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50 Questions to Ask Your Mentor

I get it; your corporate journey is a blend of ambition, self care, and the occasional self doubt (maybe even imposter syndrome). Now picture yourself across the table from a mentor – someone who’s been exactly where you are and is ready to share their insights.

But where to start? How do you develop that connection and make the most of their insight? Well, that’s what this blog post is devoted to – I’m here to provide you with a bunch of thoughtful questions to ask your mentor, turning your conversations into a goldmine of wisdom. So, grab your virtual coffee, and let’s dive into these questions tailored just for you, the ambitious young professional woman!

1. Getting to Know Your Mentor

You know those conversations that start with, “So, tell me about yourself?” Yup, mentors appreciate those too! Kick things off with a smile and ask them about their journey. How did they get where they are? What challenges did they face along the way? These stories aren’t just inspirational; they give you a glimpse into their values and principles, which can be pure gold when you’re carving your path.


  • “What initially drew you to your career path?”
  • “Could you share a pivotal moment that shaped your professional journey?”
  • “What values or principles have guided you through your career?”
  • “How have your past experiences influenced your current role?”
  • “What’s something about your career that you wish you knew when you were my age?”

2. Goal Setting and Growth Questions to ask Your Mentor

Ah, the age-old “Where do you see yourself in five years?” But wait, we’re flipping the script. Ask your mentor about how they approached setting their career goals. What strategies did they use to keep themselves on track? Getting a peek into their goal-setting playbook can be a game-changer for your own aspirations.


  • “How do you approach setting both short-term and long-term goals?”
  • “What’s a goal you’ve achieved that you’re particularly proud of?”
  • “Can you share a time when you had to pivot your goals? How did you handle it?”
  • “What strategies do you use to stay motivated and on track?”
  • “How do you balance pursuing ambitious goals with maintaining a healthy work-life balance?”

3. Overcoming Challenges

Let’s face it – every career journey has its share of potholes. So, bring up the topic of challenges. Ask your mentor about the hurdles they faced and how they tackled them. Did they ever have a moment when they felt like they hit a dead-end? How did they bounce back? Their stories of resilience might just be the pep talk you need on a tough day. Plus, their advice and experience with being a woman in the workplace can be invaluable.


  • “What’s a significant challenge you encountered in your career, and how did you overcome it?”
  • “How do you manage stress during demanding times?”
  • “Can you offer advice on gracefully handling constructive criticism?”
  • “Have you ever had a setback that turned out to be a valuable learning experience?”
  • “What practices do you incorporate to maintain a sense of well-being, even when facing challenges?”

4. Navigating Office Politics Questions to Ask Your Mentor

Oh, office politics – that thing that no one wants to talk about and how it does affect your job, but isn’t actually your job. But don’t worry, your mentor is here to share some survival tips. Gently ask about their strategies for navigating office dynamics. How do they foster relationships with colleagues and supervisors? What’s their approach to conflicts and sticky situations?


  • “What’s your approach to building positive relationships with colleagues and superiors?”
  • “How do you navigate office politics while staying true to your values?”
  • “Could you share a time when you had to mediate a workplace conflict? How did you handle it?”
  • “What strategies do you use to foster a collaborative and inclusive work environment?”
  • “How do you balance assertiveness and diplomacy when expressing your ideas?”

5. Skill Development and Learning Opportunities Questions to Ask Your Mentor

You’ve got your goals in sight, but how do you get there? Cue your mentor! This is the time to ask about continuous learning. Your mentor’s wealth of experience can guide you toward skill-building resources that might not be on your radar.


  • “How do you approach staying updated with industry trends and new skills?”
  • “Could you recommend any resources or courses that have been particularly valuable in your career?”
  • “What strategies have you used to identify and fill gaps in your skillset?”
  • “How do you balance skill development with your day-to-day responsibilities?”
  • “Can you share insights on how to leverage opportunities for growth within our company?”

6. Balancing Ambition and Self-Care

Your ambitions are soaring, but taking care of yourself is equally vital. Your mentor can offer pearls of wisdom on keeping your inner fire burning while preventing burnout and give you other advice on work-life balance.


  • “How do you manage your ambitions while ensuring you don’t sacrifice self-care?”
  • “What practices do you use to recharge and prevent burnout?”
  • “Could you share a time when you had to prioritize self-care during a busy period?”
  • “How do you find a balance between work, personal life, and pursuing your passions?”
  • “What’s your go-to self-care activity after a demanding day?”

If you are looking for some self care ideas, check out this blog post with self care ideas for working women.

7. Networking and Building Connections Questions to Ask Your Mentor

Your mentor has walked many paths, and networking is one of them. Dive into a candid conversation about effective networking strategies. Trust us, their insights can be your secret sauce for making meaningful connections.


  • “What are some networking strategies you’ve found successful throughout your career?”
  • “How do you approach building authentic connections with professionals from diverse backgrounds?”
  • “Could you share a memorable networking experience that led to valuable opportunities?”
  • “What tips do you have for making the most of industry events and conferences?”
  • “How do you maintain and nurture your professional network over time?”

8. Embracing Leadership

Dreaming of that corner office? Chat with your mentor about their journey to leadership positions. You’ll discover valuable insights on effective leadership, and how to balance being a confident decision-maker with being a team player.


  • “What steps did you take to progress into a leadership role?”
  • “Can you share an experience that helped shape your leadership style?”
  • “How do you make tough decisions while considering the perspectives of your team?”
  • “What’s your approach to leading with both confidence and empathy?”
  • “Could you provide insights on maintaining a supportive and collaborative team culture?”

9. Advocating for Equal Opportunities

Conversations with your mentor should be a safe space to dive into deeper conversation. Ask your mentor about their thoughts on gender equality and diversity in the workplace. You might gain valuable guidance on addressing biases and promoting inclusivity.


  • “How do you approach conversations about promoting gender equality and diversity?”
  • “Can you share strategies for addressing bias or discrimination in the workplace?”
  • “What actions do you take to support an inclusive and equitable work environment?”
  • “Have you encountered situations where you had to challenge inequality? How did you handle them?”
  • “What advice do you have for contributing to a workplace culture that values diversity and inclusion?”

10. Giving Back and Paying It Forward

Don’t forget to give back as well! Your experiences can be just as much help to another young woman. As you wrap up your virtual coffee chats, delve into the mentor’s experiences on the other side of the table. Explore the power of mentorship and how you, too, can give back and support others on their journeys.


  • “What inspired you to become a mentor?”
  • “Could you share a memorable experience from your time as a mentor?”
  • “How do you see mentorship benefiting both the mentee and the mentor?”
  • “What advice would you give to someone considering becoming a mentor in the future?”
  • “What qualities do you think make for an effective and impactful mentor-mentee relationship?”


Remember that mentorship is a journey of growth, reflection, and mutual learning. These questions can be your guide, helping you navigate the waters of success while staying rooted in self-care and authenticity.

Now it’s your turn! Take these questions and embark on your mentorship adventure. Whether you’re meeting your mentor for coffee or virtually connecting, these questions for your mentor can help you guide your conversation to get the most out of your connection.

So, here’s to mentorship – a bridge between where you are and where you want to be. Let’s keep these conversations brewing and the wisdom flowing. Feel free to share your thoughts, experiences, and favorite mentorship moments in the comments below.


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