Figure out what you want to learn. Then figure out how to learn it. 
Rather than focusing on title, salary, or who you report to, determine what you’re most interested in learning and the path you need to take to learn it. This was a lesson Melissa describes as a defining point early on in her career. Even though she launched Google Fiber, Google Cloud Platform, and Google Play during her tenure at Google, she realized it was only legal work but missed the policy work component, which is a muscle she wanted to flex.

Building a network is important (you can’t do it all on your own)
One guarantee: “if you don’t like the people you work with, you’re going to be miserable, but even the hardest jobs become easier if you have camaraderie.”
Melissa is still friends with the staff at NYU Law, and her former colleagues at Debevoise & Plimpton and Google. (She spent 8 years at Google before joining Reddit as General Counsel in 2015). She reflected back on how often that community leans on one another. She shared that she often receives emails from other GCs of different startups saying “Hey, do you guys have a policy on X and how did you approach A, B, and C?”

Make Diversity a Priority
Melissa recognizes that the more diversity there is at the executive level (including age, background, and experience), the more diversity there is within teams. One of her guiding principals is to leave a place better than how you found it, including a company. This means she has honest communications with Reddit’s CEO about race, gender, etc. because she knows it will have a trickle down effect.

On Messing Up:
It’s OK to make a mistake but don’t try to lie about it or cover it up. When one of Melissa’s colleagues or direct reports makes a mistake, she simply asks that they own it so she knows there was thought put into it, then everyone can move on to find the right solution.

Slow Down.
This applies to written and verbal communication, especially when reacting. “Anything that happens in 5 seconds means you reacted with emotions.” Instead, take a deep breath or a literal lap around the block so that your reaction is thoughtful.

Keep it short.
Learning how to communicate and present should be skills you prioritize. While no one teaches you how to do this, the most important thing is that the other person or other people hear you. If you share something and the other person doesn’t hear you, then it doesn’t matter.
If you’re writing to people above you at work:

  • Keep it a one-liner (or 3 bullet points) – no one has time to read!
  • Don’t add facts; keep it truncated.
  • If you feel facts are necessary, add a ‘tl;dr’ (too long; don’t read).
  • For more detailed information, share it in person.

Rather than running away, run towards something. 
The goals Melissa set for herself kept her honest in knowing that she needed to be successful (especially if she wanted to buy a house in the Bay Area). When she started at Google in 2007, the company paid like a startup for a long time — she even took a big salary hit when she left the law firm to join Google because she wanted to make the jump from corporate law to in-house work. It was upsetting to leave Google and the strong camaraderie of the team when the opportunity to join Reddit was presented. However, she knew it was important to be challenged mentally, figure out new problems to be solved, and work on legal + policy.

On Practicing Compassion 
At Reddit, one of their values is to ‘remember the human.’ This means that it’s important to recognize that there are humans on the other side of every action you take, regardless of whether it’s behavior, or communication used in person or in an online forum. In turn, this means they’re more transparent with policy, communications, and when discussing what happens on Reddit’s site.

From a personal perspective, Melissa shared that being present and a voice for others, especially minorities, is what she defines as practicing compassion. “As a minority female, it’s hard to see that or be that voice when you’re not present in it.” Having an opinion and a voice is something she was trained in and a big factor of her success. She shared a proud moment of when her niece wrote her college essay that was focused on her aunt (Melissa) being one of very few black women executives.