Building a Remote Team — Learning from Failure

November 3, 2015

Usually startup advice boils down to this: build the right product for your market. Almost every problem a startup has can be traced back to that single thing. The problem is most startup advice assumes some basic things:

  1. You have a robust founding team
  2. You have some funding, or are able to live on ramen for awhile
  3. Live in an area with some semblance of a startup community

This covers probably most startups but if any of those three items aren’t entirely true in your case then you’re trying to steer a leaky ship. You need to get your team set up properly. You can overcome item 3 because there are some amazing tools out there that will connect you to anyone in the globe and let you work as well as you would if you were in the same office. Check them out if you think you already have the right team or they are currently in your hiring pipeline — don’t wait until after they’re hired!

The right people for the job

Hiring the right people has always been difficult, and it doesn’t help that hiring for a remote role is more complex and harder to navigate. When we went to first expand our team, we had no idea what we were looking for besides skill. How do you find skill in areas that you aren’t experienced in? Big names on the resume of course!

In the past, we’ve had some absolutely amazing talent on our team with big name companies on the resume. We really jumped the gun after marking the skill checkbox off the list. When hiring, you have to have set processes in place and know exactly what you’re looking for. This doesn’t only mean skill, but also a complete match in values, personality fit. Have an open mind, but when it comes to your hiring process don’t be afraid to let someone go if they don’t fit everything you’re looking for. If you get that uncomfortable feeling in your gut, move on to the next candidate because one person not following your team structure and process will tear apart the team.

A highly skilled worker doesn’t necessarily make a great remote worker

You need to figure out what you’re optimizing for in your hires. There really aren’t many good reasons for a small team to not be optimizing for values. Every single person you add to a small team has a big impact on its culture and work rhythm. Your team is in a delicate balance that needs to be focused on shipping your product. Every mistaken hire wrecks that balance and costs you valuable time, so optimize your hiring process for values.

That’s not to say you should ignore skills entirely. That’s probably going to be your first pass on candidates. Anyone not meeting some very basic criteria should be discarded. Consider keeping this criteria basic. Do you really need a candidate who knows how to code the software for rocket launchers, or do you simply need someone with the right traits who can and will learn what you need? Find passionately curious builders who can learn to build what you need quickly, rather than discarding anyone that won’t know exactly how to build your product from day one. The old saying “there is no I in team” is trite, but especially true of fully remote teams.

Get the term “rockstar developer” out of your vocabulary because if they are out there, they’re not going to be on your unknown startup. And if they were, they’d probably hinder the culture if they don’t check their ego at the door. You’ll save yourself a lot of trouble later if you’re checking that your new hire is most interested in helping the team succeed, rather than simply helping themselves. It’s very hard in a team that is split around the world to have one person who feels they can act above the group, or refuse to shoulder the load as necessary when someone makes mistakes. Mistakes happen. What separates a good team and great team isn’t who makes less mistakes, but how the team comes together when mistakes do happen. And how they come together in tough times to meet milestones and ship great products. Your team is going to have a tough time doing that consistently if one of your handful of team members is playing king.

“My biggest mistake is probably weighing too much on someone’s talent and not someone’s personality. I think it matters whether someone has a good heart.” — Elon Musk

The second half of the puzzle is setting your hires up for success after you extend them an offer. We made more than enough mistakes in this area as we tried to implement new tools and processes after everyone was on board. It’s not an easy task to get everyone hyped about implementing a new tool to your remote work process. By having in place the process you want for your team, you’ll be able to bring on new members who you know are on board and comfortable with that structure.

Key Takeaways

  • Hire based on the right balance of values, passion & skill
  • Don’t be afraid to say “no” to a perfect skills fit who has the wrong values
  • Have your processes in place from the beginning

Communication is hard

Communication is key for a remote team. It’s hard enough that you can’t communicate in-person, but you’re probably spread across multiple time zones where you have different working hours. In our case, we even had team members as far as 12 hours apart. In this scenario, you often have to wait 6–12 hours until you get a response to questions and it drags out the development process excruciatingly long. Because of this, your team culture is bound to take a hit where you’re communicating with some team members much less than others. It’s imperative that you solidify a weekly all-hands meeting. For us, Mondays are now when we lay out the week’s work in detail so we can check ourselves on Friday to see if we’re on track.

