Hybrid work is the Spork of teamwork

Hybrid work is a compromise between our desire to cling to the old ways of working while appeasing the team’s wish to have more flexibility in their lives. When done well, it will sort of work, just like a spork in picking up bites of food or spooning up some soup. I have a hard time seeing it to be a tool to build high-performing teams though. Distributed work is more than processes and tools. It is a culture shift. I would like to share with you the various failed attempts I had in the past 10 years and hopefully, we find a better path forward together.

Try #1

When my first company was acquired, I experienced firsthand the communication challenges I feared in distributed work. The acquirer and our company had complementary products. Generally, the product and engineering teams from both sides can work separately on most features. Though there were places where connecting and integrating the products made sense. While our team was located in NYC, our counterpart was in Israel. There was a 7 hour time difference and the Israelians didn’t work on Fridays but worked Sundays. Our teams had different lifestyles. Typically the NY team didn’t show up for work until 10 am or 11 am ET and left later. The Israelians followed a more family-friendly schedule. All in all, we had about one hour of overlap from Monday to Thursday.

Coordination was a disaster. When we couldn’t squeeze in all the discussions into that one hour, issues would take hours, if not days to get resolved. Out of sight, out of mind. We just weren’t each other’s top priority. The best solution we came up with was to minimize the number of integrations and when possible, establish formal APIs like you would when dealing with external entities.

Try #2

For the next company I founded, we kept a strict in-person model. At first, we didn’t think we had the right tools to replicate the tight communication loops required to run agile teams iterating toward product-market fit. Slack and Zoom weren’t available. Then even as we adopt tools like Hipchat and Skype, we were slowed down by issues from bandwidth, tool configurations, to poor hardware.

Yet, we gave remote work another try. We were an AI company that needed deep expertise in natural language processing in 2016. Talents were extremely hard to come by in NYC. We met a great NLP data scientist who lived in Boston. We decided to make an exception to the in-person model for him. Knowing that having a remote person is challenging for the team, we did everything possible to make the relationship work. For the team working directly with this data scientist, we doubled the number of coordination and planning meetings. The data scientist would visit the office every 6 weeks. We even dedicated a workstation to him in the office where there was a live Skype connection to his desk at home. 6 months into the relationship, it was clear to everyone that it wasn’t working. Once the novelty fainted, people soon stopped visiting the “virtual” workstation. We couldn’t stop teammates in the office discussing work or making decisions while they ate lunch together or chit chat by their desks. These conversations weren’t premeditated plots to exclude our data scientist. People simply talked about work when they were at or around work. The team had trouble giving their remote teammate enough context. In turn, his suggestions and comments sometimes came off as not helpful or silly because he didn’t have all the information.

Try #3

I took a break from founding companies to run the tech team of a health tech startup in 2019. The team started off as a 100% colocated team in NYC. After years of growth and changes in people’s lives, the team organically ended up with some members in New Jersey and California. When I took over, the company just opened up a London office.

A couple of weeks in, I realized that we were in for some serious challenges. Even though the team had grown to be in different locations, team members mostly kept to processes and rituals as if they were all in one office. 8 to 10 engineers would squeeze in front of a Polycom phone to conduct their daily standup meetings. Sometimes, people couldn’t hear each other. Other times, the statuses were so brief and specific to the individuals’ work that no one but the immediate teammates knew what they were talking about. There was no plan to properly onboard the new hires in London nor ways to distribute work to these new employees.

We did as much triaging as we could. We broke up the team into smaller pods. Stand-Ups had to be conducted via Zoom with video on. All meetings with at least one member not in the office were conducted over Zoom for everyone. We bought team member headsets for those who needed one. The new engineers in London were added to the weekly task planning meetings and we started pairing them with engineers in the US. Almost on a daily basis, the pairs would spend hours pair-programming on new features. The result was ok but not spectacular. Overall, the team worked better across time zones and regions. We made significant improvements in conducting meetings, pair-programming, and communication overall. Though we never got the London team to a satisfactory performance level and ended up closing the office.


As I embarked on building NorthShore.ai a year ago, my co-founder and I decided to build a remote-first company. We started the company with me in New York and my co-founder in Colorado. Even as a small team, we take time to write down our thoughts. We implemented good Slack hygiene and a more explicit mode of communication. For example, just because I tagged a person in Slack, I don’t assume he saw the message. If I need the person’s attention immediately, I text and call him. We minimize standing meetings but frequently ping each other for a 10-minute chat when required. It is still early days but it is working well for us. I am sure we’ll face new challenges as we scale. I am excited that we are starting with a foundation and vision that takes advantage of the strength of distributed work instead of treating it like a compromise. And I have the lessons from the past 10 years to draw from.