CEOs and Leaders: Here’s how to prepare for an extended period of remote work

David Hassell
38 min readMar 26, 2020

We’re all living through an unprecedented moment in modern history, the potential scale of which hasn’t been seen in over one hundred years since the 1918 Flu Pandemic.

As I sit here at my desk writing this at 8:30pm on a Wednesday night in the midst of the whirlwind of news and uncertainty, I, probably not unlike you, am doing my very best to answer some very important questions.

How long will this last? How bad could this get? What will the impact be to our economy, to my family, and to my business? How might this change the world, for the worse, or for the better? How do I make the right decisions to navigate my company through to the other side safely, and do the best I possibly can to take care of my team and our customers, and possibly even create more value for our customers in this dire time? As a leader of a company in the midst of a crisis, I know first hand how stressful this moment can be, and my heart especially goes out to those who’ve been severely affected in industries like travel and hospitality.

One conclusion I’ve drawn is that there’s a high likelihood that we’ll be in for an extended period of remote work, and that there may be multiple periods over the next 18 months that remote working could be required (more on why I believe that below).

If that’s not how you normally run your business, having your entire team all of a sudden working from home is likely another major added stress, and I want to help.

I’ve gained a lot of hard-won expertise over the last 9 years building 15Five as a remote-first company with now over 200 employees. As a primarily work-from-home, remote CEO of a company honored to have won multiple awards for its culture, I’m also in a unique position to share how to effectively lead remotely as well.

My hope is that by sharing some of what I’ve learned, I can help you avoid some of the pitfalls and reduce some of the stress involved in trying to figure it out on your own at a time when you need to devote most of your time and energy navigating your company through this difficult time.

For background, we’ve run 15Five as a “remote-first” company since day one, despite more than half of our employees working out of one our five global offices. As a result, we didn’t miss a beat when the rest of our team was forced to move to fully remote work.

I’ll share why I believe running your company with a remote-first mindset and remote-first infrastructure is both beneficial to productivity and resilience, even if most of your company works out of a physical office. I’ll also share some simple things you can do right now to help make this transition more easily.

Despite nearly half of our team working remotely full time, we’ve placed #3 on Glassdoor’s Best Places to Work (with over 80, 5-star Glassdoor reviews), #2 on Fortune’s Best Workplaces Bay Area, and #5 on their Best Workplaces in Tech.

I’ll also help dispel the myth that you can’t have extraordinary culture if your workers are remote, and additional practices you can implement during this difficult time to keep morale up, and keep your team feeling connected, engaged, productive and focused on what matters most.

But first, let me share more about why I believe we may be in for an extended period of remote work.

As I write this on Wednesday, March 25, there are now over 68,000 confirmed cases of COVID-19 in the U.S. and over 1,000 deaths, doubling every 3 days.

Despite national guidelines of physical distancing and regional lockdowns, the rate of growth hasn’t yet abated. As a result, in the coming weeks we’re likely to see a major strain on our healthcare systems and hospital workers, which could result in increased and extended shutdowns as our government works to get the spread under control.

If you’ve read Tomas Pueyo’s thorough analysis on Medium (over 40m views) or the report put out by the Imperial College of London, you might conclude as I have that:

