An unprecedented number of organizations across the world transitioned to a Work from Home (WFH) program on very short notice recently. What counts for “business as usual” changed completely in a matter of weeks, and that upending of routines presents an ongoing challenge for many leaders.
That’s exactly why we built this resource.
In this guide, you’ll get actionable tips for improving your own WFH experience as a remote team leader, while improving the experience for your team as well.
We’ll cover these key areas -- feel free to start from the beginning, or skip to any section:
We pulled tips, advice, and anecdotes from our own experiences leading remote teams, but we didn’t stop there. We also met with other seasoned remote team leaders to find out which new technologies are changing the game, and which time-tested tools and strategies they still use today.
Our goal for this resource is for you to benefit from the learnings we’ve earned through trial and error as a long-time distributed team.
p.s. If you’re looking for some ways to improve your own experience as a remote employee, or for some tips for your team to use, check out this guide’s precursor: “WFH: How to Make Working from Home Work Better for You.”
If you're looking for a comprehensive resource that covers both working and leading from home, check out our recent eBook, A Practical Guide to Working and Leading from Home.
And with that, let’s get started!
Navigating those first crucial weeks
If you and your team are new to full-time remote work, the first few weeks can be particularly challenging. That’s why it’s so important to have as many factors in your favor as possible, from hardware to plans, tools, and protocols.
Lead with patience, empathy, and compassion
There is nothing more important right now than granting your team every last ounce of patience and empathy you can spare. They’ll need it now more than ever. Like executive coach Suzan Bond explains in her Fast Company article:
“No amount of technological wizardry or personal autonomy negates the fact–which has long been true for office-bound workers as well–that job satisfaction is still closely tied to having an effective, emotionally intelligent boss.”
Anticipate, accept, and mitigate WFH obstacles
Shifting from working in a co-located office to a WFH environment isn’t always simple even in the best of times, and the circumstances in which many of your teammates transitioned to working from home probably weren’t ideal.
Like many others across the globe right now, they’re likely dealing with myriad issues from childcare snafus to food scarcity, financial strain, and either mild or severe restrictions on movement and daily activities.
In addition to those distractions, there’s a physical element to this issue. Not everyone has a home environment conducive to work, whether they’re in a small apartment, or living with roommates who are also suddenly working from a crowded home -- and that’s just a few examples. Jules Forrest captures the mood impeccably here:
Can we do a WFH workspace setup thread, unglamorous edition?— Jules Forrest (@julesforrest) March 13, 2020
My partner and I are both working from our studio apartment. My setup is a chair in front of the front door and my desk is our clothes hamper. pic.twitter.com/5rVaqgkjjw
As for your team: assume they’re doing their utmost to cobble together a WFH setup as quickly as they can, but it might be a few days (or weeks) before they truly find their groove.
This doesn’t mean you shouldn’t expect good work from yourself and your team during this period -- it just might take a bit more time and effort than usual while everyone adjusts. As much as we’d like to expect “business-as-usual” levels of productivity during this transitionary period, most of us simply aren’t conducting business as usual, and that will be reflected here.
Instead, expect a little mayhem now and then, provide support wherever you’re able to, and if you can, try to embrace the chaos together as a shared experience.
Maintaining team morale and engagement
Even in the best of times, measuring, maintaining, and improving employee morale can have a meaningful bottom line impact. In times of crisis, this is doubly true.
Recognize the signs of low morale early on
Common signs to be aware of are things like reduced work output, increased absenteeism, and reduced initiative. But these things are all relative and based on a benchmark of normality.
It can be difficult to discern whether a teammate is exhibiting some of these signs because they’re adjusting to remote work, or for other reasons. With that in mind, it’s useful to track morale continuously over time so you have a sense of whether this is a new development, or something that has been brewing for months.
Tips for boosting morale on a remote team
Even if you don’t recognize signs of morale decreasing, it’s valuable to put effort toward maintaining or improving it. Have you ever heard of a team suffering because morale was just too strong?
Recognizing, rewarding, and celebrating great work is one of the most simple, cost-effective, and direct ways to boost morale. The keys to giving highly effective recognition are:
Frequency: Recognition is not a limited resource and it costs nothing to give, so give it often.
Timeliness: Give recognition in the moment, when it has the greatest potential for impact.
Visibility: Give recognition in a venue where others can gain visibility into the valuable contributions their colleagues make day-to-day.
Specificity/Authenticity: You have to mean it. Don’t just say “You’ve done a great job this week.” Call out what made that work valuable, and why.
