Three Years at GitHub! 🌶️

As we all know, there isn’t enough “thought leadership” content from leaders in tech, so here I am doing my part to fill the void. You’re welcome, internet.

Ok, open with a joke, done ✅

I’m celebrating 3 years at GitHub. I joined in December of 2020, finally having regained my ability to smell and taste, ready to dive into a new adventure after The New York Times.

Working at GitHub at the intersection of design and code has been a dream. As a Staff Design Infrastructure Manager leading the Primer Design team, I can list off endless bullet points of things I have had the pleasure of being involved in over the past 3 years — shiny teams and initiatives from Brand, to Global Navigation, to Accessibility. For this post, I could have written a somber reflection of how we’ve grown, evolved, innovated, and what incredible things we’ve shipped. I could have also filled infinite pages writing about the wonderful people I get to work with every day: unreal talent, incredible minds, and some of the kindest and empathetic individuals on the planet. But, because it’s my party, this post is going to be something different.

Hot takes. 🌶️ Yep, you heard me right. My love of hot takes and vaguely quotable slogans precedes my time at GitHub, as evidenced by my Shop Talk podcast with the delightful Dave Rupert and Chris Coyier https://shoptalkshow.com/434/, a love only rivaled by my enjoyment of giving the internet unsolicited advice sprinkled with sarcastic humor. So, in that same spirit, let’s do this.

I won’t trigger my own existential crisis by calculating how many hours I’ve spent in Zoom repeating myself. Instead, I’ll “open source” a few of my most repeated lines and what I mean by them. So, if you’ve worked with me over the past 3 years, odds are, you’ve heard me say one of these things:

• “Guidance, Governance, Guardrails” I’m a design system manager. Odds are, I’m going to ask questions and recommend something from one of these buckets. How are we mitigating risk? How are we maintaining and ensuring quality? How are we driving forward innovation? I will probably end up printing this on a tote bag at some point.
• “What are the incentives? Who will be accountable, and how?” Majoring in psychology is the gift that keeps on giving. Everything is people. Want to understand a company’s values and culture? Take a look at what is rewarded and who is held accountable. Want to set up a project for success? Make sure the incentives line up and someone is accountable. Ultimately, most people will take the path of least resistance or optimal outcomes for themselves most of the time. Nothing personal, and yes, this includes you and me.
• “I trust you” Hill I will die on: micromanagement is a poor coping mechanism, and is the fastest way to lose and offend talented people. Instead, hire good people, empower them to do good things, get obstacles out of their way, and if you can’t, make sure they don’t run into those obstacles.
• “No” Being able to say no effectively is a critical skill. I am okay with being disliked.
• “There’s always something clever we can do” Always bring a solution. Don’t accept defeat. Don’t brute force a solution by throwing resources or time at it, think through all lenses and possibilities. There’s always a clever path forward.
• “Us vs the Problem” I printed it in big bold letters on a giant slide during my Clarity Design Systems Conf 2020 talk, and I’m still saying it to this day. Life (and our roadmap) is too short. Let’s solve the problem together, no throwing anyone under the bus.
• “Timing is everything. Don’t fight the tide” Totally a metaphor. No one can fight the ocean. See when it’s time to focus on blue sky thinking or when it’s time to zoom in and be relentlessly pragmatic. Don’t drown, caught in the riptide, trying to do one thing when it’s really time to do the other.
• “No one reads” If you want people to do something, make it easier. Written charts, docs, process, guidelines don’t matter if they increase cognitive overhead. If your change adds complexity and is “one more thing to remember ‘’ then it won’t be adopted.
• “Constant vigilance is not a strategy” Systems systems systems systems systems. A person “keeping an eye on things” is not a system. Solve things with technology, automation, tooling, cleverness, literally anything but telling someone “that’s not a good time to take a vacation.”
• “Protect your energy” Focus on what I can control. Don’t throw your energy into the void of hope — observe what people do, not just what they say or intend, and respond to that.
• “All of this should mean something” Live your life. Don’t lose sight of the fact that people are spending their most precious, non-renewable resource — time. Time that can be spent with their children, on their hobbies, petting pets, taking care of their communities, planting milkweed for butterflies, anything. Respect that time, respect the gift of their work, and do everything you can to make sure that whenever people move on, they leave better than they arrived.

In conclusion….

Not sure how to end this other than with a message of deep gratitude to all of the people I work with. ❤ Cheers, Hubbers!