How to Manage a Remote Team: Advice from Five Experienced Remote Managers

Last week, we covered the basics of what all remote work novices need to know as they transition from a traditional office to working from home. This week, we are focused on remote team leadership, and the challenges they specifically face during this transition. Due to the circumstances surrounding COVID-19, it’s not just your average worker that has been thrust into working from home, but their managers and supervisors, too. 

When you aren’t in the same physical space, it can be easy to panic about how to manage your employees. It won’t surprise you to know that some managers will fall into the trap of micromanaging their team in an effort to feel in control of their output. However, the boundaries for remote working look a lot different than the boundaries for a traditional office. How do you structure regular team check-ins…without getting in the way of things actually getting done? How can you tell if work isn’t getting done, and how should you handle it? 

We spoke to five experienced remote team managers and asked them for their insight on how to remotely manage their team.  

Remote management tip #1: Create a daily/weekly structure, with regular check-ins

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One of the best ways to stay connected with your team and provide some sense of “normalcy” (if that’s even possible right now) is to still rely on a consistent schedule. 

Every single one of our remote team leaders mentioned daily conversation in Slack as a minimum, as well as regularly scheduled stand-ups. While some opt for just a weekly report in a meeting, others do a quick daily Slack check-in as well. 

Diana Potter, Head of Support at Qwilr, currently manages four folks, but has managed a remote team of up to fifteen people. She has worked remotely for twelve years, and has a structured involvement with her team. She shared that her team talks daily in Slack, in addition to having weekly 1:1s. The whole team meets once a month in Slack and once a month on a video call.

Senior Agile Project Manager of Alley Interactive, Jaimie Olmstead, shared a more hands-on approach: her team has a morning Slack check-in when everyone logs on for the day, but that’s not all. They also have weekly scrum rituals (refinement, planning, retro, demo), along with a daily scrum which is held over Zoom at the end of the day.

Slack is a gift to us all right now, and allows for so much flexibility with how we communicate remotely. If your team works more asynchronously, you’ll have better luck with regular Slack check-ins than say, ending the day with a video scrum. While you’re adjusting, you can also set up Slack reminders that ping everyone with a nudge to update accordingly–whether it be a morning or end of the day check in. 

Remote management tip #2: Set deadlines…and create flexible, short-term plans for long-term goals

If you’re just now managing a remote team, thinking about how to make sure tasks get done may make you sweat. Almost all of the remote team leaders we interviewed mentioned the importance of setting deadlines and the need to set and adjust schedules on a nearly week-to-week basis. 

Jaimie shared how her team plots out their tasks with a team-specific calculation: 

“Our scrum team does week long sprints. We decide the amount of work we can commit to each sprint based on our average velocity. We use velocity, or the total number of story points completed in a sprint, to ensure we’re planning based on data vs feelings or general hunches. The team understands that if we’re bringing a ticket into our sprint, we’re committing to getting it done by the end of the sprint.” 

Rachel Gertz, co-founder of Louder Than Ten, shared a more extended process that includes advance planning for any potential show-stoppers:

“We do bi-weekly sprint planning and grooming and work through dependencies so we know how to prevent blockers. We also know that our sprint task limit is approximately 7–10 ‘cards’ or major tasks.”

Remote team management tip #3: Keep priorities clear and committed, and evaluate them regularly

You may have already surmised that when you’re managing a remote team, clear communication is more important than ever. 

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Our team leaders stressed the importance of not only communicating which priorities are important with their team, but to drive home their importance through a variety of methods. 

Diana shared that her team puts all of their priorities in writing. “Especially when you’re asynchronous from your team, you have to work on that written communication and keeping things in easy to find places,” she shared. “You can’t just sort something out in Slack and then expect everyone to catch up on it. You need to summarize and share everything in another form. And keep it as a living document so they know when things change.”

Pro-tip: This is where a solid project management tool…like Cardsmith…comes in. Peruse our project template boards for ideas on how to get started and use Cardsmith for project management.

Rachel also spoke of the importance of evaluating those priorities on a regular basis, and how her team evaluates which priorities are the most important. “We’re always weighing effort vs impact and prioritizing things that take less effort and provide higher value. Then we prioritize higher effort, higher impact tasks.”

Remote team management tip #4: Take note when team members go silent or get vague 

This is the real tricky aspect of remote team management: how do you know if things aren’t getting done? When should you start to worry? 

The owner of DigiSavvy, Alex Vasquez, succinctly summed up the telltale signs you need to look for with, “They go silent, or they provide vague answers.” Diana also pointed out that, if you have clear deadlines scheduled or KPIs already documented, it makes it easy to identify when tasks aren’t being completed.

