“Welcome to Hack Week!”
There have only been two other times in my life when I have felt a greater thrill than hearing those words: when my wife said “I’m pregnant!” and “Yes, I will marry you!” (Not in that order...)
When the “Welcome to Hack Week” email goes out, you can feel the energy in the office change. A buzz enters the air as a week of boundless exploration begins. People break off from their normal teams and join new groups for the week. Impromptu brainstorming sessions happen in the kitchen, in hallways, and over lunch. Slack channels fill with questions about making X dream possible. The resounding answer is always, “That’s an awesome idea!! I can help with that! DM me.”
Exploration, collaboration, creativity, ingenuity, and optimism reign supreme.
Yet, would these qualities still reign supreme when we’re all working remotely? Would that energy still pervade the (virtual) office when we’re all exhausted from being cooped up and only seeing in-person the people that we live with? Would that collaboration still happen when it requires so much more effort to find and coordinate with people outside your circle?
Would Hack Week even work remotely?
There were many barriers, and they seemed daunting when looked at as a whole:
- How would finding collaborators work when it’s hard to make those ad hoc connections virtually?
- How well would teams be able to collaborate remotely?
- How would we, the team that produces Hack Week, translate the energy felt during in-person Hack Weeks to a remote workforce?
- How would we keep people from feeling isolated in a week when the majority of meetings are cancelled?
- How would we make a day of 80 five-minute presentations work logistically?
- How would we keep people engaged during those 80 presentations?
In hindsight, our biggest worry was whether—given these perceived barriers plus the stress of working remotely during a pandemic—people would even want to participate in a virtual Hack Week.
Embracing the spirit of Hack Week (exploration, collaboration, creativity, ingenuity, and optimism), we decided to solve these challenges as best we could, trial a virtual Hack Week, learn from it, and improve it for the next round.
Really these barriers break down into three themes: collaboration, energy and connection, and presentations. Let’s take a look at how we solved those themes and what we learned.
Collaboration
We believed that effective collaboration during Hack Week stems from people having ad hoc conversations, like talking in the kitchen or having spontaneous brainstorming sessions in the hallway or elevator. We asked ourselves, what is it about those spaces that make people so willing to have brainstorms and to partner up? Do snacks make people more open? Does coconut water? Maybe? But how does that translate to elevator rides and hallways?
We realized that all of these spaces are special because you aren’t at your desk. You’re purposefully taking a break from thinking about work. When you get up to grab a snack, or when you’re walking between meetings, your brain gets a rest before concentrating on your next task. You are mentally open and receptive to being engaged about anything.
Creating those rest spaces virtually for people in their home workspaces was tricky. We couldn’t say “go to the kitchen” or “go for a walk” because, well, then they’d be away from their computer and away from the people they need to collaborate or brainstorm with. Instead, we created spaces and opportunities within the virtual work environment to get away.
We created optional Water Cooler Chats and Hack Week Dinner meetings every day. In the Water Cooler Chats, people signed up to be paired with other engineers to talk about their projects during the week. Hack Week Dinners were a standing meeting during dinner time, where anyone could join and eat dinner with other engineers and creatives.
These meetings, like those in the kitchen or hallway, created a space for the break from work where you could run into someone and talk about what you’re doing. You could get a different perspective on a problem. You could end up connecting with the right person or team who could solve an issue for you.
The meetings also solved another challenge of fully virtual Hack Weeks.
Connection
If a majority of normal meetings are cancelled and sprints are paused during Hack Week, isolation and loneliness can quickly hit. If you don’t have scheduled time to talk to anyone, you can almost spontaneously find yourself not talking to anyone all day, for a week. That takes a toll on you mentally and emotionally. With the Water Cooler and Hack Week Dinner chats, people had the chance to just see a friendly face without feeling like they had to pull someone away from working on their projects.
We also created a JQBX station and asked for people to sign up to DJ for an hour. This allowed people to escape by creating an hour-long playlist of their favorite songs and playing it for their coworkers. It also let people take a mental break by going into the station and interacting with whoever was in the station at that time. People got to meet new coworkers and bond over something that wasn’t related to work. We learned that people who have connections to each other outside of work are more likely to collaborate during work, thus helping solve the collaboration problem as well.
