Hello Generalist
Interview

Evan, Former Youtube Chief of Staff, Ops for Google's Area120 Incubator

canva headshot of evan from presentation

You’ve likely heard Maya Angelou’s famous quote, “At the end of the day people won’t remember what you said or did, they will remember how you made them feel.”

I think we intrinsically know this is true, but research backs it up. The exact number is argued, but somewhere between 55 - 90% of all communication is nonverbal. All the data points you labored over in your deck? Almost entirely forgotten. But the feeling they left? That remains.

What would happen if you really leaned into this idea? Cliff Cate, Yelp’s GM and my former manager, was the first person I worked with who really took this idea to heart — Cliff prepares for many meetings not just with an agenda of points to make, but with an intention of how he wants people to feel on the other side (motivated, inspired, ready to fight, ready to dig in, like there’s a correction to make, I could go on). He’d optimize hard for that feeling. It was incredibly effective.

Today, I’m thrilled to introduce you to Evan Gelfand, a Hello Generalist member who’s spent years experimenting with this in his own right.

Evan’s a bonafide business generalist, with time spent as Chief of Staff at YouTube, marketplace supply lead at a Greylock-backed startup, eComm lead for a Google-incubated startup, and not to mention time as a PM, Experience Designer, and Product Marketer. These days, he’s building his fractional book of business, helping early to mid stage teams with all things ops (you can hire him on HG!).

But perhaps the best lead in I could give — While recording, Evan and I joked that an alternative title for this issue could be Zen and the Art of Startup Maintenance, or perhaps Just Make ‘em Laugh. I know you’ll enjoy!

Drop 1. Qualities that may not “fit in” can lead to unexpected payoffs

This was a competitive advantage for me, but at the time had to be extracted because I didn’t realize the opportunity! For so long, I thought fun was a distraction because it wasn’t “professional,” wasn’t what I saw all the people who were building stuff and getting shit done were doing.

I had tried to fit the mold of what I thought others wanted from me. I spent so much time trying to be someone else. And when the pandemic hit and I could express this part of my personality at work, I realized, oh! Not only is this a fun thing to do, but it’s an impactful piece of the organization, and help others work together more effectively.”

Take it back to your team:

  • Evan gives a simple, free example of bringing the fun: a rhyming email series dubbed WFH Gnome that went out to 1000s of people across Youtube. Are your internal comms buttoned up, serious, tedious to read, or are they a joy?

  • The silliness of WFH Gnome cut through — it was different, it was authentic. His team across not only participated, but reached out thanking him for bringing a bright spot to the weird first year of Covid.

  • Evan came to realize that his natural strengths - the ways he actually liked showing up - actually integrated perfectly into his role. Take the risk!

Drop 2. Using incongruence to your advantage

My model could have easily been ignored, but it contained a set of decisions that would be helpful for all parts of the company: product, operations, customers, design, eng. As I was preparing for our offsite where I would share this model, I decided to call it something memorable: I called it the THICC Model! It was one of the most remembered things from the offsite, and everyone understood what it represented for our business.

Take it back to your team:

  • Evan brought humor to helping the company learn about their marketplace’s supply quality issues — he needed the whole company to understand what was happening, as opposed to tuning out during a busy offsite. In his case, humor did the trick, but he argues for leaning into incongruences to make a bold point.

  • We typically think of the Expectations vs Reality Gap in a negative way — you miss an expectation and hell breaks loose. It’s the opposite in this example — His team expected his offsite presentation to be, well, boring. The gap between a boring presentation vs revealing his THICC model made the point really sticky.

Drop 3. Cooking (creating) vs cleaning (fixing)

I’ve realized that there’s this difference between cooking, like creating, and fixing, which is like cleaning.

When you’re cooking, you’re throwing everything in a pot, splattering sauce everywhere, and it’s super fun because you deliver this meal and everyone feels full and satiated. But then afterwards, there’s a mess to clean up, and not for some people, they love the joy of cooking. And some people love the order you get from cleaning everything up, spotless countertops, everything in it’s place.

Startups and tech really glamorize cooking. But for everything you cook, you need to clean.

Take it back to your team:

  • Startup land tends to glamorize cooking, or building from scratch. But for everything you cook, you also need to clean.

  • As Evan says, cleaning can be quite joyful: The bad thing has happened, and you now get to pick up the pieces. He makes a great point that many people overlook this clean-up work in anticipation of the things they get to build next instead. When there’s a cleanup situation, are you recognizing your team’s effort as much as when they’re cooking?

Drop 4. Turn your kryptonite into your superpower

I started as a PM, did product marketing, was a Chief of Staff, ran ops, was an experience designer… I have a very broad set of experiences! I can’t shy away from it, I can’t try and fit into the mold. It means a lot of jobs might not be a fit, but when I find people who are open to something that’s a little different, it’s clear there’s a lot that can be brought from the roles that I’ve had.

Take it back to your team:


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