What Founders Have Learned a Year Into Remote Work

Nearly a year into the “remote work experiment no one asked for,” we know a few things. For starters, we know that we can be just as much if not more productive when how and where we work is flexible. We know that even stoic coworkers are in fact more like us than we think when we see their kids enter stage left in the back of a Zoom meeting. 

And we know how we spend time with our teams is going to continue to change as a new group of entrepreneurs envision improved processes and create new tools for remote communication and collaboration. 

“When we talk about the future of work, we’re referring to a few things; we mean the tactical of operations and productivity and also what stitches teams together, remote communication,” said True Analyst John O’Connell. 

Among our community of founders, culture has been top of mind during the pandemic too. “Another important part of the future of work is how we recreate culture when companies have essentially lost many of the touchpoints that nurture their culture and bring teams together,” said True VP of Culture Madeline Kolbe Saltzman. 

“Rituals of connection are more important than ever,” she added. “Executives can downplay their importance in comparison to other business goals. But healthy, engaged culture emboldens teams. And engaged teams with outsized impact succeed.” 

An article for Harvard Business Review suggests that rituals of connection – moments of social routine – not only create a shared identity but also reduce anxiety and encourage desired behaviors. 

A ritual of connection can be as simple as a weekly standup meeting or as planful as a monthly book club. Regardless of complexity and cadence, many of the founders whom we fund agree that over-communicating to team members during times of distress and disconnection can help to fill in the gaps of distributed teamwork. 

When working remotely, over-communicate to teams 

Communicating more than you normally would if you were with your team in person may feel tedious. But a steady drumbeat of communication can help to create an invaluable, two-way street for conversation between leaders and team members. 

College career network Handshake continued to host weekly all-hands meetings throughout 2020 and into 2021 in addition to introducing biweekly ask-me-anythings with its leadership team. 

“Any Handshaker can pose questions to executives and upvote questions ahead of time,” said Handshake Co-founder Garrett Lord. “Over-communicating has been essential to keep our team aligned through both headcount growth and operating fully distributed.” 

Balance asynchronous and synchronous communication 

As you continue to lead a remote team and the line between work and home life blur further, reset your company’s balance of asynchronous and synchronous communication. 

While the trend prior to the pandemic was largely to communicate via live messaging apps – instantly and often – some teams have since leaned far into asynchronous communication tools to better accommodate employees and offset the effects of being “constantly on.”

The co-founders at Jour, an app for guided journaling, sought an alternative to Slack so their team members wouldn’t feel pressure to reply instantly to messages at all hours of day and night. Jour Co-founder Justin Bureau recalled how it became commonplace to wake up to more than a hundred Slack messages, requiring morning hours to be spent reading and translating the messages into action items. 

The team transitioned to the asynchronous group discussion platform Threads during the first shelter-in-place order in March 2020. Bureau sees the benefit as threefold.  

“To start, it’s transparent. Everyone on the team has access to info and decisions that are being made; no more decisive conversations happening in private Slack channels,” he said. “It empowers everyone to be analytical. While a live conversation is mostly an infinite chain of one-sentence-thoughts and comments, a Thread forces our team to be sharper in the way we give feedback and take action.” 

Bureau also finds the platform to be better for historical documentation. Anyone on the team can reference past posts to see why the company made a specific decision, understand the context, know the stakeholder, and see the results.

The ‘threads approach’ isn’t as extreme as Jeff Bezos’ memo culture, but both systems guide employees to consolidate thoughts and create a system of record with the intent of future use. 

Empower a collective of leaders to be the voice of the company

When you’re not sharing an office with your team, it’s impossible to have the same type of leadership presence. Look to senior leaders across your company to enable a safe and supportive feedback loop. 

In addition to communicating with the Handshake team consistently and often, Lord developed an extended leadership team (XLT) in 2020 to help reinforce key messages to the greater organization and open more gateways for two-way communication. The group is comprised of its top 20 percent of directors and senior managers,

“As we’ve grown, it’s become even more important that our extended leadership team plays an active role in relaying information to their teams and also sharing team sentiment upward to inform decision-making,” said Lord. “We now cover key strategic updates, cultural decisions, and personnel decisions with this larger body before sharing them with the whole company.” It’s one of Handshake’s best ways for understanding what’s resonating with its team members. 

When replacing real life with online events, make them interactive

“We’ve seen a massive uptick in companies hosting online events,” said Whitney Stoner of Whitney Fusion Events, an event production company based in the San Francisco Bay Area. True has worked with the company on its events for entrepreneurs, including True Founder Camp, for more than a decade. 

Last year, Stoner and her team began using Welcome, a new platform for hosting interactive, virtual events, in order to recreate the kismet of attending a conference and, say, meeting a stranger with whom you have something in common in the lobby or at a mixer. 

“You don’t want online events to feel like you’re watching TV or a webinar,” said Stoner. She noted that one of the biggest challenges with virtual event hosting, for event producers and executive teams looking to recreate cultural experiences, is keeping people engaged. 

“Whether you’re hosting an all-hands meeting or a company holiday party, you can create interaction by sending attendees engagement kits to open during the event,” said Stoner. “Have your event speaker invite attendees to use the pour-over coffee set in their engagement kit to go make a fresh cup of coffee and return to their laptop in 15 minutes. Or, do a stretching exercise together.” 

Stoner’s best advice for entrepreneurs hosting online events for their employees is to keep it short and view events as a series. Shorten online events to a third of the time you’d spend if you were in person to keep the team engaged. “Shorter content segments is key,” said Stoner. 

She also suggests building upon content from week to week. Create a connective thread between recurring online events for engagement and accountability. 

“For a founder, that might be giving employees a question to think about and asking them to bring their answer to the following week’s standup or all-hands,” said Stoner. By linking event content together over time, you can turn one-off moments into thoughtful experiences that align with your culture and leave your team members feeling connected.