Summary: Trello’s How to Embrace Remote Work

Sarah Archer

by Sarah Archer

7 min read
Summary: Trello’s How to Embrace Remote Work
Playbooks Managing Teams

The global rise of reactive remote work in 2020 spawned a proliferation of playbooks published by many of the leading remote-first companies, which open-sourced the knowledge they’ve gained from years of successful fully remote operation to help other businesses follow their lead. There’s only one problem: These playbooks are loooooong. So wkrfrce has condensed them into abridged versions—CliffsNotes, if you will. Digital nomad Sarah Archer, a passionate advocate of remote and flexible work, has combed through thousands of pages of remote-first strategies to deliver the most unique, most useful, most actionable insights to help make working remotely work for you.

Trello cofounders Michael Pryor and Joel Spolsky have long challenged the traditional office set up.

Sticky notes weren’t cutting it, so Pryor and Spolsky launched a visual collaboration tool that organizes and prioritizes projects in real time. Now 50 million users strong with employees distributed all over the world, Trello knows a little something about growing a product with a fully remote team.

Take it from Pryor—he believes that remote work has led to a better product, stronger talent, and a clearer purpose.

We dove into Trello’s playbook on how to embrace remote work as well as their blog posts to learn more about how they successfully do remote work.

Establish Ground Rules for Communication and Collaboration

When people with vastly different work experiences enter a remote-work environment, naturally, they approach work differently. For those who are new to working remotely, collaborating in a colocated environment doesn’t always translate well to online.

That’s why Trello sets clear ground rules for how their team should communicate and collaborate. These guidelines not only make projects run smoother but they also foster a happy and productive team.

  • Establish communication rules
    Identify the right time to write emails, pick up the phone, and communicate over chat. Allow remote workers to have “noncommunication” times as well—when their get-it-done energy is highest. If everyone contributes to and aligns with the same rules, everyone is more likely to be productive.
  • Preface communication with context
    You’ve done this, right? You’re preoccupied and you reply to an online message with one word. But your answer doesn’t provide context, which means more chances for miscommunication. Your colleague might misinterpret your brisk answer—for example, that you didn’t like the question, or that you’re mad at the sender. So if you’re using email, you’ll need to explain. Or try updating your status in Slack: You’re working heads-down and are not available for conversation. This can help avoid misunderstandings, not to mention hurt feelings.
  • Always be empathetic
    On the other side of the situation—sometimes a coworker’s intent gets lost over chat; you’ll navigate this more effectively if you assume that your colleague is coming from a positive place.
  • Deliver feedback with the best intentions
    List or discuss your colleague’s strengths before revealing how to make the idea better. If you consistently say something positive first, you’ll increase the team member’s mood as well as their willingness to listen to your feedback.
  • Provide constructive or corrective feedback over video
    Workers can misread even well-intentioned and useful feedback if it’s sent over email or chat. Use video conferencing instead so your intentions are clear, and so you can read your direct report’s feelings and reactions to the feedback.
  • If one person is remote, everyone’s remote
    No one likes to dial into a video call to hear the background chats of onsite participants on the other end. If everyone can’t be in the same room for a meeting, default to holding the meeting over a video call.
  • Develop video call etiquette
    Video calls run smoothly when everyone follows the same rules. You know the drill: Mute your mic when you’re not speaking, keep your video on to stay engaged (unless you need to turn it off to save bandwidth), and, if you will need to speak, avoid joining calls from a noisy location.
  • Provide the support for a great video call
    Provide (or reimburse for) headphones to ensure audio and microphone quality, cover employee internet bills to boost bandwidth, and promote using apps like Krisp to remove background noise.
  • Decipher time sensitivity
    To avoid distracting team members with Slack threads, the Trello team defaults to communicating on Trello (the product) unless the information is time sensitive.
  • Plan ahead
    Be cognizant that team members live and work in other time zones; therefore, don’t make last-minute decisions. Trello embraces asynchronous communication that doesn’t require an immediate response, and you should consider it, too.
  • Create a meeting structure
    Make it easy for anyone to follow along, no matter their location, by preparing a meeting process, structure, and agenda. Always designate a meeting lead and a note taker who captures process and decisions in writing.

Establish a Company Culture with 100 Percent Buy-In

A robust company culture requires intention. You must work to understand the perspective of others and then establish rules that everyone lives by, to create a space that welcomes all.

In addition to being intentional, shaping a culture that everyone buys into needs time. Trello culture develops from the time they take to encourage feedback, regularly review company values and policies, and recognize achievements. Here are some ways, taken from Trello’s blog, that you can build your company’s culture.

