The Secret to Building Trust in an All-Remote Startup

Kevin Borders
Mar 10 · 6 min read

The biggest misconception people have when I talk to them about remote work is that you can’t have great relationships. Not only is this untrue, but I believe trust is even more important in a remote environment than it is in an office. When you can’t see people, you have to rely on what you know about their character to have confidence they are acting in the best interest of the team.

What I have found bootstrapping Collage.com to 50 employees without an office is that it isn’t the separation itself that makes building trust difficult, but the fact that separation makes it harder to show vulnerability, which is the basis of trust. Luckily, there are a lot of things you can do to foster the expression of vulnerability in a remote workplace. This article describes how we build trust at Collage.com, which has helped me establish close bonds with many of my colleagues, some even closer than friends or family who I see all the time.

Joe (left), the other co-founder of Collage.com, and I hanging out in New Orleans during one of our all-company retreats — a key way that we build trust in our all-remote startup.

Create a Mistake-Friendly Culture

The cornerstone of a healthy remote workplace where people can express vulnerability is a culture where it’s okay to share mistakes. This starts at the top. It is very important for leaders in a remote workplace to go out of their way to communicate both publicly and one-on-one when they screw up. This shows everyone that work is a safe space where mistakes won’t get you fired. It also conveys that management doesn’t hide things from people and that they are human. Sharing publicly shows that you aren’t afraid to open up to everyone, and sharing privately demonstrates that you value your relationship with each individual.

Another great way to build trust is for managers to share what challenges they are facing, what they learned recently that they would do differently in hindsight, and what they are working on improving personally. This is a nice way for people to feel less negatively about any issues they may have with their manager, and feel more comfortable sharing critical feedback in a less personal remote setting because it will seem like they are helping their manager rather than complaining.

Retrospectives and post mortems are also powerful tools for fostering vulnerability and trust that don’t require face-to-face meetings. Rule number one of a retrospective is that everyone tried their hardest to do what they thought was right at the time. However, most people still feel uncomfortable admitting their errors in this context. One way management can help is to not allow the conclusion to be that we will just try harder next time. Management should contribute something they could have done to prevent problems, such as establishing better processes, setting more clear responsibilities, or fixing underlying problems in systems that allow mistakes to happen. The message needs to be that it’s not the individual’s fault, and that management will take steps to avoid the next post mortem.

Talk About Your Personal Life

One of the easiest things to lose in a remote workplace is day-to-day conversations about what is happening in people’s lives. Since people tend to reach out only when they have something work-related to discuss, this important type of communication is often lost, but it doesn’t have to be.

During one-on-one meetings, managers should make it a point to talk about what is going on with their family, what they do for fun on the weekends, and things outside of work that causes stress in their lives. They should also ask about these things, even if it seems a bit unnatural over a phone call/video chat. It is also important to take note of what is happening in people’s lives and actively follow up (e.g., “Is your kid feeling better this week?”), which demonstrates that you genuinely care.

We have also instituted a “How was your weekend?” segment at the beginning of every Monday stand-up. This is especially beneficial for team members to get to know each other better who don’t have standing one-on-ones. There are also various Slack channels for hobbies/interests outside of work, which are a great way to connect people across different departments who don’t normally interact.

Emphasize Common Goals

Nearly all of our disagreements at Collage.com are not fundamental in nature. People generally want the same things, but can get into arguments if they don’t know it. This can often happen when working on complex projects because each person has a different perspective.

One of the most important management skills is identifying when people disagree because they’ve failed to establish shared goals and helping them resolve their differences. This can take the form of something like: “We want to avoid launching a project with any severe bugs.” If two engineers can agree on this principle, then it makes it much easier to resolve a dispute about a code review, for example, where the author thought the reviewer was being nit-picky with a change request when the reviewer was actually worried about causing bugs. Making common goals explicit is especially critical in a remote environment because people interact less often and need to trust each other’s decisions when they’re not around.

In-Person Meetings

At Collage.com, the whole company gets together in-person twice a year. These meetings are an essential part of our culture because they give us the opportunity to have interactions that aren’t possible over video chat and allow us to establish new connections in a different environment.

Perhaps the most effective session we have during our meetings is an ask-me-anything style Q&A with me and the other founder/CEO. People have asked us some difficult questions that some people even thought went too far. But, there is no better way to lead by example and show vulnerability than to explain what personal shortcomings you have that has negatively impacted others in front of the whole company and frankly discuss what you plan to do about them.

Another type of session that works best in person is a cross-department meeting. All the steps you take to foster relationships remotely are harder to execute across departments, and large meetings over video chat are not conducive to people expressing critical opinions. In-person cross-department meetings often uncover general concerns or sentiments that may be common knowledge within a department, but unknown to others. They are also a powerful way for members of another department to express their gratitude and support for other people’s work, as well as their desire to receive better feedback. This has been especially enlightening for meetings we’ve had between other departments and the customer service team. They have been able to share valuable insights about customer concerns, and others have been able to provide better context about why they are not always able to fix customer problems right away, but reaffirm the importance of hearing about these problems on a regular basis.

Finally, there is no substitute for a late night at the bar and karaoke. At work, you are probably not singing and (hopefully) not drunk. However, a lot of people’s deepest concerns, like why someone else got fired, whether their own job is in jeopardy (even despite assurances it’s not during regular one-on-ones), or that they are worried about the behavior of their manager, are just not going to come out unless they feel like they are in a really safe environment. I have had many conversations that I would consider critical to a person’s happiness or some other important aspect of the business after 2 AM, which have led to successful follow-ups and better relationships during work hours. By sharing deeply personal things like struggles I have had with my family, I have let people know that life can be tough for everyone, and they are part of a larger family even though we only see each other twice a year.

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Kevin Borders

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Co-founder and Co-CEO at Collage.com. Software Engineer, Computer Science Ph. D.

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