While I would love to say that the DJing idea took off and was an immediate success from day one, it wasn’t. Getting our JQBX station off the ground required having a lot of one-on-one conversations to get people excited, cajoling them into signing up to DJ, going there just to listen and interact with the DJ, and creating a space where DJs felt safe showing their musical tastes. We had to recognize that creating playlists and showing your coworkers what you listen to could be a scary idea for some. Once we recognized that, we were able to build in the positive support that gave them the courage to do so. That meant always having a listener on the channel who would like or react to songs, and always having a playlist playing music of all types, even when there was no DJ signed up.
Presentations
Lastly, but maybe most importantly, we had to solve the presentation challenges. Unlike collaboration and connection, presentation challenges were not cultural, but logistical challenges that we could directly address.
With the only rule of Hack Week being that you must give a 3-5 minute presentation on what you worked on, Presentation Day is full of energy, jaw-dropping moments, and cheering for each other. While the jaw-dropping moments exist whether we’re virtual or physical, anyone who has presented virtually to a group will tell you that the energy and feedback from the crowd are hindered when you’re remote. It can be a flat experience for even the most practiced presenters, which we learned first hand at our Engineering All Hands and Q&As with Engineering Leadership events. The speakers at those events are our most experienced presenters, and even they had to work to overcome feeling flat when they presented virtually. How could we change that for our less experienced speakers?
We did this two-fold. We built an interactive tool for the audience to give real-time feedback to the presenter and we provided basic quality controls for the speakers.
The quality controls were easiest to create because we had learned so much from the recent All Hands meeting we held, as well as from our twice-monthly Q&A with Engineering Leadership. We sent out these instructions with the Hack Week presentation sign-up email, and followed up with every speaker 10 mins before they presented to refresh them:
Presentations will be fully virtual for this Hack Week. How it will work:
- You will be invited to a presenters link 10 minutes before you present. Please join that invitation muted.
- Once it is your turn to present, unmute yourself and share your screen.
- Once you are done presenting, please leave the presentation meeting and rejoin the live stream.
A few comments to make this more seamless and easy for you.
- The quality will be best if you join via Chrome.
- Share just a window or tab whenever you can instead of sharing your entire screen.
- If you have any audio or video in your presentation, make them their own tabs in Chrome and share just that tab. That will successfully share the video and audio stream.
- If you are sharing your full screen, ensure the text is large enough for people to read and see what you are doing.
- Do a quick test run with someone on Thursday using just a standard Google Meet. If it works there, it’ll work here.
While these quality controls were so important to help drive continuity and to set the presenters up for success, what really changed the day’s energy were the tools we used to encourage interaction between the audience and the presenters.
We have always had a dedicated Hack Week Slack channel, but this is the first time that we actively and consistently pushed conversations to happen in that channel. And it paid off. During presentations, the channel was ALIVE with comments, questions and praise for the presenters. A presentation didn’t go by where there weren’t multiple kudos given or follow-up questions asked. While we couldn’t hear the applause or watch jaws drop with each presentation, this was almost better. There was an energy to the channel that day and it was all palpable.
Not knowing how well the Slack channel would go, we also got a small team together to build a tool, called Party Line, to change how our audience interacted with the presenters.
Using a straightforward broadcast server and websockets to immediately send any valid message to all other listeners, we created a web app that allowed participants in the live stream to send real-time emojis to the presenters. Party Line's emojis were a preset list (👋, 👏, 👍, 👎, 🤣, 🤔, 🎉, 💯, ❤️, and❓) displayed on the left-hand side of the screen. By clicking on an emoji, you’d send that emoji to all parties with the app enabled. This created an immediate feedback system. Present something that people loved, and you (and everyone else) would see a flood of ❤️. Say “Can you see me?” and you’d receive a bunch of 👋.
So, how did things turn out?
Even with the prep and the tooling, the fact of the matter is that what made Presentation Day run so smoothly and successfully were the employees, both presenters and audience. The presenters were practiced, calm, engaging, and inspiring. They read what the presentation quality controls were and worked within that system. The audience interacted with every presentation via our tooling, but more importantly, with each other in our Slack channel. They praised and lifted each other up. They forgave technology challenges and restrictions. They followed up with each other to learn more about projects that interested them.
To put it simply, in our first virtual Hack Week, everyone fully embodied what Hack Week is all about — exploration. When you have a group exploring, there is no "wrong" or "right.” The best explorers are those who have the support system to go confidently in their own direction. We knew we had this support system when it came to in-person Hack Weeks, and we now know we have it for virtual Hack Weeks too.
The phrase “Welcome to Hack Week” can’t come again soon enough.
For a deeper dive into the history of Hack Week at Squarespace – as well as key projects that have been brought to life via the program – check out our recent video series below.
