How To Build And Manage Remote Startup Teams
In recent decades, we’ve witnessed a revolution when it comes to how and where people work together. Remote work tools like Slack, IM, and even email have fueled multimillion-dollar businesses whose team members have rarely if ever, met in person.
It’s not a universally beloved concept, however.
While several Silicon Valley startup success stories have built themselves up using remote teams, industry giants like IBM and Yahoo have scaled back their remote work policies, even going so far as disassembling their remote teams. Their justification? Greater potential for collaboration and hoping for more tight-knit groups using the traditional approach.
I’ll put it right out there—I’m unapologetically all for remote teams. I’ve built all of my businesses around them, and my current business is focused on recruiting for them.
Not to say that I don’t respect the difficulties that come with managing them, and the points raised by these executives are valid. But these are giant, monolithic companies rooted in traditional work. For startups and early-stage entrepreneurs, especially, the pros of building and managing a remote team far outweigh the cons. And the benefits are immediate. But only if you do it right.
Having built up successful companies in this manner, I’ve compiled what I’ve learned on the topic into this comprehensive guide on how to start, grow, and manage a thriving remote team for your startup.
The Benefits of Remote Teams for Startups
One of the undeniable benefits of working with remote teams is that you and your staff enjoy a better quality of life.
That goes for your employees, who are much less likely to experience burnout, but for you as well. Being able to work from home helps your family deal with the increased time you need to spend on your business. You’ll avoid a lot of office-related expenses that would be at the back of your mind, draining your energy. And we know that whether you’re starting out or scaling up, your energy is precious.
But I’d say the most overlooked advantage to building a remote team is that you get access to a much bigger talent pool. You don’t need to fight the big companies for the best people. No need to get into bidding wars for an excellent engineer or a fantastic content marketer. And the more large corporations shy away from remote work, the easier it will be for you to find a good catch.
And then there’s the diversity aspect. Do you care about diversity? Not in a “hit the right numbers and get into Buzzfeed diversity listicle” kind of way, although it’s absolutely important from an equality standpoint. But hiring from different cultural backgrounds also increases your cultural capital. This capital, in turn, means more and better ideas.
Building a local team gets you the best, second best, and third best people in your immediate area. An international team gets you the best from your area, the best from Ukraine, the best from Italy. That’s three gold medalists instead of gold, silver, and bronze.
But I get your apprehension—those are the “whys,” but there are still the “hows.” How will you keep communication smooth? How will you keep everyone motivated? How do you make sure everyone is productive?
How To Set Up Your Remote Work Policy
Don’t confuse remote work with, “do stuff whenever you feel like it.” Freedom is not about anarchy. In fact, too much freedom can backfire and throw your remote teams in disarray right from the start.
When you don’t give people appropriate rules and constraints, some will go too far in one direction. They’ll burn out or get stuck in self-management hell. Others will pick up too much of a relaxed attitude and never live up to their full potential.
By all means, be flexible, be open to exceptions on a case-by-case basis, but set up some ground rules. And be ready to lay down the law if people break them, as you would in a regular office setting.
The rule of thumb: expect from remote teams anything you would expect from local teams. The only difference should be that they don’t work in the same building.
The following are the most important policies you should start defining when managing remote teams. Remember, there are no right or wrong answers—it depends on your business and the culture you want to build. But you should have answers to each of the below.
Attendance and Official Time Zone
Official work hours may vary from person to person, but spell out what you expect. Are there particular hours the employee must be available? Or is it completely flexible as long as they meet deadlines or complete a certain number of tasks? How should illnesses or absences be reported and handled?
Does your business have clients spread all over the world? It might make sense to have remote teams staggered to collectively work around the clock, especially when it comes to people in support. Your customers will feel valued if you take care of their questions and problems in a timely manner.
It’s also worth pointing out that whatever you choose, you should have some overlap. Enough to enable you to get the whole team together for a video conference for 10-15 minutes every other day. This meeting will help make them feel part of something and combat a feeling of isolation. So what if the meeting happens at the start of the workday for some, and the end of the workday for others?
With staggered schedules comes the need to choose an official business time zone. Even if not everyone works the same hours, set a standard for scheduling meetings and deadlines.
My team works on EST. If an employee in Portugal (GMT +1) wants to schedule something with one from Ukraine (GMT +3), they will talk in EST. It saves a lot of confusion.
Here’s a tip: have your team use Google Calendar’s Additional Time Zone function. Go to Settings, and it’s the third option on the first tab. Look below the field where your employees pick their time zone. As soon as they set it to your company time zone, they will see that time zone side-by-side with theirs.
