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The Manager's Guide to Remote Employee Engagement

Featuring insights from personal interviews with CEOs and executives from leading remote-first companies:


What you'll find in this free guide:

  • Chapter 1: The purpose of employee engagement and how great managers nurture it.
  • Chapter 2: Best practices on how to set your remote team up for success.
  • Chapter 3: Remote employee engagement strategies to create a supportive distributed team.
  • Chapter 4: The checklist that will make your remote team 10x more effective.
  • Chapter 5: Helping your remote team be their best: Conversations & feedback for career advancement in a remote company.
  • Chapter 6: The 7+ deadly sins to avoid on remote teams.
  • Chapter 7: The remote manager’s toolbox.

Chapter 1: The purpose of employee engagement and how great managers nurture it.

Chances are you can probably think of a job where you were just clocking in, killing time while the hours crept slowly by, and then hitting the door as early as you could get away with.

What a waste of your potential!

Disengaged employees are bad for business

Sadly, Gallup’s research shows that waste is far too common with 52% of American workers say they’re “just showing up,” and 17% describing themselves as “actively disengaged.”

Imagine what changes you could’ve made if the leaders at that fast food joint / agency / dev shop / school had taken an interest in your career goals and found a way to align their objectives with your dreams.

As you compare your effort at that job to another position where you were in the zone and showing up every day ready to go, you know what most executives know: disengaged employees don’t bring their best selves or their best ideas to work, they don’t look for creative solutions to hard problems, and they don’t lift up the performance of their colleagues.

Happy employees lead to happy customers

On the flip side, companies with higher levels of employee engagement see higher profitability, productivity, and lower turnover. 

It’s not only about the internal effects on employee retention and productivity either. Engagement is highly correlated with customer satisfaction and brand loyalty. In short, happy employees lead to happier customers.

Just compare the traits of a disengaged employee to an engaged one and it’s obvious who anyone would rather work with or buy from.

Engaged Disengaged
Optimistic Pessimistic
Team-oriented Self-centered
Goes above and beyond High absenteeism
Solution-oriented Negative attitude
Selfless Egocentric
Shows a passion for learning Focuses on monetary worth
Passes along credit but accepts blame Accepts credit but passes along blame

Gallup has been researching the direct affects of employee engagement on profitablility for decades now, and despite the well-established links to an organization’s financial health, companies still tend to fall short.

So why the disconnect? If the research is clear that disengaged employees are costly, why aren’t more employees actively engaged in their work?

The answer: there’s a shortage of great managers.

Great managers understand motivation

Great managers understand what motivates their team, they understand human nature, and they can inspire action in a diverse group of people. These are the qualities that you can and will need to embody to be the manager you want to be. This guide will help you do exactly that.

You might be wondering, “Can I really make that big of a difference as a manager? Isn’t it the employee’s responsibility to find what works for them?”

Sure, the employee bears plenty of the responsibility for their own motivations and behavior … and great managers create and nurture an environment where employees believe their effort will be worth it.

Great managers nurture engagement

And the difference that makes is massive. Gallup’s research shows that managers account for a staggering 70% of variance in employee engagement.


Great managers consistently engage their teams to achieve outstanding performance. They create environments where employees take responsibility for their own – and their team’s – engagement and build workplaces that are engines of productivity and profitability.

Have you ever felt like you knew what could be done, you knew what should be done, but you didn’t bother because you were certain it wouldn’t matter?

What a deflating and defeating feeling!

The great news is, as a manager, you have more influence than you may realize in making sure your team members never feel that way. You can ensure that when your people know what could and should be done, they feel like they can affect change.

Great managers boost the engagement levels of the people who work for them. According to Gallup research, only 28% of U.S. employees are engaged, or are actively pursuing top performance on behalf of their organizations.”

Great managers build great teams

People want to feel valued and know that their contributions are respected. They want to know that they’re doing meaningful work, that their voice is heard, and that their ideas matter.

Not only will you get peak performance from your team when your management style allows those things to be true, but consider what will happen if you don’t.

Disengaged people who think their contributions are meaningless or have seen that their ideas are ignored don’t feel a connection to their jobs and so they’ll do the bare minimum to get by. They’ll go to a 9-to-5 time clock mentality, avoid social team activities, and hunker down in their own world. Their resentment will grow, they’ll spread negativity instead of inspriation to their co-workers, and absolutely destroy team morale.

Before long, these will be the only people you’re left with if you create this environment instead of one where co-workers would look that person in the eye and say, “Really? I don’t feel that way at all.”

And that’s what you’re going to create. You are going to build a team where people feel known, where they bring their best selves and are inspired to do their best work, where support is a cultural norm, and where strengths are celebrated!

Chapter 2: Best practices on how to set your remote team up for success.

So, what separates great managers from the rest? How can you learn from decades of research to set yourself and your team up for success?

In a Gallup study of 7,712 adults, participants were asked to rate their manager on specific behaviors. Three behaviors had particularly strong links to employee engagement. Learning and implementing these practices will ensure you’re on the better end of that 70% variance uncovered by Gallup’s research.

They are:

  • Meaningful, regular communication
  • Performance management based on clear goals
  • Focus on strengths, not weaknesses

Meaningful, regular communication

Gallup’s research shows that people whose managers have regular meetings with them are three times as likely to be engaged employees.

But that’s a chicken-egg kind of thing, isn’t it?

Because the type of manager who would create a healthy, flourishing work environment where employees are engaged and productive is also the type of manager who would meet regularly with their team to get their feedback.

