Remote Team Management #101 – Starting Your Internet Business, Part 4

Remote Team Management #101 – Starting Your Internet Business, Part 4

For the fourth and penultimate installment in my Starting Your Internet Business series, I’d like to look at how you can motivate, encourage and work well with a remote team of 2-60 people… or completely screw it up.

So, there are two ways that you can become qualified to speak on a particular topic; most commonly by having experienced wild success in a related area or by being absolutely appalling at the subject in question, having failed countless times and having figured out, to an extent, how to survive regardless. As you might have guessed, my accreditation arises from the latter.

For example, I’m so bad at communication that I started a company with a guy who I never even spoke to other than over Gchat or email, for the entirety of our partnership. True story.

Now, most people can blame it on the other party and I’d be more than happy to do that, but it takes two to tango and I accepted this opportunity to not have to engage with another person and sit behind my screen with open arms. Same for firing people. I’ve probably let go at least a couple of dozen staff over the years, and without exception, I’ve done it all over email or text. I’m just not very good at face-to-face, or even voice-to-voice communication.

Which is something I could focus on trying to get over, or not, because, in my experience, while there are certainly drawbacks to text-only-communication, there are also significant advantages and in this piece I’d like to talk about them in relation to how you can successfully manage, motivate and get by in a remote workplace, and also not. Read on!

This is the fourth post in our five-part series about getting started with an online business.

First, You Need to Be Able to Manage Yourself…

A lot of people claim that email is the root of all evil. I couldn’t disagree more.

And when it comes to managing yourself in managing a remote team in the most efficient way possible, there really is no substitute to email done well.

In the wrong hands, it can be a nightmare, a place where information goes to die, a never-ending pile of work that just squeezes down on you by both constantly reminding and rendering you incapable of doing the work you need to.

And I kinda felt like that until I discovered inbox zero – and then modified it completely to work for me and Gmail, specifically, following these rules:

  • Your constant goal is to get your email inbox down to nothing
  • Have email on, pretty much all of the time you are at work (but not before or after… I usually keep pretty good 8am-6pm hours)
  • If you can deal with an email that comes in, deal with it straight away
  • If something needs to be done, always leave the ball in the other person’s court… Archive, archive and archive again
  • Use your inbox as your to-do list (using Gcal is awesome for this. It’ll email you reminders that you can’t remove until you’ve done the job)
  • If something is too big, transfer it to paper by your keyboard – don’t let it clog up your pursuit of inbox zero
  • Use stars liberally to indicate day-to-day importance so you can easily prioritize on the run
  • Use filters to collect incoming email (like job applications) into labels and auto archive them so you can batch deal with them
  • Be OK with not reaching 0. I regularly have 4-5 that need more attention (or thought) than I can give them
  • And unsubscribe to all those email newsletters (except ours, of course ;)

This is because email is the crux of how you communicate and manage your team.

Email Tool: Gmail

…Then Worry about How Everybody Else Is Feeling

The thing as a manager that I probably like most about chat is that it gives me pretty much an open door, both to myself and also so that I can reach out and have a quick conversation with pretty much anyone I need to. It’s a nice, easy way to get things done, and it saves on the sacred space that is email.

And it’s tacit, interpersonal, touchy-feely, emoji-laden, nice.

And that is a really important and perhaps the most important thing to get right when it comes to working with remote teams, not only for yourself but also within and amongst the teams themselves.

Yes, you are in danger of being absorbed into a world of sharing nonsense all day long but you can also turn it off (shock!) and there’s a certain efficient collegiality about sharing that stuff that, IMO, gives a remote team a kind of coherence that you’d get in a real office, in probably less than half the time it’d take people chewing the fat around the water cooler

And, of course, while using chat you can also be doing other stuff, which, if it’s mundane, is a pretty awesome way of multi-tasking.

Which has all been given an upgrade by Slack.

Gchat was great, Hangouts was better, but to be able to easily form and manage groups the way Slack allows you to do is absolutely awesome. It’s the quickest $5k I’ve ever parted with (and for something we were previously using for free).

I’ve never experienced a better tool for creating connections, groups and communicating (and thus managing) in an authentic ad hoc way.

Chat Tool: Slack (obviously)

And How Your Team Gets Things Done…

This is probably the hardest part of managing a remote team because you miss out on all the tacit, intra-personal and face-to-face reassurances and catches that you need while you’re putting together a new project, no matter how good your chat app.

And it’s also probably the area we’ve moved through the most tools and ways of working, and are still trying to evolve.

