Going Beyond Basics: Advanced Questions for Effective Mentor-Mentee Interactions

So, while you're eager to conquer your own goals, lend an ear to your mentor's journey - you might find gems of wisdom...

Are you feeling anxious about your first conversation with your mentor? If you're afraid that the conversation may be dull or that you will struggle finding interesting questions to ask, then never fear – MicroMentor has just the thing for you! Here are some key questions that will open engaging dialogues, prove useful in sparking business advice, and give insight into a successful entrepreneur's past. So if you're stuck for a stimulating chat at your next mentoring session - let us be here to help! And even if you’re not feeling stumped for conversation, these are still great questions to ask at any time throughout your mentorship. 

Did you have a five or ten-year goal? Did you achieve it?

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Ever wondered how your mentor reached where they are today? Ask them about their five or ten-year goals, and you'll discover fascinating stories of passion, persistence, and adaptability. 

Some may have climbed the ladder they set out to reach; others might still be climbing. A few might be walking a new path instead, embracing the twists that life threw their way. 

So, while you're eager to conquer your own goals, lend an ear to your mentor's journey - you might find gems of wisdom that illuminate your own path to success! Hold onto enthusiasm, hope, and openness to truly appreciate their experiences and possibly help reshape your perspective. 

How do you embrace and recover from failure?

Let's face it, nobody likes failing. But guess what? It happens to everyone, no matter what path you're on. Luckily, your mentor is there to guide you through the tough times. 

By observing how they handle their own missteps, you'll gain insight into how to handle your own pitfalls. Not only that, but you'll get a sneak peek into how they'll handle any bumps that might come up during your mentorship. So don't be afraid of failure, it's just an opportunity to learn from your mentor's wise ways.

What’s your motto/what do you live by?

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While not everyone necessarily has a motto, almost everyone has a certain set of rules or a moral code that they live by. When choosing a mentor, it's worth finding out what kind of moral compass they have and whether or not that is someone you are interested in investing in a long-term relationship with. 

A good follow-up question is whether they apply the same motto to both their personal and professional life. Some people may adopt a certain moral code when dealing with friends or family, but are a little more cutthroat when it comes to business. It's up to you to decide if that's a dealbreaker or a match made in mentorship heaven.

Which pieces of art have inspired you?

Getting to know your mentor’s passions not only humanizes them, but it opens the door for more engaging conversations.

Let's change the channel on this mentorship conversation and talk about something that might surprise you - your mentor's interests! Sure, they're knowledgeable in your industry, but did you know they moonlight as a film critic or have a library that rivals Belle's in Beauty and the Beast? 

Getting to know your mentor’s passions not only humanizes them, but it opens the door for more engaging conversations. Plus, it'll make them seem a little less intimidating and more relatable. So don't be afraid to break those barriers and get to know your mentor on a personal level.

Have you experienced a major career shift? What happened and how did you deal with it?

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Life is all about change and growth, and your career is no exception. Whether you're swapping job titles like they're going out of style or planning for a future that includes both work and family, you're bound to experience a major career shift at some point. Luckily, there are ways to make the transition smoother and less stressful.

Acquiring fresh tools from your mentor to help you adapt to these changes can make all the difference. Plus, who wouldn’t want to know how their mentor handles pressure? Asking these questions will hopefully bring up some strategies to help you tackle career transitions with ease.

Is there a skill that has been particularly helpful to you during your career that you didn’t expect would benefit you as much as it has?

Entrepreneurs are always on the hunt for the latest and greatest skills to add to their arsenal, but sometimes the best inspiration comes from unexpected places. Maybe your mentor learned how to crush the competition through some killer tap dance moves or got a valuable lesson in business strategy while practicing karate chops. 

Who knew that a hobby could turn into a professional asset? Hearing about your mentor's surprising experiences is not only fascinating, but it might even help you uncover your own hidden talents.


Meeting with your mentor can be intimidating, especially at first. But by having some good questions in your back pocket to pull out, you’ll know exactly what to ask when you don't know what to say. Hopefully these few question suggestions will help you foster more meaningful conversations with your mentor and make the most out of your meetings! Who knows, with a little insightful conversation you might be able to make an even bigger impact on your career! Ready to get started? Sign up for a mentor today on MicroMentor.org and see what opportunities arise!

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