SERENDIPITY IN QUARANTINE PART 1: Building a new culture of introductions and ideas – in 2hrs or 2weeks.

I’ve never felt comfortable during happy hours at the office.  If you’re not an extrovert, it’s awkward, but I get the point. On the surface we want people to take a break, enjoy a moment together. But the undercurrent of happy hours, free coffee, a shared kitchen is all about manufacturing serendipity. Smart leaders hope people bump into each other, spark connections and mingle across teams, pay grades and disciplines. They hope through these casual moments, employees will build trust and be more willing to reach out for help on the next big idea. 

So, in the era of Covid-19, where the office backdrop has been ripped out from under our feet, what is happening to serendipity?  When there is no longer a physical workspace to meet, and people are virtually zoomed out, how might we manufacture at- a-distance spontaneity ? How might we drive people to connect creativity and generate new, bold thinking? 

Space can no longer manufacture casual collisions, but people can still curate connections. As sociologist Mark Granovetter wrote about in “The Strength of Weak Ties”, it’s critical to cultivate and maintain spontaneous connections, social networks and weak ties. Whether you have 2 hrs or 2 weeks, with some planning and permission, in person or remote-  here’s two simple ideas of how you can move past the happy hour to make valuable connections within your organization. 

First, establish your purpose. Why do I want to connect my people?

Serendipity in Quarantine Goals:

  • Invention, innovation
  • Better problem framing 
  • New strategic thinking
  • Partnership with peers
  • Learning new skills
  • Sharing your expertise
  • Connecting across disciplines, regions, titles, tenure
  • Making work more human

Secondly, establish your format. What people, resources and time do I have? What kind of event or engagement will be popular and rewarding for the team?

Third, find an executive sponsor to advocate your initiative and get going.

Here are two examples of how you can curate new connections in your organization:

2hr workshop: A Mentorshop 

Purpose: Uncover and match up teaching and learning new skills within your own team or across teams. ‘Market’ and ‘Shop’ people’s skills and match make across teams, tenure, seniority, locations and disciplines to make meaningful connections while also building new capabilities.  

What is it: A ‘time boxed’ skill fair- with 3 to 5 skills that are relevant and low hanging fruit for the team you’re working with. Participants come with a mentor/mentee attitude and a giving mindset- what skills and time do I have to offer? But also a receiving mindset- What am I looking to improve to better myself professional development? 

How it works: 

Prework: Facilitation team works with the workshop sponsor (Head of a department, head of a studio, location, business line) to determine the mentorship themes- what do we need to focus on the business to make our teams more engaged, stronger on the job? Develop these into ‘posters’. Each poster is one theme. So you should make 3-5 posters for the session. At the top of the poster is the header. For example: BUSINESS DEVELOPMENT. The left side is the prompt: SKILL TO SHARE: I AM AN EXPERT IN THIS AREA. The right side is the prompt: SKILL TO LEARN: I WOULD LIKE TO LEARN FROM AN EXPERT IN THIS AREA.  Posters can be made on digital collaboration platforms like Google slides or Mural space to allow for multiple participants in the same virtual whiteboard space. 


  1. 10-15 minutes, INTRODUCTIONS and PROMPT: At the beginning of the session, walk participants through the ‘mentorshop’ themes. Help clarify the poster statements and answer questions to participants. 
  2. 10-15 minutes, SHOPPING: Give time for ‘shopping’. Allow participants to add their name to either the Skill TO SHARE or Skill TO LEARN section of the poster. Ask participants to elaborate on their post-it or under their name more specifically under the theme what they want to learn or contribute. For example: “Steve Jobs: I know a lot about making good pitch decks and public presentation skills”
  3. 30 minutes, REVIEW: Close the ‘market’ and spend time reviewing the posters together with a facilitator guiding the conversation. Look for common themes, happy surprises, clarifications. Reflect on patterns across posters. Where did we have a lot of volunteers, where do we have gaps? Ask people to speak on their post to spotlight a variety of voices. Allow time for larger discussions around bigger organizational or professional goals. Often a personal skill building discussion leads to healthy open forum business reflections. 
  4. 45min BREAKOUT: ask 2 EXPERTS from each of the poster themes to lead a breakout discussion. Use a virtual platform to create breakout rooms. In this round assign LEARNERS to specific rooms to make sure all topics are covered. Give the EXPERTS a facilitation guide (3 questions to ask the group) and use this time to allow for learners to ask questions around the topic, expressing specifics around what they would like to know more about. Have one expert facilitate and the other take notes. This helps everyone understand the needs and gaps of the community and to get a feel of what future mentorship themes and goals for the organization could be focused on. 
  5. 15min SUMMARY: Have everyone come back to the shared virtual room and ask each expert to summarize the conversation. Take about next steps for the participants and thank everyone for their time. 

