75+ Great Questions to Ask Your Mentor (The Ultimate List)

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Did you find a great mentor, but you don’t know what to ask them?

Here are some good questions you might want to consider:

Hannah Gentile

Hannah Gentile

Entrepreneur | Mindset Coach

“What was the process you used to find your ‘why’?”

This tells you a lot about how your mentor approaches meaning and purpose. You could take something from their process.

“Have you seen other processes of finding your ‘why’ you found interesting?”

Just because a technique doesn’t work for your mentor, doesn’t mean it won’t work for you. Good mentors will have collected tips from others which they will be able to share with you. It is like having a group of mentors!

“What values drive you?”

It is handy to know you have some cross-over or similarity in driving factors. It is also nice to have differences. Differences allow you to reflect on the strengths and limitations of your own values, and ways to balance that out.

“How do you approach risks?”

A personal favorite. You probably don’t want someone who is overly cavalier helping you out! But neither do you want someone so adverse to risk that you can never take action. Approach to me is a fascinating insight into how someone calculates, mitigates, and acts upon, risk.

“Do you have a goal-setting process you believe in?”

Not everyone likes the idea of goals. Have a think about whether you want a mentor who can suggest a solid structure for your goals, or whether you want to be introduced to a different approach entirely.

“What has been your biggest failure / what did you learn from it?”

There is no hiding from the fact that we learn more from failure than success (although success is an important learning tool too). Many an amazing Phoenix has been born from the most heartbreaking of ashes. You don’t want your mentor learning from your failure…so find out where they’ve gone before you and how you can avoid the same mistakes.

“What has been your biggest challenge? How did you approach it?”

To be honest, the challenge is less important than the approach. Most challenges can be faced in similar ways – to find out what process your mentor has for tackling those tough times.

“What has been the most valuable lesson you’ve learned?”

Another favorite. Every person you meet knows something you don’t. Your job is to find out what that thing is. Your mentor has hopefully built up a treasure trove of these little nuggets. Start digging.

“What is one thing you wish you would have done, that you didn’t?”

A survey of people close to death found that one of the biggest regrets people had, was not what they’d done…but what they had missed out on doing. The risks they did not take, the paths they did not go down.
What is something your mentor wished they had taken up? How can you make this relevant to you?

“What is something you thought was important but has turned out not to be?”

All too often we get caught in a rabbit hole of the one thing you must do to make millions. Or to be a success at ‘this’ or ‘that’. You can avoid all that time and energy but finding out what your Mentor spent unnecessary time on.

Matt Edstrom

Matt Edstrom

CMO, GoodLife Home Loans

“Has there ever been an instance in your career where you felt like you weren’t successful? How do you rebound from failure?”

Inquiring about past instances of failure with your mentor can be a great technique for establishing a good rapport. It’s a great question because it leaves ample room for an open-ended response, which is a great way to break the ice with someone you may not yet be comfortable approaching & chatting with.

By inquiring about something pertaining to their career, you are demonstrating an interest in them. The question appeals to the notion that most people enjoy speaking about themselves, and if you can somehow tie the question into something that directly pertains to their career, it can further benefit you if you ever come across a similar problem during the course of your career.

You could even follow up the question by asking about an instance where they felt most successful if you’re trying to find a balance, and not focus solely on their past failure(s). The takeaway is that asking a question that can be answered in story form is a great way to encourage a mentor to talk about themselves.

Related: Overcoming Fear of Failure (Avoid these 3 Mistakes)

“I tried to execute a task and it didn’t go as planned. Could you perhaps help me identify where I went wrong, and how to avoid the issue in the future?”

Being able to approach your mentor about things that went wrong for you when trying to execute something at work is essential for learning & growth. It shows that you are not only comfortable enough to approach them with an issue rather than hoping it will take care of itself if ignored, but also that you trust your mentor to the point where you want to heed their advice.

Demonstrating transparency is a trait that should not be ignored. Being able to show you value your mentor’s opinion builds the bond and trust in the relationship. There is also a lot to be said about possessing a strong sense of self-awareness rather than deflecting, which demonstrates your ability to recognize when you did something incorrectly in the first place. Having that self-awareness enables you to more easily recognize when you need to reach out for assistance.