Inclusivity: Recognition should reach and originate from everyone in the organization, from last week’s new hire to the CEO.
Value Alignment: Give recognition in a way that highlights and reinforces the connection between the work you’re praising, and your organizational values.)
For more details on giving recognition effectively, check out The Guide to Modern Employee Recognition from our friends at Bonusly.
Support and encourage “frivolous” social interaction
Why encourage people to waste their time posting GIFs and talking about their day? Because those activities are not a waste of time. As Arlene Hirsch explains in her article for the Society for Human Resource Management (SHRM):
"According to VDI data, the greater the virtual distance, the higher the negative impact on the team in terms of innovation effectiveness, trust, work satisfaction, role and goal clarity, and project success.
Team leaders can reduce virtual distance by creating an environment where team members feel emotionally and psychologically connected to one another and to the business...An open channel for communication in a technology platform gives remote team members a “meeting place” where they can go to socialize."
Activities like sharing pet photos, dinner recipes, jokes, and anecdotes help teams to build camaraderie around a shared positive experience. For example, one of our dedicated social channels, #pawlly, is a surefire cure for even the worst case of the blues.
In co-located offices, random social interactions happen as a result of sharing a physical space. Remote teams don’t have any traditional areas that encourage chance encounters, or “collisions,” as they’re referred to in Ben Waber, Jennifer Magnolfi, and Greg Lindsay’s Harvard Business Review article “Workspaces That Move People.”
While you may not be able to build collisions into a physical space for your WFH team, it’s easy to bring them into our collective digital domain.
OK, so how do you do that?
Here’s an example:
For sure! We're making a lot of room for fun diversions to stay motivated. We just held our first team lunch over Google Hangouts, @stacy_tumarkin will be hosting a yoga class via @zoom_us this Friday, and we're running lots of goofy @polly_ai polls on @SlackHQ. 🎩🦁🐍🦅 pic.twitter.com/ADd1rtcOi6— Bonusly (@bonusly) March 18, 2020
We’re always looking for more ways to connect as a distributed team on a regular basis. Sometimes that means using tools in an off-label format. Here are a couple examples of things we’ve tried lately:
Remote pizza party
We recently celebrated the release of AgilePolly for Microsoft Teams. Since we’ve gone entirely remote over the past couple weeks, we decided to hold a remote pizza party. Every team member got to order a pizza of their choice (or buy ingredients and make a pizza of their choice).
We shared our creations in Slack, then everyone hopped into a Zoom chat to share in the celebration. Periodically, we’d separate into random break-out Zoom chats, then everyone would congregate in the full-team chat again.
This was a really fun experience for everyone. It gave us a venue to celebrate some truly amazing work on a project that touched every arm of our organization.
Zoom coffee break-outs
After our most recent remote all-hands meeting, we’ve added some extra time for everyone who wants to have a “Coffee break” together. Everyone took part, because it was a welcome chance to chat and see everyone’s faces again.
Keeping a persistent two (or multi) way videochat running across different offices can help to bridge physical distance between those offices (so long as everyone is ok with it). If you want to talk to someone in a different office, you can simply walk up to the wormhole and start talking, just like you might in a colocated office.
Establish a process/protocol (and stick to it)
When everything’s turned upside down, it’s immensely helpful to have protocols in place that people can trust in. Even something as simple as a steady communication cadence can provide support and sense of normalcy in an otherwise bewildering situation.
You won’t be bumping into each other in the office, so it’s crucial to have a process established for regular face-to-face (or screen-to-screen) communication.
Dave Lewis, VP of Marketing at LINQ, and a 12-year veteran of distributed team leadership shares some of his strategy here:
“I have had remote teams as large as 10 and as small as 4. For me, I have found that I need both a weekly team meeting and a weekly one-on-one.
Slack has been great for those needed conversations you’d usually get by stopping by another employee's office or cubicle. You can share your work, quickly get answers to those simple questions and even better you can create specific channels in which to communicate with specific groups so you can share and discuss projects with multiple people at the same time.”
Weekly Team Meetings
“In our team meeting, my goal is to ensure that the entire team is on the same page with everyone’s individual projects. I will make sure that everyone is clear about who is working on what, and when things are due.
I like to give each team member five to seven minutes to provide an update on their projects and to remind other team members about any deliverables owed.
I use Google Docs to not only store our work in an organized way, but my team is able to share and comment on projects.”