  • This is the most severe respiratory illness to hit the world since the 1918 Flu Pandemic; it is highly contagious and spreads quickly in part because it’s a novel virus to which no one has natural immunity.
  • While most cases are mild and survivable, it’s severe enough for some that we simply don’t have anywhere near the medical capacity to treat even a fraction of the people who would need care if we let the virus run its natural course; without mitigation, we will quickly overwhelm our systems, many more people could die, and we may end up forcing our doctors and nurses to have to make unfathomable decisions about who lives and who dies.
  • The only way we get out of this (where the rate of spread is low enough to not be problematic) is by getting to herd immunity. That means that either a large percentage of the population need to contract the virus (and survive) or we need a vaccine. Due to the nature of clinical trials for vaccines, it appears that we’re at least 14–18 months away from a vaccine.
  • The limiting factor is our health care system’s capacity, hence the need to “flatten the curve” to avoid a level of human tragedy our society is not willing to accept (which I both agree with and support). Without treatments that can help keep people out of the ICU or reduce the need for ventilators, we must control the rate of spread and that requires mitigation through physical distancing.
  • Current measures may not be enough. Yaneer Bar-Yam, an MIT-trained physicist and complexity scientist who studies pandemics and who recommended protocols that helped stop the spread of the 2014 Ebola epidemic, recently called for an immediate five-week national lockdown to defeat the virus in the US. Further, Bill Gates has just said that we missed our opportunity to avoid an extreme shutdown, and that we will need one that could last six to ten weeks before we can go back to normal.
  • There’s also the chance that even if we get the spread under control now, we may (or very likely will) have additional waves of outbreak until we’re able to get a vaccine in place, causing further shutdowns regionally or even nationally.
  • The big wild card, and potentially saving grace, is whether we discover any drug treatments that help keep people out of the ICU or reduce the need for ventilators until we find a vaccine, in which case we may be able to relax some mitigation measures and allow more people to naturally contract the virus faster.

The last point is a big “if,” and while I certainly hope that happens, it’s not something I want to bet my business on. In light of this, we’re preparing for the worst case scenario while keeping a close eye on how things progress.

Even if your country or region decides to relax physical distancing guidelines in the coming days and weeks, some number of your employees who are in a vulnerable at-risk group or area (or have close relatives who are) may feel anxious about commuting and working from an office, and may prefer to continue working from home. Or, you and your team may just decide that you really like the flexibility and benefits that come with even part-time remote working.

Given that, we all need to act now to prepare ourselves for this being the new normal for an extended (and potentially recurring) period of time.

Some things that are different than 1918, like our dependence on global supply chains and just-in-time inventories, are concerning in this kind of crisis and only add to the uncertainty and stress.

Other factors, like the nearly ubiquitous access to cheap, fast Internet and an incredible toolset that sits on top of it, makes it possible for us to effectively communicate, coordinate, and stay socially connected even though we need to practice physical distancing (which evidence shows is one of the most effective approaches to slowing the transmission of COVID-19).

All things considered, we are massively blessed that this is the case!

If done and managed well, remote work can be as if not more productive than working in an office.

So, let’s get to it.

My objective here is to create somewhat of a comprehensive guidebook that you can reference as you work to put in place the optimal and essential systems and practices for leading a team remotely.

I’m going to break this post down into the following areas:

  1. Remote Mindset — how do you need to think and act differently as a leader when learning and managing a fully distributed, remote team?
  2. Company-wide Tools & Practices — how do you ensure you’ll have the visibility you need and ensure that your company’s goals will be achieved, while designing a structure of interactions that have your employees feel socially connected and like they’re part of a single team?
  3. Manager/Employee Practices — what are the best manager practices for managing a remote team?
  4. Individual Work Practices — what are some key considerations for every person from your SDRs to the CEO to make remote work, work?

Remote Mindset

Here are a few key ideas that I’ve found helpful in thinking about remote teams and how to have them work well.

1) Embrace putting in place remote work systems as a long-term net benefit, even if you ultimately revert to mainly office-based working.

If done right, having a remote-first infrastructure will give you the best of both worlds. You can still get all the benefits of working in an office if you choose to, while also allowing you and all your employees to have the flexibility to be productive wherever, whenever.

Having a remote-first mindset and infrastructure also opens up the ability to hire the best people regardless of locale (perhaps even in lower cost areas than where your company is headquartered), and gives your organization a high degree of resilience should anything like this ever happen again.

2) Focus on building a thriving and socially-connected culture by intentionally designing for the same interactions that would otherwise happen if people were together in the office.

