06How to lead a great remote team: the importance of letting go

All teams start out small. There is a certain kind of security, comfort and an extremely high level of personal investment that comes with working with only a handful of people you trust completely. It’s a nice feeling—and very much a bonding experience for everyone involved. However, as your business takes off, you’ll inevitably need to start scaling your team to make sure you stay on top of the game.

As your team grows, so do the challenges that come with arranging the workflow and making sure everything runs smoothly. If you don’t have any previous experience with leading a team of more than a few people (or even if you do), that step may seem intimidating and overwhelming—and rightfully so.

However, an important thing to remember is that leading a large team isn’t in any way worse compared to a small one—it’s just different.

Team having a meeting in an office
As more organizations embrace new ways of working, managers will have to do away with the misconception that remote teams only work when they stay small. Teams that embrace structure, transparency, and a culture of knowledge sharing can—and do!—scale just as efficiently as co-located teams. Emily Bonnie, Wrike

In this chapter, we’ll go over some things to keep in mind when leading your growing team and making sure you don’t lose touch with your employees, and manage to retain the cohesiveness that keeps you together—whether you’re five, fifteen, fifty, or a five hundred people strong.

Dealing with structure changes

As your team grows, the structure of it has to change, too. In very small teams, the CEO is usually the person that everything goes through—the one who deals with the high-level coordination of everything from engineering to marketing to business development.

When your team starts growing, this arrangement will become more unreasonable with every extra person. It will slow work down, create longer decision times and communication loops, and put an overwhelming amount of stress on you—which is not what you want.

Every CEO, at some point in the lifetime of their company, needs to learn to avoid being the centre of everything. As your team grows, you’ll need to empower other people in it to make decisions, regardless of whether they are related to product, hiring, or anything else.

Photo of Annika Helendi
You have to trust your employees in a remote team. Letting go of your own control issues might be the biggest challenge in leading a remote team, especially if you started out with a more "traditional team". Annika Helendi, Toggl Plan

It can indeed sound like a challenge, but is actually mutually beneficial for both you and your team. Letting go of some control in the team is also something mentioned by Alari Aho, CEO of Toggl Track, in a positive note:

Photo of Alari Aho of Toggl Track
I don’t know everything, I don’t want to be that guy. This is what has changed in Toggl Track over the years—our role as founders in the actual product is getting smaller and smaller.

To achieve big things, you sometimes need to let small things slip. That has been my personal challenge—being a control freak. I guess personalities can change over time, so my OCD is getting better as time goes by.

So, how do you start out with not being the centre of everything, while still being sure that everything runs smoothly and there are no gaps in work or communication?

First, consider creating teams within a team. This is the first and foremost thing that goes hand-in-hand with not being at the centre of every decision-making process. At a certain point, when you have enough people working in similar positions, you should consider forming a team (or teams) within a team, and putting someone else in charge of it, giving the group at least partial independence to make their own decisions, and therefore speed up workflows.

Instead of micromanaging the work of teams, put extra effort on making sure communication works. If you’ve managed to hire the right people, you should already know that they’re qualified and have the skills required to do their work efficiently—which means that whether the right decisions are being made isn’t something you should be constantly worried about. What you should make sure of, though, is that you’ve provided your team with the right tools and mindset of communicating efficiently while in the process of managing themselves.

Photo of Michael Krapf of WooThemes
As the company grows, the challenge of maintaining relationships grows as well. Since success in business is highly dependent on successful relationships, we’ve had to adapt by becoming more intentional about our team sizes and communication flows. Michael Krapf, WooThemes

Making sure communication works does not mean spying on your team members’ personal conversations or pressing your nose against the virtual window when they’re discussing anything. It means:

  • getting to know your employees—through both team conversations as well as one on ones;
  • learning to recognize the signs of something being “off”;
  • encouraging employees to be open about how they feel by creating a judgement-free environment;
  • gently nudging any conflicts to be solved in a reasonable manner;
  • setting up a regular communication schedule both between you and an individual employee as well as the employee and the rest of the team;
  • encouraging the use of team messaging and collaboration tools;
  • nurturing familiarity between team members;
  • avoiding any “them vs us” moments.

Manage expectations —as much as your team members need to be able to manage themselves, one of your main duties as a leader is still to set clear expectations and goals, and define how communication about delivering these goals should take place.

Clear lines of accountability can be established by setting regular (monthly, quarterly, yearly) performance goals, checking in every now and then to see what the progress is—and lending a hand if something is not going as expected.

