Reflecting on #CaaSH: Looking Back on the First Time I Helped to Organize a Hackathon

It has now been a week since CaaSH, the City as a Service Hackathon kicked off. I had such an exhilarating time, and won’t soon forget the first hackathon I helped organize. From the organizing team, to all the new project teams, it has been amazing to see these collaborative groups come together. I am very excited to see what the teams have to show in a couple weeks, after a month long sprint. This will focused on my experience with organizing the event-so far.

My last post was an attempt to let people know I was still active, dropping a line to touch in. These last couple months have been a lot of fun, albeit at the expense of many items on my to-do list. But, that’s one of the reasons I’d do it again in a heartbeat.

My original interest in joining the hackathon planning group was to offer help the day of. To arrive early to move things, get set up and help check people in. Well… I did do that. But, I ended up doing more. A lot more.

On a daily basis, my agenda had time critical actions. It became a second job for me, forcing me to learn how to effectively manage my time both at work and at home. (My wife may disagree, but I’m getting better!) My time as a teacher helped with this, but that was one job. This project felt as if I had two jobs. Also, teaching was more of an individual endeavor, whereas CaaSH was a team project.

My office utilizes shared drives and shared documents, but we do not use much else for collaboration software. We use SourceTree for Git, but my role doesn’t offer me a chance to make commits often. Working with CaaSh opened my eyes to Slack, and wow is it fun. I’ve used Slack some with my other Code for Philly project, Leverage, but much of the hackathon planning happened through our dedicated Slack channel. The group has a great sense of humor, and I learned the fun aspects of Slack like custom emojis and giphy posts. But I also learned about polls and how to archive important posts and integrate tools.

Slack is fun and incredibly useful, but there were other tools used that aren’t as snazzy. Google Docs/Hangouts, Trello, and Uber Conference allowed the team to share information in real time and meet without having to be in the same room.  Far quicker and in a more organized fashion than had we relied on emails or in person meetings. Many of the organizers met in real life for the first time the day of the event.

Making the logo was an exercise in patient iteration. As I mentioned before, being an art teacher, especially at multiple schools at once, much of what I did felt like it was working in isolation. I would do what I could to help with overall climate and single school objectives, but my classroom was my classroom. It was the only one that was an art room. Planning the hackathon was a great team project. I was able to feel as part of a team in a professional manner more so than any other time I can remember. Every time I submitted a new iteration of the logo design, I felt that I needed the team feedback more than I needed to be finished. What I was doing would represent the project as a whole, and by extension, the people who were working so hard to help plan. I needed to hear their voices for me to feel finished. No matter how good the design might be, if they didn’t approve, it didn’t matter.

I guess you can see how much of an impact this team approach left on me. While most of this post has been about what I learned, this project was about the team’s efforts. Dawn McDougall, the Executive Director of Code for Philly set the tone early. Dawn has been organizing hackathons for Code for Philly nearly by herself, so this was a chance to delegate one for the first time. She made sure to celebrate each person. She also allowed some autonomy for taking the lead on anything someone wanted to work on. That isn’t how most companies work-at least not those that where I’ve worked. The fact that I had a chance to explore areas that I might find interesting was an invaluable experience. Each person on the team contributed based on their interests and skills. Not based on job title. As someone who often gets frustrated with bureaucratic workflows, this was a breath of fresh air.

There were mistakes along the way. Nothing I can think of as egregious. More like learning opportunities. I did end up doing what I originally set out to do, but am so thankful for the chance to do so much more. I had no intention of creating a logo, taking the lead on social media, or running a twitter chat. Both personal and team success from this event means I’ll be looking to work on another hackathon soon. Or, maybe I already am…

Reflecting on #CaaSH: Looking Back on the First Time I Helped to Organize a Hackathon