  • Hold a company-wide town hall
    Traditional quarterly speeches are retro and not in a good way. Instead, hold a monthly open forum that anyone can contribute to through questions, discussions, and team presentations.
  • Schedule 15-minute side chats
    Trello randomly pairs employees each week so they can get to know each other. Trello encourages employees to recap their meeting with a summary of what they learned about each other.
  • Sponsor a choose-your-own event
    Offsite team events are costly—and not practical with a distributed workforce. Instead, Trello offers a choose-your-own-adventure day: Employees have a budget to spend on their own adventure such as sailing a boat, rock climbing, going to the beach, or whatever suits them best. Adventurers build rapport by recapping each adventure and posting pictures in the virtual town hall that follows.
  • Recognize employee achievements
    Make sure to notice and celebrate work anniversaries; doing so shows your appreciation for employees’ dedication to the team and business. You also can create a birthday committee that sends a cake or surprise to all employees on their birthday.
  • Promote bonding
    Set aside time in virtual meetings to chat about life outside work, play ice-breaker games, and catch up on company news. In every agenda, Trello includes a “bravos” section that highlights each person’s positive contributions to the team and a “gossip” section to help everyone feel connected to what’s happening in the company.
  • Create transparency
    Make information accessible to everyone, regardless of their time zone. Trello documents decisions made in side chats, records all video meetings, and shares all notes in public forums.
  • Introduce virtual team-building activities
    Trello uses a variety of activities to build camaraderie among the team. For example, employees show team members what it looks like outside their window, do a desk show-and-tell, play two truths and one lie, or have a team lunch over a video call.
  • Create interest-related channels in Slack
    Trello encourages conversations about life outside work through common-interest Slack channels such as for recipe-sharing, musical interests, and exercise tips.

Motivate Employees by Being Transparent About Career Growth

Trello strives to support all employees by being transparent about how they can progress in their career at the company, and beyond. However, the company also keeps goals open, as individual potential can always expand.

Below are ways that Trello prepares a growth path, learning process, and progress-tracking plan to ensure every employee has the opportunity to grow.

  • Create growth tracks
    Public-facing growth tracks show employees how to progress over time and how managers can support that. Individuals use these tracks as a guide, then personalize them to match their own development and goals.
  • Set performance metrics
    Managers establish quantifiable goals with direct reports and constantly refer to them in weekly one-on-ones.
  • Promote accountability
    Employees write daily, weekly, and monthly goals for themselves in a physical checklist. This practice helps them take small steps toward larger goals.
  • Establish a sense of purpose
    When employees know how their work is benefiting larger business goals, they’re more likely to be emotionally connected and happier at their job. So, go beyond sharing the what behind an employee’s role to why it matters to your company.
  • Share an employee directory board
    Trello provides an employee directory with everyone’s name, title, and fun facts about them. Employees easily can find the person they’re looking for so they can explore opportunities, find mentors, and get to know the company better.

Adapt Tools to Become a Virtual Office

Endless lists boast the “best 50 remote tools,” but which one works for your team? Trello identified the following tools that solve teams’ pain points and easily integrate with one another.

  • Chat tools
    Slack goes beyond other chat tools with its “social” features that integrate GIPHY and emoji reactions. And communicating through Slack channels confirms that no decision is ever lost and lets team members contribute on their own time.
  • Video call software
    Effective remote work starts with video conferencing, and Zoom has proven to be a reliable solution that supports hundreds of participants at one time in a gallery view, in addition to allowing custom backgrounds.
  • Collaboration and status tools
    Trello doesn’t just promote its product; teams use it. Trello (the product) offers real-time collaboration with status updates, projects, meeting agendas, and more in one place.
  • Communication and documentation tools
    Working remotely requires documentation, and Trello relies on Confluence to outline policies, take meeting notes, and share ideas. For collaborating externally with freelancers, Trello teams use Google Docs.
  • Time tracking app
    A time-tracking app like Harvest can break up your day and identify which tasks are taking up too much of your focus.
  • Calendar and timeline app
    Calendar apps like Planyway allow users to manage team schedules, workloads, and due dates visually and in one place, making it easy to oversee multiple people and projects simultaneously.
  • Document storage
    If one team stores in Dropbox and another on Google Drive, at some point you’re bound to develop an organizational hiccup. Pick a storage tool and stick with it. Trello uses Google Drive for seamless integration with its tool.

According to Trello, a recent survey revealed, “77 percent of people see increased productivity when working remotely compared to working in an office setting.” And Trello, a remote-first start-up that turned into a $425 million business within a decade, provides solid proof that remote work, works.

Learn how other top remote companies embrace remote work through our remote playbook series.


Summary: InVision’s Remote Playbook

The global rise of reactive remote work in 2020 spawned a proliferation of playbooks published by many of the leading remote-first companies, which open-sourced the knowledge they’ve gained from years of successful fully remote operation to help other businesses follow their lead. There’s only one problem: These playbooks


Summary: Toptal’s Suddenly Remote Playbook

The global rise of reactive remote work in 2020 spawned a proliferation of playbooks published by many of the leading remote-first companies, which open-sourced the knowledge they’ve gained from years of successful fully remote operation to help other businesses follow their lead. There’s only one problem: These playbooks