The remote tools we’re using

When I first started remote working, I ran an entire website through Wordpress drafts, AIM, email, and a shared spreadsheet. I was 23 years old, managing a handful of freelance writers, and life was awesome. (Whether I was doing a good job or not is debatable… I was 23.)

The available tools are much more advanced now, but I’m here to report that things are only marginally better. Too often people think tools are a cure-all for poor communication and collaboration, and that a fancier series of kanban boards will create that aspirational “culture of shipping.”

So please, don’t use this post at a template to get your remote team to the next step. The tools are just the tip of the iceberg—longterm success comes when you hire right, train right, clearly define duties and projects, and fail so many times that you, by process of elimination, learn how to succeed.

With further ado, here are the tools we’re using. (I’ll add to the list over time, there are some more granular tools we use that a developer will have to explain once things calm down a bit.)

Basecamp for team management

There are a million team and project management tools on the market, and they all do things differently. My advice is to find the one you find easiest; not the one with the most features.

For my money, Basecamp is the best of the bunch. To-do lists are easy to enter and easy to assign, the message boards work as they should, the calendar is nice and clear, you can toss documentation into any room you create, and the search function is incredible. Best of all, it doesn’t feel flimsy. I know that’s subjective, but I rarely find myself wondering what’s going to happen if I push a random button in Basecamp. The options are simple, properly labeled, and just work.

It’s certainly not flawless though. The WYSIWYG is severely underpowered (instead of H1, H2, H3, etc., you just get a single “Heading” button), there aren’t any fancy kanban tools, and exporting files is a real headache.

Still, it’s the best we’ve come across, and we’ve gone through so many platforms.

A note about project management

A good project management system will do two things clearly:

  • Quickly show people what they need to do
  • Quickly show people how their part fits into the broader strategy

No matter which platform you use, if the overall project is opaque, you’re either limiting the creativity of your team to fill in the inevitable blanks, or you’re going to find yourself dealing with a lot of duplicated work. It’s nearly impossible to plan every detail of a project before it’s started, so the better you frame the scope of each task, the more concise the improvisation will be (having multiple people trying to solve the same unforeseen problem is a huge waste of time).

The moral of the story is that if you’re managing a remote project, you should write everything down for everyone to see. When you do things that don’t make sense—even if they don’t make sense for a very valid reason—productivity and belief in your leadership abilities will suffer.

Zoom, FaceTime, and Slack for video chats

The best video chat tool is the one that works. We used Google Chat for a long time, but the connection tended to get less and less stable every time we added someone else to the team. So we moved to Zoom a few years back, and it’s been wonderful, aside for the occasional audio glitch.

We typically create Zoom rooms in Slack using a bot we created, but due to it being 2020, the 5 seconds it takes often seems too long for 1-on-1 meetings. Instead, we usually use the built-in Slack video chat or FaceTime, depending on the situation. I typically prefer FaceTime, but, for example, there’s always an echo when I’m calling Kevin at home. But Slack works fine. Whatever.

Again, use the one that works.

A note about Zoom security

Zoom has been in the news a bunch lately for its questionable security practices, and that’s a real concern. Fortunately, we use Zoom only for broad discussions and social chatting—specific problems are generally solved over text so there’s a clear paper trail, and because we’re an asynchronous-embracing remote team.

Based on how we use Zoom, finding a new solution has been a fairly low priority, but once things cool down a bit, we might reassess.

Slack for text chats

When I first started at iwantmyname, we used HipChat for everything. And it was… fine. It didn’t feel modern, it wasn’t sexy, but it generally did the job. In 2017, Hipchat moved to a platform called Stride, but a few of us had been pushing for Slack for years, so we went in that direction.

Admittedly, there was a bit of an internal fight over going with a big Silicon Valley company over a smaller company (or a big Australian one) that might share a bit more of our ethos, but we never found an alternative solution that fit better better. Slack is just so easy—everything works, and there are a million ways to extend it to do just about anything you could want.

Also, because we use chat so much and for so many things, we felt like we needed a platform that would stand the test of time, and be geared towards our specific use case. Stride was a brand new (unproven) thing, Google’s Gchat/Hangouts feel like they’re just waiting to be canned (Google seems to can everything eventually), Microsoft Teams is wound up in an ecosystem we don’t use, Discord doesn’t really have business tools, and RocketChat just doesn’t have the polish yet. I’m sure there’s more out there, but Slack seems like the brand that’s pushing the space forward, and it admittedly feels nice to use a best-of-class product when it makes sense.

