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Updated March 23, 2023You’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.
There are plenty of benefits to meeting in person occasionally as a remote company, especially for fostering meaningful connections and building trust. But there are associated costs and potential downsides worth considering when thinking about how often people get together.
Connection. Getting together fosters human connection and helps build trust.
Collaboration. Activities like planning and brainstorming are generally easier and more productive when conducted in person.
Speed. Communication and collaboration happen much more quickly when an entire team is in the same place. Some companies send new employees out to work with their onboarding buddy or mentor to making onboarding as quick and effective as possible.
Fun. Getting together isn’t just about business. Many people like offices because they’re also social spaces. Team lunches, happy hours, karoake sessions, and much more are only really possible in person, and most remote workers only get these opportunities with coworkers when they have the chance to get together.
Cost. Flying a few people to meet occasionally might be feasible for a small startup, but as companies grow, these costs can escalate quickly. A retreat for a company in the hundreds can cost hundreds of thousands of dollars*—Automattic spent $3.3M to host 800 employees in Orlando for their annual retreat.
Inconvenience. Traveling can be fun, but it can also be inconvenient. The burden of travel falls particularly hard on employees with specific physical or mental health needs, those with families or caretaking responsibilities, and for those who live far from the destination.
Safety. Some locations will be less safe for women, LGBTQ+ folks, and/or members of racial, ethnic, or religious groups to travel to or through. It is essential that companies take steps to keep all of their employees safe, by choosing locations that do not present risks of injury or harm to any employees.
Have a realistic budget. Retreats can get expensive, but a successful retreat doesn’t have to be extravagant.
Respect people’s time. Account for total travel time such that people aren’t gone for so long that caregiver and other responsibilities are strained.
Visit the section on offsites and retreats for all the details on bringing everyone together.
There’s a plethora of tools that we have at our disposal for different kinds of work. Tools like project management software, collaborative design tools, distributed source control for code, and others, become communication channels when we’re doing distributed work. Many of these types of tools support commenting, assigning people to tasks, and other means of communication that cross over with the other channels we’ve already covered—and many tools are aiming to handle a broader spectrum of uses, blurring these lines even further. We can’t cover them all here, but a few examples include Basecamp, Asana, Trello, and Jira for project management; Google Suite for documents, spreadsheets, and presentations; Figma and Sketch for collaborative design; GitHub and GitLab for code source control; and many other options.
Purpose-built. Tools can be better at serving a specific purpose than general-purpose work suites are. For example, project management tools that support collaborative teamwork are generally preferable to trying to keep track of everything in a spreadsheet.