☕️ (R)emote Expresso #72

☕️ (R)emote Expresso is global. Remote. Slightly feral. Weekly.

A reader sent this through the feedback poll at the bottom of a previous issue:

That vote shows up in my dashboard as "Bad."

It's one of 230 votes I've gotten over the last year. 66 of them registered as Bad. At least one of those Bad votes was love that the system couldn't display.

This March marked a year of writing this newsletter in my own voice. It was also a year of a lot of other firsts I'm not going to list here. (You don't need that essay. I might write it later.)

For most of that year, those three buttons were the only signal I got. Bad. Fine. Loved it. I'd hit send on a Monday night and watch the numbers trickle in. Three options. The whole point of writing into a community is the part of it you can't multiple-choice.

I believed those buttons more than I should have. Which makes sense if you've spent your adult life as a corporate lifer where buttons are the language. Press the right one and the system tells you you did the right thing. Press the wrong one and you get retrained. Multiple choice was my native tongue.

It also makes sense if you have the kind of brain that registers anything short of effusive love as rejection. Mild reads as cold. Fine reads as bad. Loved it reads as polite. So when 29% of the votes for the year said Bad, I had a brain that took it as proof.

A couple of weeks ago, I got admin access to the community.

There are actual humans with actual thoughts on the other side of that send button. I can read them now. They have things to say. They've been there the whole time.

I don't actually know how many of those 66 Bad votes were love. Could be one. Could be twenty. The point is the system can't tell me, and I was reading it as if it could.

This is what most of remote work runs on. Three buttons.

The thumbs up someone left on your message because they read it but didn't have time to write back, and you read it as terse. The calendar decline that came in twenty seconds after you sent the invite, which felt like a slap and was actually someone whose kid was throwing up. The Slack message that shows up at 10:12 PM your time and feels like an emergency and is just someone in another time zone clearing their inbox before bed. The "okay" that means okay, the "okay" that means I am furious, and the "okay" that you can't tell apart from the other two because you're reading it on a phone on the train.

We do this everywhere. Pressing the only buttons we've been given. Reading other people's button presses like they're the whole sentence.

Most of us are doing this all day.

So I'm done guessing.

Today I'm opening a chat channel in our R Generation Circle community. It's called The Bad Button. There's one prompt pinned at the top: name a button you wish you could have pressed. On this newsletter, on a Slack thread, on a meeting invite, on anything. Just the button. No explanation needed.

It's an open room. Nobody has to be in there for you to leave something. Drop a note. Leave. It's passing notes in class. It's writing on the bathroom stall. You don't have to wait for anyone to read it.

On Thursday, Isabel Novaes Machado is leading a session on a method for this. Not for misread Slack messages specifically - for the larger thing underneath: how to design a small experiment in your own life when the buttons you've been pressing aren't giving you what you need. Details below.

April was about what you can't say at work. This is the last issue for the month. Some of what we can't say is sitting between Bad, Fine, and Loved it.

Some of those Bad votes were love. I'm not mad. I'm just going to give you more buttons.

Three buttons aren't enough. So I'm collecting the ones that should have existed all along. What button do you wish you could have pressed - on this newsletter, on a Slack thread, on a meeting invite, on anything? Drop the button name in the channel. No explanation needed.

A working glossary of compressed signals. The system can't tell you what these mean. Use at your discretion.

SIGNAL 01: Auto-reply that reads "I'll respond within 24 hours." System reading: 24 hours. Also possible: 72 hours. Six days. Never.

SIGNAL 02: A Loom video lands in your inbox at 6:47 PM your local time. System reading: same-day expectation. Also possible: 11:47 AM their time. They will not check on this until Friday.

SIGNAL 03: Status indicator showing green for six uninterrupted hours. System reading: they are at their desk, working. Also possible: they walked out, drove to a doctor, picked up a prescription, came home, and have not yet moved their mouse.

SIGNAL 04: Hand-raise emoji left up in the meeting after the question has been answered. System reading: lingering question. Also possible: they forgot to put it down. They are reheating soup. They have been raising their hand in life since 1987.

SIGNAL 05: A reply from someone who normally writes paragraphs, returning as one sentence with no punctuation. System reading: cool distance; rejection of some kind. Also possible: phone. Train. Hospital. Both hands occupied with a cat.

SIGNAL 06: The "Hey" message with no follow-up text, then forty minutes of nothing. System reading: forty minutes of dread. Also possible: a meeting ran long. The dog got out. They forgot what they were going to say. They are debating whether to send the rest. They have moved on entirely.

SIGNAL 07: 🤣 from a member of your leadership team you have never seen laugh. System reading: joy. Also possible: this is cause for concern.

Things you've actually said back to this newsletter. Anonymized. Permission given when you hit send.

This month's guest creator is Isabel Novais Machado, a design leader with 15+ years across telecommunications, finance, data, and startups, currently running design at a data privacy company - which sounds dry until you realize she's spent her career chasing one question: how do you get from a spark of an idea to something real that people actually use?

That question isn't just for products. How you design a product, how you design a team culture, how you design a life - the mechanics are pretty much the same. You start messy. You explore. You narrow. You ship. You explore again. Rinse. Repeat.

Thursday April 30.

11 AM CDT | 12 PM EDT | 5 PM BST | 6 PM CEST

Miro Community Event. Hands-on. The piece I'm watching for: you map what gives you energy and what drains it, then dig into one of them until you've hit something underneath.

The Bad Button is the fast version. This is the slow one, with a method.

Paste this into whichever chatbot you prefer. It'll ask you two quick questions and then invent five buttons that should exist in your job.

Retroactive plot summary: I've been writing to you for a year. You've been writing back the whole time. I just started getting the mail. Worst postal service in history. Caught up now.

— The (R) Generation Team 💻 🧡 🫶

PS: Lurking is also a button. I should know - I've been pressing it on my friends' newsletters since 2024.

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☕️ (R)emote Expresso is published weekly for R Generation - a global community of remote professionals, designers, product people, facilitators, consultants, and freelancers who believe remote work should fit the human, not the other way around.