Equipment and Connectability
It might seem obvious to you that someone wanting to be part of a remote team should have access to good technology. Don’t take it for granted. Once, I found myself trying to interview someone for an engineering position. This person was on a farm in the middle of nowhere. The connection was so bad I could hear the cows mooing in the background more often than I could hear him!
Think about the relationship you want to have with your remote team. And about the relationship you want the team to build among themselves. Communication is the most important factor when creating and managing remote teams. So never, ever allow your employees to skimp on gear or connection.
Everyone should be video-conference ready. A camera—face-to-face is irreplaceable—and a good microphone is mandatory. Enforce the use of headsets, too. Echo and feedback can become a headache during remote meetings.
Finally, access to a proper connection should be mandatory. Part of the appeal of the remote work lifestyle is that each employee can work from wherever they like. But if that happens to be granny’s house, and granny’s house is on top of Mount Kilimanjaro, then, sorry. Granny will have to settle for a postcard.
When your team is remote, the internet is its lifeblood. Employees are responsible for maintaining a sound signal during all working hours.
The good news is that you can test for this at the interview stage. When you are getting ready to hire someone, never settle for anything less than a video meeting. If the candidate seems reluctant to accept, that’s fine; maybe you caught them traveling. Reschedule at their leisure, and while you’re at it, explain the points above.
Pay attention to the quality of the call during the interview. Could you communicate without flaw? Remember, a job interview is a moment where everyone makes their utmost effort to be at their best. If it didn’t go well then, chances are, it never will.
Security and Data Protection
It’s easy to gloss over security—it’s a super annoying topic! That is until a hacker kid steals your user database and you have a PR crisis on your hands. Then it’s not boring at all; it will be a super exciting time in your life! But not a fun one.
The amount of security that you’ll want each member of your remote team to adhere to will depend on their position, and the access they have to core business systems. The guy writing on your company blog doesn’t need to be as careful as the person who handles banking. But that’s not to mean he should use the unsecured Wi-Fi connection at the corner pastry shop.
At the very least, insist that your remote teams use secure internet connections, and steer clear of free wireless hotspots.
And enforce good password hygiene. Way too many people, even tech experts, still go with the time-honored “Admin / 12345” combo.
Of course, that’s easier said than done. Even with stuff like LastPass, (an app that randomizes passwords and keeps track of them), people still fall into their old patterns.
Minimally, get your remote teams to follow two password security rules. First, make each password unique. Second, make it a passphrase, not a password.
Welcoming Remote Teams Home: Onboarding Strategy
The optimal period for onboarding remote staff is the first week. It’s during those first seven days that expectations are set. It’s when the new employee is the most amenable to learning and embracing the company’s culture.
Good people will always be ready to learn and adapt, but first impressions matter. The first week will set the pace for your employee’s further development.
There’s a lot to cover about onboarding remote employees, but what follows are the top three, must-do actions for that first week.
Meet The Team: Video Edition
When that “hey, meet our newest team member” email arrives in an overflowing inbox? Most people will shrug and mark “read and archive.” Some will report you for spam! Sorry, that doesn’t work.
If you want people to care, and you should, you need to set up a video meeting. You’ll use it to introduce the new member to the team live. Explain what they will be doing on the team. Finally, encourage them to share something personal about themselves.
We usually do this during our weekly “all hands on deck” meeting. We interact in video format every day, but once a week, we make an extra effort to get everyone in a meeting. Here, we talk about the general direction the company is going.
If you decide to do the same and integrate introductions into your regular meetings, that’s fine. But make sure the meeting in question isn’t right at the end of the week. It’s no fun to have the new person be a stranger in your remote team for those first critical seven days.
Introduce Them to Your Remote Team’s Tools
When we’re talking about managing remote teams, it’s easy to take for granted that everyone will use their tools. After all, most people have their own processes. Trying to force a change may decrease their productivity, one of the reasons you hired them in the first place.
But there must be some standard for tools that your remote team uses to interact. It’s no good if a third of your team uses Office 360, a third uses Google Docs, and the rest does everything on Notepad++.
Unlike the policy points that we’ve covered before, this is something that will emerge as you grow your team. As people work together, you ’ll be able to see which tools are working out better. Once you’ve figured it out, standardize them across the whole team.
And as popular as your tools of choice is, it’s not a given that a new employee will be familiar with them. So this is the first thing we take care of when a new person joins us.
Our key-master also takes care of adding newcomers to our paid service teams. She’ll create and hand them business accounts when appropriate.