Conversations that would normally be a quick chat in person, perhaps not thought of again, become something that feels much more formal, more negative. You then have to set aside time with this person specifically and not everyone handles constructive criticism well, especially if it’s not face to face. You have to commit to having the hard conversations early, and make time to have them be face to face via video. Don’t just email someone saying they’re doing something wrong. Always default to a face to face conversation on Sqwiggle or Skype. There’s a great list of tools for remote teams that will help you to communicate efficiently and transparently in this setting.

There’s a really cool movement going on called The Open Startups Initiative which speaks to the importance and benefits of transparency in a company. This is even true down to the bare bones of the business in every interaction you do. One area we noticed this was a few months after bringing on two team members. There was a misalignment of expectations because we unknowingly failed to clearly convey our expectations of them. Let prospective hires and current employees know exactly what you expect of them, and let them know what they should expect from you. It’s a two-way street, so do this early and always to lead by example.

“Transparency breeds trust, and trust is the foundation of great teamwork.”

Key Takeaways

  • Have the right tools in place from the start
  • Set aside an hour or two a week for an all-hands meeting
  • Always be clear and transparent in your communication

Accountability is key

“Processes” is a bit of a dirty word in startups. It implies you aren’t moving fast and breaking things. Yet, for a remote team, having a few basic processes is absolutely crucial to setting the expectations you need to make sure your project moves along on-time and (if you’re paying) on-budget.

Get your team in a regular rhythm that lets you check up on progress. This should definitely include live builds. You’ll probably want to use an agile development process anyways, so keep your sprints relatively short so that you’re never going too long without seeing updates that could be hiding a big issue.

The hardest thing to do is realize that someone is just not the right fit for your team in terms of how you’re operating. If you find yourself in a repetitive cycle of constantly having to re-explain expectations, then it might be time to think about what your team would be like if you weren’t spending so much time on this basic task. You’d be moving faster, and you’d have a far more productive team. So just as fast as you’re willing to bring the right fit on, be willing to realize that you may have been wrong and need to try again. Hire carefully, fire quickly.

Key Takeaways

  • Find your team rhythm
  • Realize when you’re wrong
  • Move quickly

Time spent on hiring is time well spent

Going through a hiring process for what is just your little side project or brand new company is scary. You probably don’t even have a product fully built yet, no customers, no users. Your product is your baby at this point — it hasn’t been exposed to the world. You find yourself going through dozens of candidates because, let’s face it: the initial interview is as much about them figuring out whether you’re even worth working for as it is about you making a potential hire.

When you finally do find a few people who are as excited about your baby as you are, it’s pretty exhilarating. You want to call up the team and gush about how this talented person thinks the baby is great. Here is the part where you need to take a step back.

You’re going to be tempted to find every reason why they should be brought on as soon as possible. The risks in bringing on the wrong fit for the team are so much greater than the risks of taking your time to find the right hire that I’m going to repeat, when you find a candidate you’re excited about you need to slow down, take a step back, and bring in the team to do some validation. Don’t muddy their view by telling them all the reasons you think they’re a good fit. Just say there’s a candidate you want them to look at.

Then check to see if this candidate is going to pass the test of the key areas we’ve described: are they going to communicate well, are they going to commit to the basic structure the team operates in, are they excited about your product and values, and are they going to lift up the team before they lift up themselves? If you aren’t enthusiastically saying yes, yes, yes, and yes, and you have asked them all the right questions, then take a pass.

As hard as it is to jump back in the gantlet of interviews, do it anyways. Do it over and over again until you find the right person. Your small project is going to cause you many a sleepless night and take up a significant portion of your life. The people in it with you become like family. You’re hiring someone who’s going to not only build your product, but someone that will potentially be in your life for years to come. So take time to get it right.

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