“What types of skills should I be aiming to hone in on?”

Asking about building up skills that pertain to the job shows your mentor that you strive to improve your skills to become a better employee. This helps notify your mentor that you are serious about wanting to grow rather than just complete the bare minimum. Most of the time, your mentor will start providing resources for you that relate to whatever skills they said would be wise to improve.

These resources can serve as incredibly valuable, and can potentially carry over to other jobs in the future. The tenacity to learn more is a common trait among those in leadership roles. By demonstrating that sense of tenacity, it may cause your mentor to consider you for leadership roles down the road.

Jason Patel

jason-patel

Founder, Transizion

“What was your biggest failure and how did you overcome it?”

Learning from failure is the hallmark of greatness. You want to know what high-performing people went through and how they overcame their challenges. Perhaps you can take struggles from their life, relate them to your own journey, and apply their solutions. Learning from others’ mistakes is a great way to minimize your own and save time.

“Do you recommend graduate school?”

Some of us are destined for graduate school, while others are not. Your mentor can show you the way and give you feedback on whether your professional path necessitates graduate school. A good response from your mentor can have you applying to graduate school soon or saving your money altogether.

Yaniv Masjedi

Yaniv Masjedi

CMO, Nextiva

Here are a few of my top questions for a mentor:

  • “If you could do it all over again, would you change anything? If so, why?”
  • “What are you most proud of?”
  • “What were your goals at the start of your career?”
  • “What would you do if you were me?”
  • “Did you ever land a role that you weren’t fully qualified for? How did you prepare yourself?”
  • “How did you become such a good public speaker?”

The questions you ask your mentor will depend on where you and your mentor are at in your respective careers, and what each of you aims to get out of your relationship. The above questions should be useful to an early stage professional paired with a senior executive.

Mentorship can provide one with answers to both personal and philosophical questions, as well as practical how-tos for gaining new skills and overcoming challenges.

Larry Sternberg

Immediate Past President, Talent Plus, Inc.

The questions to ask your mentor will inevitably shift over time as both your mentoring relationship and your situation evolve. Here are a couple of questions you can ask near the beginning of the relationship (when you might not yet apply the term “mentoring”).

Ask these questions in your own words and style. It’s the concept that’s important, not the precise words.

  • Tell me about some of your mentors.
  • What can I do to ensure that you feel this is a valuable use of your time?

I am aware the following are not questions, but here is some advice to get the most out of your relationship with your mentor.

  • Implement his or her advice. Otherwise, your mentor will become disengaged. As my wife says, “Don’t buy a dog and bark yourself.”
  • Come prepared with issues/questions to discuss, so that you can make the best use of your time.
  • Don’t just bring problems. Celebrate successes, too.

Angela Connor

Angela Connor

Founder and CEO, Change Agent Communications

Ask your mentor the things no one is going to teach you – about incorporating who you are outside of corporate America, into a space that doesn’t always embrace the unfamiliar, unique or what may seem different or “out-of-place” in the work environment.

I had to learn on my own how to bring all of who I am so to speak into the work environment as I climbed the ladder and moved into senior and ultimately executive roles. If someone had told me sooner that my authenticity and (a girl from Detroit attitude) is what made me personable, relatable and human in an industry where relationships matter and chemistry is important, I may not have been as hesitant early on. Too many times we hide some of who we are thinking we need to be two different people, especially African-American women.

No one wants a robot, so if you don’t inject personality and never reveal anything about you that sets you apart, you can’t win as big.

It’s important to develop enough trust with a mentor to touch on those emotional pieces and not be so fixated on how to get promoted, or how they can be a sponsor to connect you to the right people. 

With teen daughters, I’ve seen how dependent they are on technology for relationships, so I make them do what’s uncomfortable. I don’t always let them order food online or through an app for instance. That’s small, but I make sure they are talking to people face-to-face.

I believe that Gen-Z is going to need more mentoring on interpersonal relationships, so those are some of the things that will have to be covered as well – talking about being present and connected in an increasingly connected, yet disconnected world.

