A reader emailed in to ask:
We are in the process of trying to move to working remotely more often. I know that your team for the most part are all pretty remote and also work remotely with a lot of your customers. Just wondering if you could give me a list of what technologies you use for conferencing, team meetings, etc. Also maybe some pros and cons and\or issues you have run into.
Here’s my favorite apps:
- Slack for chat – we used to use Stride (formerly Hipchat), and it was alright, but Slack gained more traction
- WebEx for client meetings – because we need something that allows copy/paste between machines, support for Windows and OS X, and both computer audio and phone support
- Dropbox for file storage
- Github for source code control
- Expensify for expense reporting & approval
And that’s pretty much it. We try to run as lean as possible.
Remote work issues we’ve run into
Working by yourself can be draining. If you’re a people person, you may miss being surrounded by other folks and having water cooler chats. Slack mitigates that for me today, but years ago, I preferred coworking spaces.
Get face-to-face online weekly. Every week, we get together on video during our Office Hours podcast and talk shop. We accidentally learned that it keeps us on the same page, lets us have fun conversations, and reminds us that our coworkers are humans.
Get together in meatspace too. Once a year, we go on a week-long company retreat with no client work involved at all. We look forward to planning it and doing it, and we get excited to hang out with each other. (This might not work for every company because after all, the bigger you get, sometimes there’s folks you don’t actually want to hang out with for long periods of time.)
Your Internet will fail, and usually at the time you least expect it. Be armed with a phone, tablet, or hotspot so you can pair your computer to it for brief periods of time.

De-prioritize your communications. Whenever possible, stick to asynchronous, non-personal communication methods that don’t require specific people at specific times. Here’s my preferred order:
- Slack message (not direct message) just saying something that anyone could answer or fix.
- Email message directly to a person – so they can get to it whenever.
- Direct message or name mention in Slack – because someone gets an immediate, interrupting notification. This is bad form – don’t do this unless it’s urgent.
- Text – because this interrupts someone no matter where they are.
Set expectations for at-work hours. Employees pick their default working hours (mine’s 8AM-4PM Central), and they’re expected to be around Slack during those times. If you won’t be around, just let the rest of the team know.
When management wonders what remote people are doing, have them swing into Slack and watch. They’ll be able to see what’s happening, and see that work really does get done. (Although also, just like in-person offices, a lot of friendly goofing off happens too!)
Set expectations for off-work hours. When you work remotely, it’s really easy to just keep going for just another 10 minutes, just another 10 minutes, and next thing you know, you’re divorced and your children refer to you as “my DNA relative.”
10 Comments. Leave new
Excellent post as usual and the timing is perfect since I am setting up a remote office in an office hotel the coming few weeks. I understand that you focused on the IT of remote working but you did forget one piece of equipment that keeps (almost) all IT offices running. The Coffey Machine!
Ha! I use a Technivorm Grand:
https://www.williams-sonoma.com/products/technivorm-grand-glass-carafe/
He you explored office 365 at all feels like a no-brainer of a business case to me, especially with Teams for “free”
Ross – nah, we’ve been using these services for quite some time. O365’s new Teams functionality might be interesting when it starts developing the kind of community following you see today around Slack – take https://SQLSlack.com for example, where thousands of community folks are active.
Serious coffee like: http://www.coffee-a-roma.com.au/store/p28/Rocket_Espresso_Giotto_Tipo_V_or_Evoluzione_R.html
WOW, that’s a work of art. I even love the little rocket-shaped feet. That’s beautiful.
Having had to use Skype for business for the past year (UK, USA) I would rather use a tin can and string!
Del – yeah, I’m with you, it’s pretty bad.
Have you tried [Redacted]? It is online project management and collaboration software that teams can use to run their day, their projects and their work-life. With [Redacted] it becomes effortlessly easy to collaborate, and manage remote teams without breaking a sweat.
Vartika – you just magically found that, huh?
Your email address is the same company you were promoting.
That’s called astroturfing, and it’s a great way to get a really bad reputation. Reconsider what you’re doing. https://en.wikipedia.org/wiki/Astroturfing