editione1.0.2Updated September 6, 2022
You’re reading an excerpt of The Holloway Guide to Remote Work, a book by Katie Wilde, Juan Pablo Buriticá, and over 50 other contributors. It is the most comprehensive resource on building, managing, and adapting to working with distributed teams. Purchase the book to support the author and the ad-free Holloway reading experience. You get instant digital access, 800 links and references, a library of tools for remote-friendly work, commentary and future updates, and a high-quality PDF download.
If I had to pick the one thing to get right about any collaborative effort, I would choose trust. Yes, trust. More than incentives, technology, roles, missions, or structures, it is trust that makes collaboration really work. There can be collaboration without it, but it won’t be very productive or sustainable in the long run.Larry Prusak, Senior Advisor and Faculty, Columbia University, author, Working Knowledge*
In most organizations, trust goes in many directions. The organization trusts the individual to perform their duties, and the individual trusts the organization will provide the means to do their work, and will also fulfill their end of their agreement, such as paying for that work. There is also a network of trust among employees. Organizations that rely on knowledge work are built on the expectation that individuals will fulfill their duties to each other, so that collaborative work can happen. We trust that everyone will play their part, on time, so we can all perform well.
It’s harder to build trust when teams are separated. Remote employees don’t have access to serendipitous opportunities to physically spend time with coworkers, like having lunch or going out for ice cream or happy hour. Being in the same space makes it easier to bond, so distributed organizations may need to be deliberate in how they build and maintain relationships that foster trust with their employees, and also may need to strive to create a culture and environment that enables employees to build trust with each other.
Trust isn’t just about good feelings or liking the people we work with. Building a culture of trust makes a meaningful difference in both employee engagement and company outcomes by enabling higher productivity, better-quality products, and increased profitability.*
Many in-person organizations use physical presence as a proxy for trust and may not in fact have a deeper ethic of trust within teams. In remote companies, employees need a shared understanding of how to think about trusting their teammates and leaders.
Doist defines trust by a set of core values:*
Leaders are credible.
Employees are treated with respect as people and professionals.
The workplace is fundamentally fair.
Transparency builds trust. Many companies—especially remote organizations—value transparency because it improves credibility and lowers the chances of miscommunication. Monzo, a hybrid remote team in London, calls this “transparent by default,” and in addition to being internally transparent, shares a lot of information directly with their customers. Buffer identifies transparency as its first overall value:
“As individuals, we view transparency as a lifestyle of authenticity and honesty.
As a team, we view transparency as an effective way to work remotely and establish a culture of trust.
As a company, we view transparency as a tool to help others.
We strive to make all communication clear and avoid making assumptions.”
A couple of tactics for maintaining transparency—beyond the broad strokes of detailed, asynchronous documentation and communication—include:
Keeping employees informed. Surprises erode trust. Telling employees there’s a new hire on the day they start, or many sudden changes of plans, isn’t a good way of maintaining employee trust. Whenever and wherever you can, it’s best to ensure everyone knows what’s coming up, especially when it’s not just good news. When teams are kept in the loop, they can lower their defenses. If things go wrong, they will then trust that they will know about it with sufficient time to react or to understand how change will affect them.
Acting on feedback. Collecting feedback through employee surveys and anonymous forms is a useful way of learning about employee engagement. The value of this feedback isn’t in the collection of it, but is rather in the action that follows it. Once the company knows about any problems, it faces the choice of acting on them to maintain trust and improve engagement of their workforce, or risking eroding what trust they do have.
In our remote setting at Doist, we’re never on the clock. We don’t have dedicated hours you need to work and we’re not using team time-tracking or screen monitoring tools. With this setup, you’re measured purely on output. It’s about what you produce, not how many hours it took you or whether you did it at 6am or 6pm.Fadeke Adegbuyi, Marketing Manager, Doist*
Since it is almost impossible to observe if employees are working or not, most successful remote companies tend to shift their focus toward results. This entails granting people the autonomy (and associated tools, documentation, and organizational support) to make decisions and solve problems on their own as much as possible. It also involves a general level of trust that people are doing their best and getting their work done. Scott Hanselman reflected on the pressure he felt as a remote worker at Microsoft, where he often felt that a lack of trust drove him to work long hours to prove that he was doing good work:
Working remotely requires your company to trust you can do the work not only without them seeing you, but also without constant physical interaction with your teammates.*
A few key tactics that help improve autonomy and build trust in remote teams include:
Retiring the punch card. Traditional organizations believe that compliance, and even trust, can only happen if there’s presence. Distributed work requires that organizations free themselves of this notion. By definition, the organization must trust that work will happen when they can’t watch. Not trusting your employees will not only cost you as you build structures and processes for compliance; it will erode engagement, productivity, and the quality of outcomes. To build a modern company, it’s imperative that you free yourself from archaic notions of how work is supposed to happen. This means retiring the physical, virtual, and mental punch cards, and working on giving employees clear goals, healthy communication practices, and a thriving collaborative environment.
