Top Takeaways from Google’s Sprint Conference 2019

Insights, tools, & wisdom from leaders across the design sprint community

Taylor Cone
8 min readOct 7, 2019

Last week was the 3rd annual Sprint Conference, hosted this year by Google in Boulder, Colorado. Top facilitators, designers, innovators, and change-makers of all kinds convened to share tools and methods for getting the most out of sprints and out of a team in creative collaboration more broadly.

Closing out Advanced Facilitation with Daniel Stillman

Below I’ve informally recapped my biggest takeaways — the methods, quotes, and frameworks that stuck with me and that I plan to utilize moving forward. Some will be useful mostly if you’re a facilitator or coach, and some will be useful if you’re a leader within an organization. There’s something for everyone here.

My experience at SprintCon ’19 began with an all-day Advanced Facilitation workshop with Daniel Stillman, who is a conversation designer and masterful facilitator.

He shared a ton of great material, some of which I was able to record and transcribe here.

  1. A journaling framework to support both individual reflection and conversation design/scaffolding:
  • Facts: What happened?
  • Feelings: How did it make me feel?
  • Insights: What did I learn or discover?
  • Potential: What’s the why? How do I want to embrace this and incorporate it into the future me?

2. The Conversation OS Canvas is a helpful tool to bring intention and awareness to the design of your conversations. (Note that ‘conversations’ include collaborations and design activities, which are rarely done without any type of verbal communication.) The Canvas invites you to consider, as you’re thinking about a conversation you’re designing:

  • People (who’s involved?)
  • Invitation (how are they being invited into the conversation?)
  • Power (what power dynamics exist, and how might you influence or shift them?)
  • Turn Taking (how will you manage the division of speaking time?)
  • Interface (through what medium will the conversation take place?)
  • Cadence (what will be the pace and energy profile of the conversation?)
  • Threading (how will the content of the conversation evolve and interplay?)
  • Goals (what are the desired outcomes of the conversation, for each person involved?)
  • Error & Repair (how will we handle issues and instances of tension or trust-breaking?)

3. Daniel had us reflect on the narrative arcs of the experiences we design. He shared a handful of classic narrative arcs, like the double diamond, the triple diamond (which the Google design sprint is a version of), the hero’s journey, the 5 E’s (Entice-Enter-Engage-Exit-Extend), and the “four seasons.” This last one was newest to me and I decided to dig into it more.

The Four Seasons narrative is a way to map the experience you’re designing (a workshop, a sprint, a conversation, etc.) to the four seasons we all know:

  • Spring (Plant the Seed) — this is when we imagine and inspire, when create the conditions for a successful experience
  • Summer (Tend the Crops) — this is when we execute, when we’re doing the work, when we’re lost in the experience
  • Fall (Celebrate the Harvest) — this is when we deliver and celebrate the work we’ve done
  • Winter (Rest the Soil) — this is when we reflect on our experience and give ourselves time and space to replenish and rejuvenate

I invite you to try thinking about the next experience you’re designing through the four seasons lens. It gave me a new way to organize my thinking as I lay out a workshop or a sprint, and it empowered me to bring more intention and awareness to the energy in each phase.

We did so much more too…

Learn more about Daniel Stillman and The Conversation Factory.

The next day, I attended a session entitled “Creating a Workshop Culture” with facilitator, speaker, and author Alison Coward.

The motivation for the session was the tension between the effectiveness of workshops to achieve specific goals and the challenge of maintaining that level of effectiveness over time. Great workshops are like bursts of productivity, creativity, and effective collaboration. How might we sustain that beyond the workshop?

Alison’s point of view on building a workshop culture centered around three phases:

  1. Meetings as workshops (how might we view/design our meetings as workshops instead, with clearly laid out desired outcomes, agenda, activities, etc.?)
  2. “Workshop Culture” workshops (when the team begins to take ownership of building habits that will result in a workshop culture)
  3. Embedded in culture (point at which no more workshops or “offsites” are necessary because it’s part of what you do every day…very rare to reach this point)

Where is your team/org on this journey? How might you shift into the next chapter?

Learn more about Alison Coward and her company, Bracket.

Rodney Evans, an org designer and coach focused on the future of work, gave a keynote and led a workshop on reinventing your organization.

She kicked off by making a hilarious(ly sad) point. She showed a slide listing a handful of behaviors that sounded a lot like a typical organization (or bureaucracy). She then asked where we thought they came from. The answer? The CIA Simple Sabotage Field Manual. That’s right — many of the teams and organizations we find ourselves to be a part of are skilled at the key behaviors that spies use to make sure enemies don’t succeed. Oops.

Her talk focused on the complexity of organizations, and how we might approach that complexity in a way that effectively wrangles it. She made the point that bureaucracy is a complicated answer to a complex problem. (If you’re not familiar with the distinction between complicated and complex, read about it here.)

Rodney shared the “OS Canvas,” a tool her company uses to assess and design culture. Rather than recapping it here, check out this post by one of her colleagues that gives a comprehensive overview.