Adapting to new solutions

As your team grows, you’ll need to take more and more advantage of different technical solutions to help everyone get their work done effectively in a remote environment, regardless of how many people you have in the team. There are two things to keep in mind and check every now and then:

Are the tools you’re using suitable for both small and large teams? There are certain tools that don’t work very well for larger teams—for example, at some point you’ll probably run into trouble when it comes to video calls—some conference call tools are just not built to accommodate more than a certain amount of people, and will start to get glitchy if too many people join.

Are the tools you’re using the best option for you financially? Cost efficiency is also something to keep an eye on—many tools start rapidly raising their prices as you add more people.

We’ve talked about the importance of having your internal communication guidelines written down in an easily accessible document. This should also include a list of all the tools you use in your remote team.

First of all, it’s great to use when hiring and onboarding people for simple information sharing, but it also has the benefit of being there so you can go through it every once in a while, see how much you use/need/pay for them, and perhaps make some decisions or look for alternatives in case one of them isn’t really working that well now that your team has grown.

Creating trust

Establishing trust and transparency in your team means you can nip any issues in the bud before they turn into big ones. Trust is important in all directions. As much as horizontal trust (between team members) is absolutely crucial for your team working efficiently together, you should also never forget about vertical trust.

Employees need to be able to trust their CEO, team lead, supervisor or anyone else “above” them to know that management has their back and they can talk about any issues they have without being judged or punished for it.

Here are some ways to make sure there are no communication barriers between you and your employees:

One on ones: in the environment of constant (written) communication that comes with a remote team, face-to-face, one-on-one conversations might feel redundant, and maybe even a waste of time. Don’t make the mistake of believing this.

Regular one-on-ones are about personal development and problem-solving, and make the individual you’re talking to the number one priority. Make sure you have regular conversations with your employees to see how they’re doing—on both a professional and a personal level alike.

Woman working in office while on the phone
I’m a firm believer in trust but verify. Each team and position should have some trackable metrics that indicate the level of productivity achieved. The difference in choosing to trust first is that when you see an issue, you ask questions versus assuming that someone is taking advantage or otherwise intentionally underperforming. Carol Cochran, FlexJobs

Many managers tend to make the mistake of having one-on-one conversations with their employees only when a problem has already surfaced. There are two issues with this: firstly, at that point it’s most likely already too late, and secondly, having one on one chats only when something is wrong will make your employees scared of them.

Aim to make your “hey, let’s chat for a bit today” something to look forward to for the employee, not a “what have I done now?” moment.

Honest feedback: don’t underestimate your team members’ ability know if you’re not being honest about sharing feedback about anything regarding them, including their work performance as well as any personal issues. Honesty, however, doesn’t mean judgement.

Stay open-minded, listen, and offer help where you can without over-managing. If there is something that needs to be corrected when it comes to the work, attitude or mindset of the employee, try to be frank, but not intimidating. Constructive criticism is fine. Aggression and threats are not. Say it, don’t spray it.

Encouragement: you shouldn’t feel obliged to constantly pat every single one of your employees on the back every time they finish a regular task, but it is important to take the time and say how well they’re doing every now and then.

This is especially important in a remote team because spontaneous praise tends to naturally happen when chatting in person and in an informal setting—which isn’t often in a remote team. So, don’t forget to give your team members a virtual pat on the back every now and then if they’ve done a good job. It’s more important than you think.

Avoiding burnout

Burnout is often used as a hype word, but it’s a very real issue—especially in startups and smaller teams, where everyone shares a ton of responsibility. The workload can and will start getting to people eventually, unless it’s carefully prevented.

A 2012 study of 500 IT administrators from various firms by Opinion Matters revealed that 72% of respondents were stressed, 67% considered switching careers, 85% said their job intruded on their personal life, and 42% lost sleep over work. These are scary numbers, and call for careful thinking about in any team.

The transparency and open communication we’ve discussed a lot comes into play here a lot—if you’ve managed to establish a team culture that is accepting of openly talking about issues like this and expressing it when something isn’t right, you’ll know about it before it’s too late.

Some signs of impending burnout to keep an eye out for, regardless of whether it’s you or your team members, include:

Increased irritability: overwhelming feelings of not being in control can eventually lead to lashing out on others around you—whether at work or at home.

Poor work performance: burned-out employees often need to exercise a lot of extra effort to get their stuff done—effort that they often don’t have the energy or motivation for. A noticeable drop in performance when it comes to work-related tasks is a certain sign of something being off.

Working too much: as opposed to not getting enough done, doing too much can also potentially be a bad sign. When people feel like their control over their achievements is slipping, they can try and overcompensate by working a lot more to make sure they get everything done.

Constant exhaustion: difficulty sleeping and feeling rested, perpetual tiredness and low levels of energy regardless of daily activities can be a sign of many health issues, but are also a common symptom of burnout.

