We Tried 5 Famous Mentor-Mentee Routines: A Mini-Documentary
What was the secret behind the legendary relationship between Warren Buffett and Bill Gates? How did Steve Jobs guide a young Mark Zuckerberg? And what can Maya Angelou’s mentorship of Oprah teach us about our own careers?
We hear about famous mentorships all the time, but the actual how often remains a mystery. Their routines are treated like secret formulas for success.
So we asked ourselves a question: What if we could actually try them?
We spent a week stepping into the shoes of some of history's most successful mentor-mentee pairs. We took their core philosophies, applied them to our own real-world work challenges, and documented the results. Some were surprisingly effective; others were... not for us.
This is our mini-documentary. Here’s what happened when we tried 5 famous mentor routines.
1. The Buffett-Gates Routine: "Radical Focus on a Single Goal"
The Famous Routine: Warren Buffett is known for his intense focus. He once asked his private pilot to list his top 25 career goals, circle the top 5, and then—brutally—avoid the other 20 at all costs, calling them distractions. He shared this "two-list" strategy with Bill Gates, helping him focus Microsoft's strategy.
We Tried It: Our mentee, "Alex," felt overwhelmed by a long list of Q3 goals. In our session, we applied Buffett's method. Alex listed 15 goals, we debated them, and circled the top 3. The other 12 were moved to a separate "Forbidden List" for the quarter.
The Verdict: This routine is shockingly effective but requires discipline. The immediate feeling was relief. Alex reported a 50% increase in productivity on the top 3 goals within a week because there was no more "decision fatigue" about what to work on. This style is perfect for ambitious people who feel scattered and need a ruthless framework for prioritization. It’s less suited for those in purely creative or exploratory roles.
2. The Jobs-Zuckerberg Routine: The Philosophical "Walk and Talk"
The Famous Routine: When Mark Zuckerberg was facing pressure to sell Facebook, he often met with Steve Jobs. Their meetings weren't in boardrooms; they were long, meandering walks around Palo Alto. Jobs didn't give tactical advice; he helped Zuckerberg think about Facebook's mission, values, and long-term vision.
We Tried It: We took a real-world problem—"Should our team pivot its Q4 marketing strategy?"—and instead of a Zoom call, we did a 45-minute "walk and talk" around a park. We were forbidden from discussing tactical details (like budgets or specific ads). The entire conversation was about the "why" behind the strategy: "What is our mission? Who do we serve? What feels right?"
The Verdict: This is a powerful tool for getting "unstuck" from a tactical problem. Removing the screen and adding movement changed the quality of the conversation, making it more open and philosophical. We didn't solve the problem, but we returned with a clear set of principles that made the tactical solution obvious in a follow-up meeting. This is ideal for founders, leaders, and anyone facing a major strategic decision.
3. The Angelou-Oprah Routine: "Mentorship as Identity Work"
The Famous Routine: Maya Angelou was more than a career mentor to Oprah Winfrey; she was a guide for her life. She helped Oprah navigate fame and public scrutiny not by giving business advice, but by asking questions about her core identity: "Who do you want to be?" Their mentorship was about aligning Oprah's career with her deepest values.
We Tried It: In our session, we ignored a specific work problem. Instead, the entire conversation was guided by one question: "When you're at your best, what values are you honoring?" The mentee, "Sarah," who was stressed about a project, realized her best work came from a place of "creativity" and "connection," two values that were missing from her current task.
The Verdict: This routine is like therapy for your career. It's incredibly effective for high-achievers who are on the edge of burnout because it reconnects their work to their purpose. It’s not for solving an immediate crisis but for building long-term career resilience and fulfillment. It requires a high degree of trust and vulnerability from both mentor and mentee.
4. The Miyamoto-Reggie Routine: "The Student Becomes the Teacher"
The Famous Routine: Shigeru Miyamoto, the legendary creator of Mario and Zelda, mentored Reggie Fils-Aimé, the former President of Nintendo of America. Miyamoto's style was to give his mentees immense ownership and then challenge them by asking, "Why is this fun? Explain it to me." He forced them to deeply understand and defend their own ideas.
We Tried It: Our mentee, "Ben," presented a new project idea. Instead of offering feedback, the mentor's only job was to act as a curious student, asking clarifying questions for 30 minutes straight: "What is the core idea here? Explain the user's emotional journey. Why is this better than the alternative?"
The Verdict: This is an intense but highly effective method for fostering ownership and critical thinking. Ben reported that being forced to articulate his ideas so clearly exposed the weak points in his own plan, allowing him to strengthen it before presenting it to a wider group. This is perfect for developing future leaders and product managers.
5. The "West Wing" Barlet-McGarry Routine: "The Loyal Challenger"
The Famous Routine: In the fictional but brilliantly written world of The West Wing, Leo McGarry's mentorship of President Bartlet was defined by one role: to be the one person who would tell him the unfiltered, hard truth when no one else would. He was a loyal challenger, stress-testing every decision.
We Tried It: We role-played a scenario where the mentee had to make a tough decision. The mentor's sole job was to be the "devil's advocate," respectfully challenging every assumption and poking holes in the mentee's plan. The mentor wasn't allowed to offer solutions, only to identify weaknesses.
The Verdict: This is not for the faint of heart, but it's an invaluable tool for de-risking a major decision. It creates what's known as "psychological safety to dissent." The mentee felt more confident in their final decision, knowing it had survived a rigorous stress test. This style is essential for any high-stakes leadership team but requires a strong, pre-existing foundation of trust.
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