So, it’s not enough to just throw some 1:1s on the calendar and expect things to improve. You gotta be sure those meetings are focused and well-prepared. And structure them in a way that makes it clear you’re interested in knowing them as a person and understanding what makes them tick; not that you’re simply making sure all the boxes are checked this week.

Gallup’s research shows that people whose managers have regular meetings with them are three times as likely to be engaged employees.

The only people who will be satisfied with that sort of relationship are people who don’t want more for themselves and don’t have the option or talent to look elsewhere. That’s not the team you’re going to build!

Sure, status meetings have their place. But those transactional interactions aren’t enough to maximize engagement. People want to feel known and they value a manager who cares about more than just their current projects.

It shouldn’t take a study to prove this, but yes, the Gallup study shows that employees who feel as though their manager cares about them as a person are more likely to be engaged in their work.

Here is a list of relationship-building questions you can add to your upcoming 1:1s:

  • Any vacations coming up that you’re looking forward to?
  • Listened to any good podcasts or read a book recently?
  • What was one of your funniest moments at work?
  • How does work feel to you right now? Energizing? Draining?
  • Anything we can do to help your overall well-being?
  • How do work-life boundaries feel to you right now?
  • Do you ever feel lonely or isolated at work?

Great managers (like you!) take the time to get to know their team and make them feel comfortable talking about any subject that’s on their mind. People can’t do their best work with something heavy weighing on them, and sometimes they need to be able talk it out in order to get on with their day. A safe, productive workplace is one where those conversations can happen and it takes a proactive, caring manager to make that happen.

Performance management that is clear and consistent

The awkward annual performance review is such a meme now that many managers and employees alike dread them or avoid them altogether.

If employees are unclear about their role and their manager’s communication is infrequent and haphazard, these annual review conversations feel forced and pointless.

But! It doesn’t have to be this way!

From Gallup:

“… when performance management is done well, employees become more productive, profitable and creative contributors. Gallup found that employees whose managers excel at performance management activities are more engaged than employees whose managers struggle with these same tasks.”

“Engaged employees are more likely than their colleagues to say their manager helps them set work priorities and performance goals. These employees also more likely to say that their manager holds them accountable for their performance. To these employees, accountability means that their manager treats all employees fairly and holds everyone to the same standards, allowing those with superior performance to shine.”

So, what sets great performance reviews apart from their lame-o punchline counterparts?

Clarity and consistency.

According to Gallup:

“[we] discovered that clarity of expectations is perhaps the most basic of employee needs and is vital to performance. Helping employees understand their responsibilities may seem like management 101, but employees need more than a written job description to fully grasp their role. Great managers don’t just tell employees what’s expected of them and leave it at that; instead, they frequently talk with employees about their responsibilities and progress. They don’t save those critical conversations for once-a-year performance reviews.

To ensure your team understands their goals and is crystal clear on their progress toward them, set goals with the following rules in mind:

  • Involve employees from start-to-finish
  • Goals should align with business goals
  • Goals must be clear and easy to understand
  • Goals must be accepted and recognized as important by everyone who will have to implement them
  • Progress towards goals must be measurable
  • Goals must be framed in time, with clear beginning and ending points
  • They should be challenging, but achievable
  • They should be adaptable and dynamic

For example, here is a terrible goal:

  • Increase social media reach

And here is an excellent goal:

  • Increase our Twitter following from 10,000 followers to 15,000 this quarter by engaging in more conversations, automating evergreen posts with MeetEdgar, and writing one new article per week

Work with each of your reports to develop short, medium, and long-term goals with those recommendations in mind and you’ll be on your way to building a stronger, more engaged team.

Focus on strengths, not weaknesses

The researchers at Gallup have spent decades studying employee engagement and behavior and it’s clear that the most effective strategy to help your team grow is to build on your employees’ strengths rather than focusing on improving their weaknesses.

“… managers tend to focus on finding and fixing a person’s weaknesses. This leads to reviews and development plans that focus on negatives— where the emphasis is on “improving” a person into someone [they’re] not. In contrast, great managers emphasize the development of their [reports]’ unique strengths so as to help further their talent, while finding strategies to support their weaknesses.”

I’m firmly in the “sports is a metaphor for life” camp and I think this is one of those places where we can observe how this works on the field. Great coaches will often tell their players to “play your game.” Which means: don’t let your opponent dictate your style. Do what you do best and put your points on the board.

Of course you’re going to address your weaknesses and do what you can to improve all the aspects of your game, but the focus is on putting people in positions where their unique talents can shine.

… managers tend to focus on finding and fixing a person’s weaknesses. This leads to reviews and development plans that focus on negatives— where the emphasis is on “improving” a person into someone [they’re] not.

As Gallup’s research shows, working through whatever weaknesses are surely present will be far more successful when there’s a strong foundation of confidence. When managers help their team grow and develop through their strengths, employees are more than twice as likely to be engaged. 

Chapter 3: Remote employee engagement strategies to create a supportive distributed team.

In my interviews with CEOs and executives at Gitlab, Buffer, Doist, Baremetrics, Zapier, FullStory, and more, some common strategies to build and support engaged remote teams have bubbled to the top.

Pull from this list and work them into your team’s dynamic in the ways that you think make the most sense.

And remember, don’t give up if you have a few false starts! Success takes time, work, and several iterations. So allow your methods to adapt and evolve along with your team and you’ll eventually find the mix that’s right for you.

Small Talk & Socialization

Second only to communications struggles, loneliness is the most consistently top-tier challenge remote workers report year in and year out. Human beings are social animals; we’re meant to work as a team.

