Design Sprinting in a Remote World

by Eric Smith - Head of Business Design

At High Alpha, we’re in the business of building businesses with a laser-focus on taking B2B SaaS ideas to market in a high-velocity, repeatable fashion.

Our core forcing function for building businesses is Sprint Week, a quarterly exercise that showcases our best ideas, world-class co-founder candidates, and the cross-functional talent from our studio team in a pressurized week-long journey to birth our sharpest thinking with passionate and visionary leaders.

It’s intense. It’s exhausting. It’s exhilarating. For one week, we effectively lock ourselves in an office and dive deep on problem statement refinement, customer validation, and solutioning. It requires a tremendous amount of team coordination, clear expectations, endurance, and leadership. And at the end of just one week, we decide which business concepts will be formed and funded. This process is the lifeblood of our studio and it must be done excellently every time.

Running design sprints effectively is a challenging endeavor in normal times, but when you add in the complexity of conducting one remotely due to our worldwide pandemic battle, the challenge is quickly amplified. Part of my role is to oversee our Sprint Week process. Leading up to our first virtual sprint, I had many sleepless nights sorting through whether the virtual sprint was possible, advisable, and if we could still produce excellent results virtually. We’re not ones to shy away from a good challenge and so, once the decision was made to move forward virtually, we got to work. 

This month, we (successfully) held our first virtual Sprint Week with approximately 60 participants spread across five teams. Here’s what we did, how we did it, and what we learned along the way in hopes of helping others navigate the current reality.


Technology would be integral to facilitate our virtual design sprint, but it would not be relied on to address all our challenges. Crisp communication, clear expectations for the week, grace, and flexibility would be keys to our success  — we all have different variables to contend with while working remotely from blurred lines between home and work to children running into conference calls. The list goes on and we would not fool ourselves into believing that work and team collaboration conducted in an office could be replicated digitally.

Organization and Expectations

Over communicate. And when you think you’ve gone far enough — communicate some more.

Coordinating a large group in a way that allows things to flow smoothly during the digital week required planned down to the most minute detail. What time should the sprint start? What do meals look like? What do breaks look like? How long should the day be and how do we know when it’s over? How (or should) there be digital socializing? How frequency should the broader group come together for check-ins? Where am I supposed to go to be with my team (more on that later)? What should the deliverable look like? How should final deliverables be presented?

We sent participants a simple, light schedule for the week detailing different all-hands events and when teams had time to break out. We held a kickoff meeting to set the stage at the start of the week and closing remarks at the end of the week once presentations were completed. We held all-team check-ins during the week — this was a quick, fun way to hear how other teams were progressing and dealing with the uniqueness of the digital sprint. We presented a template to help guide the final deliverable to ensure a baseline level of uniformity. We provided contact information and a virtual place to go in the event that any sprinters encountered technical issues. 

However, we were cautious of being overly-prescriptive and acknowledged that each team would develop their own workflow and identify based on the respective team members and their work styles.

Connectedness

One thing we told ourselves repeatedly leading up to the sprint: don’t try to replicate an in-person Sprint Week. 

Sprints are intricate processes and we felt we needed a way to facilitate these intricacies. To do so, we brought in a leader to help us construct a purpose-built design sprint tool that would enhance the team interconnectivity, reduce friction in how they connected, and improve collaboration and document sharing. We tied together chat, video, documents, and whiteboarding to create an environment where each team could see where everyone was, what they were working on, and how to reach them. We needed a sense of presence and togetherness.

The tool that was built and used didn’t have a final coat of polish, but it painted a vision for what the future could look like – a very exciting future in our eyes. This tool took our virtual sprint to the next level by addressing a fundamental conundrum in virtual work: where am I in relation to those I’m working alongside, and how do I collaborate with them? It truly made us feel less isolated and, in doing so, raised our spirits, energy, and productivity.

Software can help make our jobs easier, but great leadership will always be at the core of a great sprint week. A purely digital world can feel anarchical if the leadership isn’t visible and accessible. It can be very helpful to have sprint teams pre-meet prior to the start of the week to align on objectives, roles, and expectations because once the week starts, things go fast and the team needs to know the chain of command.

Conflict management is also trickier when done virtually. In our sprints, we believe in healthy conflict — in fact, we encourage it to sharpen and pressure-test the best thinking. In a virtual world, nuance can be lost and healthy conflict can turn into something unintended. Be exceptionally mindful of this and go to great lengths to ensure communication is delivered and received as intended. Seriously.

Energizing a Remote Team

If you’re not an experienced design sprinter, the intensity and required endurance can catch you off-guard. Even for experienced design sprinters, it’s challenging to focus so intensely for so long. Video fatigue in the virtual sprint added another hurdle to overcome.

Not only are you deeply focused, but you’re doing it while physically alone, staring at a computer screen for 12 to 14 hours (or more) each day. Fatigue is a real concern and, to combat this, we rolled out “Operation Surprise and Delight.” Each day, special deliveries were made to each sprinter’s home containing coffees, dinners, snacks, swag, and, for the last day, a celebratory cocktail. It was an incredible experience and breathed life and camaraderie into the week. It’s shocking how something as simple as a bagel delivery can make an individual feel like they’re part of something special. It’s also shocking how much planning and logistics goes into making these deliveries — special kudos to our studio team members who stepped up to make these deliveries a reality.

Lessons From a Remote Sprint

There were so many! Here are the six that continually surfaced during the week:

  1. Encourage teams to take frequent breaks. Screentime fatigue is for real.
  2. Be careful scheduling digital meals, check-ins, and socializing events. They may sound good but are hard to manage without very specific agendas. Use that downtime to be away from the computer to recharge vs. scheduling more gatherings.
  3. Make sure your tech tools are up to the task and ensure everyone on the team is comfortable with how to use the tools. For us, we built our own tool and took the time to ensure all participants were familiar with it prior to beginning the sprint.
  4. Digital happy hours are fun in small groups but can feel forced in larger groups.
  5. We had a special musical guest close out the week for us with a live virtual performance. Find ways to make the week feel special and try to inject a few surprises along the way.
  6. It was my first virtual design sprint and there are many, many things I would do differently next time — it’s ok to feel uncomfortable.

The Outcome

Not just one, but four incredibly exciting concepts successfully emerged from Sprint Week. The talent, grit, humility, and adaptability of a truly incredible group of people made it possible. Their patience and nimbleness as we navigated the virtual world will be forever appreciated. If I were to do it over, sure, I’d do many things differently — this was far from flawless. But in the midst of these unprecedented times, we adapted and we created. You can too.

Care to hear more? I’d love to chat about our virtual design sprint experience or the remote work tool we built specifically to help us navigate these challenges!

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