Running an Enterprise Hackathon

Chase Doelling
CA\rABU Life
Published in
7 min readMay 5, 2016

Hackathons are beginning to emerge within larger organizations to give passionate engineers an opportunity to show that they can solve tough problems, explore new ideas and remove roadblocks to make their day jobs easier.

Before you start organizing an enterprise hackathon, take a peek at some key ingredients I’ve found that will help you set up a successful environment for innovation — versus coercing your employees to stay later than usual.

1. Safe Pitches and No Secret Backlogs

Allow employees to create and define what they want to see in the world and in the company. Nothing kills a passion to solve problems faster than scoping the work down into a defined user story. A hackathon is a chance for people to learn new technologies and test ideas, not get to Monday morning faster.

Trust them to work on the most important things. Not everyone will agree on what is “important” to either the business or the development team. Every hackathon project isn’t right the first time and likely takes some iterations to see what works and what doesn’t. If the project is too audacious or too technically challenging, teams will know and adjust accordingly because done wins every time.

2. Everyone Demos

How will I know people are actually working on projects versus goofing off for two days? The proof is in the pudding and the hungry will show up. This is a chance for some limelight that doesn’t usually occur in most organizations; many people are eager to show what they can do technically and how they can contribute to the organization. Having everyone demo represents a commitment to the event and to your peers.

3. Stack the Judges

When setting up the judging panel for the event, aim for the highest titles possible for organizational visibility. This will increase the visibility a group gets to show off their thinking and simultaneously allows senior management to see rising talent. There’s also the side benefit of seeing if any of the projects might have potential to become its own product or service.

4. Not Just for Engineers—Involve Others

Communicating the perception that a group within the company is going to get food, prizes, and energy drinks—and get to build things they want—puts you an advantageous position. Use it to invite others. Great hackathon teams that create value in a small amount a time are not lone wolves. It takes a team with a cross section of skills, talent and knowledge; and more often than not you need to look outside your group and department. Can sales tell you if it would make customers excited? Can marketing spruce up your presentation? Can UX help simplify your demo? Go ask.

5. Create Hackathon OGs

OG: Original Gangster

If you are like most organizations and can only run events like these annually or every six months, put a date on it. The detail is subtle but if hackathons become an ongoing event, people will want to show that they were there at the beginning. They’ll hang on to that shirt, poster and plaque with a sense of pride. Note: if you want people to wear it more than once, invest in quality shirts. Expensive, but table stakes; make room in your budget.

6. Healthy Code, Healthy Snacks

Credit: Mashable

Hackathons have gotten a bad rap lately that they’re fueled by pizza and beer and unhealthy habits that result in a coding hangover. And it’s true. You can’t function as a human if you don’t eat human food. When organizing your hackathon, aim for protein bars, nuts, fruits and treats that don’t make you sound like a German scientist when you read the ingredients. Sugar and carb crashes don’t help people intently focus for long periods of time.

7. Watch for Poachers (Food and Toxic People)

This one might seem silly, but if you’ve ever worked in an organization that goes past Dunbar’s number, people come out of the woodwork to take food, swag, time and attention. Treat your hackathon (or any special gathering) like a nature preserve. You don’t feel special if Steve takes snacks and goes back to his cube. You don’t feel special if Stephanie comes in to ask the same question from an email. If you can, take your event offsite, even a room in a different department will drastically reduce the poachers.

8. Don’t Skip the Small Things: The Most Expensive Part is Over

If you’ve created the time for people to learn and improve, don’t get caught up in the hard costs. Its easier to track food, snacks, prizes, etc., but those are usually a factor of 10 smaller than the cost of people’s time. People know when you get bad T-shirts, people know why you get just pastries for breakfast, people know why you get Starbucks gift cards. If you take the time, make it special.

9. Facilitate Like a Boss : Timing is Everything

Hackathons are just time boxes—the deadline is what makes it special. You must be the champion of the deadline, set the rules, set the agenda and stick to it. The difference between the enterprise and the weekend startup is projects that are successful must fit the timeline. Teams don’t have the luxury to keep going on the side. Make sure teams walk away with something scoped and tangible. Note: Be especially strict about demo time because people like to explain every nuance.

10. Permission for the Unique

Better chilled, unbearable warm

Creating space for innovation doesn’t come very often, so bring in unique elements that become their own artifacts. A good friend of mine started bringing in Bacchus-D to hackathons. Now we try to get a bunch of random food and drinks for people to try. Not sure what to order? Try a food truck. Get a local massage therapist to come in for breaks. Have $30? Buy a flying shark to fly around. It doesn’t take much.

11. The Best Prize? Funding.

Drones, awesome. VR Gear, sweet. Smart watches, why not? But the best prize an enterprise team can get is funding. We helped a well-known software accounting firm run a hackathon last year and the CEO stood up and granted six months of time and funding to the winning team to vet the idea. The room was deafening. Not only was the team ecstatic, but it sent a clear message to the entire R&D organization that innovation will be rewarded.

12. Water Cooler Success Metric

One of the first questions I ask customers when working with them to set up their internal hackathons is: How would you measure success on the investment? The best answer I got was from an international storage and cloud computing company executive, “If it changes the conversations at the water cooler, I’ll be happy.”

Shaping the culture of large organizations is a job for consultants with many acronyms following their names. It’s hard, and often the best way to improve the relationship is like any other: actions speak louder than words. A hackathon (done well) can be one of those small actions—a catalyst to influence the water cooler and shift to a culture of creation.

13. Show Your Awesomeness

Record the demos and share them. Make it GitHub public. Send winning announcements wide. Show your stuff. Talk about it. Take pride in what you built, what the teams built and what you can do.

14. Go Zombie Hunting: Fake “Hackathons” Hurt

Tell it Inigo

Hackathon is a buzzword, no argument there. Like any other buzzword fate, people use them to make other events sound cool and exciting. Hackathon is probably one of the biggest offenders in organized tech events. I’ve attended “hackathons” internally and externally that are time-boxed death marches. They suck.

Be judicious. Gathering the troops over a P1 bug is not a hackathon. Working on what a large customer needs is not a hackathon. Putting people in the same room to solve X problem is not a hackathon. Shit happens.

Its OK to stop everything to stop the bleeding. Its OK to have war rooms. Its OK to kill hackathons to solve actual problems. But call it what it is. People will appreciate the transparency and come better armed.

--

--