What have you learned?


We were sitting around a big table at 9am, and our meeting moderator (for lack of a better word) asked us what we’ve learned from our time at iwantmyname. These sorts of questions always lead me to the same initial response — a deep groan — but I marched on.

What I’ve learned at iwantmyname is that people in small teams naturally try to fill in cracks. In large organizations, there’s redundancy everywhere, but when the team is lean, people are forced to step out of their comfort zones. And that presents a huge opportunity — if you find success in those new roles, your career, and the company can blossom. But if you don’t find success, and if the team doesn’t have the skill or the time to help you succeed, it can make the entire company struggle.

Small teams are strange animals.

The second thing I’ve learned is that remote teams don’t function well when your idea of planning is to get into a room for a few hours and come up with a plan that’s going to perfectly guide you into the following year. And honestly, that might not even be a remote-team issue — perhaps this took me far too long to learn, but successful projects require a guiding hand at all times. Like raising a child, everything is messy, always. You can provide a rock-solid framework, but without patience, flexibility, communication, and some real creativity at key moments, even the simplest tasks can slow to a crawl.

Without management, reality is sort of like the Lord of the Flies. You don’t need a military-like structure, but someone has to have an overview of what’s going on, and someone has to be in a position to make hard decisions when forks-in-the-road occur.

The third thing I’ve learned is closely paired with the other two things I’ve learned — when hiring, you can’t place enough value on people who simply want to do a particular task very well. I think it’s natural for startups to yearn for unicorn employees that, by force of personality, will take the company to “the next level” or something, but ambitious dreamers often require some structure to confine that creativity. And when it doesn’t exist, it’s like a leaky hose. Ideas splatter all over the place, but there’s less water at the end of the day to feed the plant.

Sometimes I think I fall into that category — I spend so much time plotting the future that I naturally don’t have as much output at the end of the hose. Perhaps in the right structure I wouldn’t be so leaky, or perhaps my hose is on the wrong hose socket. This all makes sense in my head…

Anyways, what’s important is that balance is key. A team of doers will do, but can often come up short when it comes to thinking out of the box. And a team of planners can often plan themselves to inaction.

My opinion? Society has molded us to all want to be the next Steve Jobs, but we all can’t be f-ing Steve Jobs. Honestly, most of the great things society has produced don’t come from a deity-at-the-top structure. The best things in the world come from artisans who can rely on a management structure to clear their plates of all the bullshit that takes their minds off their work. Creative freedom with a guiding hand produces the best product, nearly every time.

So when you’re hiring, be very clear about what you actually want. Do you find yourself posting jobs for “full-stack devs” when all you really need is a focused CSS specialist? Are you looking for a “marketing rock star” (ugh) when all you really want is a talented media buyer? Generalists can be quite useful, but it’s not all that hard to be pretty good at a lot of things. What’s hard is to be really really good at exactly one thing.

Be clear. Be focused.