Great, so bureaucracy stinks and organizations are complex. What’s new about that? When it comes to transforming an organization, Rodney says, the key is disciplined experimentation. (I couldn’t agree more!) She describes an experimentation loop that she calls Continuous Participatory Change. It goes:

  • Tensions: the pain point
  • Practices: what’s currently being done
  • Experiments: what you try in order to change things

Finally, I loved the term operating rhythm to describe what organizations need in order to move from experiment to habit. You must have accountability, milestones, deadlines, and regular reflections in order to make something part of your culture. And it all must be done in a disciplined way.

Learn more about Rodney Evans and her company, The Ready.

Bree Groff from SYPartners gave a wonderful keynote on “Managing Grief and Loss in Organizational Change.”

Why are people so opposed to change? Bree offers the perspective that that question misses the point. She says, “People don’t resist change. They resist loss.” Taking care of people through that process of loss is a great framing for change management.

Bree shared six types of loss that we experience during change:

  • Loss of CONTROL
  • Loss of PRIDE
  • Loss of NARRATIVE
  • Loss of TIME
  • Loss of COMPETENCE
  • Loss of FAMILIARITY

Change management, she says, is about respect for this loss. But how?

First, understand what the process looks like. To start what’s next, you must acknowledge the ending of what came before. Begin by honoring what you’re saying goodbye to — memorialize it, celebrate it, and name it. Validate the feelings associated with saying goodbye to something we cared (or still care) about. Acknowledge that the work that’s been done is what got us where we are.

“In order to do something new, you must let go of something you once valued.”

The second step Bree shared is called adjustment. After addressing the loss, beginning to adjust to a new way of seeing your work, your team, or yourself. Finally, step three is to celebrate the new beginning. Create a well-defined, concrete opportunity to turn the page to the new chapter. If steps one and two were done well, step three will be much smoother.

Learn more about Bree Groff and SYPartners.

Dana Mitroff Silvers led a great improv workshop.

Sketching credit: Deb Aoki

I was so involved in the actual activities that I didn’t write much down…but it was fantastic and one of the key takeaways was: do everything you can to bring more improv into your daily work. It unlocks creativity, it lowers barriers between people, and it makes us all feel happier.

On the topic of improv, I will share that I recently launched an online version of activity cards that a colleague and I created at the Stanford d.school. Check them out here: www.stokedeck.io. (For the brief history of the stoke deck, read this.)

One of my favorite things to come out of this workshop was one of the participants describing improv as “useful silliness.” Absolutely perfect!

Learn more about Dana Mitroff Silvers and her company Designing Insights.

The last keynote of the conference, presented by Tricia Wang from Sudden Compass, focused on Data-Driven Sprints.

Tricia’s talk grappled with the growing tension over the last several years of wanting to infuse big data into business strategy, design, and innovation while still including the critical human element in the development of new products, services, and businesses. She began by challenging the assumption that more data & technology equals more innovation.

She introduced quantification bias — the unconscious belief that the measurable is more valuable or true than the immeasurable. To be clear, she sees big data as valuable — she just emphasizes the importance of using it to augment thick data (her name for qualitative data), not replace it.

She poses: How might we empower humans in a data-driven world? She offers:

  • Operationalize the difference between optimization and discovery
  • Integrate qualitative and quantitative data
  • Bring decision-makers and customers closer together

Tricia then offered a 2x2 she calls “Integrated Data Thinking” where the axes go from Unknown to Known and Quantitative to Qualitative. To use this 2x2, you’d write questions you have on post-it notes and then place them into the quadrant corresponding to space they represent.

Learn more about Tricia Wang and her company Sudden Compass.

My last session of the conference was Beyond the Prototype with Douglas Ferguson. In it, he led a conversation about how to carry the momentum from a sprint forward after everyone goes home.

The key question Douglas posed was: How might we bridge the gap between ideas and outcomes?

Douglas offered six steps for addressing this question:

  • Wrap it up (close out the sprint with clarity and intention)
  • Share your story (be clear about what the narrative is, who’s telling it, and who’s hearing it)
  • Chart the course (outline what’s next and who’s involved)
  • Expand the inner circle (identify who else should be included in conversations and collaborations moving forward)
  • Cultivate the culture (identify what behaviors are most critical to the team and how you’ll support them)
  • Get guidance (identify gaps in experience or expertise and find help)

Learn more about Douglas Ferguson and his company Voltage Control.

I learned a ton, made lots of new friends, and deepened friendships with others. Thanks to everyone for making it such a rich week.

There’s quite a bit I didn’t get to put in this post. If you’d like to hear more or learn about my approach to all of this, you can learn more about me and my company Lightshed. And if you’d like to chat about how I can help you and your team get where you’re trying to go, you can schedule time with me here.

I’m Taylor Cone. I’m a collaboration designer, coach, and Founder & CEO of Lightshed. I thrive on helping teams solve problems and innovate better, faster, and more collaboratively. Book time with me here if you’d like to chat.

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Taylor Cone

A curious character committed to creative collaboration. Co-founder & Head of Experience @ Compa.