Rachel backed up these observations, stating, “Usually, people who aren’t getting things done are tough to reach and you’ll have a tough time seeing visual timestamps or realtime progress (deadlines get missed, meetings delayed, deliverables are slow or low quality).”

There is a rhythm and flow to remote communication, just as there is in person. While some folks on your team may be chattier than others, you’ll start to notice subtle shifts in the way a person communicates. 

If someone normally reports their tasks in great detail and then suddenly starts to be more vague, that may be a sign it’s time to check in. If someone is normally more cheery in tone, but then gets more short or blunt in their responses, that may be a sign to check in. It will differ from team member to team member, but if you follow the approach outlined above and have regular conversation/scheduled updates amongst your team, you’ll be able to notice shifting tones and updates quickly. 

Remote team management tip #5: Approach missed deadlines with a direct, but positive approach and a plan 

Lina Calin, Project Manager at Sparkbox, shared Sparkbox’s use of pairing to help problem solve and stay accountable: 

“I’ll start with asking what that person needs to help unblock their work or move it along. Then I’ll ask if they’ve paired with anyone to help them. Sparkbox is a big proponent of pairing for good reason; it really works to help solve problems. In this conversation, I’ll suggest folks I know who would be good to pair with. I’ll check in later that day to make sure they’ve set up a pair and ask them to share how it went and if additional pairing is needed afterwards to unblock them. 

She went on to mention that tasks not being completed are not necessarily a sign that your team member is slacking off. Sometimes, it’s that their workload is a little too big for them to handle. You’ll notice this if you see work progressing, but not at the rate you originally hoped for.

Lina advises, “When you suspect that [what they’re working on is too big], it’s good to help your team member break the task up into smaller pieces that are more manageable for the creative team and can show progress better.” 

Rachel agreed, “Most of the time, [missed deadlines are] due to overwhelm or an inability to let go of less important things (we’re all guilty from time to time).” She recommends, “The best way to address lower productivity is to ask your teammate directly what’s happening, what’s blocking them, and what you can do to remove that block. Having your teammate restate their goals and priorities is also super important and will allow you to be candid and maintain trust.”

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Diana folds these sometimes tough conversations into their pre-established coaching sessions. They already have them on the calendar, and she regularly checks in with her team and how things are going with what they are working on. She suggests approaching any missed deadlines or concerns in a straightforward manner, but during a regular meeting, which helps take the pressure out of the conversation. 

Jaimie also emphasized the importance of walking into these conversations without assuming the worst: 

“Always assume positive intent. If you’re working in a scrum team, understand that you live and die as a team. Focusing on individuals and their personal struggles won’t help the team to move forward. Instead, discuss the challenge as a group. How can you support your team member? Could they pair up with someone? Do they need time with family? There can be multiple factors, so it’s important to teach your team to hold each other accountable but also be supportive and work as a team to overcome obstacles.” 

Remote team management tip #6: Trust is everything

Lina emphasized the importance of having a safe and healthy relationship with your employees, especially before having hard conversations about what’s going on with their workload: 

“Trust is CRITICAL. If you haven’t done the work to build trust with your team, all of these steps won’t feel like you’re helping them to do their best work. It likely feels like you’re henpecking them while they’re trying their best. It is incredibly important for you to take the time to build trust with your team before something like this comes up. If you haven’t, you’ll have to put a lot of time into walking alongside them step-by-step, sharing your thoughts and feelings as you go, to show them that you are in this with them, not just bossing them around.”

Trust helps you avoid remote manager pitfalls…which we detail in the next tip.

Remote team management tip #7: Avoid the classic mistakes

We asked all of our remote team leaders what they thought were the most common mistakes made by novice remote managers, and what they wished they had known when they first started managing a remote team. Trust and compassion were common themes. 

We could break this down further, but what they have to say is so valuable, we are presenting it in full: 

“First of all, remember that everyone is struggling right now. People who have been remote from years and folks who work on entirely remote teams are all struggling to focus and stay productive. This is a challenging time for many reasons. If you have a team member that is struggling right now, it is not necessarily because they aren’t good at working remotely. We’re all having a hard time adjusting to this new reality. And don’t assume everyone works how you do. Each person will adjust to remote working in their own way. 

Recognize when folks are doing good work, even if it looks different from what you thought it might look like. Grace, flexibility, understanding, and encouragement are some of the most important tools in your arsenal right now. Also, set the example for over-communication. This is not something we all may do naturally, and is something I’m working on every day. But if you set the example, your team will follow suit AND have a model of what you mean when you ask for more frequent or thorough communication.

