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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.
Remote work breaks down when we try to mirror physical processes in the virtual world. Instead of trying to skeuomorph our way into collaboration, we should focus on the outcomes of any process we use and find alternatives that can help us achieve these outcomes.
Whiteboarding is the process of drawing on a whiteboard on a wall (typically with dry-erase markers) in order to visualize ideas or concepts. It can be used to demonstrate or explain something to other people, or more collaboratively as a tool for brainstorming and coming up with new ideas.
Notably, we call this technique “whiteboarding” because it’s rooted in a physical process that is simple and easy for almost anyone to use. When trying to show someone a complex or hard-to-follow idea or process, our natural instinct has long been to grab a writing instrument and say, “Let me show you…”
It’s effective because it combines all the benefits of in-person interaction—such as facial and emotional cues and rapid and collaborative discussion—with visual information that is easily updated, deepened, and improved. A quick in-person whiteboarding session can help map out an operational process, diagram a technical architecture, or explore pricing and packing ideas. For in-person interaction, whiteboarding is an amazing Swiss Army knife.
importantBut, in-person whiteboarding lacks one thing that remote work is increasingly skilled at creating: an asynchronous artifact. A physical whiteboard is designed to be easily erased, and usually is—on purpose or accidentally. If you want to iterate further on some whiteboard idea, you have to take a picture and recreate it somehow online, or draw it on the board again later on. There is a better way.
Many early approaches to whiteboarding for remote teams amounted to ways to share one person’s actual whiteboard (or the whiteboard in a conference room) with others via another screen. This approach is tantamount to sending around the picture of a whiteboard. In an unsophisticated remote setup, the office employees will work on the physical whiteboard, take a picture, and circulate it to the remote workers in chat, where they can’t actually contribute to it, and it’s often hard to read. When operating in a distributed environment, it helps to (metaphorically) throw the physical whiteboard out the window and start over.
In general, we’ve largely conflated whiteboarding with brainstorming. So let’s focus on brainstorming instead, and start from first principles. You’ll want to ask yourself these questions when you have the itch to whiteboard something:
What are you trying to achieve?
Who needs to be involved?
What information do you need?
How could you most easily represent, alter, or adjust that information?
What do you want to do with it once you’re done?
When it comes to brainstorming, fully distributed teams have one advantage in that everyone is forced to use a digital tool. For example, while a marketing team might use sticky notes on a whiteboard to generate ideas for social media campaigns, what they’re doing is collecting a set of ideas that can be easily moved around, grouped, and categorized during brainstorming. In that case, a remote team might choose a collaborative project management tool that supports kanban-board functionality that many teams are already familiar with, such as Trello.
Sometimes, you simply need to get some really basic ideas down first for people to react to, which you might do in a collaborative document like Google Docs, Dropbox Paper, or Notion, which makes it even easier to move content around in chunks. A team meeting to brainstorm can all be in the doc or tool at the same time, working together to adjust and iterate.
importantRemote brainstorming requires an even greater focus on allyship in meetings. The person running the meeting should ensure everyone gets a chance to speak, ask questions, and contribute. It may help to assign one person as facilitator to be responsible for ensuring that the end result reflects everyone’s ideas and input.
The output of an initial session might then move into a different tool where you can better visualize or draw ideas if needed, such as tools like Miro or Mural that take some of the physical principles of whiteboards and virtualize them. Modern design tools like Figma or Sketch with Abstract also make distributed design collaboration much more effective by treating design iterations like ‘branches’ similar to software. This allows multiple people contribute and keep track of current state and past iterations.
Even with tools like Miro or Mural, there are cost and experience implications for how remote brainstorming might work for an entire team. These tools work best when people have physical equipment like iPads plus Apple Pencil or a Jamboard (which can be remarkably expensive), and you’ll want to consider whether it’s worth the investment to ensure your entire team is equipped to participate equally in brainstorming activities.
The clear upside to remote brainstorming is that each step of the way, you’ll have an asynchronous artifact that you can share easily and as widely as needed.
importantWhile we can’t cover all the ins and outs of brainstorming techniques here, one key tactic that is important and likely intuitive to experienced remote teams, is to have people brainstorm individually first before you get together as a group. Research shows that asking people to brainstorm individually before the group gets together generates more unique ideas than brainstorming as a group first.* In groups, people are subject to groupthink and might converge on one idea too quickly without healthy debate.
“How We Overcome Location Bias When Brainstorming With Remote Teams” (SuperAwesome)
“Remote Whiteboarding” (Medium)
“6 Types of Meetings That Are Actually Worthwhile” (Atlassian)
“How to Stop Wasting Your Time—and Everyone Else’s—in Meetings” (The Economist)
“How to Make Meetings Less Terrible (Ep. 389)” (Freakonomics)
“The Ultimate Guide to Digital Meetings” (Slack)
“How to Run an Effective Meeting” (The New York Times)
“Cracking the Code of Sustained Collaboration” (Harvard Business Review)
“Group Conversations” (GitLab)
“The Silent Meeting Manifesto v1: Making Meetings Suck a Little Less” (Medium)
“The Art of Async: The Remote Guide to Team Communication” (Twist)