Meeting Your Mentor for the First Time? Here Are 15 Must-Ask Questions to Consider
Back before I started Reframed Coaching – and when I first started seeking guidance in my career – I quickly realized the immense value of having a mentor.
A mentor can provide insights, support, and advice that can be crucial for your professional growth. What’s more, mentor relationships facilitate positive perceptions of equity in advancement opportunities – According to Gallup, 58 percent of employees with formal mentors are more likely to say their workplace gives all employees equal opportunities to advance to senior management.
If you’re wondering what to ask a mentor in your first mentoring session, here are 15 must-ask questions to kickstart a productive conversation.
Let’s dive in!
What’s the difference between a mentor and a coach?
A coach is a paid professional who helps a person gain clarity, remove blockers, and progress towards their future goals. A professional coach does not offer advice. Instead, they ask the critical questions to help individuals dig deep and find the right answers within themselves.
Unlike a coach, a mentor-mentee relationship is often unpaid. It’s a great way for someone with more experience to share personal insights, advice, and recommendations to help the mentee gain knowledge on how to address specific challenges in their professional journey. Usually (but not always), a mentor has “been there” and “done that”, which is why they can be a very resourceful advisor for the mentee.
Making the most of your relationship with your mentor, however, often comes down to asking the right questions! These questions will not only help you gain a deeper understanding of your mentor’s experiences, but they’ll also provide actionable advice that you can apply to your own career.
Through my own journey and conversations with many seasoned professionals, I’ve compiled a list of the top eight must-ask questions for your mentor.
Let’s dive in!
1. Can you tell me about your career path and what led you to your current position?
The truth is, people love talking about themselves. If you approach your mentor relationship with the mindset of "What do I get out of this?" it will not work. Instead, you should think, "I want to build trust." Starting with the right attitude is important for success.
This type of question is a great way to establish rapport with your mentor. It shows them that you're interested in who they are as a person, their personal history, and how they made decisions along their path. It also helps you see the career path they took to get where they are. This gives you context and inspiration for your own career.
Tip: Write down what stands out to you. Ask follow-up questions about the challenges they faced or the unexpected opportunities they took. Cherry pick what you want from this response and apply it where relevant to your own growth plan.
2. What are the biggest lessons you've learned in your career?
Everything is a lesson, and every person learns a different lesson based on their own individual experiences. Perhaps your mentor learned the art of navigating relationships after losing a big account when they were up and coming. Or, perhaps they understood the art of delegation after burning out while working 80 hours a week.
Hearing your mentor talk about their experiences is very helpful, and you can learn from their lessons and avoid their mistakes. Essentially, you’re able to learn crucial lessons without ever having to assume risk or be held accountable!
It’s in these lessons you’ll find ways to make more informed decisions as you grow in your own role.
3. What skills do you think are most important for someone in my position?
Chances are, your mentor has accumulated the relevant experience you’re looking for, and they've walked down the path you’re intending to take.
A good relationship with this person, then, is key. It helps you find the hard and soft skills you need. And these skills will help you create more value and speed up your career. In an ideal situation, your mentor will be able to identify your strengths, acknowledge your blind spots, and support you with growth in the areas they feel will most benefit you.
4. Can you recommend any resources or activities that could help me grow?
This is a great follow-up to question number three. It forces your mentor to provide you with something concrete and tangible that you can go and explore.
Whether it’s specific podcast recommendations, in-depth coaching programs, online courses, or simply just a useful blog article or two, this question gets straight to the heart of a mentor-mentee relationship: knowledge transfer.
Here’s the secret to asking this question: If you want to deepen the bond with your mentor, you need to actually take action on the advice they give you.
Asking for advice and NOT taking it is the best way to show someone you do not value their opinions and recommendations. You want to do the opposite with your mentor.
If your mentor suggests a book, read it.
If they suggest a podcast, listen to an episode.
When you’re done with a particular resource, go back and talk through what you learned.
Positive reinforcement works, too. If your mentor feels they're helping you, they're more likely to keep giving advice, support, and opportunities.