Paige Arnof-Fenn

Paige Arnof-Fenn

Founder & CEO, Mavens & Moguls

Career

  • “What was your path?”
  • “How did you know it was right for you? Would you choose it again today?”
  • “What has been your best and worst job?”
  • “What has been your best worst boss?”
  • “Do you have any career regrets?”

Life

  • “Is there ever a life balance?”
  • “What is your biggest source of pride and joy?”
  • “How have you recovered from failure?”

Personal

  • “What do you do for fun?”
  • “What is your favorite quote?”
  • “What is your favorite movie?”
  • “What is your favorite book?”

Brad Ormsby

Brad Ormsby

Owner, Colorstone Marketing

One of my favorite questions to ask my mentor is how they arrived at a certain idea. Written another way, how do you think about this situation?

My mentor is successful in business and a serial entrepreneur. And one of the things that fascinate me is how he identifies opportunities I never would have thought about. But I want to figure out how he thinks about things. His patterns, how he fuses ideas together, and how he spots trends. Instead of finding out about a specific situation, I want to train my mind to think this way.

So I ask about the mental process that led to that decision rather than the decision itself. I think it’s important to learn to think like your mentor (assuming they’re living the life you want) so you can eventually become the mentor and pay it forward.

Dayne Shuda

Dayne Shuda

Owner, Ghost Blog Writers

I find that mentors often give advice that is counter to their own journey to success. One example I’ve often heard from successful people is that they wished they would have gotten their college degree.

So when I’m chatting with a mentor or someone that’s successful I like to ask them their experiences and then pull my own lessons from their stories.

It might start with a question like, “What was the first year like?”

Then it might get into, “What helped get you to the next level?”

And then I’ll throw in, “What was a big challenge at that point and how did you respond?”

There are all kinds of questions you can ask, but the key is to focus on their story and pulling your own lessons from that story. Focus more on the actions they actually took over what they suggest or tell you that you should do.

Dane Kolbaba

Dane Kolbaba

Co-Founder, Watchdog Pest Control

Things they realize in hindsight. For any big decisions, they’ve made throughout the years, for the bad and perhaps the not-so-bad choices they’ve made. This would give me a better idea of what to expect for any similar decisions I’d be needing to make in the future, for what possible reward and fallout there would be.

What they could tell their younger self, for each milestone of their adult life. We tend to be so consumed with our own lives — what we need to do, what we want to do, where we need to go, where we want to go — that we neglect to stop and think about what it is we’re really doing and why. I have plenty of things I wish I could have told my younger self, and a mentor who’s further along in life would no doubt have invaluable insight.

Their biggest regret professionally, and if they’d share it, even personally. Something they did but wished they could undo or take back, but more importantly, something they wish they did do but lacked the courage to do so.

Rachel Richards

Rachel Richards

Finance Analyst | Founder, Money Honey
Author, Money Honey

In my experience, it’s best to ask your mentor questions that stand out. Stay away from the overly-used and too-broad “What’s the best career advice you can give me?” or “What are your best management practices?” Questions this vague are difficult to answer.

Try one of these instead:

  • “Was there a clear turning point in your career? What happened and how did you navigate it?”
  • “What’s one of the most challenging conversations you remember having?”
  • “What suggestions do you have for asking for feedback from my peers and bosses?”
  • “What do you see as my areas of improvement?”

Also, ask them about themselves. As Dale Carnegie once said, “To be interesting, be interested.” Your mentor will be more partial to and open with you if you ask them personal questions about their background and successes.

Try one of these:

  • “What was a trying time for you in your career and how did you overcome it?”
  • “You make it look so easy. What aspect of your career was more challenging than most people realize?”
  • “What do you wish you’d known 15 years ago?”
  • “What one decision have you made that has impacted your career the most?”

Joe Bailey

Joe Bailey photo

Operations Manager, My Trading Skills

I would focus my questions on my mentor’s failures throughout their lives, and how they ended up getting back up after these setbacks. As such, some of my questions would be:

  • “What has been your biggest failure to date, and what effect did it have on you, your goals, your vision, and your future decisions?”
  • “Which are the biggest lessons did you learn from this failure, and how have you implemented these lessons?”
  • “How did you get back up after this major setback? Did you ask for help?”

Bottom Line: Learning from your mentor’s failures will help you prepare for and possibly avoid major pitfalls on your journey.

