2020 Design Sprint Retrospective

2020 Design Sprint Retrospective

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The following is a summary of the roundtable conversation had between myself and my team members at Crema. Watch the full conversation below, and click here to view the Miro board we worked from!

Recently, I had the opportunity to sit down with some of my wickedly talented peers: a group of product designers, product managers, and facilitators that have been a part of several design sprints this year. I asked them each five questions, and we discussed them together. Below are the questions, their responses, and some additional commentary.

Question 1: What did you see to be the most valuable aspect of the Design Sprint for the clients?

Product Manager: The ability to test and “fail forward.”

Designer: The amount of time dedicated to uncovering the root of the problem with the voice of every stakeholder present.

Designer: Having stakeholders together choosing a direction to a solution that works for all.

Product Manager: The ability to jump-start product development quickly and confidently.

Director: Getting this crew in the same room and committing time to figure out the problem, not just a solution.

Designer: Being able to identify the problem, a potential solution, AND see that solution brought to fruition to be tested in such a short amount of time.

Facilitator: Primary: time dedicated to leaning into the problem space, not just justify a hunch/potential solution. Secondary: Learning that collaboration & innovation are not contingent on offices & conference rooms.


The process works because it gets the right people together for a long period of time to focus not only on potential solutions but also on the problem they’re trying to solve in the first place. It’s one of the best possible ways to kick off a project or product. (Seriously, listen to our clients talk about the value they found.)

Clients across multiple industries all agree: sprints work.

Question 2: What was the most challenging aspect for you during your Design Sprint? (for Designers)

Designer: The balance to create a prototype that is strong enough for testing, but that doesn’t create an emotional attachment in the client — something they may want to dump if it fails. We know that you can’t create a product in 3 days, but do they understand that?

Designer: Gauging the level of fidelity possible & most valuable to design at in the amount of time given.

Designer: Before Design: Not designing ahead in my mind. As you hear the client team discuss their ideas in the first few days, it’s hard to not get invested in certain ideas more than others. During Design: Prioritizing and not perfecting.


It’s hard to be a designer during a sprint. You’ve got to know how to say “no” to perfectionism and precision in order to say “yes” to helping the client answer their problems.

A day’s worth of designs for one of our Design Sprints in 2020.

Question 3: What did you see to be most challenging for the clients during your Design Sprint? (For Facilitators)

Product Manager: The learning curve around virtual tools. (Zoom, Miro, and others)

Facilitator: Forgetting preferences & personal passions in order to pursue the goals the team decided on.

Director: Committing the time & headspace for the exercises and discussions.

Product Manager: Trusting the process. The exercises build on each other generally leading to significant “aha!” moments about half-way through the Sprint. Yet, the early exercises are key.


Design sprints are hard enough (with people doubting the process, staying on their soapbox, or not being fully present), let alone when doing them digitally. And yet, the process still works. Trust the process, and don’t let the difficulties of the first couple of days get you down.

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Our digital summary of a week of good, hard work.

Question 4: What’s one thing you would do differently if you were to do your Design Sprint again?

Product Manager: Emphasize that our Design Sprints are not only a trusted process, but also a guideline: we can and have iterated mid-flight to get the best outcomes for our clients.

Designer: Continue to ask myself if I’m designing toward the ultimate goal. I found myself getting stuck designing details or specific UI patterns and forgetting the big picture.

Facilitator: Have a mandatory “Design Sprint Intro” session where we use a fake business model to show the full process as opposed to only saying, “trust the process.”

Director: Pay even more attention to the outliers & non-consensus inputs.

Designer: Try to understand the client team dynamics and individual skills beforehand, not just the focus of the Design Sprint. Knowing how an existing team interacts allows you to see where gaps need to be filled.

Product Manager: Have pre-workshop session that utilizes all of the tools and features of the design sprint.

Designer: Prepare a content outline if we need content from the client first thing during “prototype day”. Pay equal attention to all attendees. I was a bit distracted by the decision maker’s input.


It’s not about you, it’s about them. The more time you spend beforehand preparing the workshop, training on the tools, listing requirements, and listening to your clients, the better. To facilitate & partner with clients in a sprint, you must be flexible, empathetic, patient, and curious. Anything other than that will not get them what they need.

“Short Term + Full Time > Long Term + Limited Time.”

Question 5: What was your biggest take-away from your Design Sprints this year?

Designer: Design sprints require commitment and open-mindedness to stay focused on the long-term goal.

Designer: A small, dedicated group of the right people coming together for a design sprint can solve problems in a week that would take months/years. Short Term + Full Time > Long Term + Limited Time.

Facilitator: Don’t be so married to the process that you aren’t willing to make the “pit stops” or “detours” that come up — and then get back in the process you intentionally crafted. (Also, having strategic co-facilitators and designer provides exponential value to clients).

Product Manager: They provide a validated way forward and alignment across teams.

Product Manager: In our world of distributed work, the work we do in our Design Sprint lives on with our Miro boards after the fact. This has been so valuable for effective collaboration, even after the Design Sprint ends.

Designer: Dedicating time to defining the problem before the solution with the right people, enables faster, better work. Also, as a designer, take ownership over what you don’t know yet.

Director: Committed cross-team discussions can change the ways people and teams see their role in getting things done.


Design sprints are powerful tools that expedite problem-solving, align teams, and change the way people work. Especially with digital tools, they’re more accessible than ever. When you put a team of thoughtful facilitators and designers together with them with a team ready to try something new in order to speed up, take risks, and get unstuck, you’re not going to look back.

Check out a video case study of one of our 2020 Design Sprints below!

Justin Mertes is a Coach & Design Sprint Facilitator at Crema. If you have any specific questions about facilitation, workshops, or Design Sprints, or simply want to get in touch, reach out to him on LinkedIn.

Appendix: Our Digital Design Sprint Tools

The following tools were used by Crema to ensure a productive digital Design Sprint:

  • Miro (digital white-boarding & collaboration)
  • Figma (our favorite design & prototyping tool)
  • SessionLab (for creating workshop agendas)
  • Zoom (our go-to video chat platform)
  • Loom (for asynchronous communication)
  • Slack (for internal conversations)

Last updated
Jan 20, 2024

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