These are just some things to look out for, and can be related to many other things besides serious burnout. However, it’s always safer to ask and be sure than let it happen in the background and risk serious consequences for both the individual and the whole team.

There are several things you can do to prevent burnout, including:

An open vacation policy: a lot of remote teams, including Groove, Buffer, Zapier, etc, have opted for an open vacation policy, which basically means that people can take time off whenever they need it (granted that they are aware of their responsibilities and dependencies when it comes to other team members’ work).

Mental health days: regarding why take some time off, feeling “out of it”, generally unmotivated or down should be enough of a reason to take a day or two, without officially considering it “vacation” or “sick days”.

Providing options for a healthy lifestyle: many companies offer paying for their employee’s gym membership or other activities among other perks, should they request it. Getting enough exercise, fresh air, and time to yourself is extremely important in a fast-paced job, and offering to support that shows that you care about your employees’ mental and physical health.

An open and accepting environment: if team members feel like they’ll be judged, punished or looked down on when they discuss their problems, they won’t come to you. Make sure to make it very clear that you’re there if there’s any issues, and willing to really listen.

Spending (as much) time (as possible) together: remote teams don’t have many opportunities to hang out and do fun things together, which is why occasional team retreats are super important. Hanging out in person builds trust and personal relationships, which can then be later maintained online.

As a fun prevention method, Mattermark uses puppies (yes!) to keep stress levels down:

Four cute dogs huddled together
You can find an endless supply of puppies running around our office. It’s normal to see someone sprawled out on the floor, getting her face slobbered on by a dog at least once a day. When we hit walls, we step away from our computers and play with our furry friends. Sam DeBrule, Mattermark

An endless supply of puppies.

Whichever actions you take to make sure your team members are healthy both mentally and physically, the most important thing is to openly communicate about these issues within the team, and encourage your employees to reach out to you if needed.

Measuring performance

Measuring employee performance is a difficult thing in any organization, regardless of whether it’s remote or not. Many companies take the road of measuring hours worked as the main indicator or performance. This might seem to make sense in traditional, nine to five office jobs, because it’s pretty easy to see whether an employee comes to the office at a certain time and leaves at another.

Remote teams are more complicated. First of all, simply because it’s pretty tedious to track hours worked with remote employees, unless you make them virtually clock in and out or track their hours and then report them to you. You can obviously do that if you find important. We don’t recommend it, though. Why?

Keep in mind

Hours worked is irrelevant to output: showing up to work is simply not the same as getting work done. If you have agreed on certain goals and/or a measurable output, and if the employee delivers, then who cares if they work 8 or 6 hours a day, or which hours of the day they are? If you think about it, this should apply to any kind of organization, but unfortunately it isn’t the norm of thinking yet.

Trust is important: being able to trust your team members to have a large amount of self-discipline and get things done is an integral part of remote teams. If your team members feel like you don’t trust them, or that you’re constantly hovering over them, they’ll start to resent their work after a while.

Clocking systems and vigorously reporting hours waste time: smart teams spend time on what actually matters. This means that as long as your team members are delivering what they should be delivering and work processes are running smoothly, there’s absolutely no reason to spend your or your team members’ time on reporting their hours worked and regularly checking them. Here are some alternative things that make a lot more sense to talk about when measuring your remote team members’ performance:

Output: as long as an employee is delivering quality work, keeping up with the rest of the team, hitting deadlines and goals and being productive, it doesn’t matter when or how long they actually work. This, however, implies a pretty concrete set of measurable and agreed-on output.

“I’m a firm believer in trust but verify. Each team and position should have some trackable metrics that indicate the level of productivity achieved. The difference in choosing to trust first is that when you see an issue, you ask questions versus assuming that someone is taking advantage or otherwise intentionally underperforming.”

Carol Cochran, FlexJobs

Personal drive and enthusiasm: is the employee personally invested in the team’s common goals and activities? Do they work well and cohere with the rest of the team? Do they participate actively in discussions about the team’s business goals as well as culture topics?

Self-improvement: do they constantly thrive to improve themselves and their work? Do they set ambitious goals and work hard to get there? Are they excited about learning, growing and improving when it comes to both work and life in general?

One of the best things about working remotely is the option to work when you feel most productive and “on”. If you find your most productive times of the day, have the flexibility to create a healthy work-life balance and take care of yourself, and feel personally invested in and excited about your work, you’ll be more productive.

Being more productive means that you’ll get more work done in a shorter time and hit goals sooner. Therefore, it makes sense that hours worked is definitely not a good unit of measurement.