TLDR: most people ask hard, annoying questions of people they admire; instead, start a dialogue and don’t outsource your thinking
In college, I desperately wanted a mentor. I set my eyes on Sheryl Sandberg. Who better to take me to the next level?
What I failed to ask: why would Sheryl want to mentor me? What had I done to earn it? Absolutely nothing. I hadn’t even bothered to read her book, Lean In.
Then I came across an interview where she shared her most dreaded question: will you be my mentor? Clearly, my wish was naively shared by many others.
Years later, I finally get what she meant. Being on the other side of the table has exposed the silly mistakes we make in chasing someone’s orbit.
Let’s consider a more effective approach.
Prestige vs. learning
I chose Sheryl for the prestige. I loved the idea of being in the orbit of someone ultra-successful. But prestige for you gives the other person little reason to reciprocate.
Here’s a test: if the information you seek can be found on the internet instead of an in-person conversation, would you be happy with that? If you’re driven by learning, this is great news! If not, you’re chasing the prestige of proximity. Wanting to build a relationship with someone you admire is ok, but there’s a better path to getting there: it starts with learning.
Access to the most distilled thoughts of the best minds is only a click away. In my case, I could’ve dived into the Sheryl archives and learned a lot. By doing the work, I could have generated unique questions fun for her and others to answer.
Studying what’s in the public domain gives you a better shot at connecting in the private domain. When a vague wish turns into a specific ask, you become more worthy of mentorship.
Psychology of a mentor
Will you be my mentor? or even Can I pick your brain? are tainted questions.
Here’s what people hear: will you blindly commit to spending 1:1 time with me even though I have given you no reason to do so, and don’t even have a real question?
Here’s what people do like:
You engage with their work (e.g., share a thoughtful summary of their book, post an insightful response to their Tweet)
You use their ideas / product, and give useful feedback
You understand what they’re interested in, and share useful resources
You ask a specific question not easily Googled and best answered by them given their expertise in X
These steps turn you from a complete stranger into someone high-potential. You don’t need to do everything, but the point is to demonstrate you are resourceful and appreciative. Both are signs you’re not going to waste their time.
If they do respond with advice, take action! Then follow up with results. Let them know they made a difference.
Perfecting the ask
The less familiar someone is with you, the less committed they are to responding. If you want to hear back, make it a no-brainer.
To do this, take note of the Question Spectrum, which spans a range of difficulty for the respondent. Easy questions are about their life; medium questions are their take on a relevant topic; hard questions are what they would do in your specific situation.
Here’s the catch: easy questions are also satisfying to answer. Letting the other person talk about themselves is fun for them. The hard questions are usually annoying to answer. They feel like work and place a burden of responsibility on them to say the right thing.
Easy and satisfying questions are also more likely to start a dialogue, rather than open a can of worms. That’s how a college student connected with Randy Komisar and Eric Schmidt. Start with easy asks.
Perils of advice
How much context does someone need to answer your question? If they require multiple paragraphs of your life story, you’re asking the wrong opener.
Personal advice is heavy and nearly impossible to give unless someone knows you well. You’re better off talking to a person more familiar with you.
Advice is also heavily inspired by personal anecdotes. The more different you are from that person (in age, experience, background), the lower the odds that what worked for them will work like magic for you. This is why you can learn more relevant details from people just a few steps ahead than from a mogul.
Before you copy someone’s playbook, ask yourself: will this apply to my life?
Ultimately, learning from others should turn you into the best mentor for yourself. Nobody has a bigger stake than you.
Mentors you sort of know
Observing, absorbing, and asking thoughtful questions also apply to people who are in your orbit. It’s infinitely easier to get access to your VP or CEO, which is another reason to spend time carefully picking your local pond.
Examples of useful questions:
How did you know X was a good idea?
What was your decision process for Y?
What’s your biggest concern about Z?
People who run companies usually love working, and by extension, love talking about work. Being curious about their work can get you on their radar. It still helps to start with easy questions, but you do have more leeway to explore the heavy stuff if they have context on your situation.
However, none of this changes the inevitable truth: your peers and direct manager still wield disproportionate influence on who you become because you spend the most time with them.
Board of mentors
The real magic of mentorship is not outsourcing your thinking. Having a board of mentors (formal and informal) helps you see multiple perspectives, uncover blind spots, and ideally gain more empathy along the way.
But the real magic comes from filtering their perspectives to make better decisions for yourself. When you think independently, you go from chess piece to chess player.
The very nature of mentorship has changed. Valuable information used to be exclusively locked up in the heads of a few people. Direct 1:1 mentorship was required just to get past the starting line.
Today, anyone with the hunger to learn can bootstrap their start. A level playing field means adding value and asking specific, timely questions are more in vogue than ever.
To learn from the best, you no longer need to meet them, you just need to absorb them. Ironically, it also happens to be the best way to eventually meet them and earn their respect.
Give this a try, and let me know what you think!
Will be launching it on Product Hunt next Sunday. To mark the occasion, next week’s post will come out earlier, ~12 AM PST on Sunday. Stay tuned ❤️
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Thanks for reading,