5. How do you handle work-life balance?
Work-life balance is as important (if not more important!) than the work itself! A typical career could span ~50 years, so learning how to work sustainably is vital to continued growth and development.
A great mentor will have a lot to say about work-life balance and its impact on productivity and mental wellbeing. Asking them how they handled difficult periods of “all work and no play”, and what they did to implement the right boundaries to regain control over their work-life relationship, is a great way to discover the tactics that will address burn out, before burn out even happens!
6. How do you stay current in your industry?
If a career is ~50 years long, one important factor is keeping up with the rate of change in your industry and knowing how to continuously provide value!
In content marketing (my old field of expertise), artificial intelligence is quickly changing how content is created. In HR, new generations entering the workforce are changing the landscape of business culture. And finally, economic upturns and downturns force businesses to adapt their models in order to survive.
Quite simply: Staying informed about industry trends is crucial for remaining competitive and relevant in your field. Ask your mentor how they’ve adapted to change and remained relevant – you might be surprised with what you learn.
7. How do you approach networking and building professional relationships?
Your career growth will come down to a few key areas, one of which is networking and relationships! Strong relationships are the cornerstone of career development and professional growth (your relationship with your mentor is a great example of this!).
Learning how to network well is therefore very important. It helps you grow your professional connections and create new opportunities. Ask your mentor about how they’ve approached relationships in their career, and follow up by asking for advice on where to look for new relationship opportunities. Oh, and don't forget to action on their advice!
8. How did you develop your leadership style, and how has it evolved over time?
Leadership is not the same for everyone. Each leader develops their style through personal experiences, successes, and mistakes. Ask your mentor how they first approached leadership — were they naturally confident or did they struggle with delegation and decision making?
Understanding your mentor's early leadership journey is a great way for them to show (not tell) you how leadership skills develop over time. You do not just inherit them!
Their response can also highlight how leadership styles evolve based on team dynamics, industry trends, and personal growth. Maybe they once led with a directive style but shifted to a more collaborative approach after realizing the value of empowering others. These insights can help you shape your own leadership philosophy while avoiding common pitfalls.
9. How do you approach decision-making when faced with uncertainty?
Not all decisions come with clear right or wrong answers, and navigating uncertainty is a skill every professional must develop. Ask your mentor how they approach tough choices, whether they rely on data, intuition, or seek guidance from trusted advisors.
Understanding their framework for decision making can help you refine your own approach when faced with ambiguity.
Additionally, you can learn about any major decisions they made that didn’t go as planned and what they learned from those professional experiences. Did they regret waiting too long to make a move? Or did they take a risk that ultimately shaped their career? This will help you figure out how to balance analysis and action when making career-defining choices.
10. What habits or routines have had the biggest impact on your success?
Success is often the result of small, consistent actions rather than big, singular achievements.
Be sure to ask your mentor about the daily or weekly habits that have made the biggest difference in their career. This might include learning how they structured their morning routine, their approach to regular self-reflection, or how they approach strategic networking.
This can help you identify habits to implement in your own routine that will support long-term career growth.
11. How do you handle professional setbacks or failures?
Every career has moments of failure. This can include missing a promotion, losing a big client, or making a bad decision.
Ask your mentor how they’ve handled setbacks in their career and what mindset they adopted to move forward. Their response can offer a practical roadmap for dealing with disappointment while staying focused on your career objectives.
12. How do you approach advocating for yourself at work?
Advancing in your career often requires more than just doing good work. Much more! You also need to ensure the right people recognize your contributions.
Ask your mentor how they’ve successfully advocated for themselves in different stages of their career. Did they proactively seek promotions, negotiate for raises, or leverage their network for new opportunities? Their insights can help you become more strategic in how you position yourself within your organization.
13. What’s one piece of unconventional career advice you swear by?
This is a fun one.
