Meeting Your Mentor for the First Time? Here Are 8 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.
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!
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 go into your mentor relationship thinking “what’s it in for me”, instead of “I want to build a strong, trusting relationship”, your mentor relationship will be doomed from the start.
This type of question is a great way to establish rapport with your mentor. It shows them that you are interested in who they are as a person, their personal history, and how they made decisions along their path.
It also allows you to understand the career path and journey they took to get to where they are, which provides context and inspiration for your own career. 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 from your mentor about their experiences and understanding the lessons they took from them is a great way for you to avoid making the same 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 have walked down the path you’re intending to take.
A strong relationship with this person, then, is the key to identifying the hard and soft skills you need to develop so you can create more value and accelerate 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 like they are adding positive value to your life, there is an increased probability they will continue to provide advice, mentorship, opportunities, and recommendations.
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 the art of effective networking and how to expand your professional connections and generate opportunities for yourself, then, is invaluable. 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. Finally, action on their advice!
8. 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.