Take a Lesson. Caroline V. Clarke

was something that I felt was really important and also a little bit counter to my personality. I still struggle with having to go up to people in work environments and start conversations socially. I've had to practice that and it totally drains me. But to learn how to do that well not only helps in every facet of your life, it truly makes you a better executive.

My reserved personality is grounded in not feeling completely comfortable with myself when I was younger. As you get older, you learn to appreciate who you are and not worry so much about what others think. I also have noticed, through observing other leaders I respect, that there is not one successful personality type. Mark Zuckerberg, as an example, is not somebody who's the center of attention in every room and I think he appreciates the quiet confidence of somebody who is really good at what they do but is not necessarily trying to always be talking.

      People appreciate authenticity, so it is really important that you always try to become a better you, not someone else or someone you're not. It's about gaining confidence in what you're good at, letting that show, and building relationships around that. That enables people to tap you for opportunities that you might not even have thought were within the realm of possibility.

      That was the case when I first heard from Mark about the CFO role at Chan Zuckerberg Initiative literally two weeks after I had my youngest son. I had no plans to leave PayPal and that's not a time when you want to add a lot of change to your life, anyway. You're happy with things being steady so that you can just survive that particular moment. But then I started to learn what he and his wife, Priscilla, were doing, and I've always wanted to be able to drive change at scale, doing good in the world in a way that is good business.

      I assess opportunities based on what is going to add to my learning and development, and am I going to enjoy it. The am I ready question almost always pops up too, and sometimes the answer is, I'm not ready, but I'm going to do it anyway. Fighting imposter syndrome is something that you have to keep cranking at every single day.

As women, we question ourselves too much. I have seen so many situations where the guys are signing up for opportunities that they are not prepared for and they go in with full confidence. We need to learn from that. No one's ever totally ready. If you think about any CEO out there, it was a leap for them to take that position and that is relevant at every single level in a company. Your boss, your boss's boss, even the most powerful leaders struggle with the same thing. And it can help to get to a point where you decide to think, What are they gonna do, fire me? Don't do me any favors!

      You also have to have supportive people in your corner that will push you. My husband is much more extroverted than I am, so he's always pushing me to make that phone call or go to that meeting or take that chance. This was really important when I was first approached to be on a [corporate] board because my first thought was, I've got little kids and I have this job and I don't have one more minute in the day for one more thing. But my husband said, “If you've got opportunities, grab them. The timing is never going to be perfect. You're always going to feel like you can't put one more thing on your plate but the last time you thought you couldn't get something done, you got it done. So, just do it.” He was right.

      What happens for women, and for Black women specifically, is you don't often have either the relationships or the roadmap to show you what you should expect. We don't necessarily have a plan laid out for us that says, here's what you do when you're going for that regional sales leader position, here's how you should be advocating for yourself, here's financially what it should offer, and here's how to spot a progressive position.

      Eventually, you start to realize how to leverage what you offer and to recognize if your value is not being appreciated. That requires listening for opportunities in the office and in the market, even if you're not interested in changing jobs. And don't be afraid, when you're having conversations about your career, to say, I'm an ambitious person, someone who's always thinking about whether my career is progressing the way it should. I would love to continue to grow my career within this company but if it's not going to happen, I am going to consider my broader opportunities. That causes people, if you're delivering the message right, to say, wait a minute, maybe we should think about what your next role is or how we add to your compensation. You should take this approach, even when times are uncertain—maybe, especially then.

      This last almost two years has been nothing that any of us could have imagined. The beginning was just chaos. We had a son in second grade, a just‐turned four‐year‐old with a 10‐minute attention span, and a 23‐year‐old who was studying finance in New York and ended up at our house in California trying to do college virtually with these little ones that worship him wanting to be all up in his face. Trying to navigate all of that was crazy. But I will say that not traveling all the time, being able to do board meetings and events virtually, and to have dinner with the family much more often was great. So there was a certain comfort with the chaos and, on a broader scale, I do think there will be parts of this that we will sustain.

      In some ways this is our time, as Black women. The conversation around the business case for diversity has gotten a lot clearer. The focus has shifted to building products that are relevant to customers, and why diversity of perspective, experience, and background that reflects the customer that you not only serve today but that you want to serve, is essential.

There still is a problem of having the right sort of awareness of all the rich talent that is out there. There's also an issue of leaning into the tried and true versus giving people that first opportunity. We can always help others, regardless of where we are in our career, but you do get to the point where you are getting opportunities that you can pass on to others, or you have a powerful voice in decision making that can enable people to get opportunities. I'm on two public boards and we're only allowed to be on two. So I find myself building my list of amazing Black women and amazing Black men who are ready for that next opportunity. We need to continue to do that for each other and to position ourselves to be both ready as well as in the conversation so we can infiltrate these pipelines to companies and corporate boards.

      When I'm recommending people for boards, I very deliberately ask, If you were hiring a white guy, what qualities would you want? It's great that you want to have a board that looks more like our world, but what are the specific skill sets that you're looking to round out, because I don't know who to recommend if I don't know that. And if you don't know that, then are you actually giving someone a seat where they can make an impact?

      The same is true as a relates to progression within a company. Being able to home in on additive skill sets within the goal of diversifying is key to making sure that we're giving people opportunities to be successful. The advice I always give is: Continue to work on yourself, always make sure you're prepared, and don't let anyone ever tell you that you're getting a job because they're filling a [diversity] slot.

      Honestly, it doesn't really bother me when I get racism from the white side, because whether it's offensive comments or not getting the opportunities I deserve, I view those people as either insecure—worried about losing something they don't deserve—or just ignorant. I am hurt more by people of color who make assumptions about my life and who I am.

We're all made up of the experiences we have lived and the perspectives we've been exposed to, so I do not purport to understand what every person of color's experience has been. I had a different upbringing than most other Black people and there were probably times when I had it easier than others because of that. But it is hurtful when people make assumptions around whether I've had the experiences to be able to know what it really means to be of color or the perspective to speak on certain issues. If you don't know me, you don't know my experiences or my heart.

      This all informs how I lead and how I think about my responsibility to develop each individual on my teams. There are some quirky people in Silicon Valley—quirky and super talented. I have met some of the coolest people after thinking at first, They seem odd but let me just stay open and listen. The best teams are made up of people who can truly bring their best selves to the team. And in order to get the very best out of each person, you have to be open to understanding what makes a person who they are, what motivates them, and what makes them prosper on a team versus not.

      It's