Mentor Mistakes Fixed - Lollipops & Laptops

Like most students, I was pretty wise to the concept of getting a mentor from early on. I read a lot about how to find a mentor. I was good at pursuing the relationships. And yet, I let a few potentially incredible mentors slip through the cracks because I didn’t properly cultivate the relationship. Luckily, I’ve adjusted my approach and been able to find some fantastic mentors despite my initial mistakes. Keep reading for some of my worst mentor-seeking offenses and how I’ve succeeded at finding a few great mentors since.

The Business Proposition

I worked part time during my last semester of college for a guy who owned a luxury spring break company. I stayed in touch with a twice-per-year email after I stopped working for him, just as I had been taught. When I finished law school and sent him my biannual email, he asked to meet with me. When we got together, he told me about a business idea he had and wanted me to do some of the up-front research, and, if it had legs, to run that business for him. It took me by complete surprise. For one, I did not expect him to want to go into business with me. What’s more, I wasn’t as into the idea as he was. I went home and did some cursory research, sent him a this-is-what-I’ve-found-so-far email, and never followed up.

Instead of thanking him and being honest about my interest level, I looked like I totally dropped the ball. He’s an alumni of my university, and a well-connected entrepreneur, and it was a total bomb not to follow up.

You think he ever reached out again? Let’s put it this way, 8 years later, I’m not running one of his companies. Moral of the story: be up front but continue to follow up. Take interest in their pursuit even if it’s not for you. You never know when that might become an interesting idea to you or another opportunity arises that they’ll pitch you.

Mentor Mistakes Fixed - Lollipops & Laptops

Great tips via Foundr

The Empty Meeting

I connected with one gentlemen through my brother. This guy was a lawyer who never practiced law–what I was hoping to be as I was leaving law school hellbent on avoiding the practice of law. He was running an economic development nonprofit in Los Angeles and was bright, charismatic, and full of great advice (like suggesting my then-fiance and I should forget about jobs and travel the world for a year as our honeymoon, which, in case you’re wondering, we never did, though we still daydream about the idea today). We didn’t discuss specific job opportunities or career moves, so when I left, I felt like that was kind of the end of the line.

If my experiences have taught me anything, it’s that every connection is a good one. This was someone that could have helped me work through my career plans, opened the door to new contacts, or even created a job opportunity. It just required a little follow up.

The Wrong Industry

I met the head of a commercial real estate company just after law school. Although he didn’t have any job openings at the moment, he gave me some valuable life lessons. In fact, one of them has become my personal mantra as it relates to my perfectionism (In life, a 92 is an A). Still, I wasn’t interested in pursuing a career in commercial real estate, so I didn’t follow up. Imagine the irony as I happily come to work these days managing commercial real estate. Wouldn’t it have been nice to be connected to the CEO of a power player in my industry?

The point is, if you have a connection with someone, who cares what industry they work in? Maybe you won’t end up in that industry the way I did, but a man who I regularly quote after only one one-hour meeting almost a decade ago would have been worth keeping as a connection. Don’t underestimate the power of a great relationship. And don’t drop the connection just because they don’t have anything to offer you right now.

The Success Stories

I’m a consummate student. I made some glaring mistakes and missed out on a few great opportunities. Despite my rocky start, I learned from them and have since managed to successfully cultivate a few great mentor relationships.

Mentor Mistakes Fixed - Lollipops & Laptops

While on maternity leave, I connected with a colleague who worked in a different division of my company, and we hit it off both personally and professionally. I followed up with her every few weeks whenever an interesting article came up or a mutual connection was recognized for an achievement. This follow up was critical to my career. In fact, she ultimately helped architect my promotion to the division where I currently work. What’s more, she continues to be a champion for me, and is currently supporting me as I pitch a company-wide initiative.

I have also fostered a great relationship with an executive in my former division. This woman is successful, intelligent, and has a lot of great insight in terms of career growth. She agreed to meet once a quarter for an hour coffee chat, so I do my homework ahead of time. Although we spend plenty of time casually talking about whatever comes up, I’m always armed with recent industry information and questions about the direction of the division and her career experiences. I don’t ever want her to feel like I’m taking her time for granted, and having an outline of discussion ideas also helps fill in the gaps in case of an awkward silence.

I’m continuously working on cultivating other professional relationships. It takes a lot of effort, but I refuse to ever lose out again on a professional relationship because of a lack of follow up or an unclear direction about how to connect with them.