Learnings From Remote Work

Raven Jiang
Aug 24 · 11 min read
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I had the opportunity to join the team at Bain Capital Ventures for my MBA summer and collaborate primarily with partner Sarah Smith. One of Sarah’s recent areas of interest has been centered around remote work needs, and the ways in which technology can support teams forced to work remotely due to the pandemic and beyond. I joined Sarah the past three months in conducting a number of deep dives on how the need to adopt remote work is changing the way people think about their HR, recruiting and collaboration needs, and spoke with dozens of startups that are responding to the call for change. This article is a summary of the questions we found over the course of these conversations.

For years, companies have cautiously evaluated remote work with mixed results. While there are obvious benefits to employees, such as avoiding the commute and greater flexibility at home, there are also many unsolved challenges.

Despite some early commitments by several big name tech companies to support full remote work after the pandemic, the corporate world is hedging its bets. In a recent Gartner CFO survey of 317 CFOs and their direct reports, only 6% believed that 50% or more of their workforce will remain permanently remote post-COVID.

Sarah and I both experienced managing teams at high growth startups with generous work-from-home policies. We decided to look at lessons learned from natively remote companies such as GitLab and InVision and talk to startups working on making remote better. Across these conversations, we saw four major challenges emerge:

  1. Transparent Communication
  2. The Water Cooler Problem
  3. Building Social Capital
  4. The Hybrid Challenge

In each of these areas, we see opportunities both for companies to adopt better policies and for startups to innovate and build better tools.

1. Transparent Communication

The point here is that informal communication is expensive when it comes to remote teams. Even with modern tools like Slack, the overhead of waiting for a reply means that it takes far longer to clarify ambiguity, adding to the iteration time at every step of a project. The goal is therefore to reduce the need for such communications by making what has already been discussed widely available.

Solution: Document Important Conversations

Among remote companies, the solution to this problem has been to document important conversations and decisions in a formal and public manner.

GitLab, a provider of software development tools, has over 1300 employees located in 67 countries and is the world’s largest all-remote company. Its employee handbook contains an extensive section on its remote culture:

The Remote Manifesto
All-remote work promotes:
1. Hiring and working from all over the world instead of from a central location.
2. Flexible working hours over set working hours.
3. Writing down and recording knowledge over verbal explanations.
4. Written down processes over on-the-job training.
5. Public sharing of information over need-to-know access.
6. Opening up every document for editing by anyone over top-down control of documents.
7. Asynchronous communication over synchronous communication.
8. The results of work over the hours put in.
9. Formal communication channels over informal communication channels

A quick glance through the manifesto reveals that over half of it is really drilling in on the need to document conversations. Preferring asynchronous communication (e.g. emails, shared documents, wiki) over synchronous communication (e.g. video conference, phone call) caters both to multiple time zones and the need to leave an evidence trail of every business decision so that costly communication is minimized. Some existing tools that we consider to be in this space:

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Tools for leaving a record of important conversations

Creating a communication trail comes at a cost. It can feel impersonal and can itself introduce friction to workplace communication. Nobody enjoys taking meeting notes, but at the same time automatic transcription may not always have great usability. Therefore, there is opportunity here for better services and tools that improve both the experiences of creating these paper trails and searching for relevant details in the firehose of information that they create.

The ideal solution in this space should not only make it easy to create lasting documentation based on low-friction conversations, but retrieve or highlight relevant information for future readers. It is an information retrieval problem as much as a logging problem.

2. The Water Cooler Problem

Hiring and training young inexperienced employees has also long been recognized as a challenge by fully remote companies. Bjorn Freeman-Benson, the former CTO of all-remote InVision, said in an interview, “It’s basically impossible to hire junior people in a distributed company.”

The issue he identified is that junior developers at InVision were unable to see other developers at work and did not feel comfortable asking questions. They tended to get stuck until they were explicitly asked about their progress. In addition to being a source of new ideas and social bonding, casual conversations also help to keep the ball rolling for inexperienced employees.

Solution: Virtual Water Cooler

There is a great deal of thinking around the Water Cooler Problem and the current solutions in this space to try to make casual conversations in remote teams less formal and easier to initiate. In essence, they attempt to recreate the sense of being in a shared space for remote teams. Conversations without calendar invites.

These tools typically feature easy screen-sharing, lightweight UI to initiate audio conversations with teammates and some fun and social features to encourage casual chit-chats. In order to protect blocks of time for focus, they often employ various UI cues to help your teammates understand if you are currently open to having casual conversations.

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Tools for spontaneous conversations between remote teammates

Most organizations cannot and should not be 100% focused on execution. Execution without alignment can often be counterproductive in the long run. Team meetings and water cooler talk help to naturally and incrementally realign the team, but striking the right balance in the virtual setting is difficult. A Zoom meeting scheduled intentionally as a time for casual conversations may be too formal and awkward for organic conversations, but also distract from valuable focus time.

For teams and companies that are used to working as a tight-knit group in person and frequently communicating, tools like Pragli and Tandem can be helpful in the post-COVID remote world by making it easier for remote team members to initiate conversations without the overhead of scheduling meetings.