Some of the best career advice comes from real-world experiences that challenge conventional wisdom. Ask your mentor if they’ve ever received or discovered a piece of advice that seemed counterintuitive at first but ultimately made a huge difference in their career. Their response might shift your perspective on success, risk-taking, or professional development.
They might have learned that saying “no” to some opportunities helped their career. They may also find that moving to a different role can lead to surprising growth. Based on these answers, you can broaden your own thinking and gain new ideas on how to approach your career with a fresh perspective.
14. If you were in my position today, what would be your top priorities?
One of the most valuable perspectives a mentor can offer is a sense of direction. Ask your mentor what they would prioritize if they were in your exact situation! Would they focus on building technical skills, expanding their network, or improving communication?
This question is also a great way to identify blind spots you may not have considered. Your mentor might highlight an area you missed, which could greatly affect your career path.
15. Finally, what do you wish you had known when you were in my position?
Finally, understanding your mentor’s hindsight can provide you with valuable foresight! If your mentor was in your seat again, what would they do differently? What knowledge can they pass on to you so you can excel faster, smarter and in a way that works best for you?
As the old adage goes: Hindsight is 20/20. Listen closely here.
How to find your mentor
Unless you’re lucky enough to be in a position where your current manager is also your mentor (it happens sometimes!), you’ll need to initiate the search for your mentor on your own.
Here are a few ways to help you find a mentor:
1. Explore resources like First Round Capital's insights on finding a mentor.
2. Start from the top down. Identify leaders in your organization whom you admire and would like to learn from. Mentors don't necessarily need to come from the same career track – a product leader can mentor someone in sales or marketing, for example.
3. Consider your manager’s manager. While reaching out to your manager's manager can be tricky (although skip level meetings are considered normal), be transparent about your intentions, whether it's learning about their career journey or gaining insights into their daily life.
4. Initiate conversations! If you're new to the company and need to establish connections, don't hesitate to request meet-and-greet sessions with senior leaders. The worst they can say is “no, I’m busy” and you can move onto the next one.
Top tip!
When initiating conversations, we recommend reaching out within the first two weeks of the job or new role. Reach out to all the senior leaders and ask to book a 30-minute meet and greet with each one. Here’s a sample request:
“Hi [INSERT NAME]!
I’m new to the company and I’d love to meet with you for 30 minutes. I’d love to learn about your journey into the company, what your goals are, how I can help, and any leadership tips.”
5. Consider external mentors. Sometimes, the ideal mentor cannot be found within your company. Don't hesitate to explore external avenues. Look for mentors on platforms like LinkedIn, industry networking groups, or even at past companies.
How I found my past mentors
As Annie Duke likes to say, “the quality of your life is based on two things: luck and the quality of your decisions.” I’ve been fortunate enough to have found mentors based on luck and my own initiation.
Hopefully the ideas below will get your creative juices flowing:
Based on pure luck:
My first manager at KPMG
My manager at my first marketing job
My CMO at a tech startup
A woman I met on a neighbouring sailboat while I was cruising around French Polynesia
Based on effort and search:
A marketing client turned mentor
A former client’s husband
My peer at my first startup
An expert I found online
Other managers at KPMG who I didn’t directly report to. I sought out and built relationships with managers who had similar values to me and career paths I admired
Making the most of your mentorship: The vital link to career development
Meeting your mentor for the first time can be both exciting and nerve-wracking. I remember my first formal mentoring session and how anxious I felt about asking the right questions (I had my first formal mentor as a college student in my business program).
But, what I quickly realized is that a mentor is not just a source of knowledge, but a partner in your growth! Their guidance is invaluable and can help you navigate common pitfalls, develop essential skills, and stay current in your industry.
When I started out, I wasn’t sure which questions would yield the most valuable insights. However, by focusing on understanding my mentor’s journey, learning from their experiences, and seeking advice on skill development and industry trends, I found myself growing both professionally and personally.
Finally, your mentor is there to support you every step of the way. So, make the most of it and enjoy the process of learning and growing together!
Reframed Coaching offers a hybrid mentoring and coaching approach. To learn more, explore our workshops or contact us today.