Jason Yau

Jason Yau

VP of E-Commerce & General Manager, CanvasPeople

“What do you wish you had asked somebody earlier?”

This question will open up an extremely valuable conversation about self-awareness, growth, and vulnerability. A good mentor exemplifies all three of those things. You not only want to learn from your mentor’s successes but from their failures and things they wish they had done differently. A lesson that many entrepreneurs need to learn is that it is ok to ask for help, and any good mentor will be able to tell you that.

Stacey Berk

Stacey Berk

Managing Consultant, Expand HR Consulting

  • “At this stage in your career, how did you learn one of the following… to plan more strategically, make better decisions, focus on time management, and build improved relationships with people?”
  • “At this stage in your career, how did you learn to lead people? As a leader, how did you recruit, develop and retain your staff?”
  • “What do you think have been my core strengths as you have watched me grow over the years professionally?”
  • “What do you think I should focus on for the next 3-5 years to get to the next level in my career?”
  • “What resources do you think I need to achieve those areas of focus?”

Varda Meyers Epstein

Varda Epstein

Parenting Expert and Writer, Kars4Kids

I think the question every mentee should ask a mentor is: “How do you keep a positive attitude when things are going against you?”

This is what every mentee really wants to know because it is very easy to get depressed when things are stacked against you. Often, that’s exactly the case with a mentee, who generally needs mentoring because s/he may not have a supportive family or comes from a low-income neighborhood. It’s usually why they need mentors in the first place.

It’s easy to think: why to get good grades in school, stay out of trouble, go to college, look for a job when you’re stuck in a vicious cycle. It can feel like you work twice as hard as everyone else, but you just don’t get ahead.

The thoughtful mentor understands that what he’s being asked for is hope, and a way forward, too. The response doesn’t have to contain the wisdom of the ages. But it does have to give the mentee something to hold onto, or a step to take in a positive direction.

Related: When Life Gives You Lemons… Should You Make Lemonade? 

Stacy Caprio

Stacy Carpio

Business Coach | Growth Expert

I’ve found it helpful to ask mentors what their biggest failures have been and to hear their stories and answers in depth.

You already know your mentor has done some admirable things and maybe they have even helped or taught you to do the same.

Learning about their mistakes and the ways they have been hit hard by external circumstances or their own failures is a huge benefit you can lean on them for since learning what has gone wrong for them will often save you from going through the same negative experience yourself.

Lily Ugbaja

Lily Ugbaja

Founder, FindingBalance.Mom

The top question everyone should ask their mentor is “If you could start over, what would you do differently?”

I’ve found this question helps uncover common mistakes and major pitfalls to avoid, effectively speeding up your journey to success by at least 50%.

Most of the time we spend building is actually spent on trying stuff and failing at them. So I use this question to eliminate a lot of “smart” fail and get a leg up! Plus it seems to be an easy one for mentors to answer thoroughly.

Matthew W. Burr

Matthew W. Burr

Human Resources Consultant, Burr Consulting, LLC

“Where do you see my strengths and weaknesses, how can I improve?”

The mentor should focus on all area’s in an individual. What they do well, and where they need to improve. With concrete examples of both and a path to success. Here are recommendations to improve x, y, z.

“What opportunities will best help in my personal, professional and emotional growth?”

This one is going to be more personalized, the mentor should focus on what the person wants to accomplish and put a joint plan together to ensure there are agreement and accountability.

Megan Meade

Megan Meade

Marketing Specialist, Software Path

As a woman in business, it’s extremely important to have a mentor who can lift you up and encourage you to grow. A mentor relationship provides opportunities to advance, as well as builds confidence and reduces the prevalence of ‘impostor syndrome’ which a lot of women fall subject to.

An outside perspective improves women’s objective viewpoint of their own skill level and can reduce hesitancy about reaching for higher career goals. You and your mentor need to understand each other’s inner workings to achieve the full benefits of your relationship. One way to do this is by asking lots of questions.

One of the most important questions to ask your mentor is: “How do I measure my success against my goals?” This is a great way to ensure you and your mentor are on the same page when moving forward; the picture of what is ‘success’ looks different for each person.

