Hack Day how-to | John Schnipkoweit | Choozle UPFRONT
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Mar 27

Hack Day how-to

Hack Days have become a bi-annual tradition here at Choozle.

Our founders have been deliberate in building a company culture and team that inspires camaraderie. Combine that basic human desire of collaboration with some of the most talented people in the industry, and you become a rocket ship of growth. However, with that comes new challenges at scale.
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What is Hack Day?

The same processes that worked when you were a company of 10 people are much different when you have 50, even with top talent on board. With scale comes specialization which can be a double-edged sword for innovation. Specialization is good because instead of having one person wear five hats, you have people that wear just one hat extremely well, therefore increasing quality. The caveat to specialization is that it can create “lanes” or “silos” of knowledge. While that one person wearing five hats may not have had the bandwidth to do everything at the highest quality, the amount of information they are exposed to makes them a formidable innovator. On the development team, we focus on growing T-shaped skill sets, but cross-departmental knowledge is a vital ingredient for true innovation.

A few months into my job as Choozle’s first CTO, I asked our co-founders if I could shut the company down for a two-day long “Hack Day.” Why?

I knew that with the right people and process, a timeboxed Hack Day can accelerate knowledge transfer, accomplish a ton through deliberate focus, and plant the seeds for future growth.

Having watched Choozle’s 50+ employees in action over my first few months, I had faith that we could make our Hack Day supremely valuable, and I knew that we could push the limits of time with this group.


Designing our first Hack Day: A five-day Design Sprint in two days

The GoogleVentures Design Sprint is a framework that takes a team through a journey to solve a problem—through prototype to customer feedback—in just five days. The book on the subject, Sprint, explains why five days is a good time span. (Mainly, the required mental energy is best divided into six-hour segments.) I knew we could remove and streamline certain elements, but the core idea behind a Design Sprint is necessary for a successful Hack Day. Spoiler alert: We ended up taking cues from these sprints and crafting our own unique process called Design Week.

We identified the following core elements:

  • Understand
  • Research
  • Diverge
  • Decide
  • Build
  • Validate

In order to give participants the necessary time to fully engage in those exercises, organization and process efficiency was key. We wanted to synchronize facilitation across all groups and remove any overhead that would normally be created by instruction. Keynote and iCloud were our saviors here—we created a guide in Keynote that included instructions, examples, and timers on each page.

P.S. We weren’t sure how a 350+ megabyte Keynote file would synchronize on iCloud, but it worked beautifully.

After reviewing the guide and how to use it with everyone in a short workshop, we could make changes as questions came in from each group, maximizing my time as a facilitator of five separate teams and syndicating updates to everyone involved. It was up to each team captain to walk the groups through each exercise and lead through decisions.

Modifiers: solution pitches, self-organization, and bits

We kicked off our first ever Hack Day with 11 sixty-second pitches (anyone company-wide could pitch an idea) and, using an anonymous dot-mapping system, our team picked their favorite five. The preselected captains had a draft meeting to create a balanced team of eight. There were some competitive discussions between the captains and while not every captain was 100 percent satisfied, it seemed like everyone felt like fair compromises were made.

The general method of a Design Sprint is intentional analog—to the extreme that laptops aren’t allowed during most of the process. While technology did help us streamline the in-person experience, we had a few remote participants, and the experience did not translate as well for them. If your team has a remote team or lots of remote employees, a potential test you can run would be to create an entirely remote team, or just host it during a time when all of our remote employees are present at HQ (for us, that’s during one of our bi-annual all-team summits).

Actors: deciders, customers, and the “mom test”

Unlike a typical Design Sprint, the Hack Day team captains became the deciders for each team, and the CEO and CPO met with each team as experts during exercises geared towards understanding the problem & opportunities. While actual customer interviews are part of the Design Sprint magic, logistically it was impossible to schedule and conduct them on our timeline. Instead, after their prototype was built, teams interviewed other employees on adjacent teams. This is another area that we will review for future Hack Days, but overall, the feedback collected during those interviews did provide useful validation.

Finally, we wanted to have one external set of eyes, so after validation, each team was given six minutes to pitch to our experts (CEO & CPO) and a special guest… the mom of one of our employees! Two reasons for this:

  1. Our marketing team led the company through an exercise at our summer summit to explain what Choozle does, so that even your mom could understand. We wanted to tie in this same idea to the opportunities our teams were presenting on.
  2. One of my favorite entrepreneurship books is Rob Fitzpatrick’s The Mom Test, which helps you understand how to ask the right questions to get authentic validation, even from your mom. Ad tech is an unnecessarily confusing industry and part of Choozle’s DNA is to simplify digital advertising for our clients (or for our moms).

What comes next? Iterating process and empowering people

While our judges did pick a winner and the employees voted, too, all five of the projects went into consideration for our next product roadmap. Our next—and evergreen—task was to bridge the gap between prototype and full production deployment with a focus on process and people, and our Hack Days continue to be an energizing, enlightening, and empowering experience for not only our product and engineering teams but across the entire company.

About The Author

John Schnipkoweit has founded multiple technology companies, leading innovative teams to scale engineering, products and operations. Working closely with his business partners, John's creative problem solving, design thinking and experience have been instrumental in bootstrapping startups into profitable ventures, with his most successful growing beyond 50 employees and over 20 million users.

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