The Greenest Person in the Room

As a broadly curious and enthusiastic leader, how do you make decisions about opportunities to challenge yourself? Do you have a go-to framework to evaluate networking opportunities, mastermind groups, or professional development events? 

In 2017, after almost five years spent flourishing in my dream role, I began the emotional process of trying to decide what came next. I had grown exponentially, along with the company, from employee #4 and Chief of Staff into COO. I began my discovery process by networking my butt off and using each new meeting to identify what about my experience was most valued in the marketplace. I knew I wanted a role in tech and I consciously kept myself open so that I could maximize the chances of finding the best leader to join. I started to describe my search as “looking for a new set of teachers”, a phrase that resonated with my new connections and prompted discussion about which subjects I was hoping to learn. 

I found my new set of teachers in tech and had gotten what I wanted most: an opportunity that would force me to level-up in every area.

Somewhere between my two favorite pieces of advice “be the dumbest person in the room” and “you’re the average of the five people with whom you spend the most time”, I settled on my personal philosophy to try to always “be the greenest person in every room”. “Dumbest” isn’t allowed in my self-talk track and I like that greenest implies both naïveté and fresh perspective. 

In my new role, I was truly the greenest person in every room. I was new to the industry, to enterprise software, to the company culture, and to a leadership team that had bonded over the previous 4+ years. I prided myself as Chief of Staff in being able to hold my own at every table: finance, marketing, product, people ops. I came into my new organization fluent about what worked best at my last company, but unable to immediately plug-in and keep up. It was excruciating and humbling. 

If you’ve worked in a startup environment, you’ve likely witnessed (and perhaps enjoyed!) title inflation. You were probably more proximate to the highest levels of decision-making than you would have been in a corporate job. These are just some of the reasons we pursue roles in startups. They’re wonderful opportunities to accelerate your leadership skills by doing, rather than observing. But as we continue our careers, I caution us to “check” ourselves. Just because we held a big title, it doesn’t mean we made it. To meaningfully challenge ourselves we have to check our egos, jump into a bigger pond and adjust to life as a smaller (for now) fish. 

Unsurprisingly, I’ve learned the most (and the fastest) when I’ve been most uncomfortable. Earlier this year I landed a role that is forcing me to level up again. Six months in, I’m still out of my depth with my brilliant subject-matter expert colleagues. But that’s the fun of it all, isn’t it? 

This is exactly why I’m committed to maintaining my “greenest person in the room” philosophy for the rest of my life, in all areas of my life. 

I want to be a better reader, so I joined a virtual reading group full of absolutely brilliant people. 

I want to hone my skills now so I can be an effective board director in the future, so I’m proactively connecting with powerhouse directors to learn from their journeys. 

I’d love to know: have you consciously put yourself in a situation because you knew it would force you to grow? How did you find that situation? Did it work?