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Hacking Hackathons: Our Best Practices for Inventing the Future

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Posted in:  Best Practices

Six months ago, I was tapped to lead Highspot’s first virtual Hackweek – a weeklong hackathon where teams from across the company come together to push the boundaries of our product.

At the time, I wasn’t sure what to expect – I had never organized a corporate event of any kind. Nonetheless, I responded to the request with, “Yeah! I’m down!”.

One week later, the results were in. Normally, hackathons are a great way to drive innovation and take risks with your product. Even so, this year’s hackathon results surprised me: We saw three times our anticipated participation from internal teams, unlocked numerous new and useful proofs-of-concept (POCs), and deepened our already strong collaboration between our product and go-to-market teams.

How can you achieve similar results with your next hackathon? Here are the dos and don’ts we learned from our most recent event.

What We Learned from Our Hackathon

Loop in leadership

Successful hackathons require executive buy-in. Hackathons take time and require teams to step away from their normal jobs to focus on the event.

Getting buy-in from leadership makes this possible. Our leaders worked with us to clear a week and create space for our event. Ultimately, this helped employees feel empowered to participate, as many had voiced concerns with having to balance their day-jobs and the hackathon.

Plan, plan, and plan some more

Early on, I thought we could organize and execute the event with just a handful of people. But the more I dug into the details, the more it became apparent that we’d need additional help.

Eventually, we consolidated a team of twelve to help us manage and drive the event. Responsibilities included recruiting participants, providing infrastructure support during the event, managing Zoom logistics, and emceeing the event – to name a few. All these details are critical to a successful hackathon – make sure you figure out who your facilitating crew is early on in your planning process.

Create guidelines instead of rules

Originally, I envisioned strict rules around team composition, team size, and so on. But through listening to employees, I learned that rules may actually act as a deterrent for the event. So we pivoted.

Instead of using rules to achieve perfection, we provided guidelines that inspired creativity. Ultimately, I felt this increased event participation and contributed to a positive, friendly atmosphere – every employee enjoys a chance to color outside the lines.

Get feedback along the way, and adjust as needed

We approached Hackweek as a collective effort between the organizers and the participants. To ensure we created space for this collaboration, we opened up our draft of the Hackweek plan for feedback.

The goal of this exercise was to ensure employees had the opportunity to have input on what the event would look like. I’ll admit, I did have concerns about losing momentum if we tried to incorporate too much feedback. My fears turned out to be unfounded; ultimately, sourcing feedback from participants helped bring them along for the ride and contributed to an atmosphere of inclusion.

Running a virtual event will have unique challenges

In a virtual or hybrid world, hackathons are still possible. They just require a little more thought. For us, this event was a learning experience – there were some things we got wrong and some we got right.

For instance, on Day 1 of the event, we had people pitch their ideas, then let participants reach out to pitchers if they wanted to work on their idea. However, this proved difficult for new employees who had joined during the pandemic and had never met many of their co-workers. Creating teams this way became a little awkward and a reminder that what may have worked for an in-person event, doesn’t always translate to virtual ones.

My recommendation here? Examine each step of your hackathon process from a virtual-first lens: does anyone get left out of the conversation? Does anything become overcomplicated? Does any form of communication become difficult? Thinking ahead will help you deliver a more seamless event.

Have fun and make an impact

This final point should be obvious, but it’s still important to remember: Hackathons should be fun! While we did have category winners, we didn’t emphasize winning as the most important aspect of the event.

Instead, we focused on delivering impact for our customers – something we could all rally behind. Thus, one of our goals was to actually ship projects with impact. This meant participants’ efforts translated into projects that can go to production in the future. The ability to drive innovation creates value for our hackers, regardless of whether or not they won.

Innovation Starts Here

Our virtual Hackweek hackathon was an incredible chance to live our Highspot values — from Collaborating Across Boundaries to Inventing the Future. And we’re just getting started. Already, we are thinking about how to leverage the learnings of this past event for our next one.

If this sounds like the kind of team-driven atmosphere you’d like to join, then I’ve got even better news: We’re hiring. Explore open roles on our product team here.

See you at the next Hackweek.

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