Ride the Wave of Better Conversations.


Do you care about how your work life affects your wellbeing? So do we. Working from home has its obvious advantages, but it also has some tradeoffs that we can’t afford to ignore if we care about our wellbeing. Remote employees are becoming more isolated, less connected and more susceptible to burnout

At its core, the problem is rapid migration to remote work has decreased meaningful social exchanges and increased task and work-related interactions between coworkers. Microsoft collected data in 2021 that confirmed weekly team meetings have more than doubled, while recent survey results from showed that 69% of remote workers reported burnout symptoms including exhaustion, little to no motivation for their job, feeling irritable or anxious and a potential dip in work performance. 

This is where DeepDiive comes in. It is a web app that minimizes the effort remote workmates need to put in to have meaningful social connections by providing a virtual deck of question  cards that dig deeper than typical icebreaker questions. 

User Research and Pain Points

To validate the depth of this problem, we ran 5 user interviews and assessed 18 survey responses targeting remote workers at tech startups. The key takeaway was: Since the pandemic, remote work has disrupted the social landscape that once existed for coworkers who worked in-person. Most remote workers reported feeling unsatisfied with the number of meaningful interactions with workmates. 62% of surveyed remote workers ranked their satisfaction with meaningful interactions at work with a 3 star rating or less out of 5. Some users shared their experiences: “Relationships feel very thin and work-related”  and “It’s rare to have 1:1 convos with people because you aren’t passing them in the hallway” 

Here’s a list of the top 5 pain points mentioned:

  • Focus on work has reduced time set aside to socialize
  • It takes more effort to plan social encounters online than in-person where there are natural bump-ins at the office
  • Sometimes it’s difficult to gauge what to say on calls when shallow ice breakers don’t satisfy social needs
  • Location and cultural differences can act as a barrier to social connection
  • Overused tools resulting in slack and zoom fatigue.

We asked research participants to share examples of interactions they found meaningful at work. They shared how getting to know a coworker in a meaningful way can extend to productivity. A number of research participants also suggested that social interaction makes work easier, more comfortable, happier and more motivating.

We also used research to validate how people define “meaningful interactions.” 

  • Most users mentioned talking about things outside of work.
  • Other trends included personal and less generic conversations, authenticity and effective information exchange.

Landing on a solution

To arrive at a solution we’ve asked ourselves: how might we increase meaningful interactions for remote workmates? Studies support that employees with friends at work are overall happier with their jobs, so we know there’s a real opportunity to improve professional and personal well being in this space.

Rigorous prioritization:

We had a short timeline (~7 weeks) to conduct research, run usability testing, and develop a product we were proud of. To execute this, we needed to make some tough calls when deciding which features we’d implement first. An example of something we deprioritized was incorporating video chat for users in-app. We had to reconsider this due to the heavy engineering lift and time constraints. During our initial user interviews about the pain points of socializing remotely, 53% of responses were related to users not setting aside social time and being too focused on work.  As a result we wanted to include integrations with Google calendar and slack to help users to schedule and protect their social time. Due to the additional engineering lift it would take to build these integrations, we decided to build a lean MVP by focusing on the end to end web app experience first. 

Data driven decisions:

When curating the questions deck, data was key.  Our PM used studies and user research to gauge what makes conversations meaningful and questions were picked based on their ability to have at least 1 of 3 desired outcomes: trigger a range of emotions among users, help users to learn something new from each other and enable users to share resources and help each other with a goal. These outcomes were informed by a qualitative analysis assessing the responses of 4,600 people across the United States, India, and Japan. 

Design and UX Considerations:

For the product design, accessibility was front-of-mind. Since DeepDiive is meant to bring co-workers closer together, our team did not want to create a product that excluded folks because of its UI. Our product designer thus applied inclusivity principles with high color contrast, especially on the question cards, and clear, simple microcopy. 

The visual design was also guided by specific user insights. Almost all interviewed users said that they sought relief from an exhausting day spent on video chat. Our solution was including colors that are both calming (blue) and energizing (yellow, orange). Our designer applied this palette in a relaxing wave motif, which led us to our product name: DeepDiive.

