This Remote Working Experiment Failed And Succeeded – At The Same Time

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A version of this article previously appeared in Forbes.

Self-aware startups often learn more from their failures than from their success. Timehop, the photo album for the digital age, is no exception. Created by Jonathan Wegener and his Co-Founder Benny Wong, the company has over 16M+ users. To put this in proper perspective, more than twice as many people access Timehop each day than read the New York Times.

And Then The CEO Said, “Go Home”

Timehop recently executed a radical experiment. With winter raging outside, it closed its NYC office for two weeks and made all of its employees work remotely, preferably not from their homes. Many of the employees took off for exotic, sun-drenched locales.

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Even though the experiment did not yield the results the management team expected, many of Timehop’s employees enjoyed the experience. For instance, Software Developer Kevin Steuer noted that, “Working remotely gives me more control over a concentrated blocks of time each day to code. This has been awesome for productivity.” Co-Founder Benny Wong echoed a similarly positive sentiment, saying, “No commute reduced a lot of the anxiety of running late, especially if I want to exercise in the morning.”

The experience was decidedly mixed, as an number of employees felt distracted and disconnected by the hiatus. According to iOS Developer Evan Coleman, “I’ve been struggling with separating work from relaxation. Since I’m already home, I can’t justify getting up from my laptop and relaxing. My logic is that I’m working from home, so when I’m home, I should be working.”

Developer Rajesh Shenoy felt that the great flexibility did not adequately offset the value of the casual social interactions experienced in an office setting. Per Rajesh, “I missed talking to everyone. Social interactions help take your mind off work for a bit and I believe helps prevent burnout.”

To dig deeper, I reached out to the company’s CEO, Jonathan Wegener. What follows is an excerpt of our conversation.

John Greathouse: You’ve just raised $10 million in funding, basically tripled your company headcount in a matter of months and you decide to kick everyone out of the office. What the heck?

Jonathan Wegener: Hah, yea, it sounds crazy. Back in December, I flew to Wisconsin to visit one of our remote employees. I worked out of his home for a few days and the experience was eye-opening. I was so much more productive and focused than I was in our noisy NYC office! But I also found it really hard to communicate and collaborate with the team back in NYC, even with the latest video and remote tools.

As a company, we always strive for better. The remote experiment was about capturing the best parts of remote -- focus and concentration, while improving the worst parts -- communication and collaboration. We saw a chance to improve the working habits of everyone, not just our remote folks.

We also knew that if we could improve things for our remote employees, we’d be able to hire folks from places like Wisconsin and everywhere else that talented folks live around the world. So we’d be widening the talent pool. And we could also potentially make "work from anywhere" an official job perk for everybody and build a truly flexible workplace. Plus, February in NYC is just terrible. <laughs>

Greathouse: How’d the team react to the idea?

Wegener: Most people were excited to book flights to warm places... but others were concerned about productivity or that we were turning into a company where everyone is just a head on a laptop. Our team is close knit and the idea of not seeing each other for two weeks made some folks sad.

Folks went to Orlando, Dallas, Denmark, Puerto Rico, the Dominican Republic, and someone even got a small studio in Venice Beach with views of the Pacific Ocean (and yes, I admit, that was me).

Greathouse: Was it a total free-for-all or did you had some ground rules? If so, what were they and what was your reasoning behind them?

Wegener: We established “Core Hours” of 1-5pm EST. Everyone needed to be online and available during those four hours. All meetings were scheduled during those hours which opened up the rest of the day, creating long stretches of uninterrupted work.

Outside of those core hours, when you worked was up to you. Work longer in the morning, work longer in the evening. Whatever you need to get the job done and be at your most productive. We also moved our weekly All Hands meeting to 1pm EST on Mondays and everyone conferenced in. It was kinda surreal to see all these faces from all around the world on your screen.

Greathouse: What were the immediate things you learned? I imagine such a shift exposed quite a bit very quickly.

Wegener: Within a couple days, we all noticed that our focus and concentration improved. But collaborative tasks became much more difficult. Meetings had more overhead to setup and were less productive. The team missed being around each other, and lack of facial and body language sometimes led to misunderstandings...

People who had fled to warmer places also found it distracting to rebuild their lives elsewhere -- finding a new place to buy groceries and toiletries, eat lunch, mail a package. Even finding reliable high-speed internet was difficult, especially for people who traveled internationally.

The people who stayed in NYC and worked from home really enjoyed it for a few days. Working from PJs without a commute freed up more time to work. But eventually folks got tired of it and wanted more work/life separation.

Greathouse: Let’s talk about some of those remote technologies. What were the tools your team uses to stay in sync?

Wegener: Slack is our office chat, and it works great. We used BlueJeans and Google Hangouts for video chat. Dropbox for design assets. Github for our engineers. We tried a few other more cutting edge tools like Sqwiggle and Screenhero but they didn’t stick.

We also setup ground rules for communication channels. For example, don’t @channel the team chat room in Slack unless there’s an important time-sensitive announcement -- it creates an obtrusive popup that interrupts 20 people across multiple time zones. That’s terribly distracting, and not something we had previously thought much about.

Greathouse: And besides the ‘product’ problems of technology still not being 100 percent ready for replacing day-to-day interactions, you mentioned some people problems that came out pretty early. Can you talk more about those?

Wegener: Remote work is skill that takes practice and requires a certain level of patience. Simple things like talking over a design sketch are much harder to do without a whiteboard. We also found that chat and text messaging leaves more room for misinterpretation which sometimes caused tension -- especially between employees who didn’t know each other very well. Apple has a mantra of “assume positive intent,” which means to assume people are always acting in the interest of the company or to improve something. We love this, and made it part of our value system as well.

Note: This concern was shared by Lead Architect Kevin Cantwell, who told me, “The longer I spend without in-person interaction my perception of individual signals like tone and body language dull. I'm less aware of the team's mood. Not having those small social queues make remote communication a bigger effort.”

Greathouse: So, knowing that remote working is a skill that must be developed, what were the lessons learned? Did you guys implement any changes?

Wegener: Ultimately, we decided we’re not setup to be a fully distributed team and we won’t be offering that as a perk.

Instead we’re doubling down on NYC as our home. If we find extremely talented remote employees who can’t relocate to NYC, we’ll consider that on a case-by-case basis, especially for people can get things done and are OK with occasional trips to our NYC office to bond with the team. We’ll also be buying some new equipment to improve audio and video for existing remote employees.

We’ve embraced occasional working from home which is great. It's interruption-free, productive, commute-less, and a welcome change once in a while. We've decided to create a silent library in our next office space for interruption-free work.

Overall, it didn’t have the outcome we anticipated, but we learned a ton and at the end of the day it’s made us a better place to work.

Follow my startup-oriented Twitter feed here: @johngreathouse. I promise I will never tweet about killer burritos or cuddly kittens.

John Greathouse is a Partner at Rincon Venture Partners, a venture capital firm investing in early stage, web-based businesses. Previously, John co-founded RevUpNet, a performance-based online marketing agency sold to Coull. During the prior twenty years, he held senior executive positions with several successful startups, spearheading transactions that generated more than $350 million of shareholder value, including an IPO and a multi-hundred-million-dollar acquisition.

John is a CPA and holds an M.B.A. from the Wharton School. He is a member of the University of California at Santa Barbara's Faculty where he teaches several entrepreneurial courses.

Note: All of my advice in this blog is that of a layman. I am not a lawyer and I never played one on TV. You should always assess the veracity of any third-party advice that might have far-reaching implications (be it legal, accounting, personnel, tax or otherwise) with your trusted professional of choice.

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