Jonah Greenberger
Startup Contributor

Mentorship in the 21st Century

By Jonah Greenberger | Thu, 01/21/2021 - 09:23

Look at any successful person – Elon Musk, Oprah Winfrey, Jeff Bezos – and you will find they have benefited tremendously from one or more mentors in their life. No one achieves on their own. But getting a great mentor and benefiting is often a happenstance and informal process, and great mentors are still in very short supply.

Mentorship involves two elements: 1) a trusting, fluid relationship and 2) powerful insights. I’d love to argue that a modified form of mentorship involving outsourcing insights in a highly structured way could create more leaders like the above on a greater magnitude. Let me explain why.

Personally, mentorship has helped me tremendously, particularly from my CEO coach Alberto Carvalho over the last couple years. We have high trust, mutual deep caring and an easy and frequent method of communicating. He knows my strengths and weaknesses and he has highly refined judgement that he can impart to me. However, half of what’s been most helpful felt so obvious at the time I’m surprised I needed help on it. Diving in, it’s often because what greatthe best mentors really help with is focus. They navigate to exactly the one thing you need to learn at any moment.

For instance, when I was faced with hundreds of challenges a couple years ago, Alberto instructed me to go through each of my direct reports and rank each from “keep,” “keep and develop” or “let go and replace.” He completed the advice with a story of when he did something similar, what the result was and how elements of that story applied. Without this advice, I may have been tempted to solve all of the tasks directly and exhausted myself (particularly since I may not have known how to do 75 percent of them and only have time for 10 percent of them). So, great mentorship in this case was paramount, but the content of the advice conveyed was something I could have read about. In this case, replacing the one department head and then mentoring the new head solved the problem. The advice was spot on.

However, today there is a plethora of high-quality content. In fact, there’s so much content that eager learners often get overwhelmed and often discouraged. I personally have had to retrain myself to set down content that doesn’t apply at the moment, even whenif it was really well-written and insightful.

What if a mentor’s job was really to point you to one piece of high-quality content you needed at that time? Stated differently, what if a mentor's role was to use their experience and judgement to help figure out what a mentee needed to study at the time, but not to create or deliver the content themselves. They’re a guide but not the map author. To be clear, I believe building the mentor-mentee relationship would be just as critical if not more critical. And the frequency of meetings would not need to change. But the one thing that could be scaled is the delivering and creation of content. A couple of elegant results could occur:

  • Mentors could spread their scarce time across more mentees (note that it takes massive skill to know the one thing a person needs to focus on so we’re still in short supply)
  • Great mentors could become much more accessible (cheaper and easier to find) as much of their time would be freed up
  • Mentees could spend as much time as they needed with the content, and with different types of content from different people to see what resonates
  • The content delivered could be from the very best across the world (a la Sal Khan of Khan Academy versus your typical middle-school teacher)

To test this, I’ve started an experiment to enable this type of “highly leveraged” mentorship with a searchable content repository of the best content I’ve received over the years. Every piece of this content has been transformational to me or someone I know, but only when delivered at precisely the right time. I’ll be using it with the company I help run, Bright (, which works to enable homes and businesses by letting them power themselves with cheaper and cleaner rooftop solar energy. I’m hoping that with this repository, they will also be able to enable their direct reports, coworkers and friends with better decisions and management.

I would love your thoughts on how to make this most useful or where you see it being most helpful, particularly if you are a mentor or working to help someone with a hard challenge.

Imagine what would be possible in a world where anyone could get mentored by someone of the caliber of Warren Buffett, Steve Jobs, Ruth Bader Ginsberg, Obama, etc. And if there were more future leaders who then turned into mentors, a virtuous circle could emerge with more great leaders becoming mentors, creating more leaders who then became more mentors. Who knows if it’s possible, but it’s a future I’d love to try to shoot for.

If you’re interested in working on this as well, I’d love to hear from you.



Photo by:   Jonah Greenberger