Many of the world’s most successful people—from Steve Jobs to Oprah Winfrey—point to one common factor in their success: They had a mentor.
A mentor is someone further along the path than you who can help you navigate the “invisible” rules of your industry. They help you avoid the mistakes they made, introduce you to people you’d never meet on your own, and push you to see potential in yourself that you didn’t know existed.
But how do you actually find one? And once you have one, how do you make the relationship work? In this final deep-dive of 2023, we’re exploring the art and science of the mentorship relationship.
What a Mentor Is (and Isn’t)
Before you go searching, you need to understand the role.
- A Mentor is: A guide, a sounding board, and a source of wisdom. They clarify your vision and challenge your assumptions.
- A Mentor is NOT: A career coach (who you pay), a therapist, or a “job finder.” If you go into a mentorship asking for a job, you’ve missed the point.
1. Where to Look: The “Circle of Three”
Don’t just look for the CEO of a Fortune 500 company. Instead, look for people in these three categories:
I. The “One-Step-Ahead” Mentor
Someone 2-3 years ahead of you. They still remember what it’s like to be in your shoes and can give the most practical, “in-the-trenches” advice.
II. The “Industry Veteran”
Someone 10+ years ahead. They understand the long-term cycles of the industry and have a massive network.
III. The “Opposite Perspective” Mentor
Someone in a different department or even a different industry. They can help you think outside the box and spot your “blind spots.”
2. The “Organic” Approach to Finding a Mentor
Avoid the “Cold Ask.” Walking up to someone and saying “Will you be my mentor?” is like asking someone to marry you on the first date. It’s too much commitment too fast.
Try this instead:
- The Small Request: Reach out for a single, specific piece of advice (the Informational Interview we discussed in previous posts).
- The Implementation: Actually follow the advice.
- The Feedback Loop: Email them a month later and say, “I tried what you suggested, and here was the result. Thank you!”
This small loop builds trust. If the conversation flows naturally after 2 or 3 of these interactions, the mentorship has already begun—no formal “title” needed.
3. How to Be a “High-Value” Mentee
The biggest mistake mentees make is being “passive.” You are the CEO of your own mentorship.
- Bring an Agenda: Never show up to a meeting and say, “So, what should we talk about?” Have two or three specific challenges you want to discuss.
- Be Respectful of Time: If you scheduled 30 minutes, watch the clock. Being the one to say, “I want to respect your time, we have 5 minutes left,” shows immense professionalism.
- Offer Value Back: Even a senior leader likes to be “in the loop.” Send them interesting articles, offer a perspective from a younger generation, or help them with a small tech task if you have the skills.
4. The “Board of Advisors” Strategy
The most successful people don’t have just one mentor. They have a Personal Board of Advisors.
- One mentor for technical skills.
- One for interpersonal/leadership skills.
- One for work-life balance and mental health. By spreading your questions across multiple people, you get a more balanced view and you avoid “burning out” any single mentor.
5. When to End a Mentorship
Mentorships aren’t usually forever. They are often for a specific “season” of your career.
- If you find you’re no longer learning from them, or if your career paths have diverged significantly, it’s okay to let the relationship drift toward a casual friendship.
- Always end with gratitude: “I can’t thank you enough for your guidance over the last year. I’ve grown so much because of our conversations.”
Final Thought: Pay it Forward
As soon as you gain a little bit of knowledge, you become a potential mentor for someone else. You don’t have to be a VP to mentor a student. You don’t have to be a Senior Dev to mentor a boot camp grad.
Teaching what you know is the best way to master it yourself.