Follow Up: Workshop facilitators review the posters and breakout sessions for 2 patterns 

1) which themes got the most traction? This helps tell sponsors where they might need more focus. I’ve done this workshop a number of times and the “I am skilled at business development…” is often the least posted on and trafficked.  This helped tell the leadership team in a very honest way that staff didn’t feel expert in this area, yet this was a critical skill for keeping the company afloat!
2) Develop longer term mentorship pods, match making between individuals or small groups that express skills TO SHARE and skills TO LEARN. Follow up with YOU”VE BEEN MATCHED! Give groups an outline for how mentors and mentees can organize time to best learn and share new skills virtually. Time box the mentorship pods and ask for them to focus on specific goals and give them time in the business schedule to meet (eg. 1hr, once a month on a Friday). Do this as regularly as it remains interesting and useful for your team (quarterly, annually etc)

2wk Hackathon: The Future of_ Competition

Purpose of Internal Hackathon: New introductions and ideas through a curated and time-boxed design challenge. 

How it works: 

Prework: With your hackathon sponsor (eg. head of Product, head of Innovation, head of Sales, head of Tech) outline the purpose, themes and intention of your internal hackathon. Make sure people are energized by the topic and the timeline. Understand time commitments, assign specific roles:

  • Hackathon facilitator and organizer (~2people). The facilitators develop the timeline, goals, teams, structure of the competition and meet directly with the sponsor to report on progress and deadlines. They also provide positive support, tips and feedback on how to be successful during the challenge for participants, judges and experts. 
  • Judging panel (~3-5 people. The judges are typically senior managers or directors of disciplines or areas of the business. They are seen as fair leaders with insight into the business. They likely have busy schedules so this allows for participation without a huge time commitment. 
  • League of experts (~5-10 people). The league is typically made up of subject matter experts who can offer specific insights into certain topic areas. Often people who cannot commit to full participation, but amazing resources for specific questions, skills or guidance. 

Hackathon:  A hackathon structure can take many forms, but make sure the timeline, milestones, purpose and rules for participation is set and clear. Ask for participation, don’t demand it. To maximize serendipitous moments and idea generation make sure you are mixing teammates in new and interesting ways.  

A) Curate who is on each project team. Make teams of 3-5 people across regions, disciplines and seniority. Let more junior staff take on team lead roles, mix teammates that otherwise don’t mingle professionally, or could learn from each other. Make sure time zones are manageable. 

B) Create a layer of mentorship and coaching. Create a league of experts who can serve as advisors to teams. These can be subject matter experts, senior people who want to participate but don’t have much time. They can offer office hours, or advocate and coach assigned teams.

C) Based on number of participants consider having gates in the competition (aka. Prelims and Finals). Narrow down the competition to a manageable number of teams for final presentations to be judges and voted on. This also allows for a shorter sprint upfront (say, 2 days) that everyone can participate in but then allows a smaller group to further sprint for another 2 weeks. This allows for the competition to exist without having a large number of staff preoccupied with the competition for 2 weeks time.  

C) Create some urgency and public celebration of the work done. Have an internal pitch presentation for the judging panel. Guide the teams with examples of good process framework and guides for pitching- storytelling, visuals, presentation structure. Remind teams and judging panel on judging criteria (eg. innovation, user delight, back by evidence, business viability). Let everyone tune into the pitch live and let viewers vote too to draw a larger audience. Make sure to create a judging rubric that is clear and fair (eg. votes are weighted 80% judges, 20% audience). Announce winners and focus on the impact of the ideas generated- Can the idea be further developed? 

Follow Up: Within a week, debrief with judges and leaders, was it considered a success? Issue a follow up survey to participants. Ask questions like: Was it a positive experience? Was it a useful way to generate new ideas? Was it worth my time? Did I connect with colleagues? Did I contribute to the director of our company mission? Learn and report to leadership the feedback and use to improve on weak areas for next time. 

Great companies know- Serendipity in the cafe or a hallway is not the end-goal, it’s creativity and innovation. Designers of serendipity have leaned on successful workplace narratives like MIT’s Westgate West, Pixar’s central atrium, Google’s Micro-Kitchens or WeWork’s collaborative workspace as the ‘model case studies’ to generate innovation. But serendipity does not depend on place making alone. It’s the people that make the connections. As Jacob Morgan, who writes and researches the business value of employee engagement, three environments that matter most to employees: cultural, technological, physical. As a leader in workplace strategy I have guided many clients on which physical and technology workplace investments will help foster serendipitous moments. But as a leader in design research and internal innovation I have also worked under all types of constraints to build meaningful cultural engagements that help connect people. Don’t think you need multitudes of help or resources to get started. A lean effort with a few focused individuals and leadership sponsorship is the best way to get going.