I’m speaking as a 70% introvert, those among us who want nothing to do with our colleagues are most definitely the exception. Don’t optimize your team interactions for the small percentage of folks who want to login in the morning, punch away at a keyboard for eight hours, and logout.

Strong teams perform best when people feel known, so make space and time for personal conversations to happen.

To be clear, I don’t mean, “Tell me about your relationship with your father.” I mean, “Read any good books lately? What hobbies do you enjoy outside of work?”

The most common practical implementation of this I’ve observed teams practice is creating a Slack channel dedicated to loves, celebrations, and weekend updates.

Install a Slackbot that asks, “What’d you do this weekend?!” every Monday morning. It’ll be a simple and easy way to help your team get to know one another casually over time.

Some companies also leave a Zoom “Water Cooler” room open that people can hop into and out of throughout the day just to chat. That’s a great idea, but it’s passive and might fall flat if you’re a small team.

  • Create a Slack channel for loves, celebrations, and weekend updates.
  • Allow time before and after the “real” meeting for small talk. Let those moments flow and don’t view it as wasted time.
  • Install a Slackbot to ask, “What’d you do this weekend?” every Monday morning.
  • Create a Water Cooler Zoom room and encourage employees to stop by on breaks.
  • Assume video on by default for meetings. Faces are friendly.

Make Time for Face-to-Face

COVID-19 complicates this for the time-being, but scheduling company and team onsites is a great way to solidify friendships that begin online.

Some companies do these quarterly, some annually, and plenty of others do some combination. When I interviewed the CEO of Edgar, Laura Roeder, she told me that they started off meeting quarterly but then then pulled back to once or twice a year because the feedback they got from their employees was that it was difficult for people with families to be gone for a week every three months.

You’ll need to figure out what works best for your company structure, but it’s almost a given that to create a real sense of community and company culture, a team onsite is a must-have.

I’ve heard some variance among successful companies as to whether these on-sites are work-focused, hi-fidelity sprints, or if they’re purely centered around relaxation and team-building. Again, there’s no cut-and-dried right or wrong answer here. It comes down to how well you understand your team and their needs.

Be sure to plan well enough in advance to consider the impact that an onsite will have on every department. 1SecondEveryday wanted to be sure that the whole team could be fully engaged and present for their onsite so they came up with a creative solution for customer service. They shut down customer service from Monday-Thursday and on Friday, the entire company jumped in to help triage and resolve all the tickets that had accumulated.

  • Use that money you’re saving on commercial real estate to take your team somewhere amazing once per year.
  • If you’re a large organization, consider an annual onsite by team/department and an all-hands annual retreat.
  • Find the cadence that works for you and be sensitive to the impact quarterly travel could have on some employees.

Overcommunicate to Ensure Clarity

It’s almost impossible to over-communicate expectations. When employees are asked about their greatest frustrations with their boss or with jobs where they are actively disengaged, “Lack of clarity” ranks near the top.

And when it comes to helping employees be more productive, when those employees see gains in the “knowing what’s expected” question, it correlates with a 5%-10% jump in productivity.

“A confused mind always says, ‘no’” is a famous sales & marketing axiom, but it applies here to employee productivity. When your people are confused about what’s expected of them, their mind will look for a dopamine hit from a sure thing. Twitter, solitaire, personal email. Anything that’s a surer thing than whatever muddled mess is on their plate at work.

This requirement for over-the-top certainty doesn’t only apply at the micro level to specific projects, but at the macro level as well.

I heard Jason Fried speak at Business of Software a few years ago and he encouraged the audience to think about your company as a product. How would people use that product? What’s the UX of that product?

Is it obvious how we use email? Is it clear how to ask for feedback or who to get help from about a payroll / vacation / reimbursement question?

This sort of poor User Experience is frustrating in an office, but it can be downright paralyzing in a remote company.

What do great remote companies do? They document everything.

Great products have great documentation and so do great remote companies.

When a question comes up that isn’t in the handbook, add it! And if you’re a software company, consider following Gitlab’s example and turning your handbook into a markdown repo.

See more examples of remote companies public handbooks.

Onboard with a Pair

First impressions matter. Getting your new hires onboard with a feeling of comfort is key to their short-term engagement. The faster someone is up-to-speed on the mechanics of the company the better, and the less likely they are to become confused or disillusioned before they’ve even had a chance to see what makes your team great.

Great managers and great companies onboard their new hires with a mentor or “pair.”

Zapier calls their approach to pairing new hires their “Zap Pal” program.

“Every new hire is assigned a Zap Pal, who reaches out to them in their first week, sets up at least one Zoom call with them, and continues to check in throughout their first month or so. It gives everyone a guaranteed 1:1 relationship, which is so important when you’re spending most of your time alone in your house. Plus, there’s a bonus for the company: it can bring about cross-functional ideas. You’re getting people who might not normally interact to chat, and you never know what will come from that.”

Some companies give their new hires two pairs, a culture pair and a team pair. The culture pair is someone outside of the new hire’s department who can answer questions practical questions about HR docs, communications preferences, etc. The team pair is someone they’ll be working with in the long-term who can be available to answer any questions they may have about their current expecations or any roadblocks they might be running up against.

The reason to split these in two is so that the new hire doesn’t feel like they’re constantly bugging their new teammate with every little question under the sun and will feel more comfortable asking questions about their role.

Of course, 1:1s with their manager during their first week is also critical, but setting up these pairs or “work buddies” to get over the inevitable hurdles in the first couple months will save your company buckets of time and money.