Reducing bureaucracy. In a distributed team, getting approval or permission to spend money can take a long time because communication can be slower. If employees are trusted to use their own and other people’s time responsibly, then why not do the same with actual money? You can do this with the policies you create for travel, expenses, and tool procurement.
cautionHowever, the shift of the burden to the employee to manage their own time can often lead to people feeling overworked. Here’s Martin De Wulf on the challenge of always needing to show output:
I am not naïve, and I know that in the end, in software engineering, most jobs are really about results (you will get fired in the end if you produce nothing), and not means; but in remote working, since people are not seeing you work, you might feel more obliged to show results everyday, even if it forces you to work way past eight hours a day.*
For all the emergent popular culture about the wonders of remote work, there remains one inextricable issue which goes largely unacknowledged: Great teams need human connection—and human connection does not happen through computers.John O’Nolan, founder and CEO, Ghost*
Happier teams are more effective teams. Regardless of your internal wiring—introvert or extrovert—people strive for connection, and remote work can have a tendency of fostering cabin fever and isolation, which affect productivity as well as well-being. There’s a demonstrated link between the amount of social support people have at work, and having lower rates of burnout and higher productivity and job satisfaction.* Buffer found that remote workers who went six months without seeing any colleagues experienced significant dips in motivation, a symptom of burnout.
Many remote companies understand the ROI on this connection and invest hundreds of thousands of dollars each year to bring their entire team together.
Formstack brought all 120 teammates to Colorado Springs.*
Buffer brought 85 “Bufferoos” to Singapore, costing $380K.*
Automattic brought 800 employees to Orlando.*
GitLab brought 260 employees to Cape Town.*
Expensify brings together their team for a month-long retreat each year.*
Retreats tend to focus on building connections, engaging in planning or hands-on experiments, presentations, learning, and celebrating achievements:
GitLab gets together once every 9–12 months in an event they call “Contribute,” which is a mix of workshops, presentations, and company awards. The goal of the off-site is to “get to know the people in the GitLab community better” as a way to build relationships for collaboration. Employees are able to bring one guest or significant other to attend events with them.
Buffer shifted from twice-a-year retreats to once a year as the company got larger. It held a 5-day retreat for all employees in 2019, which included a “day off” for exploring with colleagues. The focus of the week is to help people form more direct personal connections with each other, and realign everyone with the broader mission of the company.
Zapier has run 10 retreats for “team sizes of 7… to 185” people and had to shift its focus as it has grown. Early in the company’s history it paired the retreat with a “mini-hackathon” to solve company problems. In 2019, they shifted to replacing it with an “unconference,” letting employees self-organize around a number of topics and breakout sessions.
Basecamp meets at its office in Chicago twice per year to share company updates and give employees space and time for informal meetups, working sessions, and presentations. During the meetings the company also sets aside an hour for anyone to stand up and appreciate their teammates’ “accomplishments or general awesomeness over the previous six months.” Outside of the retreats, teams can schedule their own “mini-retreat” once per year to work in-person on a project.
Trello didn’t have a big retreat for the entire company, but instead supported smaller team-selected offsites, giving them budget to choose an event best suited by availability and location.
When planning retreats, there’s a few things companies can do to ensure their success and enjoyment for everyone:
Convenience. While fun, exotic locations are definitely desirable, you will also want to factor in ease of travel and logistics, including requirements around passports and visas. Especially for employees with families, multi-stage trips to far-away locales can require significantly more time away.
Safety. Some locations may not be safe for LGBTQ+ employees, either as a destination or a stop-over. It’s imperative to do a bit of research to ensure any location you’re sending people to (or through) won’t put anyone at risk.
Inclusivity. Yes, Vegas ticks the boxes for convenience, and general safety. But it’s not so great for people who don’t drink or want to be around all Vegas has to offer. And Bali might work for everyone, but many people won’t want to hang around their colleagues in bathing suits, so group activities and events should stick to acceptable norms for professional gatherings. If you have people with disabilities or other specific needs, you’ll need to account for those as well.
Families. A big benefit of remote work is people being able to spend more time with and be closer to their families. You will want your budget to include provisions for partners and kids to come along, and to have child care and activities available for them as well.
importantIf you have one or more offices, consider having office visits for remote employees, which which may be more effective for collaboration than retreats or offsites.* If there’s no physical office, companies can enable teams to get together on their own.
Hotjar, for example, gives employees a €2,000/year “Work Together Budget,” where employees can fly around the world to connect with their coworkers. (This is in addition to their €4,000 Home Office Budget, €2,000/year Holiday Budget, €1,000/year Personal Development Budget, €200/month Working Space Allowance, and €200/month Wellbeing Allowance.)* Doist flys new team members out to spend a week working in-person with their onboarding mentor.*
Although you get to know people in a certain way by spending time with them, you can also connect deeply with people by getting to know them in their own natural habitat. When you meet regularly over video and see each others’ homes, families and pets, you can easily understand them more fully as people than you do in a limited workplace setting.Sarah Milstein, Senior Director of Engineering, Mailchimp*
If your company can’t afford retreats just yet, all is not lost.
