Dr. Selflove or: How I Learned to Stop Worrying and Love Mentoring

Mel de Leon
6 min readNov 15, 2019

Early this year, my mentor referred a newer female product manager to me for mentorship. As a self-professed “mid-career PM” I did not feel capable of the task, and forwarded her onto a more senior female leader at my company. I didn’t mull it over, or toss and turn at night to ask myself “did I do the right thing?”. It was instinctual, immediate. I could not offer the guidance needed and truly believed I was not ready to be a mentor.

Around the same time my hairstylist of several years ghosted me and everyone she knew when she moved across the country during a painful divorce. Her replacement stylist, was very, very talkative. This was different for me. What I liked most about my old hairstylist is how much she didn’t talk. The relaxing silence was precious to me since half my job is talking, and I know I’m not alone in this since they’re charging clients in London for silent service. I was hesitant, but she won me over almost immediately. My current hair stylist is a delightful, intelligent, black woman, born and raised in Oakland with an incredible talent of disarming those around her with kindness and humor. I didn’t immediately tell you she is beautiful, because it shouldn’t matter if she is beautiful. But if you must know, yes, she is beautiful. She quickly zeroed in on the fact that it was easier for me to talk about work, my career, and my passion for tech and video games. What began as smalltalk eventually evolved into a recurring AMA session. Gradually over time, our hour long appointments every 6 weeks changed focus to her goals in owning her own small business, and long-term plans of opening her own salon. I began encouraging her to take classes, do research, focus on her health, and even take control over her relationship that was sapping away her energy and not replacing it with happiness.

And after a few sessions of this, something interesting happened. She began to quote me.

In my last appointment, she quoted something I had said months before. I was telling her about my plunge into a new role last year as a Product Manager Technical, leading a team of backend engineers with a big focus on data architecture. As a self taught casual front end developer, I felt woefully unprepared to be a thought leader in a space that was focused on micro-services, operational excellence, and scaling to meet big data problems. This role, however, was not thrust upon me as an unwilling participant. I had not only asked for it, I had created it. I saw the need for it, pitched it, and volunteered for it. My stylist was confused. She had asked me how I wasn’t afraid of failure, and I casually answered “I just assume I can do something, until I try it and fail spectacularly. I haven’t failed yet.”

Now I realize this isn’t an eloquent quote that will be embroidered on pillows, or included in the preface to an inspiring best seller about women empowerment in the workplace. It was something said earnestly to a friend in a moment of honesty. But it stuck with her. It is a sentiment that she has used to construct her mental model of how she makes major decisions in her career and life. She recently went away to Arizona to take a master stylist class, something she had been initially nervous to do but thanks to this little nugget of word vomit, decided it was something she wanted to take on. I realized in that moment that I had become a mentor.

So, since I’ve come to this realization, let me explain and rephrase that quote my mentee latched onto in a way that is a bit more formal. In a bias training I took at Twitch this year, we were asked to share instances in our careers where we think bias impacted our daily lives. One woman offered up that she felt like she had to do a job for 6 months to a year in order to be promoted into that role. She believed her male counterparts did not do the same. As someone who has done this for the vast majority of my career, it resonated with me. When I was an entry-level ad trafficker at Pandora, I began tackling bigger AdTech issues and defining company-wide process improvements for half a year before they moved me to the AdTech team. As a people manager on that team, I took responsibility for my direct reports before they reported to me. And as a project manager at Twitch, I had written five product specs before they began interviewing me for a product management role. I believed I had to check all the boxes for a job before asking for the money and recognition of that role. Moving into a backend role was the first time I had taken the plunge into the unknown.

I believe we are quick to doubt our abilities to adapt. When I began the role that I am in now, I felt a lot of discomfort. I think a lot of people categorize this feeling as imposter syndrome, but I think this is a bit of an over classification. It’s not that I had checked all the boxes required to do this job well, and wasn’t recognizing that. I hadn’t checked all the boxes. I was, however, more than capable of checking all those boxes, and it took internal convincing to decide “I will occupy this role while I’m checking the boxes, because I genuinely believe I can do this job better than anyone else.” In my case the discomfort was a signal to me, a way to identify where my weaknesses were and reinforce my abilities where they were lacking. I started taking online courses in SQL, Airflow, and reading the iconic O’Reilly book Designing Data-Intensive Applications. I shifted from reading customer-obsessed product blogs to articles about big data, scaling and application security. I filled the gaps, all the while producing for my team the other things I knew I did well, like defining user stories, creating compelling product documents, and knowing the advertising ecosystem better than the vast majority of my peers in the industry. And I didn’t fail spectacularly! I thrived. The challenge helped me grow and gave me a new reason to want to do well at my job.

I had to actively and purposefully take the plunge to build a role that I wasn’t over-qualified for. This is instinctual for a lot of people, and instinctual for a higher percentage of men than women. It’s not entirely our fault, a lot of it comes from a systemic overestimation of men’s expertise and a chronic underestimation in the skills of their female peers. In a study done by Women in the Workplace, it was found that replacing a woman’s name with a man’s name on a resume increased the likelihood of being hired by more than 60%. We have generations upon generations of learned behavior working against us, and it’s up to us to convince ourselves we’re capable of things we haven’t done yet. It’s not a quick fix, it’s a slow and consistent exercise that needs to be done repeatedly, over time. By constantly challenging ourselves to delve into the unknown, and giving ourselves the benefit of the doubt that we can catch up, we can do a good job even while filling our skill gaps.

I learned to take this plunge by, you guessed it, being mentored by a woman who was confident in her abilities to tackle challenges. I didn’t apply this belief to my ability to mentor when my colleague asked me to step up and advise her. I will not make this mistake again. I had the amazing privilege this week to do a few rounds of speed mentoring at the 2019 Women In Product Conference, and was pleasantly surprised how I could speak to a lot of the issues they faced and questions they had. I will attempt to turn around and take all the other things I’ve learned from my incredible mentors and pass it along to my hairstylist, and now to the other women I’ve met with through WIP and other connections. I am going to take my own advice and try to mentor as many women as I possibly can until I fail spectacularly.