S2 E13 – How to Learn from Mentors Instead of Mistakes

Why Mentorship?

No matter your field, interests, or life-stage, mentorship is the fast pass to growth.

As Oscar Wilde put it, “Good judgement comes from experience and a lot of that comes from bad judgement.”

Mentors let you learn from the experience of others rather than suffer your own bad judgement.

The Best Mentors

Steven Spielberg said, “The delicate balance of mentoring someone is not creating them in your own image but giving them the opportunity to create themselves."

The best mentors recognize this.

Rather than tell you what to do, they ask questions, offer various perspectives, and tell personal stories instead of giving direct advice.

The 6 Myths of Mentorship

Myth #1: Mentorship is a one-way relationship

Mentorship is not just the mentee learning from the mentor. The relationship goes both ways.

Mentees provide mentors with a sense of significance and can also offer “reverse mentorship.”

Reverse mentorship might include:

• Bringing energy
• Explaining modern trends
• Providing distinct perspectives
• Demonstrating new technology

Myth #2: Mentors are hard to get

The opposite is actually true: it’s harder to find a good mentee than a good mentor.

Our instant-gratification culture heightens young people’s distractibility, leaving them unfocused. Contrasting this culture will help you excel, and making it easier to get a mentor.

Myth #3: You need to find the “perfect” mentor

All successful people reach their success by prioritizing some things over others. That requires sacrifice. And since it’s implausible that anyone has made the exact sacrifices you want to make in every area of life, the perfect mentor likely doesn’t exist.

Instead of seeking a perfect mentor, build a network of mentors with different areas of expertise.

Myth #4: Mentors are for amateurs and people just starting out

There will always be people ahead of you throughout life, especially in distinct domains. You’ll continue to benefit from mentors as you grow in different areas of life.

If you keep seeking mentorship, you’ll keep finding mentors. You just have to look.

Myth #5: Mentorship needs to be long-term, time-consuming, and face-to-face

Mentorship can take a wide variety of forms, depending on the needs of mentor and mentee.

For example, entrepreneur Derek Sivers has been mentored by people who don’t even know he exists. He asks himself what one of his “mentors” would say whenever he faces a dilemma, and since he’s read enough of their work to know how they think, he often reaches a solution.

Myth #6: Mentorship and Coaching are the same

Coaches are good at helping you think through things, but they don’t need firsthand experience.

Mentors have been there, done that, and can show you how to do something.

Both relationships are valuable, but they serve different purposes.

The 4 Stages of Successful Mentor/Mentee Relationships

Stage #1: Self-Assessment

The first step in finding a mentor is evaluating yourself.

First, ask if you’re a good fit for mentorship:

• Do you have a growth mindset?
• Would others want to mentor you?
• Would you want to mentor you?

Once you feel ready for mentorship, it’s important to assess your goals.

Where are you now? Where do you want to be?

Contrasting a clear vision with a current self-analysis reveals upcoming challenges. These challenges will point to the people you want as mentors.

Communicating relationship objectives also help secure mentor buy-in.

Stage #2: Matching

Once you know what you’re trying to accomplish and which challenges you’ll face, it’s time to create a “hot list” of potential mentors.

Don’t just target people at the “top.” It’s crowded up there, and thus harder to get mentorship.

Instead, try asking this question:

• If I’m unable to reach this person, are there alternative people who could help me reach the same outcome?

For example, it might be a lot easier to reach a bronze medalist, even though they were just marginally worse than the gold medalist.

It’s often more helpful to find mentors who are 2-3 steps ahead anyway, since they clearly remember your current stage and have good advice.

(One exception: people miles ahead can see the big picture. They might be able to help you avoid unnecessary detours on your road to success.)

Once you have this “hot list,” begin reaching out.

Cold outreach can be scary, but there’s almost no risk compared to the very high rewards.

Stage #3: Exploration

The next stage of mentorship is highly individual, based on your personal relationship, but here are a few high-level tips.

First, start small.

Your initial outreach can be as little as asking a nuanced question based on an article they wrote or thanking them for how one of their teachings impacted your life. Little interactions like this can increase mentor buy-in without requiring major commitments. Then you can go deeper and make bigger requests as the relationship progresses.

Second, be prepared to put in the work.

Many mentors test mentees by assigning work and seeing if they go above and beyond. Jayson recommends spending two to three times as much time preparing as you do meeting. This might include reviewing meeting notes, completing action steps, and formulating good questions.

Putting in the extra time shows your dedication to and appreciation for their mentorship, which helps the relationship grow and thrive.

Third, if your mentor is comfortable, record your conversations.

This way you can go back and catch any details you missed, while also focusing on making your mentor feel heard by asking clarifying questions. Sometimes you’ll disagree with feedback when you first hear it but come to agree with it the second or third time around.

Stage #4: Closure and Reimagining

If a mentorship isn’t working out, communicate that. (But don’t burn bridges!)

Sometimes you’ll accomplish the goals you had when you began the mentorship. If so, take the opportunity to celebrate, then evaluate appropriate next steps.

If you do end a mentorship, be sure to honor the relationship by continuing to help your mentor.

This might include:

• Sending relevant articles and resources their way.
• Introducing them to people who they may enjoy meeting.
• Sharing stories of how their mentorship helped you (both privately and in public).

You should also send the elevator back down, by mentoring others.

Final Thought: Mentorship as Data

One final thought related to mentorship comes from Aristotle. He said, “It is the mark of an educated mind to be able to entertain a thought without accepting it.”

Mentorship—and any insight it provides—should be seen as data.

Listen to it. Consider it. Mull it over.

But ultimately, you decide what to take and implement.

Further Reading:

If you want more information on mentorship, including outreach scripts and troubleshooting tips, check out The Definitive Guide to Mentoring by Todd Herman. It’s a short guide like this one—his is 30 pages—specifically focused on mentorship.

Download the Full Book! [PDF]


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