Make Meetings Effective

Bad meetings kill morale. Poor morale leads to terrible retention. Low retention kills morale.

Don’t make people sit through bad meetings.

Keep them short. Insist on agendas and lead by example on this.

And don’t let off-topic conversations derail the meeting. Be polite but firm, “That’s important for us to discuss. I’m going to note that topic so it doesn’t slip through the cracks while we stick to our agenda here.”

Your people will love you for this.

Recognize & Celebrate Wins

Overlooked work is one of the unexpected challenges remote teams eventually face.

People are ready for the timezone thing to be confusing and they figure it out. Communication issues show up every single day and people get motivated to solve it. Loneliness is a tough one to solve, but the community is getting better at making sure that conversation gets the attention it deserves.

The one that sneaks up on folks is realizing how easy it is for individual contributions to go completely unnoticed if the team member or their spokesperson/manager isn’t a natural promoter.

As a manager, you have to make sure that nobody’s work is invisible. If they aren’t going to brag on themselves, you’ve got to be the one to do it for them. Share wins regularly and celebrate effort just as often!

Rewarding and recognizing great work and great effort is table stakes when it comes to making sure your team is engaged. That can happen serendipitously in the office, but it’s unlikely on a remote team. Be sure you’re in regular communication with your team and boosting their renown score on a weekly basis.

Chapter 4: The checklist that will make your remote team 10x more effective.

Have you ever heard of the Joel Test? It’s a remarkably helpful series of questions to help software teams measure their quality.

Joel Spolsky shared it with the world in the year 2000 and since then, it has helped countless software teams improve their build processes and ship better software.

Joel himself originally described the test as “highly irresponsible and sloppy” but time and the Internet disagreed and to this day teams are improving their quality by following those suggestions.

The great thing about the Joel Test is that all it takes is answering 12 Yes or No questions and in less than 3 minutes you’re on your way to improving your team.

In that spirit, I’d like to offer the Headlamp Test for Remote Teams.

The Headlamp Test for Remote Teams

  1. Do you have a company handbook?
  2. Do you have a communications guide?
  3. Do you always turn video on for calls?
  4. Do you record and share all-hands meetings?
  5. Does everyone dial into video calls on a separate screen?
  6. Do you enable work visibility and sharing as a default process?
  7. Do you share working hours and normalize ignoring notifications outside of working hours?
  8. Do you screen for self-motivation and communication during hiring?
  9. Do you provide a co-working / home office stipend?
  10. Do you schedule time for team socialization?
  11. Do you have at least one onsite per year?

Give your team 1 point for each “yes” answer.

Similar to the Joel Test, a score of 11 is perfect, 10 is tolerable, but 9 or lower and you’ve got problems.

Vision Still Matters Most

I’m going to paraphrase Joel:

These are not the only factors that determine success or failure: in particular, if you have a great remote team working toward a vision nobody cares about, well, people aren’t going to stick around. But, all else being equal, if you get these things right, you’ll have a disciplined team that can consistently deliver.

1. Do you have a company handbook?

Handbook, Wiki, Notion Workspace. Whatever it is technically, just make sure it’s easily accessible and stays up-to-date. Nothing kills legitimacy faster than a document that gathers dust and gets ignored.

Your handbook should cover the basics to give a new hire a lay of the land (Values, How We Work, Company Culture, Getting Started, etc.) and provide a source of truth for how your team will collaborate and create a healthy work environment for everyone.

It should also include a Company Directory to enable team members to contact one another directly for the rare (but inevitable) cases when waiting for a response on Slack could harm someone or the company.

Don’t try to be as comprehensive as Gitlab out of the gate. They’ve been working on that puppy since 2014.

MeetEdgar and Basecamp offer fleshed out examples you can use for inspiration without feeling overwhelmed.

2. Do you have a communications guide?

This should be included in the company handbook but it’s important enough to get its own question.

Communication is hard enough when you’ve got five people in the same room. Spread those same five people across five timezones in different work environments and the possibilities for misunderstanding can be amplified. One person might be expecting a response to their email within a few hours while their coworker makes it a point to check their email once in the morning and once at the end of the day.

Your communications guide should make it explicit which tools should be used for certain types of requests and what the expected response times are within each of those tools.

Notice that I’m not prescribing what your guide should say. I have opinions on that, but ultimately it’s whatever your team leadership decides will be the culture at your company. What is most important is that the expectations are clear and not left to chance or emergence.

Start simple with this outline.

3. Do you always turn video on for calls?

Video on should be the default because it provides important visual cues for the speaker, it helps the participants avoid distractions and the temptation to multi-task, and it gives everyone a brief glimpse into the worlds of their remote team members.

In the same way that it was fun to decorate your desk at the office with knick knacks and symbols of your personality, dress up the wall where you typically take your calls and make it a frequent conversation starter!

4. Do you record and share all-hands meetings?

It can be difficult to accommodate worldwide timezones and nomadic team members, and just as difficult to ask someone on the other side of the globe to dial into an 11pm call.

But, if you’re recording your meetings and making them available in a company directory by default, team members who aren’t able to join live can watch on demand.

Additionally, folks at Gitlab have shared with me that on their synchronous calls (not just all-hands meetings), the attendees collaborate to capture meeting notes in a Google Doc, documenting the proceedings so that people who aren’t there can follow along without having a recording.

5. Does everyone dial into video calls on a separate screen?

As a rule, if one person is dialing in, everyone dials in. This puts all participants of the call on equal footing.