“In our weekly one-on-one, I will go into the specifics about every project and gain agreement on priorities and due dates. For these meetings I have found that video conferencing is unquestionably the best method.
I feel that seeing your team helps you feel more connected. And with most video conferencing technology you have the ability to share your work. So now my team and I can share our work, timelines, priority lists, and more during our weekly meetings.
There’s no better way to keep your remote teams connected and engaged than simply meeting at the same time on the same day every week. Everyone has a voice, thus everyone feels like they are part of the team.”
Tips for holding more effective team and one-on-one meetings
It is incredibly valuable to meet face-to-face to discuss projects and collaborate, but you can help improve the efficiency of those discussions by keeping a consistent dialogue going asynchronously with your team in the meantime.
Delegating ownership is one of the core skills any good leader must have, but it’s especially important for WFH teams. When people aren’t encountering one another in the office, learning about what each other is working on, it’s easy for things to get lost in the mix.
As LINQ’s Dave Lewis shared:
“It’s imperative that each project has one owner even if several team members are involved. One person who is ultimately responsible for delivering that project on budget and on time.
Too often if a single owner is not established, assigned work and deliverables become unclear and productivity declines because no one truly owns it.
I have found this especially true with distributed teams. Additionally, owning a project whether a new employee or a tenured one, fosters leadership, builds teamwork, and instills accountability.”
Outfitting your team and investing in WFH success
While a distributed work environment can lead to some meaningful savings in real estate, snacks, and a litany of other costs associated with a co-located office, it’s important to make sure you’re still providing the best possible work habitat for your team.
So while a remote team may indeed provide cost savings, your remote work program is one of the last places to look when cutting costs. Instead, consider re-investing some of the resources saved by not co-locating into a stellar WFH setup.
Something as small as an extra monitor or a mouse and keyboard can mean the difference between a comfortable, productive setup, and one where you’re just “making do.”
In addition to hardware, some companies provide a stipend for internet and phone service, so they know their employees always have a solid connection.
Having good software can mean the difference between an excellent WFH experience, and a non-starter. Even with the best software, remote teams still face some unique challenges, so please, try not to add to those challenges by skimping on your software budget.
Find out what your team needs to be effective as a distributed force, and do your best to make it happen.
With that, let’s review some of the technology you can use to build an outstanding experience for your remote team.
Even just a few years ago, managing a remote team posed a greater challenge because there were less purpose-built tools available to serve this need; however, there are hundreds today -- each with its own strengths.
The communication/collaboration tool you choose is one of the most crucial decisions you have to make as a WFH team leader. Luckily, there are a few excellent options, depending on what ecosystem you’re already working in.
Slack brought a whole new way of collaboration to teams across the world. It’s a place for employees to chat, collaborate, share documents, and more. In addition to these features, Slack’s app directory makes it possible for you to extend its native toolset by bringing third-party tools directly into your workspace. Take a look to see which of your favorite software tools have a Slack app, and of course, check out Polly while you’re there! We've built native Slack experiences geared toward keeping remote teams together and on the same page.
Microsoft Teams is another priceless communication tool -- one which you and your teammates may already have a license for if you’re Office365 users. Teams also has a full-featured video chat feature and a library of third-party functionality to unlock within App Source. If you need a tool for gathering continuous insights on your people-driven processes, check out Polly. If you need a tool geared toward running efficient check-ins and standups in Teams, check out AgilePolly.
Zoom is the bellwether for video communication. Even if you have video calling capabilities included as part of another software, it may still be worth giving Zoom a try.
There are several options for document storing and sharing available, with Google Drive and Microsoft’s Sharepoint being some of the most popular options; however, there are also several other more specialized document sharing systems, like Adobe’s Creative Cloud.
Your WFH tech stack
While all of these tools are immensely helpful on their own, that’s just the beginning. The true benefits are unleashed when you begin to connect these tools and processes together.
For example, you can connect Slack with a tool like Google Calendar in order to set your status automatically when there’s a meeting booked on your calendar. That way, your remote teammates will know you’re busy, even if they can’t see a meeting happening in your office.
You could take this a step further by connecting something like JIRA Service Desk to Slack, immediately bringing critical data directly to your team in the context of their work.
You could take this even further by connecting JIRA Service Desk with Slack and Polly in order to automatically survey the service ticket’s participants for qualitative information about the resolution.
Coordinating WFH across timezones
There are some cases where you’ll be collaborating with colleagues across the country, or even across the ocean. That’s not a problem at all in itself but if you don’t have a communication plan, it can get complicated quickly.
