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Several grumpy opinions about remote work at Tailscale, Hacker News

Several grumpy opinions about remote work at Tailscale

As a “fully remote work” company, we had to make some choices about the technologies we use to work together and stay in touch.

We decided early on – about the time we realized all three cofounders live in different cities – that we were going to go all-in on remote work, at least for engineering, which for now is almost all our work. As several People have pointed out before, fully remote is generally more stable than partly remote. In a partially remote team, the remote workers seem to always end up treated as an underclass, overlooked in meetings, bypassed for promotions, fired when they eventally refuse to relocate because the remote work policy inevitably changes (hi, Yahoo!), etc.

The good news with our plan is the founders could “dogfood” a few different remote work ideas ourselves before we ever hired anyone. So we decided to try some stuff. Here’s what we discovered.


We’re using Notion as a team wiki and note taking app. It’s … okay. I mean, it’s probably the best tool for the job, and it’s great in some ways, but it’s severely limited in others.

Things I like about Notion:

      Great for quick to-do lists and milestone planning

    • Easy to make persistent hyperlinks between docs
    • Easy to arrange docs in a hierarchy (but not as organized as good old
    • GracefulTavi )
    • Tables and Kanban board views are pretty awesome
    • Just the right level of formatting. When I paste text into Notion, I never worry about it coming out in a weird font or color.

    Things that drive me crazy:

        The “show me what changed” view is nearly useless; tons of updates about   tiny clutter changes, but no good way to give me a deduplicated list of   all the docs that changed. Virtually any wiki’s RecentChanges view is   better.

      • Doc comments miss the point of doc comments, by being almost invisible and   creating no incentive to resolve them. (Trivia: Rumor has it that Google   Docs comments also sucked until an intern showed up and made them insanely   better as a 90% project.) There are so many ways that the greatness of   Google Docs comments has failed to be copied by every other tool   (including, for example, Google Sheets). Everything else sucks. When we   want to wordsmith stuff as a team, we move it from Notion into Docs.

      • Support for to-do lists and “reminders” is there, but pretty weak. For   example, there’s no way to make repeating reminders or get a consolidated   list of to-do items across multiple pages, so people request a separate   to-do list app. So far we’ve resisted, but we won’t be able to for much   longer.

      • No API means you can’t fix any of the limitations yourself.

      Anyway, as they say, there are the tools you complain about and the tools you don’t use. I’ve tried a heckuvalot of content managers and they’ve all been worse, so Notion it is. To be fair, it’s a very big area and hard to please everyone. And I’m really picky. But they’re

    so close …

    Keybase to Slack

    At first we tried using Keybase to manage our secret keys, and coincidentally its built-in team chat feature for our team chats. Keybase has a bit of a bad reputation because of some of their early cryptography missteps and their (very unfortunate) recent association with cryptocurrency. But whatever you think of their security or business model, their chat system is surprisingly one of the best. You can make channels and securely confirm identities without stupid QR codes; message expiration rules are clear; the notifications are A . Among other things – and this completely dazzled me – when I read a message on any of my devices, the notification for that message disappears instantly from all my other devices! I did not even know it was possible to auto-remove obsolete notifications, so seldom is it done.

    Which, of course, led me to wonder why it isn’t done . In my cynicism I’m sure I can guess why; auto-removing notifications never increases your “engagement” metric. Whereas a completely bogus chat notification from four hours ago, already dealt with four hours ago on a different computer, drives engagement every time. I respect the Keybase people for choosing the path of user happiness, except I suspect they’re soon going to need paying users instead of happy users, because that’s the world we live in.

    However, keybase had some problems for us. First, it guzzles absolutely epic amounts of CPU and memory. If you think Slack is bloaty, Keybase outdoes it by like 2x, plus it has giant memory leaks so you have to restart it all the time. There’s no web UI (they’re too paranoid about security), and the android app just crashes for me on ChromeOS. In other news, I’m pretty sure I never ever want to hear about a “security and privacy” tool that includes MB) of Electron (aka “Chromium but with the security and privacy features turned off “).

    Also, nobody but us uses Keybase, and it does support popular cute things like Github integrations. So unfortunately, we had to give up on it and switch to Slack. Y’all know how Slack works so I hardly need to describe it, but I would summarize it as “absolutely terrible at everything except user lock-in, “and here we are. There’s a business lesson in there somewhere.

    I eventually turned off Slack notifications entirely, after experimenting with many different variations. @here is an abomination; notifications in each “other Slack instance” need to be set separately; it spams your @ # $ !! phone with every single message anyone types, even while you’re on your PC. Forget it, notification privileges revoked, and I’ve been much happier since.


    For a while, we tried to run our own email server (in the name of being free of “big tech” for our core systems) but it didn’t work out. Gmail’s UI gets worse every year (correlated with decreasing information density, though the causation lies elsewhere), but at least it’s mostly familiar.

    Interestingly, because of Notion and Slack, we hardly use email at all between us internally. It’s almost exclusively used for customers and Investors.

    At the advice of the excellent book Great CEO Within , I followed the instructions in Andreas Klinger’s guide to Gmail Inbox Zero . His combination of Gmail configs is pure genius; it completely changed how I do email, and makes Inbox Zero easy and achievable, by separating the triage and work phases. Highly recommended. I also learned about several Gmail options I did not know existed.

