Does Your C-suite Still Need to Live in the Same City?

October 7, 2020

In November 2018, I gave a presentation at the Lean Startup Conference about the “future of work.” In the presentation, I made the claim that the future of work had already arrived, because trends that are changing the way we work were already visible. 

Hugh Molotsi, CEO of Ujama

One of the trends I discussed is the way technology is changing what’s possible in how companies are organized. Specifically, you are starting to see more and more companies that have forgone having a central office for their headquarters and instead work completely remotely. These future-ahead companies have fully embraced using videoconferencing and tools like Slack to collaborate.

In the presentation, I joked about how our grandchildren will be amused that their ancestors used to battle soul-crushing congestion five days a week to get to work and return home. What I didn’t realize at the time was that in less than two years, we would be facing a once-in-a-generation pandemic that is accelerating the decentralization of the workforce. Whether you were prepared for it or not, almost all office workers are now working from home and have learned to master videoconferencing. Zoom has become a verb.

So does your C-suite need to live in the same city? Well, clearly based on 2020, we have learned that perhaps working in physical proximity with each other was somewhat overrated. A common reaction I hear from friends is their surprise that their productivity hasn’t suffered, even though all their work interactions have been virtual. 

In fact, having a globally distributed C-suite will give your company access to a much deeper talent pool — not to mention the tremendous cost savings and no need for a relocation budget.

I believe an even better question we can ask is: “How should your C-suite adjust to a fully remote world?” Answering that question starts with acknowledging what we’re missing out on when we no longer get to see our colleagues in person every day. The two that come to mind for me are team building and serendipitous discovery.

Team Building 

When we no longer are physically sharing time with colleagues, we start to miss out on the conversations and shared experiences that develop interpersonal relationships. Interactions, like sharing stories about your kids’ Little League game with colleagues at the water cooler or eating lunch together, deepens personal connection and rapport. Team members become “real people” and not caricatures, which is necessary when you have to work through difficult and contentious problems.

So how do we address team building in a remote world? Use some of the money saved from not paying rent on regular and well-organized team offsites. These offsites are an opportunity to bring the whole team together, flying in employees from around the world if necessary. 

Having fun at these offsites is not just an optional component — it should be intentionally designed into the agenda. The more that coworkers can experience with each other outside their professional relationships, the better. Don’t scrimp on the planning, and don’t be cheap! Paying for an event planner and facilitator, and holding the team offsite at a nice destination will make the experience unforgettable and impactful.

One of my favorite offsites was when I was working at Intuit and our team went sailing in San Francisco Bay with J World Performance Sailing School. Our team was divided into small groups, with each group assigned a sailboat and a professional sailor. After being given a crash course on sailing and each member assigned a role, we were on the water and racing each other. The activity took all of us outside our comfort zone, but made for great bonding and a memorable experience.

Having fun at offsites is not just an optional component — it should be intentionally designed into the agenda.

Serendipitous Discovery

Perhaps the biggest benefit of physical proximity is serendipitous discovery, where breakthrough interactions happen between colleagues that are completely unplanned and unscheduled. For example, someone in an adjoining cube overhears two colleagues discussing a customer issue they have been unable to resolve. She joins the conversation and mentions she had a similar problem and had found a solution. Her interjection saves her colleagues several hours of frustration.

I’m guessing anyone who works in a product creation role has a story of a great feature idea that happened in the kitchen, where they bumped into another colleague who just happened to also be refilling their cup of coffee.

In fact, the trend to create open-office spaces was not just driven by the desire to save money by squeezing more people into less space. These serendipitous conversations lead to productivity that can never be accomplished through scheduled meetings.

In a virtual world, replicating this chatter is much more challenging. Highly functioning virtual teams use Slack and similar tools to communicate with the rest of the team frequently in almost a “stream of consciousness” mode. Teams maintain social contracts that messages should be responded to within an agreed upon timeframe. The noise from the collaboration tools can be counterbalanced by having quiet hours and using “do not disturb” features. 

In my own startup Ujama, I feel we are still learning how to master serendipitous conversations using Slack. One practice we’ve been trying to encourage is having more “stream of consciousness” posts. Specifically, if you are an engineer about to research the answer to a specific problem, you post what you’re looking into before you start your search. This way, if another team member has the answer, they can respond and save you time. Others who are interested in learning what the answer is will be on alert for the resolution.

Learn from Others

If you are considering going fully remote, take heart in the fact that several companies have already made the leap and have lots of experience on best practices. You don’t have to reinvent the wheel as you figure out how to operationalize a decentralized team. HubSpot has even put together a site on remote work with sections for beginners, intermediates, and experts. (Search “HubSpot” and “remote work.”)

Many companies are not going to switch back to the old way of working once the pandemic is over. The future of work is accelerating, and it’s more important than ever that you figure out how to make it work for your company before you get left behind.  


Hugh Molotsi is CEO and founder of the startup Ujama, where parents team up to share rides and playdates. Previously, he spent 22 years at financial services company Intuit. He is a co-author of the book The Intrapreneur’s Journey: Empowering Employees to Drive Growth.

This piece is a part of the Fall 2020 special issue of IL’s magazine, which collects advice and insights from 25 contributors. Read the full “Innovation Matters More” magazine.