A common complaint of remote members on hybrid teams is that they’re often treated like second-class citizens.

“Donut party in the kitchen!”

“Happy Hour at the taco bar after work!”

Another way remote members feel isolated and separate from the rest of their team is when they’re the only face on a video call while everyone else is huddled up in the conference room. Make sure everyone is in the same boat with a one screen per participant rule.

6. Do you enable work visibility and sharing as a default process?

Work visibility and celebrating contributions are important for morale and for encouraging upward mobility within the company. Much of this responsibility lies with the employee and managers should be coached on encouraging this during their 1:1s.

But, the fact is, some people are more comfortable and better at promoting their own work than others.

To ensure that talented but naturally quiet members of your team aren’t overlooked, make sharing and celebrating contributions a part of your process. If you use Slack, integrate a bot that asks your team to share their work every Friday morning. Or, incorporate a show and tell into your standups. Whatever makes the most sense for your organization, as long as you are proactive about ensuring that everyone’s contributions are recognized.

This isn’t about making people feel good for the sake of it. It’s about ensuring that you don’t lose talented contributors who feel isolated and shut out because they aren’t as boisterous as those who are used to taking up space.

7. Do you share working hours and normalize ignoring notifications outside of working hours?

The facts are that remote workers don’t work less than their colocated counterparts. They work more. Some of the cheerleading around remote workers being more productive is tied to the fact that we’re probably putting in more hours.

All that output might feel good in the short-term, but it will lead to burnout.

The great thing about remote work is that we create the conditions that allow us to work anytime from anywhere.

The unhealthy thing about remote work is that we have created the conditions that allow us to work anytime from anywhere.

Creating boundaries, maintaining them, and enforcing them for each other is vital to protecting our mental health and stamina for the long haul.

Model communicating a time block of working hours to your team and then don’t send emails or respond to Slack outside of those hours.

8. Do you screen for self-motivation and communication during hiring?

Remote work is easier than going to the office everyday in a lot of ways. But, it’s also a little more difficult in others. Or at least, it requires more discipline and better communication skills than the same role in an office.

As for communication, Jason Fried summed this up quite well in a New York Times piece:

Our top hiring criteria — in addition to having the skills to do the job — is, are you a great writer? You have to be a great writer to work here, in every single position, because the majority of our communication is written, primarily because a lot of us work remotely but also because writing is quieter.

Getting into a comfortable rhythm and finding the right conditions to do your best work is not as easy as it might sound. Are you looking for candidates who have worked remotely before or demonstrate signs of being an independent self-starter?

9. Do you provide a co-working / home office stipend?

The space you work in matters and you should make sure the members of your team have a dedicated, comfortable space to do their best work. You don’t want your employees working from the kitchen table or their bed everyday. In fact, this is something you should be screening for during the hiring process as well.

Be sure your employees have a dedicated home office or help them find a co-working or shared office nearby

Convert offers their members a $150/mo+ productivity budget to start to put towards whatever will help them create a more focused work environment.

10. Do you schedule time for team socialization?

Isolation and loneliness are always in the top tier of challenges for remote workers. It doesn’t affect everyone, in fact, for many, the alone time and solitude of the home office is a great comfort.

You don’t want to take that away from anybody or be overly forceful, but it is important to find ways for your team members to connect and share a little bit more about their personal life. The sorts of conversations that would typically come up around the coffee pot in the morning or over an impromptu team lunch.

It can be as simple as an automated message on Monday morning to ask everyone what they did over the weekend or by integrating a tool like Donut into your Slack workspace.

And if you don’t have an HQ but happen to have a number of members in the same locality, create a bi-weekly co-working day to build deeper relationships. Zapier is a fully remote team but there is a cluster of employees in Portland, so they get together every so often to get to know one another even better.

11. Do you have at least one onsite per year?

The great thing about being a remote team is that you’re saving a lot of money on real estate. You can put those savings towards a four-star company retreat and still come out ahead.

The team at 1 Second Everyday shuts down customer support during their week-long company retreats so that everyone can unplug from work and be present. On Friday, the whole company dives in on support to get all of the tickets closed before the week is up.

High-performing remote teams have structured their retreats in a number of different ways, so like the handbook and communications guide, it is difficult to prescribe a recommendation here. Some teams set the entire week aside for excursions and social time. Others dedicate the first few days to all-hands workshops on a topic of interest.

The important thing is that at least once per year, your people get to meet their co-workers face-to-face. We are, after all, social animals.

Chapter 5: Helping your remote team be their best: Conversations & feedback for career advancement in a remote company.

In the arena of attracting and keeping your best talent, career conversations are a manager’s secret weapon.

Right Management found that 82% of people said they would be more engaged in their work if their managers regularly discussed their career aspirations and 75% said they’d also be more likely to stay at the company.

But most managers either aren’t familiar with that research, ignore it, or get caught up in the day-to-day grind and fail to give long-term goals the attention they deserve.

In fact, only 16 per cent of employees say they have ongoing conversations with their managers about their career, according to Right Management’s research.

Career Conversations Are Your Secret Weapon

That’s a staggering disconnect! By having fruitful career conversations with your team, you’re immediately putting yourself into a position to have a more engaged, productive, and long-tenured team. And as we’ve already discussed, engaged and productive employees lead to happier customers which leads to a more profitable business.

Russ Laraway, Chief People Officer at Qualtrics puts it this way:

“I’ve seen this play out in practice over and over and over. People are surprised that they can grow towards their dreams and stay put in their current role. [Career conversations] reduce any ants-in-the-pants of wanting to leave or be promoted. As a manager, one of your prime jobs is to help the people on your team develop. Your people will grow with or without you. The question is who will they grow into?”