    Streak CRM

    We reviewed several CRM tools. The consistent advice we received was, “You’ll end up on Salesforce eventually, but don’t do it yet.” Ok, sure, I can take advice.

    Streak was appealing because I wanted something that would integrate extremely tightly with my email. Streak does what I want: I associate an email thread with a particular customer or helpdesk ticket, and then it’s magically shared with all the other Streak users in your domain, and it continues sharing as new messages are sent and received, and it’s 100% inside the Gmail UI. Not bad at all.

    The underlying concept of Streak is what I would call “batshit insane from top to bottom. “It has a tough learning curve at first, but so apparently does every CRM. It has scattered features all over that just look like extra buttons or tabs in the Gmail UI. The frustration their dev team must have endured as they implemented this, and the frustration they must continue to endure as they keep it up to date, must be nearly intolerable. But the end result is quite remarkable; these are devs who care about keyboard shortcuts, highly efficient workflows, and making short work of huge batches of emails. I’d say Google should buy them and just integrate the whole thing into standard Gmail, except then Google would kill them with love by accident, as megacorporations usually do with acquisitions, and we’d all be worse off. Oh well.

    Anyway it works, I like it. And besides sales, it’s quite a remarkably good support / helpdesk ticket system, which it seems to have only tangentially been designed for. Customers don’t even know they’re in a ticket system (is that better or worse?) but it lets us collaborate on tickets, make sure tickets don’t get lost, and so on, just like a good ticketing system should. Except without having to learn yet another new UI.

    (Uh, just because we have a good ticketing system doesn’t mean we can actually keep up with emails some days. Sorry. We try. Life at a startup is exciting.)


    In a remote company, meetings are essential. There are all kinds of subtle issues that affect the way humans interact on the call. This is the area where we experimented the most; unfortunately, although videoconferencing has come very very very far in the last years, there is still no perfect answer.

    Let’s enumerate some imperfect answers, in vaguely chronological order:

    Short answer: we use Whereby for most internal meetings, and Zoom for externally-facing meetings. We would prefer to use Whereby for everthing, if It gets a bit better.

    Videoconferencing hardware

    As a fully remote company, we don’t have “meeting rooms,” so Zoom Rooms are not a thing that makes sense for us. Which is fine, because despite what you might guess, the latency is not better with Zoom hardware than with a general purpose computing device.

    We tested a few different setups looking for a good combination of latency, video quality, and reliability. It was definitely not as cool as any of Dan Luu’s latency tests , but this is the apenwarr blog, not the danluu blog, and you get what you pay for. Sorry.

    What we learned was:

        PCs of any sort (Linux, macOS, ChromeOS, Windows) all have higher latency   than dedicated iPhone or iPad devices. (We did not bother testing Android   video latency because, well, let’s be honest, it’s not going to be an   improvement.)

      • Most (but not all) front-facing iPad cameras are not great. They’re okay,   but not great, especially in low light. If you have a lot of meetings, a   bit better video quality is nice to have. The very latest iPad) Pro   has a pretty great front-facing camera that works in low light (the best   kind of light), so that’s what I use now.

      • Older iPhones (like my aging iPhone 6S) go into CPU throttling with some   video codecs, notably Whereby’s, so the video quality starts off good but   degrades after a few minutes when it gets hot. My new iPad Pro does not   have this problem. I think my coworker has an iPhone X and also did not   report it.

      • You absolutely should use some sort of “personal microphone” whenever you   do a call. The state of echo cancellation is pretty good now (except in   Hangouts), but there’s nothing a single screen-mounted microphone can do   about ambiant noise. The single best favor you can do for your call   partners is to use a personal microphone. Airpods include two personal   microphones that work great.

      • Airpods (when connected to iPhones or iPads) have very low latency, not   detectable by humans. They’re not any worse than a wired microphone, which   It is a pretty good technical achievement (one of the goals of Bluetooth 4.x   I gather … but goals don’t always translate into reality). Because of   this ultra-low latency, they do sometimes glitch out when there’s a 2.4   GHz noise burst, but it’s brief and generally worth the tradeoff just to   not have your head wired into your computer.

      • Warning: Airpods (and all bluetooth devices) have higher and highly   variable latency depending what you connect them to. macOS is definitely   not perfect about latency (and tends to have worse videoconferencing   performance overall, for whatever reason, than an iPad). Windows bluetooth   varies from great to absymally terrible, depending mostly on the driver   but also the phase of the moon. Linux bluetooth is hahahahaha sorry I   forgot what I was going to say.

      • I mounted my iPad above my monitor, at the so-called “selfie angle,” using   a $   iPad mount I bought from Amazon . Mounting it this way has two   advantages: I look slightly up at the person I’m talking to rather than   down, and when I type notes into my computer, it doesn’t look like I’m off   to the side. This is aside from the separate benefit of using an iPad for   calls: I can have the call visible at all times, without obscuring my   computer desktop.

      We did not get all fancy with green screens and pro-quality microphones and all that stuff that other people talk about. Maybe it would be better, I Don’t know, but it definitely sounds like too much work to dump on every employee.

      Short answer: iPad Airpods Whereby is a really great combination in . And it also works well with Zoom, which is good because you’re stuck with it.

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