Stop, Collaborate, and Listen.

Ron Pragides
5 min readMay 16, 2021

Companies across the globe are embracing a new reality: more work can be done remotely. This trend is not new. Companies like Automattic (founded in 2005) and GitHub (founded in 2008) were intentional in hiring a completely distributed workforce.

Due to the COVID pandemic (and social distancing mandates), employers learned to rely online collaboration tools. Videoconferencing has been around since the days of Skype. But in 2020, companies worldwide scrambled to embrace the latest incarnation — Zoom became a household word and synonymous with the concept of remote meetings. Videoconferencing provides a replacement for in-person, real-time synchronous team meetings.

Similarly, a host of online tools exist to enable asynchronous team collaboration. Recently, our leadership team discussed the need to be intentional in our use of these remote collaboration tools.

Humans have evolved over millennia to work in small groups to achieve specific tasks. New collaboration tools seduce us with their promise of instant communication with anyone in the organization. But it’s a double-edged sword: If every employee is compelled to be hyper-responsive at every moment, it leaves little time for the deep thinking required for knowledge work. I have strong opinions on the pros and cons of these tools.

Collaboration Tools I Use Most

Email vs. Slack: Once upon a time I was very diligent at Emails, but then Slack came along and seems to be how most organizations are run these days. Therefore I’m far more responsive on Slack — despite the fact that Slack is the equivalent of 100 Inboxes. However, my preferred way of working in this environment is to have a few important standing channels for groups that need to communicate with each other frequently. An analogy would be instead of an email d-list to have a standing Slack channel. I’ve found this works quite well, and is something I encourage for every team.

Email for internal communication is now relegated to the kitchen sink as every tool dumps stuff into an Inbox. While I know that we can filter and route emails to different folders/tags, I find that the juice is usually not worth the squeeze. However, Email is absolutely the preferred way to interact with external 3rd parties. Email is a good place to document items for future reference (again, a younger me earlier in my career was very diligent in maintaining these timestamped records of decisions). But with newer collaboration tools, I believe there are better ways to provide this documentation. (See below.)

Google Docs are remarkable for collaboration (both real-time and asynchronous) but is nearly impossible to find the right documents in the massive pile of Google docs that inevitably get created. Google Docs are also — aside from Google Sheets — usually transactional, in that they serve a particular purpose (a specific presentation or meeting) and then quickly become superseded.

Google Drive helps in some regard to organize the mass of documents, but my preference is to combine Google Docs with some external index into them (such as Notion or Confluence pages). I’ve found both Notion and Confluence I’ve found to be a great way to build an intranet / internal Wiki, with Spaces organized by Department, Team, etc. Each of the Confluence pages can, in-turn, link out to specific Google Documents. In many cases, having Confluence pages as the anchor and index to Google Docs helps with organization and discoverability.

Asana is a tool I’ve seen used well for maintaining standing topics for meetings, priority lists and commitment dates, and cross-team collaboration with sub-tasks that link out to department specific tools (e.g., JIRA, Salesforce, etc).

How I Work Best

Slack is the best way to communicate with me, and I’m generally more responsive with DMs or @ mentions in channels. I like having some key Slack channels with groups that have to communicate often — an analogy to an email d-list. I’m also a big believer in using Slack threads to organize conversations by topic. I’ve recently learned about the /remind feature in Slack, which can be useful and a replacement for Calendar reminders (see below).

Calendar is visible for scheduling but with meeting details kept private. I specifically block out time for Lunch and Focus time — Clockwise is helpful in this regard. I’m open for a meeting whenever my calendar shows availability. In fact, I like it when milestones or due dates (e.g., filling out this form) are scheduled on my calendar as reminders and in the past I’ve done that for my teams as a 15 minute “REMINDER: XXXX [No Meeting]”. This is a practice I haven’t done in awhile but have found it effective in the past for my teams.

To-Do/Notes in the old days I had a habit of sending myself a ToDo email every morning. I don’t actually do that anymore but instead — if I’m organized in my thought — will set calendar notifications for me as reminders to finish a task. I have also recently started using Slack as a way to take notes for myself: creating a private channel where I am the only member. (This can also be accomplished by DMing yourself, but sometimes I like to use the private channel to also preview a message that I intend to post on Slack).

Clockwise is a useful tool for reserving essential lunchtime (which is too easy to overlook) as well as dedicated Focus Time. Clockwise also has a useful feature to put meetings on “autopilot” and automatically find the best time for all attendees. I think it is worth paying for a corporate license.

Google Sheets are a useful & flexible tool, but often a purpose-built commercial tool is better for the long-run. (I’m also particular about trimming unused columns and rows from Google sheets).

If There Was A Problem, Would You Solve It?

Ultimately, all of these tools are only useful so far as they provide employees a workflow that enables focus. It’s far too easy for companies and employees to fall into the trap of incessant communication, preventing them from achieving a state of flow. This is the hazard that Cal Newport of Georgetown University describes as The Hyperactive Hive Mind:

A workflow centered around ongoing conversation fueled by unstructured and unscheduled messages delivered through digital communication tools like email and instant messenger services.

Problem solving is what we expect of knowledge workers. Communication plays a major role in identifying problems and aligning on goals. But incessant communication is literally “too much of a good thing” — Activity is Not Progress. The deep thinking required to solve problems can only happen if periods of high-bandwidth communication are balanced with dedicated focus time.

So go ahead, “collaborate” and “listen”. But don’t forget to also “stop” long enough to actually solve problems. After all, isn’t that the point?

Vanilla Ice shares his perspective on collaboration.



Ron Pragides

Led pre-IPO teams at @BigCommerce @Twitter @Salesforce. Follow me on twitter: @mrp