5 Project Management Lessons Learned at the Overnight Web Challenge

by: Myles Dannhausen

The sun was peeking over Grant Park and into the windows of Chicago’s Roosevelt University, but the web pros taking part in The Nerdery’s Overnight Web Challenge on November 18th weren’t yet ready for the light of day.

They were 21 hours into a crash course in project management.

At 9 a.m. the previous morning, 10-person teams of web pros were assigned a nonprofit to work with, charged with re-designing the organization’s website – for free – in 24 hours. The process would normally take months, and cost anywhere from $15,000 to $40,000.

I sat in to observe much of the session, stealing coffee, donuts, and a turn on the Donkey Kong arcade game brought in for the night. Here are five valuable lessons in project management I learned at the Web Challenge.

1. Dive Deep Early, Save Time Later

It’s natural to want to get right to the design of the site, but even with just 24 hours to work with, the teams at the Web Challenge each took at least an hour to learn about their nonprofits and what they needed to get from their website. That guided every decision – and every valuable “no” – throughout the project.

“The most successful teams usually have someone who serves as the nonprofit wrangler, who can communicate clearly,” explained Nerdery Vice President of Marketing Mark Hurlburt. “This is often not a techie, because the tech guys can sometimes lose the nonprofit.”

Copywriter James Cardis was part of the Midnight Reapers team that worked with the North Lawndale Employment Network (NLEN), which helps inmates who are recently released from incarceration to find jobs. As I nosed in on the group about two hours into the challenge, Cardis outlined the feedback NLEN executive director Brenda Palms-Barber gave his team. “They vet all of the employees, and they pay the first three months of their salary to incentivize businesses to hire them,” Cardis said.

The team was pressing Palms-Barber for more specifics. “We want to sell our services as a good business move, not as just some nice thing an employer can do for people,” Palms-Barber explained. “We can help them reduce turnover, lower costs, and find good people. We want employers who visit the site to know that, and we want clients to sign up for our events.”

Cardis said this feedback was invaluable. “That’s important for us to know as we design the site,” he said. “They’ve defined their expectations very well.” By being thorough at the start, the team lowered the risk of having to throw work out the window halfway into the project.

2. Designate A Decider

If you don’t want your project bogged down by minutia, you need someone to go to who can make quick decisions. In nonprofits – where boards, donors, and staff all demand input – it’s even more critical for one person to take responsibility. The Nerdery requires that each nonprofit send someone empowered to make decisions.

“You can’t do this by committee and accomplish what we want to accomplish in 24 hours,” said Mark Malmberg, The Nerdery’s communications manager. The Nerdery also limits nonprofits to just two representatives. This keeps discussions focused and eliminates time-wasting tangents, important in projects of 24 hours or 24 weeks.

 3. Know Your Limits

Keep the project on scope, and make sure your client knows what that means. If you want to complete the project on time  (and who doesn’t?), don’t waste time on ideas that are far beyond the budget, your capabilities, or the client’s resources.

“We told our nonprofits not to ask for the Taj Mahal,” Malmburg said. “You have to manage expectations somewhat so you can leave here with a quality site, not a ton of unfinished business.”

Patrick DiMichele, assistant director of user experience at Manifest Digital, was taking part in the Web Challenge for the second time. He served as project manager for the A-plus team, which worked on the site for Court Appointed Special Advocates of Cook County (CASA).

“Right away we identified their short-term and long-term goals for the site,” he said. “That helped us carve out a wish list so we could prioritize what we could do in 24 hours, and what they could build into the site down the road. It’s important to give the client clarity on that from the start.”

4. More Isn’t Always Better

The Nerdery Web Challenge features teams made of 10 members, but even with so much to do so fast, DiMichele said 10 might be too many. “We’re not convinced we couldn’t go further with half as many team members,” he said. “Two people working on the same aspect isn’t always most efficient.”

That’s because one skilled person with a strong vision can go a long way when they don’t have to sell it to another person.

5. Hide Your Mess

DiMichele said it’s extremely helpful to have the deciders in the room to make key decisions and provide feedback, but there’s a limit to how involved they should be. “We pulled our back-end developers apart early on,” he explained. “What they’re doing looks like a shit-show – until it doesn’t. We don’t want the client to freak out at the work-in-progress.”

As the saying goes, nobody wants to see you make the sausage – they just want to taste it when it’s done.

A New Development Model?

As I watched the teams do so much, so fast, so efficiently, I wondered if this condensed process could work as a business model. Being on the client end of many web projects, I would be more than happy to sign up for a development marathon if I walked away with a quality site the next morning.

Malmberg and Derheim each chuckled when I suggested this. “We haven’t really considered it,” Derheim said. “It’s an interesting idea, but I don’t know how long we’d keep our engineers if we asked them to work this way all the time.”

About the author Myles Dannhausen @MylesPulse
Myles Dannhausen is a writer living in Chicago who has contributed to Running Times, Gapersblock, Chicago Athlete, and several other publications. He is also a content strategist at Lightspan Digital. A former restaurateur, basketball coach, and proud small-town news editor, he also helped launch the Door County Half Marathon. You can find Myles on or connect with him on Twitter and Linkedin.

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