More inclusive, impactful company hackathons

If you’ve worked at a software startup, you’re probably familiar with internal hackathons: timeboxed competitions that highlight much of what’s good, bad, cool, and weird about working in tech.

Done well, these events represent the best of startup life: tight feedback loops, unrestrained creativity, inspired problem-solving, open collaboration, and joyful work. At their worst, they’re wasteful, exclusive, and unhealthy—for individuals as well as the organizations that sponsor them.

Many of these events are simply a pressure-release valve for engineering. We all need an occasional break from the agile hamster wheel, but internal hackathons can be so much more meaningful. With a bit of thoughtful design, they can be one of the most inclusive and impactful events in the life of a startup.

In this article, I’ll share seven ways to take your hackathons from ordinary to excellent—each a lesson learned from organizing and/or participating in seven hackathons over five crazy years at Stitch Labs (“Stitch”), an e-commerce company since acquired by Square.

Involve the whole company

If your hackathons only involve product, engineering, and design, you’re missing out.

Take inspiration from Pixar and involve everyone. By the early 2010s, Pixar had grown to over 1000 employees and was starting to struggle with organizational rigidity and narrow thinking. To combat this, they created Notes Day, a full-company event where people chose organizational problems they cared about and worked collaboratively to solve them.

The biggest benefit to including all employees is that it reinforces something essential (and under-appreciated) about startups: company-building is everyone’s job. At a startup, everyone needs to help improve how things get done; no one should be content to execute against an unchanging playbook. Full-company hackathons help bring this expectation to life. They also put the focus back on problems and opportunities rather than code as a potential solution.

Full-company means full-company. That includes new hires and remote teammates. Make it remote-friendly, or better yet, bring people in for the event. Encourage new hires and make it clear that fresh perspectives are especially valuable in events like this. If you can, point to past hackathon projects that were successful and included or relied upon new hires.

Aggressively timebox

Every venture-backed startup is in a race against time. The best startups acknowledge time constraints and use them to their creative advantage.

To allow full-company participation and celebrate time as a useful constraint, consider a 24-hour format. This format is controversial because it evokes ideas of all-nighters, but aggressive timeboxing actually makes it easier for everyone to participate. The longer your event is, the harder it is to involve every role—especially customer-facing roles like sales and support.

But what about parents and people who don’t want to stay up all night? Remember, there’s nothing about a 24-hour format that requires constant participation. This isn’t a dance marathon.

At Stitch, the 24-hour format worked well for us. We’d start mid-afternoon Thursday and wrap up mid-afternoon on Friday. Staying up all night was allowed but wasn’t especially encouraged, and we made it clear that projects weren’t judged based on how much time people spent on them. In some cases, the winning projects were done within a few hours.

Plan well in advance

As is the case with most events, it pays to plan ahead.

Give your planning team at least three weeks to get ahead of the company, and give the company at least three weeks to save the date, brainstorm ideas, pitch those ideas, and form teams prior to the start of the event. If you have a salesforce, you’ll also want to ensure that the hackathon won’t interfere with end-of-month/quarter sales goals.

At Stitch, we experimented with a variety of planning timelines, but found that a two-month planning runway with events held mid-month/quarter worked best for us.

Define your goals

Be clear with yourself (as organizers) and attendees about why you do these events. Be thoughtful, write it down, and be transparent. Everyone should be clear on the why.

At Stitch, we outlined our goals as follows:

Once you’ve defined your goals, identify metrics that you can use to measure success. At Stitch, we measured participation rate, collaboration rate across departments, and employee satisfaction as measured by a post-event survey. We’d review this data in an event retrospective attended by organizers to help identify improvement areas for subsequent hackathons.

Clarify what good looks like

Have an opinion about what good looks like (“this, not that”) and make it clear to everyone involved in the event. 

Use award categories to celebrate different types of excellence; use project criteria/guidelines to clarify boundaries—the things you expect from any project.

Award categories can be tied to company values, business objectives, organizational themes, or any concept that carries organizational meaning. When these categories already resonate with your people, it sets things up nicely for these awards to be determined by popular vote.

“Best in show” is another category worthy of consideration. At Stitch, we experimented with awarding this category by popular vote as well as by a panel of judges. Ultimately, we found that a judges’ panel (made up of a cross-section of company leadership as well as outside perspectives from investors and other portfolio companies) worked best for the top prize.

Project criteria help keep the event from going off the rails. Some will bristle at the idea of setting any sort of guidelines, but done well, these reinforce the goals of the event and help—rather than hinder—the creative process.

Here’s some example criteria:

Flip the org chart

Take steps to encourage fresh thinking, different perspectives, and lesser-heard voices. Don’t miss out on an opportunity to challenge your organization’s typical way of working and relating to one another.

At Stitch, we especially wanted to encourage personal agency. If you had an idea that excited you, you were encouraged to pitch it—even if it required skills you personally lacked. On the other hand, Hax Day was not an event for suggesting ideas without personally involving yourself. It was an event for putting your money where your mouth was.

We encouraged everyone to vote with their feet. People were encouraged to find a project that they really cared about and politely say no to ones that didn’t. If someone pitched a project that didn’t get buy-in from others, they were free to go it alone, but encouraged to join a more viable project.

We also made sure to limit the influence of folks who typically had a seat at the table. Because employees often had trouble saying no to a founder, founders were encouraged to support the event as judges, emcees, or participants rather than as project leaders. Product managers were similarly nudged. These roles have outsize influence every other day of the year. The idea was to democratize prioritization, product thinking, and business building, encouraging leadership from all corners—not just from the usual suspects.

Document, document, document

Assume that you’ll want to do the event again in the future and take the time to document. This includes the planning, the doing, and the retro.

Document the before (planning) and after (the event retro); this will help you and others when it’s time to plan your next hackathon. But don’t let the documentation stop there. Be sure to document the event itself! Photos and videos help capture the energy of hackathons and are so worthwhile that you should consider recruiting/hiring a photographer. At Stitch, an employee would usually volunteer and we’d give them the best camera we had.

Also, consider a simple hub for showcasing previous projects. This is a great way to celebrate past participants, highlight winning projects, and provide cultural continuity. It can also be a great place for people to be inspired by past work, sometimes even picking up projects and iterating. At Stitch, we called our hub the Hax Day Hall of Fame.

Swag can help commemorate an event, but it can also be pretty wasteful. Tee shirts that are worn only a couple times and cheap trophies that quickly find their way to a closet aren’t worth the waste they generate. Consider swag like commemorative stickers, coins/tokens, or other lower-impact choices. Give your team great memories and a small reminder; that will be enough.

In conclusion…

There’s no one right way to hold a hackathon, but I know we were onto something at Stitch. What’s outlined above is my attempt to distill the magic into something others can try out and improve upon. And no matter what the format, a good hackathon should remind everyone why they work at a startup. If these events feel anything less than invigorating, it’s time to shake things up.