It’s essential that you and your mentor are measuring progress in the same way otherwise there will be a disconnect in what that looks like. This is also important for personal goals or seemingly non-quantifiable goals, as it opens up a metric to hold yourself to and that your mentor can use to actively help you.

For example, if you have a personal goal of being more assertive at work, this would be hard to measure beyond a general ‘I think I’ve been more assertive’, but if you add a few metrics e.g. I will send out three meetings invites this week, I won’t reschedule other commitments around another person’s schedule, and I will not use mitigating language such as ‘just’ when writing an email asking someone to do a task. You can later revisit these metrics and see how you’ve performed, and then look at the impact of this with your mentor.

Success, in this scenario, may be targeted as scheduling the planned meetings, only adjusting other commitments once in a month, and only using ‘just’ 4 times in email exchanges over the whole month. This way, even if one target isn’t achieved, it’s likely there are small successes within the overall goal too.

Asking what success looks like also enables you to understand your mentor’s thought process. What seems a success to them, may not have occurred to you at all – which helps them help you to see things through a different perspective.

This is especially important in a business setting, a business mentor may set a goal and success measure you’d never thought of which encourages you to broaden your skill set and grow – which is what mentorship is all about!

Related: 22 Reasons Why Goal Setting Is Important for Success

Bernice Quek

Bernice Quek

Head Writer, Bumble Scoop

In my opinion, it’s essential to form a personal relationship with your mentor. Having a mentor should go beyond just sharing tips and tricks about navigating through your career; he/she should also be a figurehead that inspires you to become a better person.

A great question to ask would be “What made you who you are today?”.

This gives you an insight to your mentor’s journey to becoming the person and worker he is today. It may open emotional doors that you never knew existed, or show you that while he’s successful, he is also human. The way to build a closer bond is when all emotions are on the table. Only when your mentor opens himself up to you, then the two of you will have a stronger connection.

In the days ahead, you’ll always remember the heart-tugging story he shared to fuel you through any obstacle. A tighter bond will also mean better chemistry and the possibility of a mentorship turning into a treasured friendship. This will only translate to positive changes in your mindset and attitude towards both work and life.

Rishit Shah

Rishit Shah

Founder, TallySchool

  • “What is life?”
  • “Why do we do what we do?”
  • “Why are we doing so many things when ultimately we all are going to die?”

I have asked these questions to my mentor.

When we are living, it is natural to ask a question of what is life. What is the meaning of life?

Most of the people are doing a job or business just to earn money. But, when our survival is taken care of, we have these questions and we really don’t ask these kinds of questions to anyone including the mentor.

We should ask our mentor as to why we are doing, whatever we are doing. What is the purpose of it?

Related: What Is the Point of Life?

When we get a purpose, we can work towards it full-fledged with all our efforts in a single direction. Without a purpose, we cannot give our 100% to any task. We just do it for the sake of doing it. With a purpose, we know something better is going to happen and we are a part of it. This gives us a tremendous motivation to work towards our goal.

We should also ask the question of death to our mentor. It sounds frightening but we know we all are going to die one day. So why we are doing everything because we are ultimately leaving all this behind. We cannot carry anything with us after we fall dead. This is a crucial question and a true mentor will give you the right answer. This answer is different for everyone. For someone, it can be to live a good life so he or she can die peacefully. For someone else, it can be a totally different reason.

The point here is to ask your mentor the above existential questions because these are the fundamental questions of your life and when these are answered, you will realize that a lot of burdens will be off your head and you can grow in life with full speed.

Monica Rivera

Monica Rivera

Producer & Podcast Host, You Wanna Do What?

Mentorship has been one of my most significant gifts and is a valuable, untapped resource for too many people. I like to think of my mentors as sources of tough love and sounding boards for new ideas and advice. The cornerstone of these relationships is honesty.

Use the time with your mentors to ask questions and receive answers that will challenge you and grow you.

I recommend the following questions:

  • “What are my strengths? Are there any areas where I’m highly competent?”
  • “How can I leverage my strengths in my current role or in seeking a new opportunity?”
  • “Is there anyplace I’m falling short? What can I do differently?”
  • “What’s the best advice your mentors have given you?”
  • “How do I cultivate relationships in a sincere, meaningful way?”