Many of us are familiar with the 48 hour email: you send a message about a project to a colleague overseas, but at that time, they’re fast asleep. They open and respond to it first thing in (their) morning, but by the time you receive their response, you’ve been asleep for hours. You wake up, see their response, realize you need a change made, and respond again -- but of course, they’re asleep.
Keeping your communcation flowing naturally across timezones might seem difficult, but with a little bit of planning, it’s easily achievable.
At Polly, we have esteemed colleagues across the United States, and some in Pakistan, which is 12 time zones ahead of our HQ in Seattle.
To keep things in sync, we meet at a regular cadence at a time that isn’t perfect for anyone, but is perfectly acceptable for everyone.
The regular cadence by which we meet makes this arrangement work. If we expected to have these conversations ad-hoc, it could easily spiral out of control. Instead, we’re all aware of the upcoming meeting.
We plan for our weekly meeting by working asynchronously on the objectives and initiatives we individually own, then bring relevant thoughts, questions, blockers, and action items to the table while we’re all looking one another in the face.
Our team also uses collaboration tools like JIRA, Slack, Microsoft Teams, GSuite, and Polly’s own agile apps to keep track of project progress asynchronously so that when we do meet, we don’t need to spend much time catching up on where everyone is at.
Building and extending trust
Trust is essential in any relationship, and the trust between an employee and leadership has an outsized influence on engagement, productivity, and retention. While this trust is of paramount importance to build even in a co-located office setting, it’s even more crucial for remote teams.
You can’t survive long-term as a team without it--especially as a remote team.
Douglas McGregor posited a theory in which there were two ends of a management spectrum: Theory X (authoritative) and Theory Y (participative).
If you’re interested in a more detailed look at McGregor’s management theory, you can find it here, but to briefly summarize:
Theory X managers believe that employees are innately unmotivated, and require their influence (through rewards, coercion, or punishment) in order to be productive.
Theory Y managers believe employees enjoy taking ownership of their work, and find it fulfilling. These managers tend to cultivate a more collaborative and trust-based relationship with employees.
Theory Y managers (in general) are much better suited to leading remote teams, simply because their style distributes accountability and ownership, while a theory X manager leans on a command-and-control leadership style.
Just like any spectrum, there are few if any managers who sit exclusively on one side or the other; however, you may find it useful to understand where your own management style fits within that spectrum, and how that relates to sustainable remote team leadership.
Listen to your team
During uncertain times and times of crisis, it’s important to keep open channels of communication with your team.
In good times, and in times of turmoil, employee safety is priority number one. As Obaid Khawaja, Senior Product Manager at Polly recounts:
“Back in 2012-2014, there were a lot of political protests, and my startup’s office was at the heart of all the action. We made some quick judgement calls to enable our employees to work from home effectively.
We had some incredibly brave and committed folks who put their lives at risk to make it to work. I only realized how tough it was for them to make it to work after they told me their stories.
I learnt an important lesson that employee safety and health comes first, work is secondary. So we had that chat with them to let them know what the boundaries between safety and work were and that safety always comes first. It’s not even something we need to discuss.”
Listening to your team is one of the most important things you can do as a leader. It’s imperative that you have a channel for them to have their voice heard.
Doing this isn’t just in service to the team, it’s in service to your entire organization. Keeping that channel open could mean the difference between missing an important piece of information and capitalizing on it.
Providing a channel might not always be enough though - you can help prime that information flow by asking proactively on a regular basis about how things are going, and what could be improved.
Flexibility is key
Remote work may also be an opportunity for an employee to flex into a different, yet crucial role they wouldn’t otherwise have taken part in.
“We had our scrum master/tech lead step up his efforts in terms of planning and assigning tasks to the team,” Khawaja shared. “He’d run through a pretty efficient remote daily standup, code reviews and weekly demo regimen. This helped the team make progress on a day to day level.”
Leading a team is probably not the easiest thing you’ll do in your life, but it can be incredibly rewarding. Leading a remote team adds another layer of complexity; however, there are enough tools and guidance available to make it not only possible, but even preferable in some cases.
The key is to keep working toward a better WFH experience. No matter how good your team’s experience is, it can always improve. Keep learning, and keep growing as a team.
We wanted to provide a list of resources you can use to keep learning and growing, so in addition to this guide, we gathered a host of other guides and resources you might find valuable in your WFH leadership journey:
Written by George Dickson
Lives to learn and build cool things with good people.