Laraway implemented a framework for career development that led to more than a 10-point bump on engagement scores across hundreds of employees during his time at Google. His success at Google, Twitter, and as a Company Commander in the Marines Corp has helped him to become a respected leader in employee engagement and retention.

The tldr; on his approach boils down to this:

  • Leaders can retain their best people by helping them describe and work toward a long-term vision.
  • Performance reviews are backwards-looking, while career conversations are forward-looking.
  • Great career conversations happen by: getting to know their backstory, understanding their dreams, and creating an action plan that works toward those dreams.

That’s it. Like many things, it’s remarkably simple but deceptively hard.

If it’s so simple, why are they so uncommon? As I mentioned above, it’s usually because managers aren’t aware of how impactful these conversations can be, and even if they are, getting out of the weeds of the day-to-day is really, really hard.

But there’s good news! You don’t have to design a big giant automated system to start moving in the right direction. Don’t let your mind go there and then find yourself paralyzed by the overwhelming feeling of making this a “project.”

The best manager I ever had was the CEO of a software startup in Boulder. This guy had a natural ability to draw the best out of everyone around him and on reflection, we were having career conversations on a regular basis.

And here’s the evidence of the good news: he wasn’t following some robust scheduler or using a management tool to make an impact (although we would’ve benefited from some structure!), he was simply asking over lunch, “Where do you want to be in a few years? What’s your goal?” I’d answer and he’d say, “Cool buddy. Let’s get you there.”

Then he’d find ways to empower me to take steps toward my vision.

That CEO got so much effort and loyalty from me because I wanted him to be successful in return.

It is astonishingly simple. Care about your people. Care about their dreams. Find ways to align their long-term goals with your team’s business objectives and magic happens.

It’s also pretty easy to screw up career conversations. Here are four ways to do it wrong: - Don’t have them - Limit them to the near-term - Go through the motions - Underplan and improvise

But that’s not how you’re going to do it. You’re going to do it right by getting to know their backstory, understanding their dreams, and then helping them make a plan to get there.

Get to Know Their Backstory

I’m about to out myself as a total nerd, but I’ve gotten deep into Dungeons & Dragons recently. I never played as a kid but I wish I had!

If you’ve never played D&D, you’re probably thinking what I thought: it’s a bunch of dorks sitting around using make believe magic to kill make believe dragons.

Trust me, nothing could be further from the truth.

A major component of the game is role playing. You build the character you’re going to play and then draw on the character’s backstory (that you write) to decide how they would act or react to the situations they encounter. It is much closer to improvisational acting and storytelling than it is to a board game.

The backstory component is critical to making believable decisions about how a character would respond. The best characters have complete backstories and the best/most believable players understand their character’s backstory completely.

To understand where someone will go, you have to understand where they’ve been.

Laraway calls this “being their Barbara Walters.”

“Take an hour to get to know your employees — deeply. Begin with the phrase: Starting with kindergarten, tell me about your life. Then probe with more questions when they talk about pivots in their lives.”

You’ll learn a lot about a person when you understand what hobbies appeal to them, what activities they devoted time to during their formative years, and what values they’ve held onto throughout all seasons of their life.

Understand Their Dreams

This is aligned with Covey’s effective habit, “Begin with the end in mind.”

“If your ladder is not leaning against the right wall, every step you take gets you to the wrong place faster.”

Your team will be far more empowered and motivated when the work they’re doing is aligned with a long-term vision they have for themselves.

The team at FranklinCovey describes it like this:

If you don’t make a conscious effort to visualize who you are and what you want in life, then you empower other people and circumstances to shape you and your life by default. It’s about connecting again with your own uniqueness and then defining the personal, moral, and ethical guidelines within which you can most happily express and fulfill yourself.”

That’s why understanding your employee’s dreams and helping them work toward them leads to a happier, healthier workplace. Managers who think their job means telling people where to go and when via over-the-shoulder micromanagement will soon find their team resentful and annoyed.

Wise, insightful employees will come to the realization above, “If you don’t make a conscious effort to visualize who you are and what you want in life, then you empower other people and circumstances to shape you and your life by default” and they will rightfully take steps to correct that problem. One of those steps will be leaving a job that sees them as a cog in the wheel.

Dig deeper over time, but remember my story about my CEO, this can begin simply over coffee:

  • What are your goals?
  • What kind of company do you imagine working for?
  • Do you want to be a very senior manager or a very senior individual contributor?
  • What would you want to be doing at the very pinnacle of your career?

It’s that simple. The hard part is pulling yourself out of the day-to-day urgency to give attention to these less-urgent but far more important questions.

Create a career action plan

I have so much respect for Mathilde Collin and the way she’s lead the team at Front.

This is how they’ve structured their career conversations:

“Every six months, managers and employees meet to discuss career development. Ahead of this meeting, the employee prepares responses to such topics as what they like and dislike about their current role; careers they admire; where they want their career to be in 6 months, 12 months, 2–5 years; and a list of skills, competencies, and experiences that they need to develop.”

The action plan will bubble up out of that list of skills, competencies, and experiences that need development.

What can you do to develop their role to include those things in ways that align with your business objectives?

How can you build up their network and introduce them to people you know who can speak to those competencies?

Are there obvious next steps included in that list? Prioritize them!

This process creates a positive feedback loop where your team trusts that you want to help them grow, they are more engaged because they feel valued, and they want to reciprocate by helping you meet your goals.

