On The Plane

I finished the WP Engine install on the plane. Running a GCP instance, and routing through Cloudflare nameservers to test the flow. Yes, this is what nerds do on vacation.


On Leadership

Yesterday I was asked to give a presentation to the Women in Infrastructure group here at Cloudflare. They had asked me to chat about my path to Cloudflare and leadership as a woman in technology more generally. It was a nice opportunity to reflect, and I wanted to share some of the key nuggets because it really was the highlight of my day:

1. Did you have a plan for your career?

No, I didn’t have a “plan” (whether 5-year or otherwise); I have always optimized for learning, and tried to get systematically better at understanding the factors that contribute to my happiness and efficacy at work. We are all works in progress; a good career allows you to grow and change your job as you do (and that growth is rarely linear). So I tend to take an inside out approach to understanding where I am and what I want. Practically that manifests as monthly 1:1s with myself, yearly assessments of my job: what’s working, what needs to change and why, and semi-regular check-ins on what else is out there and why it might appeal, not necessarily because I want to make a change, but to see if I get excited, and if so why, so I can look for ways to build that into my job and keep choosing that path everyday. Ultimately, you have to take ownership in the outcome of your career, and if you are not reflecting on what “right” and “best” are for you, you cannot achieve happiness (you likely cannot even define it!) I have only exceled at my work when I find the intersection of my passion and what the company needs.

2. What is the best advice you received along the way?

  • Be authentic: you cannot do your best work if you are not comfortable in your own skin. This “comfort” can be hard to achieve when you don’t look or feel like everyone around you, it is a mental load that some folks don’t have to carry and that may feel less fair, but honestly I’m not sure why we expect fairness (a post for a different time). Only you can know who you are. You have to take the time to understand your strengths and your weaknesses, and try to avoid self-bias. As a leader, I have found showing vulnerability is actually a feature. I tend to be pretty open with the good and the bad, and invite my team to show up that way as well. The number one contributor to successful teams is psychological safety, and authenticity can be a critical part of that journey.
  • Build sponsorship: much has been written about the difference between mentors and sponsors, but my short summary is a good mentor will help you process what you are thinking, be a sounding board, help you reflect on whether your actions are yielding the outcomes you want (we all need these folks in our lives!); sponsor will advocate for you when you are not in the room. They are the people who will recommend you for a project, job, etc. The challenge is that sponsors cannot be sought explicitly, they really have to find you. Ideally you start with mentorship, build a relationship in context, and then that person decides they are your sponsor, and you put in the effort to maintain that relationship. So follow up, ask for advice from a person you respect, and recognize that even if it makes you uncomfortable, you have to be your own champion.
  • Bring empathy: let’s admit it, sometimes it is just hard to be. With the pandemic these past few years people have lost loved ones, had to assume more home responsibilities as schools and childcare were less predictable, have had to renegotiate the boundaries of work and home with changes in travel, socialization, hobbies, connection, etc. If someone is not showing up in a meeting exactly the way you wanted them to, maybe you can cut them a little slack. Similarly, maybe you can give yourself a little space to be less than perfect (often the folks with the least empathy for others treat themselves with little empathy as well). When we assume good intent, we give people space to be authentic, build better teams, and have better outcomes.
  • Work smart: Find what you are good at and do that as often as possible, partner with folks who excel where you are less strong, and recognize the accomplishment of the company/team/etc. is what actually matters. Success comes when goals and roles are clear: who is driving what, where are there dependencies, and seek to learn what isn’t working. Focus on the outcome the team needs to achieve, and ignore any organizational barriers that may exist. Remember we all work for the same company so the barriers are artificial: the mission is what matters, not the individual.

3. What do you wish you could tell your 22-year-old self?

Find your cohort: self-development is a journey, and you will need witnesses, cheerleaders, and coaches along the way. Even if you are an introvert, you need your people who will help you walk your path to your best self. It may be a running buddy, a friend from childhood, a group you met in your maternity class, your former colleagues from work, your sister, your mom, your spouse…when life gets busy, we often stop taking the time to connect with others, but it is our lifelong partnerships that actually help us see who we were, who we are, and ultimately guide us toward who we want to be. The best leaders seek to know who they are and have a trusted cohort who advises them along the way. If you are more introverted or just prefer a “structured” approach to this endeavor, I highly recommend Designing Your Life as a book to work through as you build your cohort.