3. Building Social Capital

This is even more true for young people who are just entering the workforce. For many fresh grads, work is their primary social network after college. It is not only where they hope to build new relationships that can last their career, but also where they want to learn how to cultivate those relationships. They want to learn to work well, which for a long time was done by observing how others work in the office.

Solution: Stronger Communities

The need to make new employees, particularly inexperienced ones, feel accepted and integrated into the team is going to be clear as this COVID-induced remote environment continues for longer than decision makers anticipated. In the short-term, organizations can survive in crisis mode and rally around a sense of urgency and need, but eventually we need more than treading water to make remote sustainable and healthy.

Here, we see a largely-untapped opportunity for tools that can help build stronger communities within the company. Services like Yammer and Facebook’s Workplace that attempted to simply transplant the consumer social network experience wholesale into the corporate world were the first movers in this space, but they did not take off in a world where workplace socialization primarily took place in person. That may be changing both as a result of COVID and demographic shift.

There are a wide spectrum of tools that fall in this space, from internal social networking to virtual happy hours to more expansive multimedia takes on the virtual office idea that promote social interactions. (Minecraft for work, anyone?)

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Tools for building intracompany communities

I think it is fair to say that none of the tools we have today have cracked the puzzle. I suspect that is because in the pre-COVID world where much of intra-company social bonding happened in person, there was simply little need for it. For any entrepreneurs interested in this space, I think it can be instructive to look at examples of purely online communities that have stood the test of time, such as open source projects and online multiplayer games.

Lessons from Online Gaming?

Online games like Minecraft and Roblox have enabled the growth of virtual communities among young people. Just as we spent time in the pre-COVID office space to do work, gamers spend time in these virtual worlds because they enjoy the game. A natural consequence of spending time together with others, whether at the office or in Minecraft, is the deepening of social bonds.

However, a purely social game without good and engaging gameplay may not keep players around enough to achieve anything, much less get to know other people. This is mostly where we still are with virtual office concepts: most of the social but not much of the work.

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Persistent community in Minecraft

A purely social tool ends up feeling too much like an unnecessary distraction from work. A sticky and sustainable product in this space will need to seamlessly blend the social features into regular work-related interactions to guarantee repeat engagement, just as the physical office space is a balance of both.

4. The Hybrid Challenge

As InVision’s Chief People Officer, Mark Frein, puts it, “If you have an office and yet a bunch of people work remote, it can be problematic, because the work experience of the people who work remote is often impoverished compared to the people working from the office.”

Remote workers in a company with in-person teams can feel like second-class citizens with a great deal of FOMO. We know that there is a strong need for communications to be asynchronous and documented in a remote team, but forcing in-person team members to follow these rules can be awkward and cumbersome. Imagine having to hold your phone out to record your brainstorming session for the benefit of your remote colleague. Or hosting a virtual happy hour on Zoom when half the team is physically in the office. It is really hard for remote workers to not feel left out and that is not a recipe for strong team culture.

It is for these reasons that Vivek Nair, cofounder of virtual office tool Pragli, often advises his customers to fully commit to remote. Yet, large companies across the US are clearly not ready to take that plunge. FOMO or not, hybrid will likely be the status quo for the foreseeable future.

Potential Solution: Next-Generation Telepresence

Given present technological limits, it is harder than in the preceding challenges to imagine what can truly bridge the gap between remote and in-person. We are dealing with time zones and the laws of physics here, but to the extent that telepresence or richer interactions can help to close the distance, remote employees can feel closer to HQ.

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Tools for telepresence and remote shared experiences

Telepresence has been an area of interest since the early days of the tech industry. When Doug Engelbart presented his visionary 1968 Mother of all Demos that described a future of remote collaboration, we imagined what it would be like to seamlessly work together across great distances. It also remains the elusive pot of gold at the end of the rainbow.

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Cisco Telepresence IX5000

The degree of visual fidelity needed to create a sense of remote presence is expensive to produce and cumbersome to consume. The amount of friction in AR and VR continue to rule out daily use cases. Greater adoption of consumer-grade LiDAR on devices like the iPad Pro may help to accelerate that future, but it is still some ways off.

The dark horse in this space may be audio. As we have learned from podcasts, the audio format can make you feel more intimate and personal than video or text. Apple’s recent WWDC announcement that the AirPods Pro will be updated to provide 3D-tracked spatial audio did not garner headline-grabbing attention, but maybe it should have. More than consuming videos with spatial audio tracks, this technology will have profound implications on audio-based remote collaboration.

Concluding Thought: Car, Not Faster Horse

In each of these areas, the natural instinct is to take wholesale what worked in the physical office and replicate the same experience online using technology as closely as possible. That may not be the right approach for everything. As companies like InVision and GitLab learned over the years, remote is different from being in the office, for good and for bad. The ultimate solution for remote work should ameliorate the bad without diminishing the good.

It may be a cliché, but it is always useful to ask yourself: Are you building a car or just a faster horse?

At BCV, we are always excited to chat with entrepreneurs about their ideas on tackling the challenge of both the future of work in general and remote work in particular. Drop me an email at raven@cs.stanford.edu or Sarah at ssmith@baincapital.com if you are working on something you are excited about!

Ideas from Bain Capital Ventures

Ideas and perspectives from the Bain Capital Ventures team.

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