That’s what a healthy team looks like and how you can be the manager you want to be!

Chapter 6: The 7+ deadly sins to avoid on remote teams.

Working remotely is different. Whether or not it’s “better” is subjective and depends on such a wide range of factors and experiences that’s it’s not a conversation worth having.

But what we can say with absolute certainty is that it’s different and it requires a different way of working. We’ve been discussing a number of ways to do it correctly, but it’s often equally helpful to invert the problem and look at ways to do it wrong. And then of course … you know … stop doing those things.

Some common mistakes remote teams make that will inevitably lead to confusion, wasted time, burn out, loneliness, and disengaged remote employees are:

  • Trying to “port” the office experience to remote
  • Overstepping work-life boundaries
  • Micromanaging time and activity
  • Not having clear communication guidelines
  • Underinvesting in remote office setup
  • Staying plugged in when on vacation
  • Allowing contributions to go unnoticed and uncelebrated
  • Remaining ignorant of isolation & loneliness
  • Never talking about personal life

Trying to “port” the office experience to remote

Jason Fried of Basecamp fleshes out a nice metaphor suggesting that remote work is a platform.

“Porting things between platforms is common, especially when the new thing is truly brand new (or trying to gain traction). As the Mac gained steam in the late 80s and early 90s, and Windows 3 came out in 1990, a large numbers of Windows/PC developers began to port their software to the Mac. They didn’t write Mac software, they ported Windows software. And you could tell – it was pretty shit. It was nice to have at a time when the Mac wasn’t widely developed, but, it was clearly ported.”

Porting feels easier, it feels familiar, and in the short-term it requires less work. But the experience is awful and the design suffers.

And a mistake that a lot companies make is trying to port the office experience onto a remote workplace because it feels familiar.

“What we’re seeing today is history repeat itself. This time we’re not talking about porting software or technology, we’re talking about porting a way to work. In-office and remote work are different platforms of work. And right now, what we’re seeing a lot of companies attempt to port local work methods to working remotely. Normally have four meetings a day in person? Then let’s have those same four meetings, with those same participants, over Zoom instead. It’s a way, but it’s the wrong way. Simulating in-person office work remotely does both approaches a disservice.”

Resist the tempation and design your team’s experience around this new context, don’t bring the office design to remote.

“The web became great when designers started designing for the web, not bringing other designs to the web.”

Overstepping work-life boundaries

I mention this in my Headlamp Test for Remote Teams, but it bears repeating here:

The great thing about remote work is that we create the conditions that allow us to work anytime from anywhere.

The bad thing about remote work is that we create the conditions that allow us to work anytime from anywhere.

When there’s no office there’s no leaving your work at the office. It’s literally in your pocket.

Enjoying a game of soccer with the family in the backyard and an urgent email from a big client comes through? It’s simple enough to pause the game, hop into the office, and get it resolved. 🙋‍♂️ Guilty.

But in the long run, this only leads to burn out.

Listen, I’ve only got anecdotes about how not to do this because I am so terrible at it. And guess what? I’ve suffered through intense periods of burn out as a result.

People benefit from unplugging and not thinking about work for long periods of time. We are not meant to be running around the clock.

I mean, sure, there are Ironwomen and Ironmen out there who can swim 2.4 miles, bike 112, and then run a marathon. But have you seen them at the finish line?! They’re done for! And what about their knees when they get into their late 50s?

(Am I bitter that I can barely crack a 9 minute mile pace in a 10k? Yes! But the metaphor still holds!)

As a leader in your company, your behaviors will set some norms whether you intend for them to or not. Set an example by communicating a time block of your working hours then don’t send emails or respond to Slack outside of those hours. Respond to yourself if you need to get the thought out! But don’t share it at 11:14pm on a Saturday.

Micromanaging time and activity

In Daniel Pink’s authoritative TED Talk on motivation, he demonstrates how important autonomy is in allowing talented people to achieve their best results.

If you want to attract and keep talent, help them get pointed in the right direction and then leave them alone.

Nobody worth keeping on the team needs a manager pestering them for updates or doing their work for them. But sometimes, managers just can’t help themselves because they aren’t seeing the results or the effort they expect.

Fair enough. Let’s talk about a strategy that is far more likely to get you where you want to go.

Instead of micromanaging that employee’s time, or heaven forbid installing activity monitors on their devices, think about the other sections of this article.

  • Do you understand what motivates them?
  • Do you know where they want to go in their career?
  • Do they feel connected to the company mission?
  • Are you meeting with them regularly to build trust?
  • Is their performance management based on clear goals?
  • Are you focusing on their strengths, not weaknesses?
  • Is your communication clear?
  • Did they have a good onboarding experience?
  • Are you recognizing and celebrating their contributions?

If you ensure that the answer to those questions is yes and you give your people space to do their work, you’re much more likely to get the results you want than through micromanagement.

Not having clear communication guidelines

When you don’t have clear guidelines on how your team uses the various means of communication in your stack, people end up in this scenario: “Uh. I’ll just throw this question/request wherever feels right at the moment” Email/Slack/Asana/SMS. Wherever.

That’s not helpful. Without some rails in place, an ad hoc communications culture bubbles up and those habits are rarely productive.

Remote teams should have a communications guide that makes it explicit which tools should be used for certain types of requests and expected response times for each.

When I interviewed Amir Salihefendic, CEO of Doist, he talked about the struggles they faced as an early-adopter of Slack without clear expectations for how the tool should be used.

