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Lessons learned building & managing a remote team

by Josh Pigford. Last updated on November 23, 2023

The cost of building a startup continues to get cheaper and cheaper, and one of the big drivers of that is the ability to build a team of people all over the world. Building a fully remote team gives you access to talent that would otherwise be completely out of reach. But it doesn’t come without costs (figuratively and literally).

Working remotely isn’t something anyone can do and building a product remotely has challenges that are very much unique to remote teams. So how do you build a remote team? How do you build a company culture around a group of people who rarely see each other face-to-face? What processes work and which ones don’t? What are reasons you might not want to build a remote team?

This guide is to help you decide if building a remote team is right for your startup and how to do it effectively.

Should you build a remote team?

The success of a remote team is rarely due solely to “process”. You can’t just throw a few tools in the mix, start hiring all over the world and expect things to magically work. It’s something that needs to be ingrained in the fabric of the company and it requires intentional work to make it…work.

And because it’s something that needs to be ingrained in the company culture, it’s very difficult to tack on after the fact. So answering the question, “should I build a remote team?” becomes crucial early on.

To answer this question, let’s actually look at the objections people have.

Your team will be far less productive

This is a matter of hiring. As I cover below, you need to hire people who are Professional Remote Workers™. If you hire people who aren’t self-motivated or capable of major problem solving, then yes, productivity will suffer greatly.

Communication is tough

Yes. Yes it is. But I think that’s a human nature issue, not a location issue. This goes back to hiring for a remote setup. If you hire people that are bad at communicating in written form, you will all hate each other within three months.

Work/Life balance is non-existent

Agreed. It’s so much harder to leave your work at work when you work where you live and live where you work. Set a culture of healthy work/life balance by having a good work/life balance yourself. Don’t work on the weekends or all hours of the night unless that’s what you want for your team (hint: you probably don’t). Encourage time off, encourage analog hobbies that get your team out from behind a desk. As long as you’re intentional about this, it’s a non-issue.

Collaboration takes a hit

This is one objection I tend to agree with. This was really evident at our retreat earlier in the year when we were all together. In person it was unquestionably easier to quickly throw things together or hash out ideas.

But that’s not to say collaboration can’t happen remotely, it just looks different and requires more work. The inverse argument is that while collaboration may take a hit, productivity as a whole is better. So I’d say it balances itself out.

Hire for remoteness

There are all sorts of things you can and should do to make your remote team work, but all is for naught if you hire people who are bad at working remotely. That’s not a knock on their abilities. They could be amazing at their craft while simultaneously bringing the whole team down because they aren’t great at functioning in a remote setting. Some people thrive in a remote setup, others don’t.

It’s imperative that you find people who fit the remote mold if you want a remote team to function. There are a few qualities I’ve found to be great indicators that someone will be a good fit for remote working.

Self-motivated problem solvers

The biggest quality you’re looking for is self-motivation. Will they get the job done without having their hand held constantly? Are they really great at problem-solving? Will they do things without asking permission and just wing it? Yes’s to all of those are great indicators of functioning well in a remote setting.

Great writers

Since most of your communication will happen over chat or email, being impeccable at writing will go a long way. Brevity is a negative quality for me (though verbosity can also be a problem). There’s a balance between saying too much and not saying enough that needs to be found and people who do a lot of writing (blogging or otherwise) tend to know that balance. A major positive for me when hiring is having a personal blog.

Non-industry hobbies

I’ve found that having hobbies outside of their field are also really positive signs. When you’re working remotely, it’s easy to feel isolated and totally consumed by work. People who get involved in hobbies outside of “programming” or “design” tend to get burned out much less frequently.

Communicating remotely

You’ve hired a great remote team, but if you don’t take communication seriously, you’ll implode.

There are a lot of great tools you can use (which you can find below), but communication is less about tools and more about intent and purpose. There’s more thought that has to go behind each interaction.

You’re no longer having passing conversations around lunch, you’re keeping your team in the loop so they aren’t left in the dark. You’re writing so that others know clearly what work needs to be done. You’re saying things that, in many cases, will be saved in the archives of your company forever.

What you say and how you say it, matters.

Making self-care a priority

One of the downsides to having a remote team is that each person can easily, without even trying, become a workaholic and totally consumed by the company. Making sure everyone on your team takes care of themselves is more important than all the tools and tips in the world for remote teams.

Here are self-care tips for you and your team to prevent burnout and make everyone more productive.

  1. Have set work hours and stick to them. Without boundaries, you’ll work all the time and get less done.
  2. Exercise every single day. Even if it’s just a walk around the block. You’ll have more energy and just plain feel better.
  3. Alternate between sitting and standing. Every study under the sun has shown that sitting all day, every day will quite literally kill you sooner. On the inverse, standing all day can also have downsides. Swapping between the two, using something like a GeekDesk, is perfect.
  4. Eat well. Loading up on sugary snacks and caffeine all day will result in a major crash in the afternoon. Keep your work area stocked with healthy snacks and eat them throughout the day.
  5. Take frequent breaks. You should be stepping away from your computer at least every hour to let your mind clear and your eyes focus on something other than a screen a few inches from your face. Usually when you come back you’ll have a clearer understanding of how to tackle whatever problem you’re solving as well.

Tools for remote teams

We use a lot of tools to keep our remote team on the same page. Here are ones we currently use and love.

  • Justworks — Payroll, benefits and other HR tools. Amazing for remote teams. Can’t recommend them enough.
  • Slack — The de facto tool for so many teams these days. It is in fact all it’s cracked up to be.
  • Asana — For product management. You can comment on just about ever single thing in Asana, making it great for asynchronous communication around projects and the product your building.
  • Dropbox: Notes — Formerly known as “Hackpad”, we use Notes for all document collaboration from ops playbooks to project briefs to blogging to company handbook content.
  • — Amazing video conferencing. Google Hangouts quite literally never worked for us. We couldn’t have a call without technical problems. We found and never looked back.
  • 15Five — Weekly team feedback. We use these to augment 1-on-1’s.
  • Abacus — Expense reimbursement.

Josh Pigford

Josh is most famous as the founder of Baremetrics. However, long before Baremetrics and until today, Josh has been a maker, builder, and entrepreneur. His career set off in 2003 building a pair of link directories, ReallyDumbStuff and ReallyFunArcade. Before he sold those for profits, he had already started his next set of projects. As a design major, he began consulting on web design projects. That company eventually morphed into Sabotage Media, which has been the shell company for many of his projects since. Some of his biggest projects before Baremetrics were TrackThePack, Deck Foundry, PopSurvey, and Temper. The pain points he experienced as PopSurvey and Temper took off were the reason he created Baremetrics. Currently, he's dedicated to Maybe, the OS for your personal finances.