Learning How to Lead

If it doesn’t feel like drowning, you’re probably doing it wrong.

For a long time (longer than I’d like to admit), my primary responsibility was mastering the craft of design. From identity to print or Web design, there was a lot to learn. Branding. Layout. Typography. Color theory. Substrates and printing techniques. Technical requirements and limitations for the Web. These are all things I could spend a lifetime perfecting, only to remember that there will always be many people who are far more talented than me.

Then I ventured into the vast world of “UX” (mostly by accident). There was even more to learn. User journeys. Site maps. Information architecture. Wireframes. Content strategy. Functional requirements. The list of artifacts and specialties were endless! My only saving grace was that I was a halfway decent designer, so my documentation looked better than most. Still, it was yet another universe dominated by extraordinary talent.

Fast forward to 2016. I somehow landed a job at a startup company with a fancy title. I had experience designing things. I could do UX stuff. And by this time I had enough industry experience to somewhat understand how screwed up online advertising had become. Only now I was responsible for doing all the design things, prioritizing projects, hiring people, and getting shit done. It all sounded very exciting and important (because it was), but leading was a new frontier.


After several months of pretending to know what I’m doing, I had a meeting with a newly-formed-but-loosely-defined team. My grand vision was that we’d figure out our Experience Design Process in a 1.5 hours on a Thursday afternoon (because, um, we never had one to begin with). Instead, I quickly realized that shit was all fucked up, people had no idea who was responsible for what, and our collective activities felt more like an exercise in chaos theory. We barely even got to the actual process stuff.

So, I obviously felt pretty terrible at my job. Again. Only this time there was no hiding behind pretty layouts and clever copy.

But you know what? It was a very good thing that happened in that meeting. I learned in that moment to embrace my deficiencies and failures. It was no longer about my portfolio, my reputation, or my experience. This was about other people – super talented, immensely dedicated, very motivated people (if I had done anything right, it was hiring). This was a mess I honestly could’t fix on my own. I needed help. Because the problem had nothing to do with “managing” people.

It was entirely about supporting them.


In the days since that awkward, very painful meeting, I’ve been focused on the team’s success instead of my failure(s). There’s still a lot to do, and much more to learn. But I’ve started by trying to understand the challenges before prescribing solutions. My job, it turns out, is not to have the “right” answers, but rather involve those who actually have the experience, skill, and vision.

After several months in this role, I’m just now beginning to grasp how limited I am on my own, and how all the help I could ever need surrounds me in abundance. They are the answer. I am not the solution.

I’ve always had a knack for learning things the hard way… But this time, the truth never hurt to good.