“We could just see so many problems. People were stressed, I was very stressed by the one-line communication model. Especially across timezones and for deep work, it just doesn’t fit together. We thought, ‘this can’t be a solution’.”

Amir’s team decided to address this problem by … well, by building Twist. The good news is, you don’t have to go that far! Twist came about because the team at Doist looked at the landscape and the natural habits that emerge within it and decided, “There’s got to be a better way!”

Twist is a product that embodies Doist’s first principles of effective communication and it’s worked wonders for their team and many others. Your first step as an effective manager should be to start the process of documenting your own team’s first principles to keep the inevitable bad habits of interruption and notification-addiction from wreaking havoc on your team.

Human Made has a nice section on communication in their company handbook.

I also like the way 1SecondEveryday lays out their communications style here.

Finally, Edgar discusses how they use their tools in their handbook as well.

Underinvesting in remote office setup

Working from your couch, dining table, or bed gets old and uncomfortable. Smart companies and smart managers want to be sure their team is comfortable and productive.

Setting up a home-office fund is an effective way of making sure your employees are able to invest in a space that helps them focus on their work.

Remote companies have addressed this in a number of ways:

  • Shopify and Twitter give their employees a one-time $1,000 allowance to set up their home office.
  • Basecamp allows their team members to expense up to $1,000 to furnish their home office, every three years.
  • Chegg pays their workers’ internet bill and provides a $500 allowance to get set up at home.

Other companies offer smaller monthly stipends to be spent on anything at all. Business books, artwork for the wall, or a one-off therapy session. Anything you need to stay balanced while working from home is fair game.

Staying plugged in when on vacation

Again, just because you can stay in touch, doesn’t mean you should. gives their employees a $250 off-the-grid bonus when they stay completely offline while on vacation because they understand the importance of unplugging in order to recharge.

There’s probably a solar energy metaphor to be had in there, but it’s not coming to me at the moment!

Be thoughtful about this and help your team feel empowered to truly disconnect.

When my dad passed away, my co-workers knew I’d need to unplug for a while, but my name kept coming up in Slack. Instead of mentioning me by name and risking setting off some notifications, they referred to me as Bryan (with a y instead of i) for the duration of my leave.

Not only was this incredibly thoughtful, but it made it easy for me to catch up on the most relevant things I’d missed while I was away by simply searching for that spelling.

Of course, giving your team license to turn off all notifications in the first place is also the right thing to do, but give some thought to all the tools your team uses and consider how you can make it easier for people to actually leave the remote office when they’re on vacation.

Allowing contributions to go unnoticed and uncelebrated

One of the traits of a great manager is that they recognize and reward the contributions of their direct reports. While overlooking achievements can most definitely happen in an office, it’s even more likely to happen when your team is distributed and impromptu celebrations in the break room aren’t a thing.

Ideally, you’re creating a culture where team members are recognizing the work of their colleagues, but the responsibility is first and foremost on the manager to be sure that a new marketing campaign, feature launch, or improved customer satisfaction scores never slip through the cracks.

If you’re on Slack, create a dedicated channel for #kudos and set the example for how it’s used.

If you have daily standups, make Friday’s a little longer and include some time to acknowledge wins that are bigger than the daily “here’s what I did yesterday” update.

Nobody likes to feel invisible, so be sure you’re the one with an eagle eye for great work.

Remaining ignorant of isolation & loneliness

Year after year after year remote workers cite loneliness & isolation as one of the biggest struggles they face.

The first step a great manager can do in response is to simply be aware of how common a problem this is.

As I’ve discussed this issue publicly, I’ve been surprised at how dismissive some folks can be.

“I’m fine. I have family and friends to fill my life.”

“Hard no for me, personally. I get my social interaction via friends/local clubs/etc. Don’t need it from coworkers.”

“I’d argue that people who depend on their coworkers for their primary source of fellowship and connection likely have higher rates of anxiety and loneliness.”

Cool, cool, cool, cool, no doubt.

All I can say is I hope those folks aren’t managers or execs. If an employee said, “Hey, my chair’s getting a little uncomfortable,” would they respond, “Odd, mine seems fine.”

Regardless of maintaing a healthy social life outside of work, loneliness & isolation are a common problem on remote teams.

I was included in a 7-part series by The 21st Century Worklife Podcast on “Connection and Disconnection in Remote Teams” and the team did a wonderful job of exploring this problem from multiple points of view. I highly recommend adding it to your podcast queue:

In my conversations with CEOs, execs, and remote workers at all levels of an organization, a major theme emerged:

Remote companies have to be deliberate and intentional about helping workers make connections and stay connected.

Interactions happen organically and with the help of serendipity in an office. It’s just not as likely when you’re remote. Make it a point to set time aside to make connections and develop relationships.

Never talking about personal life

All work and no play makes for a weak team. To know and to be known is critical in team-building.

To be clear, I don’t mean: “Tell me about your relationship with your father,” I mean: “What are your hobbies outside of work? Read any good books lately?”

As I mentioned early, a common practical implementation is installing a Slackbot that asks, “What’d you do this weekend?!” every Monday morning. It’ll be a simple and easy way to help your team get to know one another casually over time.

Chapter 7: The remote manager’s toolbox.

Plenty of “Remote Tools for Remote Teams” lists include Google Docs, Zoom, & Basecamp.

I mean. Yeah.

But those are tools that practically any modern company could utilize to operate their business more efficiently.

This toolbox assumes you’ve got email, chat, video, project management, and a wiki solved. Included here are some tools you may not be familiar with that might help your team be happier and more productive.





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