Communicating in 2016: Leave Good Messages

Communicating in 2016: Leave Good Messages

Subtitled; Never Just Say ‘Ping’

I was chatting with my friend Dan today, who works for one of the biggest publishing houses in the world. I’ve known Dan for a really long time. Here’s a picture of us from almost ten years ago:


Dan was telling me that his subsection of the company was starting to use Slack for communication at work. You know Slack right? We’ve been using Slack for a while at Automattic (for a time, the open source WordPress project was the biggest single group using Slack – or so I heard. Couldn’t tell you if that’s still true!).

At one point I tried to get all of my friends into a single Slack instance, since, like many groups of friends, we’ve ended up scattered to the four winds – Josh is in Rhode Island, Pat is in Chicago, Big Dave is down in Georgia, a dozen or so folks have their own little spots in the greater New York Megacity. It didn’t catch on, but that’s why Dan brought it up to me.

It represented a moment that doesn’t happen often for me: a time where my professional life, which is more or less surfing the front edge of what it means to Do Work On The Internet and my non-professional life, which is mostly hanging out with academics and non-tech folks. If Dan’s company starts using Slack, then it’s worth doing my part to share some lessons I’ve learned out here on the frontier of work.

(It also got me thinking; in 2016, it might be the case that every company is a tech company)

Here’s one lesson that we learned at Automattic and are still learning how to best implement – put shortly, always default to Continuation, or maybe always default to Flow, or bluntly, always default to Asynchronous.

This lesson came mostly out of working in a globally distributed company, but it turns out to make life and communication easier even when your day-to-day team all works in the same time zone, as mine does. Let me explain a bit more what I mean.

I’ll start with something that’s somewhat common and also the absolute worst way to communicate using a tool like Slack. Imagine opening Slack first thing in the morning and seeing this:


This is the worst. Let’s break this down:

  • You know that I wanted to talk with you about something.
  • You don’t know what it’s about.
  • You don’t know if it’s urgent.
  • We don’t necessarily work the same hours.

Imagine I work 9+ hours opposite you, either due to time zone changes, or differing work schedules. Even if you reply right now you may not hear back from me until I am also back online. Just saying ‘Ping’ is bad. It offers no information, and even worse, whatever task I was trying to complete in getting ahold of you, it’s now on pause, likely for 24 hours or more, until we’re able to properly connect. Blech. Don’t do this.

What about this one:


Yes, there are more words, but this is no better. In fact, if I’m your lead, or you’re my lead, this could be even WORSE! Is this a pending resignation? Is this some simmering piece of workplace rage that’s finally about to erupt? Have you messed up in some way and and now the chickens have come home to roost? Again, everyone has to wait. The flow is broken.

So, maybe:


OK, we’re on the right path here – at least you know why I’m contacting you, you know that it’s not urgent (due to the topic and the mention of the timeline we’re working on) – but you still don’t know why I’m contacting you. And again, even though this message isn’t as anxiety provoking as the previous one, we’re still breaking our flow – The Work isn’t getting done.

Last example:


This is exactly the message you want to leave for someone – it has a Topic, Task, and indicates Urgency. With a message like this, the Work can keep flowing even if we never connect in a synchronous way – and defaulting to that Flow state is key to using tools like Slack both efficiently and effectively.

Leave good messages. Do better work. Make cool stuff.


3 thoughts on “Communicating in 2016: Leave Good Messages

  1. For the sake of discussion, how do you think Slack (with the limitless history in client, unlike our previous IRC tool) is replacing our p2 communications? Pre-Slack, anything async would be on a p2. When would you suggest that a Slack message might *not* be the right venue (kicking back to a p2 or whatever other tool a company uses)?

    1. Great question! I’d challenge the premise a little – I don’t see Slack (or any syncronous tool) as a replacement for something like a P2. They’re essentially different tools with different purposes.

      Slack, both in private conversations and in busy public spaces, does not serve as a filter or an archive, whereas P2s, used thoughtfully, tagged well, and approached consistently, serve as both a filter and an archive, in that it’s easily searchable and organized in a sensible way.

      “P2 or it didn’t happen” is a saying I totally get on board with – especially w/r/t things like aggressive transparency.

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