-Lina Calin

Micro-managing is a bad habit folks pick up. I’ve seen this in my own clients with managers who are not used to working with distributed resources. Setting expectations is key for communicating check-ins and how you like to receive data from folks.

-Alex Vasquez 

Don’t assume malintent. If teammates are not meeting your expectations and you can’t (nor shouldn’t) be monitoring them constantly, it’s not because they’re awful or dumb. Usually there’s a misalignment issue where you might not have been clear enough with them about goals, or they might be blocked from doing their best work. 

Show compassion and give people the benefit of the doubt. Continuous improvement is about letting that individual guide their own outputs and have autonomy so they can help improve processes and find opportunities to support the company better. They need to know how their behaviours impact the rest of the company, but you are not there to babysit. Over-communicate and clarify your expectations and ask them to restate how they will meet them.

-Rachel Gertz

Context switching is the killer of productivity so don’t add to an already challenging situation. Limit pings to large groups. Be mindful of pings to team members. Set up communication guidelines and best practices to make sure people are clearly stating their boundaries. To help resist the urge to constantly check in, set up a regular check in time so you can ensure you’ll have an update. It’ll help you to hold off on the pings.

-Jaimie Olmstead

Don’t try and know what’s going on all the time. Trust your team. If you didn’t trust them, why did you hire them? It’s hard when you’re used to seeing people daily, but just trust that they’re professionals who will get their work done. That hasn’t changed now that they’re out of your sight.

-Diana Potter

Remote team management tip #7: Good leadership means being human first.

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These are impossibly trying times, and the learning curve of working from home isn’t the only obstacle. We are experiencing a collective, global trauma, in real time, altogether. Every circumstance we are dealing with is unprecedented. 

When asked what demonstrates superior leadership during times of crisis, all of our veteran remote managers said something similar: show up as a person first. 

Again, their words and insight are most powerful on their own, without my interpretation:  

It is important for leaders to remember that you succeed when your team succeeds. Therefore, your job as a leader is to enable your team to succeed. In ALL times, but especially in challenging times, you demonstrate leadership by treating your team members like humans. 

How can you enable their success in the specific challenges they are facing? Are they having trouble staying plugged in because their kids are home from school? Maybe you can offer flexible working hours. Is their internet not strong enough to handle video calls or sharing the bandwidth with the whole house? Perhaps your company can sponsor an upgrade for them. 

Everyone’s experience is different. Your job as a leader is to help each experience lead to the best results. The question you should be asking your team and yourself is: how can I help enable my team’s success? Not only will you help them get their work done, you’ll help them feel seen and validated. They’ll know that you care for them as a human being in this time, not just a generator of productivity.

-Lina Calin

Lead by example. Share things in asynchronous ways so everyone can catch up and know what’s happening. And especially right now, give people slack. Understand their minds aren’t necessarily all there. They might be adjusting to being at home. Or having their kids with them. Or stressed about family. Or who knows what else. Don’t expect that remote right now is what remote is always. These are trying circumstances and things are going to go wrong. Check in regularly! You don’t have serendipitous moments where you’re both passing in the halls or in the break room. Talk to your team. See how they’re doing.

-Diana Potter 

Show your vulnerability and show up for your team as a human first, owner or boss second. Everybody is scared and doing their best to get through this difficult time. It is normal for productivity to be tanking right now. Show compassion: find out what you can do to support your workers and reach out to them personally because despite the risk you carry as a boss or supervisor, your team truly keep the lights on.

-Rachel Gertz

Letting people know you’re available but also provide a safe space where people feel they can be open with their struggles. Make sure your team knows they are appreciated.

-Alex Vasquez

Hold space for your team members to be vulnerable and share their needs. Foster an environment of trust and transparency. Not everyone processes these challenging times the same, so it’s important to demonstrate to your team how they can support each other while being productive.

-Jaimie Olmstead

One of the most remarkable things about this advice is that much of it is counterintuitive to common narratives about leadership.

Many people believe that old (terrible) adage, “spare the rod; spoil the child,” and manage their teams with a heavy, harsh hand.

All of the professionals we interviewed have a collective forty years of experiencing working remotely, and all of them have managed teams for a significant chunk of that.

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You might have noticed that the common thread amongst their responses is about approaching your work and your team with compassion, dignity, transparency, and humanity. We could all use a little bit more of that right now, so if you are a leader thrust into a new position: now is the time to rise to the occasion. We believe in your ability to do it, and so will your team. 

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