How to Build Trust in Remote Startups

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When I talk to people about remote work, the biggest misconception 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 team's best interest.

9 Key Secrets I Learned Building Trust in an All-Remote Startup

What I have found bootstrapping to 50 employees without an office is that it isn’t the separation itself that makes building trust difficult, but that separation makes it harder to show vulnerability, which is the basis of trust.

Luckily, there are many things you can do to foster the expression of vulnerability in a remote workplace.

1. 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.

Leaders in a remote workplace need 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.

Sharing mistakes 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.

2. Share Challenges

Another way to build trust is for managers to share what challenges they face, what they learned recently, and what they are working on improving personally.

This is a nice way for people to feel better about issues they have with their manager and feel more comfortable sharing critical feedback because it will seem like they are helping their manager and not just complaining.

3. Use Retrospectives and Post Mortems

Retrospectives and post-mortems are also powerful tools for fostering vulnerability. 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 retrospectives.

Management can help by not allowing the conclusion that we will just try harder next time. Management should also contribute something that they could have done to prevent problems.

The message of retrospectives needs to be that problems are never an individual’s “fault.”

4. 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 reach out when they have something work-related to discuss, this 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.

Managers should also ask about each employee’s personal life over a phone call/video chat, even if it seems unnatural. It is also important to take note of what is happening and actively follow up (e.g., “Is your kid feeling better this week?”), which demonstrates that you genuinely care.

5. Have Consistent Personal Discussions

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 who don't have standing one-on-one meetings to get to know each other better.

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.

6. Emphasize Common Goals

Nearly all disagreements 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 something like: “We want to avoid launching a project with severe bugs.”

If two engineers can agree on shared principles, 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 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.

7. In-Person Meetings

In-person meetings are another great way to create trust in a remote startup. These meetings allow you to have interactions that aren’t possible over video chat and establish new connections in a different environment.

Sessions such as an ask-me-anything style Q&A with the founder/CEO are also a great way to let employees ask questions they're curious about. Even if the employees may ask questions that are difficult to answer on the spot.

Ultimately, there is no better way to lead by example and show vulnerability than to explain what personal shortcomings you have that have negatively impacted others in front of the whole company and frankly discuss what you plan to do about them.

8. Encourage Cross-department Meetings

Another type of session that works best in person is a cross-department meeting. Fostering relationships remotely is harder across departments because people have difficulty expressing critical opinions in large video meetings.

In-person cross-department meetings often uncover general concerns or sentiments that may be common knowledge within a department but unknown to others.

Cross-department meetings are also a powerful way to express gratitude and support for other people’s work and willingness to receive better feedback. This has been especially enlightening in cross-department meetings with the customer service team.

Customer service team members have shared valuable insights about customer concerns, while others can explain why they cannot always fix customer problems right away but reaffirm the importance of hearing about these problems regularly.

9. Have Fun

Finally, there is no substitute for a late night at the bar and karaoke!

You are probably not singing and (hopefully) not drunk at work.

However, deep concerns like why someone else got fired, whether someone’s job is in jeopardy, or concerns about a manager’s behavior will not come out unless people feel like they are in a 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.

The Bottom Line

Some people assume that you can’t have strong relationships and high trust remotely.

Fortunately, this is not true, and there are many concrete methods you can apply to establish trust in an all-remote environment.

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