In between in-person opportunities, or before they become available, companies can invest in non-transactional remote communication. Many companies know that connections are not always going to be built solely through collaborating on projects, and remote work requires more intentionality around building community—it will not form automatically, even if cultural norms and expectations are documented along with company values.
Encouraging a culture of celebrating wins collectively, praising each other for group achievements, and then taking time out for personal connection also promotes social cohesion and a sense of accomplishment, and helps fight the disconnection.* These shared rituals and joint, team-based celebrations both promote social connection, and discourage the type of individual competition that can exacerbate unhealthy work habits.
To build community, a little can go a long way. Here’s a variety of approaches used by remote companies:
Digital team lunches. These involve carving out a day per week when everyone sits down via video chat over lunch—even a hybrid company can have everyone get take-out or bring their lunches and join from a conference room or their desks. There’s even a company that handles the logistics for holding a virtual pizza party for a remote team.
Home office tours. You can encourage people to show their workspace either via photos or as a virtual tour on a video call.
Paired calls. Buffer does casual calls in pairs or threes, using an automated bot for Slack that sets up “donut chats.” Upworthy does this with “serendipity calls,” and there’s also HeyTaco! Such practices encourage people to take work time for a casual chat, where you take a break and get to know another teammate.
Virtual happy hours. Holloway has a monthly happy hour, where the distributed team gets together over Zoom and a drink of choice, no work talk allowed.
Team learning sessions. Specific teams can host their own “brown bag” or learning-focused sessions where someone presents on a specific topic of interest that they’ve been working on.
Slack channels. Most companies using Slack or other chat apps have #random, #fun, #music, #books and a host of other interest-based channels where people can visit and chat about non-work things they share in common.
Virtual games. Having fun with others builds relationships. Games can be a low-cost way of bringing people together and helping them build relationships. The Miro team has a great set of ideas for games teams can play virtually.
Informal Q&A. Basecamp has automatically running “social questions” where they ask simple, thought-provoking questions like “Anything inspire you lately?” that are meant to “grease social gears.”
Getting to know your teammates outside of day-to-day operations is important in working more effectively with them. As we cover in team communication agreements, these interactions help fill the gaps and answer questions like:
What motivates you?
How do you best learn?
How do you prefer feedback to be given?
These interactions help employees feel connected to one another and to the company and its mission. And they’re just plain fun.
importantIt’s also important for people on your team to connect with other people outside work. You can’t simply assume they have either friends or family to fill that need. A good practice is to encourage your employees to participate in local community events, reimburse their coffee shops visits, and pay for co-working subscriptions or even gym memberships. Anything that gets people out of their homes and interacting with other people will lower their mental-health risk.
Most people genuinely want to do a good job. In a remote team, there aren’t any silly rules about having your butts in a seat during certain hours of the day. This means at the end of the week you either have something to show for your week or not. This means you trust that your teammates are getting something done. But also your teammates trust you.Wade Foster, co-founder and CEO, Zapier*
Rebuilding trust when it’s damaged is an imperative for all companies. Managers of remote teams need to keep an ever-present eye out for hard-to-diagnose signs of conflict or degraded trust within their remote teams. This can include things like communication that is “business only” and never includes any chitchat or personal exchanges; team members not speaking up and admitting when they make mistakes; individuals overworking and not asking for help; and people explicitly complaining about other members on the team (either to each other or to management). We cover tactics for dealing with this in Managing Conflict in Remote Teams.
More broadly speaking, leadership at a company has an outsized impact when it comes to resolving broken or degraded trust within their organization. Buffer’s CEO publicly took the blame for mistakes when his company had to lay off several people, while invoking the company’s values and promising to uphold them in the future:
The fact is, the challenge that I created has now irrevocably changed people’s lives. I put the company in this position. I had poor judgement and took the wrong actions in many different areas. Especially at this time, I want to try to live our value of transparency and share everything about the big mistakes we’ve made, the tough changes we’ve decided upon as a result, and where we go from here.*
Setting the tone in this way likely helped to eliminate speculation about what happened, while rebuilding trust and expressing that leadership has the credibility to help turn the company around.
In my research I’ve found that building a culture of trust is what makes a meaningful difference. Employees in high-trust organizations are more productive, have more energy at work, collaborate better with their colleagues, and stay with their employers longer than people working at low-trust companies. They also suffer less chronic stress and are happier with their lives, and these factors fuel stronger performance.Paul J. Zak, Professor of Economic Sciences, Psychology, and Management, Claremont Graduate University*
“Why Good Leaders Make You Feel Safe” (Simon Sinek)
“How to Build Trust in a Virtual Workplace” (Keith Ferrazzi)
At its core, organizational culture shapes how an organization learns and solves problems. In the early stages of a company, culture may be shifting rapidly, but also be very coherent, meaning there is a clear connection between the day-to-day assumptions employees are making, and the espoused values and artifacts. Early employees understand the “why” behind most decisions as a result of the company being smaller and typically having direct access to influential decision makers.
As the company scales, subcultures may emerge, typically across specific teams, functions, or business units. Schein specifies that culture may emerge at the group level, among “a definable set of people with a shared history,” when they have:
Been together long enough to have shared significant problems;