Remote teams succeed or fail based on their quality of communication. Making sure everyone uses the same tools helps to consolidate a company-wide language. Teaching that language to a new employee is an absolute priority.
The Mentor Approach
The most efficient way to get a new employee kicking ass by the end of the first week is to assign them a mentor. Mentorship is one of the keys to unlocking anyone’s potential, even your own.
The mentor should be a company veteran. If you’re just starting, congratulations, that’s probably you!
If you’ve already got some weeks or months of working as a team under your belt, pick the person you wish you could clone. It won’t be as easy as all that, but if your new employee is to learn by example, you want to put forward the best exemplar.
Bonus points if the mentor is in roughly the same timezone as the new person.
The mentor is the ideal person to handle and organize the process from the previous points. They should also check on the new employee every couple of days. No need to be intrusive. The point is not to micromanage, but to see how they are getting along with the rest of the remote team. By checking up, we mean more than a poke in Slack. A one-on-one video chat, even if only for five minutes, is the best way to do it. More on one-one-ones in the next section.
The mentor’s primary job is simple. They should be available to answer every question, especially silly ones. As the team grows and culture develops, inside jokes and “unwritten rules” start to creep in. As a new person, it’s daunting to navigate those.
Knowing that someone has your back when you are new removes a lot of stress. The mentor will guide them through the team’s workflow, and help them understand the organization’s culture.
And here’s the added benefit: the person you pick to be a mentor will thrive with the responsibility. They will become better and better at training and at managing people. That’s something you’re going to want to have as your company grows in the long term.
Say It and Mean It: Communication Strategies for Remote Teams
I have a hunch most of the work in your company happens on computers. So what’s the real difference between having all your people in the office and having them work remotely? A computer is a computer, regardless of where it is.
The answer is communication. In an office setting, where you have people close to you, it’s much easier to be in sync. It’s easier to get the point across. And it’s easier to know what’s going through someone’s mind at a glance. Even soft skills work better in a personal context.
So the final key to successful management of remote teams is cracking the communication code. It’s making your team’s communication as close to in-person communication as possible. In a virtual meeting, there are some ways to ensure your group is communicating effectively. But communication is about more than meetings. It’s about the day-to-day operation of your remote team. Let’s go over some important points.
Aim for Over-Communication
When managing remote teams, there is no such thing as too much communication. Volume makes up for the lack of proximity. Train your people to talk. Teach them to speak with you. Teach them to talk among themselves.
The first few times someone has a question, you’ll be inclined to answer it. You want to be a real boss, and honestly, it’s nice to feel like you’re the linchpin of the organization.
But resist this urge. In the long run, it’s not sustainable. It will overwhelm you. What’s more, you’ll find out that your employees will start running everything through you.
Instead, train yourself so that your first instinct is to reply, “You should ask so-and-so. He/she is the one responsible for that info.” As you do this over time, you will be training your employees to look for the right person, instead of going through the boss every time.
The second thing to do is put in place a failsafe mechanism. Make it a rule that every piece of communication must exist in duplicate. It might seem counterintuitive, but it’s crucial for smooth communication. It’s way easier to forget about an email than about a folder sitting on top of your desk. To avoid this, build redundancy into your communications. This could be a strange concept to some, so I’ll explain how it plays out and why it works.
The specific rules will vary depending on your process and the tools you use. But this is how it works in my company:
At DistantJob, we use Trello as our starting point for any task.
A card gets created for a task, the stakeholders are tagged, and then work begins. If we need to communicate with a particular person about that task, we @ them on the card.
Then, we always send a quick poke on Slack saying “Please check this Trello card about such and such.” We submit attachments on the card to the relevant Slack conversation. Everything—messages, people responsible, relevant documents—lives on both of these platforms.
We send meeting agendas by email and paste them into the appropriate Slack channels. After each session, we write a summary in Slack. From there, action-items turn into Trello cards.
If it doesn’t exist in duplicate, there’s a good chance it will slip by someone. This is because each team member will naturally give varying levels of attention to different platforms throughout the workday.
Team Rocket might not have been a remote team, but they had the right idea: “Prepare for trouble! And make it double!”
Keep Escalating via One-On-One Conversations
Our natural state is not to want to bother people. Our culture prizes “gumption” and suffering in solitude while dealing with a problem. Going to a colleague—or worse, a boss—for advice when you’re stuck is something many employees fear.