I don’t want to make it seem like this is a universally loved app though, even in our small iwantmynam universe. Dave, just this weekend, wrote this in response to a query about why he hates Slack so much:

because you have no way to filter out the garbage from the useful. you need to read all posts to determine if it’s important. you cant do custom filtering, mark stuff as read or ignore, tag for later, save a copy for notes. above all its a walled garden where slack is the one true messaging tool. i manage with irc and email to follow several hundred useful opensource projects with less than 10m a day of pruning. slack consumes maybe an hour if you give a shit about making sure you didnt miss anything

and threads are weird af in their desktop app. hiding on the side not easy to expand to read nor sure where they live if you need to search for them. Maybe im just our resident UNIX graybeard now shouting at these skateboarding pot-smoking whipper-snappers to get off my lawn…

1Password for password management

We started with LastPass, but moved to 1Password a few years back because it was just a bit more seamless.

I’m sure all the password lockers have all the same features by now, but the way 1password handles 2FA feels really nice. Instead of having to use Authy or Authenticator, 2FA is just handled through 1Password as part of the process.

I know it’s just one additional step, but if you looked at how people interact with technology, that one step will take a huge population from dismissal to adoption. Kudos to any brand that takes the time to remove steps from any process—in a world of brands barfing out features right and left, it’s refreshing to see one that’s actually trying to make life simpler.

Dropbox, Google Drive, GitHub and Basecamp for file/document management

So this is admittedly a cluster, and is a problem I see in many companies (and on individual’s computers).

The problem we have is that organization can be a very personal thing. I was reading an obituary a few days back for Anick Jesdanun, an AP tech writer who died of COVID-19 complications (he’s kind of a hero in the tech world), and this struck me:

By example, conversation and hands-on editing, Jesdanun, working from a desk renowned for its messiness, taught a generation of AP journalists how to cover technology in ways that were understandable and accessible but unparalleled in their depth.

That little touch of humanity—that his desk was renowned for its messiness—was a great piece of writing. It stung, not just because the situation is unbelievably sad, but because it highlighted one of those universal truths. Everyone has their own way, and the way that works is generally the best one.

The problem we have is that a lot of people have had their hands on deciding the best way. iwantmyname started as a very flat company where everyone had an ownership stake, so everything was visible. As people were hired, the file structure largely got split between operations and the product. Then it got merged in an effort to re-flatten things. Then we moved some stuff to Basecamp because the Dropbox folder was so unruly. Then we started using Google Drive for some reason I don’t remember. And there’s also quite a bit of technical documentation on GitHub.

Our situation now feels a lot like Anick Jesdanun’s desk. Messy but usable. Very human. Perhaps it’ll be cleaned up one day, but it’s not really a top priority.

As far as product endorsements go, I prefer Dropbox over Google Drive because it looks nicer in finder, but it’s just a cosmetic difference. (I also really like Dropbox Paper, but haven’t been able to get others to adopt it, so the Dropbox ecosystem has been largely unproven on our end.) Also, Google creeps me out… I’ll just come out and say it. If I had my way, we wouldn’t use Google for anything, ever.

GitHub is a mess to me and seemingly every non-dev on the planet, but it seems to be essential, so shrug emoji. And Basecamp, oh Basecamp. I really want Basecamp to be the hub for everything we do, but its WYSIWYG is so underpowered that it makes real documentation tricky. And it’s really bad at retaining styles when you import and export files. It’s just kind of a mess.

But… it’s so convenient. And the Basecamp search function is a treat. I’m honestly on the fence with using Basecamp for documentation and file storage. I’m sure it can be a fine solution for the right team, but it’s hard for me to be all-in. Maybe someday.

MailChimp for non-automated newsletters

We send newsletters for a few things: newsletters (that we’ve failed to send for a long bit), price updates, major site updates, etc. We tried a few different platforms (years ago), but landed on MailChimp because… because…

Ok, the reason I landed on MailChimp really has nothing to do with the usefulness of the platform itself. There are probably a handful of services that do the same thing, and perhaps better. Unlike their competitors, MailChimp A. is delightful to use, and B. supports the podcasts I spend so much time listening to.

Honestly, if anyone out there doesn’t think targeted advertising is effective—and not indiscriminate targeting using something soulless like AdWorks, but actually building relationships with the brands and shows and platforms people care about—you should probably reassess your opinion. Advertising was the engine that made podcasting happen, and I’ll always have a soft spot for the brands that got in early (~2000-2015). The MailChimps and Squarespaces and Casper mattresses of the world weren’t just advertising, in my opinion. They took a risk on a thing that most marketing managers and company owners still don’t understand, and really made something of it. (You have no idea how many conversations I’ve had with people who’ve said, “But how can I ever track the ROI on a podcast ad spend? How do I know if it’s working?”)

The only real downside to MailChimp is that it can get pretty expensive if you don’t manage your lists well. For a time, we were using it for major system emails, meaning we kept a list that included every customer email address we had. The problem is that MailChimp charges by the amount of contacts you have, not how many emails you actually send out. You end up starting with a list that maybe has a few thousand contacts, and it costs $X/mo. It’s not cheap, but it’s not breaking the bank. When you get a list to over 100,000 contacts, you’re looking at a big ol’ bill. If you’re a Fortune 500 company, no big deal. But when you’re a small domain registrar in New Zealand, your head starts to spin.