Not every master plan is truly genius. Not every scheme works. Entrepreneurs know that better than anyone.

Last week in Brooklyn, New York, a panel at the Northside Festival explored that theme with a panel presentation called "Sh*t That Seemed Like A Good Idea At the Time But I'd Never Do Again." 

Panelists Kellan Elliott-McCrea, chief technology officer of online craft marketplace Etsy, and Liz Crawford, CTO of curated products company BirchBox, entertained the crowd with stories of lessons they learned during their years of building start-ups. 

Build Teams While Building Products

When you're starting up, keeping a step ahead on staffing up seems less important than getting your core product right. But it's actually just as central to your long-term success.

"Don't ignore team-building. Your product will change over time, and you'll need a team to support it," Crawford said. "Modify your standards for hiring to build a great culture, because engineers look forward to working with people with good personalities who are really smart--don't break that."

And on-boarding good engineers takes significant time, she says. So, you'll want to keep the great talent you do have by keeping a fun and stimulating environment--even for those engineers working remotely.

"We have 10 engineers, and three work remotely, so we keep some fun conversations on IRC (the Internet Relay Chat instant messaging system). We have a 'channel bot' that says funny things, and that makes a difference to culture. We use to listen to music together, which makes the team feel united."

Elliott-McCrea added a counterintuitive piece of hiring advice: hire from your social network. He also encouraged blogging about your culture and your team, so people who want to work for you can find you.

Celebrate Big Failures, and Don't Assign Blame

Aspiring CTOs should "Make failure, and then embrace it," said Elliott-McCrea. "One way we do that is to give awards for the best (or worst) failure of the year on our team. At Etsy, we actually give the winner a 3-arm sweater."

Elliott-McCrea explained this year's "winner:"

It was a method to try to manage site abuse. A common form of abuse is automated account creation on the site. Spammers create multiple accounts then send messages to users. If we see too many accounts from a particular Internet address, we block it, and we ban the accounts that were created. Then the next week we ran a script to test this system, from our own offices. Suddenly, everyone in the place was getting notices that their Etsy accounts had been deleted, including everyone who had ever logged in from our offices  (like our investors.) We also have a team and partnership program, and when a "captain" was banned, their followers got messages that they are 'no longer a member of the Etsy community'--including our CEO. These notes went out to millions of people before we caught it. We have blameless post-mortems, where we try to make making mistakes cheap and easy and be fast to learn from them.

Forget School: It Doesn't Match the Real World

Crawford said her advanced education seems to not have contributed too much to her success working at a start-up: "I can read lots of academic papers and categorize things and it is a great skill, but I would never do it again. I don't regret coming to America and friends I made at Carnegie Mellon, but no more Ph.D. degrees."

Elliott-McCrea added: "You learn stuff about software in school, you learn a lot about algorithms, but almost nothing about software development. You need to learn abstraction, design patterns, scaling, and working...out in the world from a team."

Do you have other tips for managing technical teams in a start-up environment? Share what you know below.

Published on: Jun 19, 2012
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