That time I girl-bossed too hard at my tech job

A little over a year ago, I left my job as a Data Scientist at Okta, and started a new role as AI Security - Principal Security Engineer at Zendesk. That new role was vertiginously above the previous one (see the levels.fyi diagram below). I went from individual contributor at the bottom of the totem pole to reporting on company-wide initiatives to C-levels.

I had become the sole AI Security SME at the company (still am) with the daunting task of figuring it all out. Every week, my morale would wobble between vertigo and imposture syndrome. Every day, I asked myself “Did I girl-boss too hard?” The meme below perfectly encapsulates how I felt:

AI Security was - and still is - a very ill-…

AI Security was - and still is - a very ill-defined field. Is it Machine Learning applied to Cybersecurity? Is it Security applied to AI products? Is it both? Either way, it is changing extremely quickly. Technically, I also didn’t have a background in Security, I had only collaborated with Security experts on ML models applied to cybersecurity. I often joked that my title (AI Security - Principal Security Engineer) has Security twice in it because Security is so important, but the dash is actually a minus. AI Security - Security = AI Engineer. 😬

And yet, a year later, I have lead the company toward being one of the first to be ISO 42001-certified, and the first company listed by Cloud Security Alliance with STAR for AI Level 1. Our AI Security posture is maturing, and I still have a job. How did I do it? I am a little bit surprised myself, so this article summarizes my reflections, in hope to inspire others to push their boundaries.

Learning is a Career-Long Journey

In that “I girl-bossed too hard” moment, I was faced with an enormous amount of things to learn, and I felt overwhelmed. Worse, I conflated “not knowing” with “will never know”.

This was until I was reminded by a mentor that the true differentiator in this job market is the ability to learn. Learn anything!? I could probably learn anything short of Quantum Physics. I know that particular limit because I enjoy science vulgarization books, and after reading three different ones on Quantum theory, (The Order of Time by Carlo Rovelli, White holes by Carlo Rovelli, and Black Holes by Brian Cox), I still don’t get it. Fortunately, I am not a physicist, so it doesn’t matter (pun intended).

Short of that, I can probably learn most things that my job actually requires. And you probably can too. All I had to do was blocking time to sit down, read, and learn. Rinse and repeat until retirement. So I did.

The Muscle of Ideation and Opinion Generation

Every week, I felt like I was running out of ideas, and that it was finally time to admit I girl-bossed too hard. As it turns out, ideation and opinion generation is a muscle that you can grow. To grow it, you must work it! Generate a lot of ideas until one sticks. You do not have to execute on each idea. Instead, take some time to think deeply and grow an opinion about the idea. Ask what others think, and listen, be inspired and educated by them.

You can rarely go wrong with sharing your ideas. Yes, some people might take them and implement them (or try to), but intellectual generosity pays off in many different ways. Ideas are cheap, work is expensive! It is a long career you have ahead of you, and you will have ton of ideas, but not as much time and resources to implement everything. Share your ideas, it’s free. Give them away like candy for Halloween 🍬. Think of ideas for other people. After a while, your ideation muscle will be big and strong, and you won’t feel like you will run out. I (almost) don’t anymore.

The more you girl-boss advance in your career and grow your expertise, the more people will expect you to have an opinion, and to voice it. I often joke that I am a professional opinion giver. Yet, having an opinion doesn’t mean dying on every hill built by that opinion. It means that you can build a reasoning about a situation, and you are able to communicate it and influence people. Of course there is a balance to find between “my way or no way” and being a push-over.

Remember that you have been hired not just to do something, but to have a professional opinion about what you do. If you are not in an environment where it is safe for you to ideate or have an opinion, then it is time to move on. I left Okta because my ideas and opinions were not just ignored, they were censured.

It’s not Time Management, but Value Management.

As you girl-boss harder and harder (aka advance in your career), the number of threads you have to simultaneously hold in your hand will increase. And it soon might feel like this:

What is valuable is not the same as what is valued - Manager Extraordinaire Liz de Moll

It was not enough to do time management on tasks. I discovered that I needed to do value management as well. If you focus your time on things that are valuable, but not valued, you are not managing your time well. Many projects and tasks are valuable, and it is tempting to work on them because you feel responsible, or nobody else wants to do it. However, if your performance tracker is full of valuable but not valued projects, you will stagnate. This becomes truer and truer the higher you go. I maintain a document, which I called “The Loom” (because of all the 🧵) to keep track of the status and details of all my threads (once a thread is done, it goes into the performance tracker. A captain knows no rest!). I sort The Loom from highest valued to lowest valued tasks. If you are not sure what is valued vs valuable, this is absolutely a conversation you must have with your manager. It is also crucial to understand who values what and why. If it is available to you, talk to your manager’s manager, and understand the larger political landscape around your projects.

Find Your People

Starting a new role at a new company - as a team of one - was very isolating. It still is. A girl-boss must rely on her network of colleagues and mentors. That’s what I did. I had a few friends from graduate school who are very knowledgeable in AI Governance, and they directed me to open source documentation, built my vernacular, and oriented my thinking and ideation. Being the captain of your own boat means to 👏 ASK 👏 FOR 👏 IT 👏, and that includes support from your network.

In the search for my people at work, I have found that being humble and honest about my ignorance and generous with my knowledge and time has fostered positive and willing collaborations. We all want to achieve something, and few can achieve it by themselves. So let your people find you too.