Don’t accept this. Don’t succumb to what Seth Godin calls “fear of escalation.” Make sure the people in your remote teams feel free to look for help as soon as they feel stuck. It’s admirable when someone tries to solve a challenge by themselves. But when you’re part of a remote team, this is more likely to cause a bottleneck than not. Work getting done well and on schedule is what matters. Who did what? Who helped whom? These are secondary concerns.
Something didn’t arrive at your desk when it should? Be comfortable with escalating. Be polite, be gentle, but be firm and unwavering.
Get to the person that you believe to be the bottleneck, and don’t lay off until you get an answer. Teach your employees to do this between themselves, too.
Escalating is hard in remote teams, as online communication lacks critical body language cues. So it can often be perceived in a harsh light. Escalating via email vs. video chat can mean the difference between being a jerk and a considerate boss. The same goes for any other interaction where someone is escalating the conversation.
You have one key tool to handle this: the video one-on-one. A video chat is as close as you’re going to get to the in-person feeling. Well, at least until Elon Musk invents remote-controlled Replicants. For our purposes, the body language and faux eye contact available through video are good enough.
Follow a simple one-on-one structure, so you don’t get bogged down in minutiae. Lead with some (genuine!) positive feedback for the first couple of minutes. Don’t have anything good to say about your employees’ work for two minutes? Either you need to pay more attention, or you need a new employee.
Then go into escalation mode. Again, be gentle but firm. Ask what’s the status on X (as opposed to “why is X not done”). Frame it as a challenge, and don’t let go until your employee states what the problem is, transparently. Make them understand that you want to help, and the first step is figuring out the issue.
Finish by collecting feedback from the employee—ask what you, or the company, could do to make the task easier. This feedback deserves close attention. It can help pinpoint flaws in your process that aren’t visible from your point of view.
Now for bonus points. Even if everything is going well, try to have a one-on-one with every member of your remote team, at least once a week. Follow the same structure. Positive feedback, inquire about challenges, ask for feedback on the company process.
Your bottlenecks will go away, one by one. Like magic.
Cultivate Casual Conversation to Unlock Tacit Knowledge
Teams work at their best when held together by a social connection. As soon as employees start forming social bonds, the stakes rise. We feel more accountable to people who are closer to us. And vice versa. Camaraderie is one of the best ways to motivate yourself and your team.
But there’s more to it. There’s a hidden secret to the best-performing teams: tacit knowledge.
These things don’t come up during formal meetings. People don’t like to butt in, and most won’t make a big deal of their previous experiences. They don’t want to appear arrogant, or maybe it just doesn’t occur to them.
This can be a problem in remote teams, which tend to communicate on a per-need basis. Meaning, you only talk to someone when you need a particular action or piece of information from them. It’s easy to see how this can lead to a shortage of tacit knowledge.
Encouraging casual conversation kills two birds with one stone. It helps nurture bonds among team members, and as they start to know each other better, they’ll develop tacit knowledge about each other’s skills.
As someone invested in nurturing your team, it’s up to you to make people feel at home and interested in each other. The first step should be establishing an “off topic” or “casual” zone in your company’s internal chat. And please don’t call it “water cooler,” or you’ll embarrass us both.
Set the example. As a boss, talk about your interests. Encourage people to talk about theirs, and engage. Interests, likes and dislikes, achievements in previous jobs—there’s a lot of ground you can cover. Of course, it should be natural. Don’t try to engage in conversation about a topic you loathe!
We’re multifaceted beings. We’ll never like the same stuff. But you are people working in the same industry, on the same projects, so there must be some overlap in interests.
At DistantJob, we’re all geeks. Geeks gravitate to the company we’ve built. So conversation flows pretty effortlessly in #general. Music clips abound, along with video game trailers and calls for testing the latest productivity software.
Along the way, we’ve discovered some cool stuff about the people on our team. Stuff that didn’t come through during job interviews and introductions to the team.
You can also nudge people into celebrating their interests. Suggest lighthearted things, like using emoji next to their names on Slack. Our VPO has a guitar. He’s learning to play. Our marketing director sports a video game controller. Guess who people are going to @ when there’s talk of a new video game console coming out?
These might seem like small things. Don’t discount their importance. We build social bonds with small blocks. But they might end up being the glue that keeps your remote team together through the hardest times.
Managing Remote Teams: The Next Step
Don’t worry about the next step. Worry about the steps above!
Most of them are not things you’ll do and then be done with. These are strategies you’ll work at for the lifetime of your business. The more you practice, the better the business will become. Stick to them, and I guarantee you, your remote teams won’t perform as well as a local team—they’ll perform better!