There’s a secret to Silicon Valley that very few people understand. It boils down to a single skill that can be the difference between your company succeeding spectacularly or crashing and burning.
The secret? Learning how to be a good mentee.
Successful startup CEOs follow a pattern—they learn on the job via high-bandwidth mentorship from their investors, board members, peers and advisors. But I’ve noticed it’s not a path that’s widely discussed outside the clubby world of venture tech CEOs.
I was privileged enough to build my mentee chops early in life. Thanks to my dad, a world-class engineer, and my uncle, a leading press critic, I had access to invaluable mentorship when I was a kid.
What I remember most about family vacations was questioning them endlessly on how internet technology would radically change the news media ecosystem and civil society. In retrospect, they were two of my earliest and most important career mentors. They taught me a love of learning, and the ability to listen, ask pointed questions and leverage their understanding of how the world works for career-making decisions.
They also set me on a path of neverending menteeship—the focused and dogged pursuit of mentors to guide me through the biggest challenges in my career and life. But you can get started at any stage in life. Here’s what I’ve learned from 20+ years of working on becoming an effective mentee.
Don’t Wait for a Mentor to Find You
Those with mentors are promoted five times more often than those without. But so many people have a Hollywood view of mentorship: The elusive and long awaited mid career meeting with a senior mentor who takes you under their wing and elevates your career to new heights. And that’s just not how it works.
Finding built-in mentorship via your employer was easier 30 years ago, when people stayed with one company their entire career and could afford to wait around to be chosen. But in this fast-paced, employee driven job market, waiting for serendipity is career suicide–especially as the head of a startup.
Whenever I speak with my friends and employees, I’m reminded how critically important good mentorship is to make intelligent career decisions. I worry about how frequently people make life-changing choices without a mentor’s invaluable insights.
The benefits of mentorship have always been clear. Studies have shown that mentors and mentees build confidence and feel more empowered throughout the process. This is why learning to be a great mentee is such a critical skill to building your career.
Be Eager, But Concise
When my company was still just a nascent idea, I cold emailed the cofounder of Heroku, James Lindenbaum. He was where I wanted to be—at the helm of a truly groundbreaking company that was transforming the way software was built and operated.
I drafted an email explaining who I was and why I wanted to meet, and quickly hit send. It wasn’t a showy production. It wasn’t a job application or essay. It was a short request designed to signal that I had a genuine purpose and reason for connecting, and that I wasn’t going to waste his time.
To my surprise and delight, it worked. He was kind enough to grab a coffee and spell out exactly what made him successful–and what I would have to do to follow in his path.
That experience taught me something that surprises most people. Yes, cold emailing is emotionally difficult and it has a high failure rate. But if your outreach is concise, genuine, personal and serious, you’ll be shocked at how often it gets a response. I’ve learned that if I am not seeing some rejection with regularity, I am not pushing myself hard enough to take risks.
Learn How to Actively Listen
The right email can get you in the door, but being a skilled listener is the key to establishing a real relationship—one that can make or break your career, or save it down the line.
I’ll never forget a key turning point in building my company when I had to make some business-defining decisions about the future. I shared my frustrations and concerns with a mentor, Adam Gross, who listened to my fears and reassured me that it was all totally normal. I, in turn, listened to understand as he laid out concrete options and suggestions for the best way forward.
Active listening is a skill that takes practice. There’s a world of difference between asking performative questions versus seeking to learn and understand. Good mentors are highly observant as to how you’re questioning them and can immediately tell the difference in intent.
My suggestion? Focus on the important questions. The questions that lead to a greater understanding are often the simplest and most obvious, but sometimes they’re the hardest to ask. Almost all of the important answers can be elicited by simply asking ‘why’. Don’t be afraid to keep peeling back the layers until you get to the heart of the matter.
Show Follow-Through
Above all, being a good mentee means actually doing something with the gifts you’re given. Nothing will frustrate a mentor more than imparting hard-earned knowledge, only to see it squandered through inaction.
At the end of that first dinner with James Lindenbaum, he looked at my co-founders and me, and said something that changed our lives: “Are you guys going to start this company or what? If not, stop talking about it.” He wasn’t just motivating us to take action. He was telling us that if we weren’t serious about our idea, he wasn’t going to waste his time helping us.
We quit our jobs a week later and founded the company.
Now more than ever, it’s crucial for people to recognize the importance of honing their skills as a mentee. And it’s not just about launching a startup or scaling a company. All careers are becoming more self-directed. The average 30-year-old stays in one position for less than three years. The average 20-year-old rarely lasts more than a year.
The path to success is never straight, and the relationships you build along the way will be the deciding factor between making informed choices, or taking detours that will cost you time, money and happiness.
Don’t wait for a mentor. Be the mentee you’d want to mentor, and one day you’ll be on the other side of the equation.
Zack Rosen is the cofounder and CEO of Pantheon, an established leader in the WebOps space and a passionate proponent of advancing the open web.
