish herself as a leader, but the prospect “almost felt like a burden,” Kryzek said. 


3. What Should I Not Do?

Mentees should be making thoughtful decisions about what not to do, said Andy Crestodina, mentor at startup lab 1871 and founder of web design and development agency Orbit Media Studios.

Successful people have the time to do what they need to do because they’ve abandoned low-value activity. They are focused because they’ve removed distractions. They capture opportunities because they choose their battles, Crestodina said. 

“Conversations with mentees typically focus on their desire to do the right things,” he told Built In. That’s good, he noted, but it’s equally important for young tech professionals to know what not to do. The question seems counterintuitive, he said, “because once you have an eye on the prize, you look for ways to get there.” 

If they’d ask this question, Crestodina would tell them that they should be honest about what they’ll never be great at, then design a life that does not include that task and lets them focus on the things they are great at.


4. How Can I Stand Out As a Remote/Hybrid Employee?

This question is key because sustaining innovation, collaboration and culture becomes increasingly difficult as companies implement remote and hybrid workplace policies, said Frank Weishaupt, CEO of Owl Labs.

It might not get asked because remote and hybrid work is, for some people, still unexplored territory, Weishaupt told Built In. Weishaupt mentors former employees and colleagues and also mentors through peer groups. He adds related questions to the main one: How to make the right impression and navigate a company as a remote-only hire, and how to encourage innovative ideas among teams that interact virtually. 

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Questions About Their Professional Experience

5. What Professional Experiences Led You to Your Current Position? 

If your mentor is currently in a position that you would also like to reach, it’s worth asking how exactly they got there. This question allows mentees to delve into the details of what roles, responsibilities and projects their mentor has taken on, and gives a wider view of a mentor’s career milestones. 

Knowing a mentor’s professional journey doesn’t mean it has to be identically followed, but it can provide some career guidance for mentees and help them chart what experiences would be best for them to take on to get to a similar place. 


6. What Is One Thing You Wish You Had Known When You Were in My Current Career Stage? 

Asking for what mentors wish they had been told in your position can help get mentees ahead of the curve in their current career stage. This information lets mentees tap into professional knowledge that may not be learned until much later, like specific tips that can be applied in the industry or resources that can help improve certain skills.

If your mentor is in a position that is several steps higher than your own, such as a manager, director or CEO, this question can also shed light on their perspective of what they expect from employees in your current position and what avenues would be best for advancement.

Additionally, even if a mentor doesn’t share the same career field, this question can still benefit mentees on a general, professional level if the answer is in regard to soft skills, networking or navigating a long-term career


7. What Career Accomplishments Are You Most Proud Of? 

This question gives mentors the opportunity to share the highlights of their professional career. A mentor’s accomplishments like significant projects, promotions or challenges that were overcome could be brought up by asking this, which can give mentees possible ideas for what to strive for in their own career. Plus, letting mentors take the spotlight can help mentees understand them better and strengthen the mentoring relationship.

RelatedCoaching and Mentoring: What’s the Difference?


Questions About Their Personal Experience 

8. What Have You Learned From Failure?

Failure in life and business is a given. Focusing only on success can skew reality. If you’re curious about your mentor’s failures, first ask permission to ask about them, then ask. 

“Knowing how your mentor has navigated failures is valuable, for background and for mentees who will inevitably face challenges of their own,” Eric Tang, co-founder of Livepeer, told Built In.


9. What Do You Still Struggle With?

Asking about struggles invites a constructive conversation and helps mentees grow by realizing they’re not alone in mistakes, said John Matlosz, CEO and founder of Epic Software Development.

Matlosz suggests developing a strong rapport with a mentor, which will make it easier to broach the tough questions, including the one about struggles.

“It’s important to admit mistakes and tackle them as a team,” he told Built In. “I try to lead by example by offering up challenges I’ve had in the past and how I worked with my colleagues to overcome them.”

RelatedHow Reverse Mentoring Achieves Employer Goals


10. Who Else Can I Talk To and Learn From? 

Mentoring also has a helpful model to follow: The more, the merrier. 

Kirsten Newbold-Knipp, CMO at FullStory, advises mentees to create their own personal boards of directors — a community of mentors who can help think through a variety of problems.

“The idea of the mentor of old, the person who says ‘I’m going to take you under my wing and I’m going to bring you along with me in my career and you’re going to learn all of the 27 things that you need to know to be successful’ is outdated and limiting,” Newbold-Knipp told Built In. 

Still, it’s tough for a protege to ask a mentor for more mentoring sources because the implication is that the mentor isn’t helping adequately. “It’s getting both more important and easier as corporate America really starts to understand the value of a diversity of opinions and viewpoints,” Newbold-Knipp said.


11. How and When Should I Reach Out to You?

Mentors are more than happy to hear this question because it signals interest from the mentee and because it gives mentors something to look forward to.

If mentees don’t set the tone for consistent communication, “the relationship begins to fall apart because the mentor gets the impression that the mentee is not invested in the relationship or does not appreciate the connection,” Desa Burton, who has mentored throughout her career as a senior officer in the U.S. Navy, a law professor and executive director of Zip Code Wilmington, told Built In. 

No One is Talking to the Mentees by Victoria Black. | Video: TEDx Talks


Questions About Growing a Company

12. What Would You Need to See to Invest in My Company?

Julie Novack wants mentees to ask her what she thinks of their business model, or key metrics used to run a business, or how to tell if a business is working.

“If you don’t know the answers to those questions, you will not be able to raise funding,” Novack, who mentors through groups such as Women Tech Founders and Women’s Wisdom, told Built In.

She loves to look critically at the business and pressure test it, just as a potential investor would. It’s the best use of her time and expertise. She asks mentees if their addressable market is big enough, who the competition is, what the moat is, what the network effect is, and other topics likely to surface in a pitch meeting. “Those meaty business questions are the best questions to have,” Novack said. “And you don’t have to worry about looking bad in front of me because I’m not a potential investor.”


13. How Hard Was It For You to Grow Your Company and Be Successful?

Mentees should be aware of how hard success is, especially in the tech business, so they are ready for the journey and prepared to put in the work, said Yoni Mazor, chief growth officer and co-founder at Getida.

When mentees ask this question, mentors can share stories of overcoming challenges and hardships that entrepreneurs face, Mazor told Built In.

“Such a learning experience can be very useful to get people on the correct mindset and stamina for long-term success.”


14. How Do I Create a Sustainable Company?

With rapid growth, culture can erode unless leaders plan intentional steps to preserve the elements that drove success, explained Sasha Siddhartha, the co-founder and CTO of Thrive Market, and who has mentored engineers for nearly two decades. 

Seldom, if ever, do entrepreneurs ask about creating a healthy, sustainable company and technology culture. “As leaders, especially in technology,” Siddhartha told Built In, “we need to think ahead to handle scale and success.”

Rose Velazquez contributed reporting to this story.

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