Take the Shot: Opening Doors By Learning to Ask

You miss 100% of the shots you don't take

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I am often asked what someone can do to advance their career or open up doors. The answer is simple - ask. 

Studies show that 15% of women and 20% of men who ask for a raise get it. That means only one in 5 or 6 people who ask get it. But you know a sure way to not get what you want? Not asking at all. 

I have mentored, advised, and sponsored many people over the years, and here are four memorable ones who took the opportunity when it came and made the ask. In each instance, they changed their own course just by putting themselves out there. 

Not Taking the First No for an Answer - Bowen Pan

During his second year at Stanford Graduate School of Business, Bowen approached me in the Paths to Power class, where I serve on a panel each year. Afterward, he emailed me out of the blue to ask for my advice about whether to take Google's PM offer or Facebook's. Our conversation led him to pick the Facebook role, with the promise that we would meet up when he arrived.  During bootcamp, Bowen reached out about the promised chat. He had been exploring commerce activities in groups during data camp and said, “I need you to take me as your RPM, and we are going to build Groups Commerce together.”  

I replied, “I am really passionate about building a social commerce marketplace here someday, but I haven’t gotten Mark’s support yet.” He pushed again and promised me that he would do anything it took to get the product off the ground. I took him on faith and brought him on, getting our engineering leader, Vijaye, gathered several engineers to work with him.  Bowen ended up being the first PM and led the launch of what is now Facebook Marketplace, a product that has over a billion active monthly users.  

Overcoming Obstacles - Sharon Zeng

In 2013, my Director of Product, Mary Ku, came to me to discuss her parental leave coverage. “I found the perfect person," she told me. "Her name is Sharon Zeng.” 

Confused, I asked her, “Who’s Sharon?”  Mary explained that even though Sharon only had a couple years of work experience and was one of the most junior analysts in the company, she was the perfect backfill. 

When I finally met Sharon, one of the first things she told me was that she wanted to be a PM, but that she had previously been rejected for the role. I was surprised, but I trusted Mary completely, so I brought Sharon on.  Not only was she a strong backfill for Mary, but she went on to lead our Payments Growth efforts, spoke at F8, the annual developer conference, about her work, and later transferred into Product.  

When we hosted our first Women in Product Conference, I asked Sharon to speak. Right before her talk was about to start, she whispered to me that one of the people who rejected her for the PM role was sitting in the audience. I replied, “And you will show her that you deserve to be here just as much as anyone else.”  Sharon went onstage and talked about how she built Safety Check in her spare time, and how that product went on to touch the lives of hundreds of millions of people. 

Sharon Zeng speaking at the inaugural Women in Product Conference

Doing Whatever it Takes - Tyler Maloney

One day I received a cold email in my inbox.  A reader of my Substack newsletter reached out to tell me about his startup. I largely ignore cold emails, but when someone is a reader, I almost always reply. Tyler reached out to ask me to join his app. Intrigued, I replied to him, and we set up time to chat. 

On the call, Tyler walked me through setting up the app. Because I am a Pixel user, we soon realized that I couldn’t download and use Faves. I told him to reach out again when he launched on Android. He replied, “Actually, I can bring an iPhone to you.”  I was caught off guard. But, true to his word, Tyler, accompanied by his new puppy, delivered me an iPhone XR straight from the Apple store. 

I felt that anyone with that level of hustle deserved an investment of my time, so I gave Tyler's app my full attention. Now I am one of the more active creators there and have invited several dozen others to join. Later, David and I invested in Tyler's seed round, and I became an advisor to his company. 

Faves App

Proving Your Worth - Jenny Truong

In 2012, I struggled to hire any PMs to work on my team on Facebook Payments. All five PMs on the team, including me, left the team or company within a year. Since my new product was failing to take off, I was asked to return to lead the team. After trying to hire a PM for months, I was desperate for anyone to help ease the load, so I opened a job role for a Technical Program Manager to do a new type of work that PMs were not already doing. Many of the engineers, having never worked with a TPM, balked.  

Jenny Truong applied for the job, and we hired her within a week. I warned her that we didn’t have the support of many of our engineers, but she was unfazed.  She told me, “My job is to prove to them that I will make their lives easier. Someday, every team will want a TPM.” This was a new role and a new function created out of necessity, so I was skeptical she could do that. But having her on the team took a huge burden off my shoulders. Over the next several months, Jenny systematically won over each of the engineering teams she worked with. Eventually, she built out the function, became the first manager of TPM on our team, and is now the head of the whole Product TPM discipline for the company. 

What these people have in common