Realizing the dream of good workplace software

After their latest episode on “The impossible dream of good workplace software,” I sent a messier version of this email to decoder@theverge.com. You can listen and read more about the episode on The Verge.

I ran engineering teams at GitHub for a couple of years, and our Slack was a mess. There were over 2,500 employees on Slack, and we had three channels for long-form writing in other apps. But due to Slack’s design, these ideas were lost in daily chatter.

I blame Slack’s product design, specifically the tiny text input that trains people to talk to coworkers like they’re DMing a group chat.

I read Stewart Butterfield’s We Don’t Sell Saddles Here and recently this thread from a Slack employee about how they use it internally.

A formative moment for me was during my last startup mid-COVID with a remote team. My colleagues were experienced and had their own deep-work projects.

Despite a watercooler channel for side conversations, everyone was mostly heads-down. I wondered, “What is everyone else doing?” I had to trust that everyone was focused, but the feeling of isolation didn’t go away.

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