Ramp up your productivity and host a hackathon. Here's how to do it.

This post is part three in a series on the features, knowledge and insight that came out of our “Practitioner Love” hackathon in mid-February. What do we mean by “Practitioner”? If you’re a writer, editor, marketer content creator or non-technical user of Contentful –– that’s you! To read more, click here.

Hackathons don’t have to be about losing sleep to create products or features that never go to market. Just weeks after hosting a two-day hackathon with the employees of Contentful, we’re releasing five new native and extensibility features that significantly improve our customer experience.

When you talk to tech industry insiders about hosting a hackathon, you’re often met with some resistance from all parties. Employees view the event as a slog; a clever ploy to squeeze more from already strained workers. Managers and those in charge might be burned from past experiences where precious hours were taken up creating non-viable features or products. When a good chunk of your workforce is tied up generating wild, speculative ideas, that’s not good for business.

Hackathon believers, Contentful included, know that with a bit of careful planning it is possible to run an event that results in tangible successes. Participant should have the space for deep and intense focus on building something they think is going to be interesting and useful.

There is no such thing as a failed hackathon project; failure is a vital aspect of experimentation and product development. We wouldn’t have the lightbulb if Edison had not conducted some failed experiments! In fact, if there are not at least a few failed projects, it probably means your teams aren’t taking enough risks.

So, how do you run a hackathon with excellent results? Don’t worry, we’ve decided to share our secrets. At the most basic level, hackathons are an event and should be treated as such. Start planning at least six weeks out, and don’t forget the follow up with a retrospective (complete with accountable parties) after the event to make the next one even better.

How to start a hackathon - one month out

Decide on a theme

Your theme is an integral part of your hackathon. In feedback from our event, more than half of the participants said that it was the reason they chose to participate, rather than the more expected motivators like prizes or time off regular work.

Your theme should be aligned to your company mission. It should be broad enough that it frees participants to choose something that is exciting and useful, whilst also guiding them towards the mission and your product road map. It helps to have a strong grip on your customer wants and needs; if you haven’t mapped this out already, do it now.

Our most recent theme was “Practitioner Love,” meaning it was time to romance the writers, editors, marketers and other non-technical users of Contentful. We wanted to have as many minds as possible obsessing over the problems our users were having with Contentful. What were the roadblocks to their productivity? How could we inject a little ease into their daily workflow? How can we boost confidence, supercharge creativity and make governance more intuitive and simple? This theme fit into our overall company mission and our goals for the year, while still giving hackathon participants the freedom to choose their projects.

Once you’ve chosen your theme, it’s time to document it and advertise around the company.

Research and preparation = viable products and features

The next step requires a little work, so bear with us. One month out, start anticipating the components you might need to deliver complete or nearly-complete products. Design components can create a significant bottleneck if you’re not including designers in the hackathon. Updating your component library helps the process flow a little smoother, and helps your teams demo their projects better. Contentful uses a design system, Forma 36, for exactly this purpose — you can check it out on GitHub if you’re curious.

Start planning your follow-up early to avoid projects being dropped after the event. This includes scheduling relevant stakeholders to help determine business value and ROI –– get in early, and be ready to weed out the good from the bad.

Think about:

• Your marketing strategy: Do you want to document and publicize your hackathon? Get organized with blog posts, videos and images. Come up with a plan for your marketing team to announce and publicize new features.

• The logistics: Book your physical space, set up your video links and organize your judges.

How to organize a hackathon - two weeks out

Smart incentives make a difference

At Contentful, we’ve seen people put in a significant amount of work into hackathon projects without substantial prizes or any prizes at all. If your employees feel loyal towards your company, they’ll work hard on a hackathon –– the ability to step away from their normal work duties is enough. Still, offering great prizes increases the stakes and makes the event even more exciting. Demos take on a shark tank-like quality as spectators root for their favourite projects, and participants are motivated to work a little harder.

Incentives don’t just mean prizes. Offer some time away from daily work duties. The worst outcome for a hackathon is that people work together for a couple of hours and then just go back to their desks. Providing a collaborative space with tables, power and displays can go a long way to keep participants focused on their projects. Give participants the opportunity to showcase their work to the whole company. Get your senior leadership team involved in the presentations; often, this is a great motivator for employees to display their skills and receive praise for good work.

Key considerations:

• Organize the fanfare: There’s nothing worse than attending a half-hearted event. Choose at least two people to be MCs. Think about how your judging panel will present the winners. How can you make this panel diverse? Will there be Oscar-style envelopes? Will all employees be encouraged to vote?

• Consider the scoring approach: What should judges value most? Sharing the scoring criteria helps teams focus on the right topics to work on. Figure out how to involve other parts of the company in the judging process. Consider adding a “people’s choice” option to involve the audience.

• Try to create urgency and hype around sign ups.

How to run a hackathon - day(s) of

Play matchmaker with the hackathon teams

If you haven't already, help form cross-collaborative teams, making sure that anyone who wants to participate has people to work with. There are a ton of benefits to making sure each team is cross-functional:

• You foster diversity of thought, leading to a diversity of products

• Assumptions are quickly validated

• Your demos will be better. Having designers, product managers and copywriters on the teams means finished demos closer to a finished product.

• Everyone gets a chance to participate

Playing matchmaker doesn’t stop when the teams are formed. You should check in on team dynamics throughout the event and encourage them to pivot if necessary. Tone down really ambitious ideas, build up anticipation about the prizes and mitigate any arguments or tension.

It’s demo and scoring time!

Your demos should put the “hack” in hackathon –– you should encourage participants to hack together a demo that is as close to a finished product as possible. This is the one time you can really promote a “fake it till you make it” mentality.

Both a judging panel and your audience should be encouraged to get involved in scoring the demos. We increased audience participation and attendance by having voting boxes and poker chips to factor in people’s choice in the judging criteria. The audience was also able to follow along on printed pamphlets from each team. Again, always be thinking about your atmosphere.

Think about:

• The after party: Throw on some music, food and drinks for your participants and audience.

• Next steps: How do you get the viable projects into market? How do you prioritise your projects?

You now have all the necessary ingredients to get started with running your next hackathon. Good luck!

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