Landing Page: Lo-Fi vs. Hi-Fi Design

Questions Screen: Lo-Fi vs. Hi-Fi Design

The Solution:

DeepDiive is not your average ice-breaker. The MVP is a web app experience that accommodates two players. The goal of this web-app is to trigger more meaningful conversations among remote workmates. Scientific study and user research was used to gauge what makes conversations meaningful and this was used to inform the questions included in the card deck. We hypothesize that there is a positive correlation between the impact of these conversations and the overall happiness at work per user. 

Three (3) key MVP features (launched early November, 2021)

  1. Easy to understand onboarding flow: When a new user initiates a game, they are prompted to enter their name and copy a shareable link to invite a workmate to play. Once complete they are given the option to see instructions for the game. Designing this flow was an iterative process heavily informed by feedback in usability testing. This includes a waiting room to pause for invited workmates
  2. Invite-only unique sessions: When an invited user joins through an invite link, they are taken through a similar onboarding flow before arriving at the waiting room. 
  3. Interactive Virtual card deck: When users all arrive and start the game, they will see ground rules to enforce safe space guidelines before they have the option to pick a card and access the deck of questions. Each player is instructed to take turns answering a question which is autogenerated on the screen.  We sockets were used so that users can see the cards change live on their  individual devices

What’s Next? 

Some users shared promising impressions of our MVP: 

“I love how simple it is! A lot of virtual activities are too confusing” 
We are always talking about work and this will push people to ask different types of questions” 
“It's the card game you can’t misplace!” 

We also received ideas from our testing sessions. 

We are excited that we could meet our goal of launching a product we are proud of. We plan to request feedback, measure success and regroup after launch to assess DeepDiive’s value and impact on users before deciding on a path forward. While we won’t jump into working on this full time, we're open to enhancing DeepDiive overtime. Some potential initiatives on our roadmap include: incorporating video or in-chat functionality and building a slack integration to change user status while they are playing the game.


Product Manager Learnings:

Dominic Stephenson

  • Perfection is a Myth - think of a lean MVP that is feasible to build, usable and valuable to the user, then iterate!
  • User research and testing is pivotal during initial discovery, but it’s a continuous process to validate whether we are building the right thing
  • Plan for tons of unknowns when building from scratch. Developing a product vision and collaborating with a cross-functional team to bring it to life through the design and development cycle requires structure and flexibility!

Designer Learnings:

Alaina Zemanick

  • Team communication is a deliberate process. In talking to our team members individually, I learned how to better facilitate meetings and conversations that are accepting of all communication styles.
  • Maintain a bias for action. Receiving team feedback during the design process is essential, but in such a lean sprint, it is also vital for team members to make decisions on their own to further our collective progress. 
  • Being user-centered is the most likely path for product success. My experience working on this real-life product reinforced how essential user feedback is. In interviews and testing, it was gratifying to remove myself from my design bubble to better understand whether my designs suited the users’ needs.

Developer Learnings:

Adedimola Ogidan

  • Team communication is important. Passing your message correctly and knowing you can have an opinion and give feedback, made us more efficient as a team.
  • It is important to prioritize the key features first and to make sure the user has a good experience even with the mvp, especially in a project with a short time span like Co.lab
  • Collaborating in a cross-functional team helped me to see product development in a whole new light, especially since my past experience was working alone or only with other developers.

Developers Learnings:

Jerrie Feng


  • Through this experience, I learned how to articulate what I want to say, and how essential transparency between team members are 
  • Working with another developer gave me experience to collaborate on how to align coding style. It was important to know when to ask for help, and the need to consistently check-in with the team. 
  • I also learned how to give more constructive feedback/comments to others.

Full Team Learning

Team communication and collaboration is key to working together successfully. We’re all at different stages of our careers, so it was important to share our situations outside of Co.lab and plan for it. It was also important to be honest about our personal bandwidth. We overcame a lot to work together as a team--- remote, different time zones, etc.---  but we’ve learned to communicate and accomplished our goals!