Startup Weekend Made Me A Better IT Leader

You'll be amazed at what you can learn when you push outside of your comfort zone.
One of the most worthwhile things I've done for my job recently doesn't have a lot to do with my job description. As an organizer for a Startup Weekend in my city, I confirmed what I know about enjoying work, learned more about business agility, networked with people who might help me in the future, and strengthened some of my weakest skill sets.

What the heck does Startup Weekend--where attendees go from idea pitch to business implementation in 54 grueling hours--have to do with being an IT leader? More than you might think.

In the dystopian world of large organizations, I run into "work sucks" a lot more than I'd care to. Well, work doesn't suck, and hanging out with 50 entrepreneurs on Friday, Saturday, and Sunday reminded me of that. As Startup Weekend facilitator J. Ramphis Castro pointed out at the kickoff of the event, "You guys just finished work, school, or whatever, and now you're here to work on something else. That's not normal!"

Among this crowd, it is normal. I can relate. When I first brought my future wife home to meet my family one Thanksgiving, she was bemused when my father and I disappeared upstairs for a few hours to repair a bathtub. Since then, she has figured out that work is how the men in my family hang out.

That's exactly what my organizer perspective allowed me to observe at Startup Weekend: Lots of people working hard, pushing the ball forward, but having a great time doing it. Some of the large organizations we work at have a sickness that makes people believe that work must suck. But when you spend time with people doing something meaningful, work is awesome, and whether or not those people matter to you when you begin, they will matter to you by the time that you accomplish your objective.

[ The startup life may be calling to your top employees. Learn How To Keep Your Best Talent. ]

Startup Weekend also taught me a lesson or two about agility. It's not that I learned about building interest and group action, or when to buy instead of build to save time, or how to rapidly resolve team issues. I was exposed to those lessons last year as a Startup Weekend participant. As an organizer this year, I saw firsthand how the large organizations we approached to sponsor or participate were paralyzed, not because they didn't want to participate, but because they couldn't get approvals in time. I'm not talking about government organizations like mine; I'm talking about large, successful, private-sector companies. Those of us who work for large organizations must figure out why things take so long and how to fix that.

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One way might be to expose yourself and your people to startups and how they operate. At the InformationWeek 500 Conference Sept. 9 to 11, the CEOs and founders of five hot startups (Appthority, CliQr Technologies, CrowdStrike, Hearsay Social, and Platfora) will take center stage to give the CIOs and other IT executives in the audience a lesson in agility--if those audience members are willing to get jostled outside of their comfort zones.

As a Startup Weekend organizer, I pushed myself out of mine. I offered home hospitality to our facilitator; Startup Weekend is a not-for-profit event, and paying for an expensive hotel room isn't in the budget. Who knew if he'd be a wild man or not! But it was an amazing experience to meet and spend a lot of time with this Puerto Rican entrepreneur, take him around town, and bring him to a business meeting before the event kickoff (where, by the way, he helped to solve a problem).

I pushed myself to acquire sponsorships for the next Startup Weekend in my city, something that I'm frankly terrible at. But I got better. Will that experience help in my role as an IT leader? Probably. If I'm honest about it, I'm just as terrible at asking for budget dollars as I am at acquiring outside sponsors. I need to get better at both.

Entrepreneur Jason Fried recently suggested that companies introduce change, like seasons, into their workplaces. His software company, 37signals, designated the month of June as "work on whatever you want" month. He says it was incredibly productive. (If you read no other book this year, read his Rework, written with David Hansson.)

Most of us can't take a month at work doing other stuff, but surely we can spend 2%, 5%, even 10% of our time on speculative projects that may have no apparent immediate benefit but have the potential to take our organizations out of their humdrum zones.

You don't have to organize a Startup Weekend. Just make an extra effort to do something new that allows you to grow as a leader at your organization and in your community.