I mean, how easy is it to throw together a spec (OK, well it’s not that easy to throw together a good spec) and then give it to a team of developers… only to get back something that is late, looks nothing like the spec, hasn’t been tested and is now scarily off-target.

And when it is released, how do you communicate bugs between support staff and developers? How do your prioritize feature requests? How do you work with developers to shift their priorities?

So. Many. Tools.

Now, you might not be developing WordPress plugins, of course, but you are going to need a way to work through a project with your remote team, and we’ve used most of the tools. Here’s are the ones we’re currently on:

Overall Task Management: Asana

Asana has been a great to-do app for us. Not cheap, or keen on cutting you a deal (boo!) but it integrates solidly with our API and at least should, if it doesn’t always succeed, let you track and manage the progress of both your own and your team’s tasks.

There are definitely alternatives but we haven’t found any that are particularly better, and you can accomplish pretty much anything with Asana.

Editorial / Some Product Management: Trello

Trello would have to be the leading contender to Asana, but whether it’d be realistic across a team of 60 people is another thing entirely. We’re keen on using it for editorial management and a bunch of staff use it for their own work or to give an extra area of really nicely visible cover for their projects.

Bug & Ticket Tracking: Custom build + Asana

If you report a bug through our Q&A or community areas then it’ll be rigorously checked and we’ll try everything we can to establish whether it’s a bona fide bug or not. Assuming it is, it’ll be tagged there, an Asana task will be raised detailing the issue and project and assigned to the appropriate developer. It’s kinda cool.

Ongoing Project Management: P2 + Online Meetings

While our current (and next implementation) of this awesome WP theme is probably about as far removed from the original as you can get, the principal is still there. And you know what we fill it with… notes from meetings! Yep, actual real meetings, well, not face-to-face, but held over Skype, Hangouts or Slack and then shared with the whole team and that project area via our own internal site.

UX & Design Discussion & Feedback: Invision

And last but not least, our latest favorite tool for presenting, analyzing, commenting on and crafting designs from the basic UX to the pixel perfect front page has to be Invision. It makes the whole process super easy and transparent and is definitely the flavor of the month at our Melbourne HQ.

And How They Communicate With Customers…

Probably the most important thing you can do early straight off the bat is to make sure you have some sort of system whereby you can look after customers.

And I can let you know now, it’s not going to be the solution we worked up for WPMU DEV and Edublogs for several years, highly customized multiple inbox setups of Gmail!

Yep, that’s four or five people just using one email box, it was pretty scary.

Until we discovered Help Scout.

I think perhaps the nicest part of setting Help Scout up was just how easy it was – take your existing email address and whack it in there; we’ve never looked back. Super easy, affordable, and, combined with Nice Reply, also easily evaluated.

And, for Edublogs Campus where we’re dealing with institutional clients, Zoho CRM is absolutely where it’s at. Costing, as it does, a pittance compared to other much more enterprise-style sales management software, it absolutely does the job for us and even connects into invoicing.

But we haven’t gotten off that easily, all of our on-site support is powered by the most custom version of bbPress you have ever seen, a step that I absolutely wouldn’t advise you to take given the complexity of supporting a 1 million+ post forum in addition to your regular security efforts.

While, of Course, Actually Getting Work Done…

This is probably the hardest part of all, summed up perhaps best of all by this Dilbert cartoon, which I fair-use a bit of below :)


You don’t want to be an asshole, but you don’t wanna be ripped off. You don’t want to distrust your staff, but you don’t want to be made an idiot of.

And I can testify to having messed this up, although primarily having been ripped off by unscrupulous staff because I pretty much gave them the scope to do it.

But even that’s not gonna make me go anywhere near any of these scary desktop work trackers, well, not me personally, at least.

Rather, when it comes to remote work we’re keen on two things: 1, that you are doing something that can be reviewed and evaluated (replying to emails, helping customers, committing dev), and 2, that you track the time you are spending on those different project and you submit your tracking and task list with your invoice.

In particular, we really like Hubstaff for this purpose and to quote one of our recent hires:

“The actual tracker is nice. It’s like walking into the figurative office. Click start, and now you’re at work.”

So what does this mean? Well, as a staff member of Incsub, when you open the app you hit the “play” button and then you switch when you are working on different projects. Your invoice and work tracking just got sorted!

Which I don’t think is too offensive or intrusive.

Of course, you as a manager then have to (at least occasionally) match the work your employees are doing related to their invoices, but this isn’t that hard (it used to be), and you always have a record so you can dip in and check up on work at any time – without it being too intrusive or that much work for you.

As ever, I’m always keen to hear how others manage remote teams and answer any questions in the comments below.

This is the fourth post in our five-part series about getting started with an online business.