Culture is what naturally happens whenever you bring a group of human beings together and have them work or live together for any period of time.

As the best organizations have learned, great culture doesn’t happen by accident but requires intentional design and influence. This is why it is so important to make your company’s mission, vision, values, operating principles, standards, agreements and social norms explicit, and to reinforce them. Doing this with a remote team is no different.

However it’s also important to understand that a key aspect of how a culture is experienced is through our emotions, which includes how your employees feel when they think about the company, you, other leaders, their manager and their peers.

The best cultures are ones where people feel a sense of connection to the company’s purpose, a sense of trust and faith in their leaders, and a camaraderie with their manager and peers.

That feeling is developed through human interaction, plain and simple. When you’re all located together, it happens naturally; whatever the culture is propagates and is amplified with each human interaction.

Impromptu water cooler, kitchen or hallway conversations, quick whiteboard sessions in a conference room, or 1-on-1 and group lunches are all things that contribute to this experience.

They’re important not only to your sense of culture, but also your team’s sense of social connection and productivity. While you can’t replicate them exactly, with proper design you can ensure those very same needs get met despite the physical distance.

As I recently shared with CNN in an article titled How to work from home without losing your sanity, it’s important to not underestimate the psychological impact of being alone. We are social beings and need connection, so getting this piece right is also critically important.

Thankfully with high quality video conferencing, text-based tools that encourage the use of emoticons and rich imagery, and a well-thought-out cadence of communication and connection rhythms, we can nearly re-create the level of emotional connection you’d experience in any office.

3) Don’t take your leadership presence for granted

When working remotely, your team will have fewer opportunities to see you face to face, and this is important to design for.

Leadership presence is always important, but in times of crisis especially critical. Your people need to feel your presence as a leader.

That means showing up in a variety of forms, regularly and consistently, despite you not being able to physically share the same space. I try to balance a mix of engaging via video in our weekly all-hands Boosts, periodic company-wide emails, presence on Slack in public channels, and engaging with our team’s High Fives inside our own product (more specifics on all of this below).

Consider the cadence and channels that you think would work best for your team and culture. To start, I recommend erring on the side of more communication rather than less, and soliciting feedback from your leaders, managers and team members to find the right amount for your specific situation.

4) Give your managers specific training, tools and practices for managing remote employees

One common fear I hear from leaders and managers is whether their employees will actually do their work, or will they just sit around watching Netflix all day.

In my experience, in most cases this fear is usually misguided, and any impulse to micro-manage based on this fear will likely backfire.

What’s the impact micro-management has on your relationships? From my limited experience, what I’ve noticed is that when you micromanage others, they learn to hide from you. They become defensive about their choices, deflect feedback, and close down. This is the antithesis of the dynamic you need to create when your people go remote, because what you need is more openness, transparency, and trust to make the whole thing work.

To that end, the formula I’ve found that works is granting trust, treating employees like adults, and then putting in place the right set of accountability and communication structures to ensure that wins, challenges, and results are being surfaced, and the right conversations are happening at the appropriate cadence.

Things like weekly check-ins and 1-on-1s are critical here, and by standardizing these practices across your organization, you can ensure a high degree of consistency and effectiveness.

It’s also important to understand some of the key principles of intrinsic motivation. When your team is intrinsically motivated, not only are they most likely to do their best work, but you won’t have to worry as much about whether they’re working either. Based on Self-Determination Theory, the idea is that there are four aspects that independently lead to someone feeling more intrinsically motivated, and those are Relatedness (with others), Autonomy, Mastery and Purpose, which some call the intrinsic motivation RAMP.

Adam Grant shared last year about a recent Nick Bloom experiment showing that if you let call centers work from home, they’re 13% more productive. Adam said, “It’s not just because they save commute time — it’s also that they’ve been given real autonomy. They have flexibility around where they work, when they work, and how they work, and they don’t feel like they’re being micromanaged.”

Good news! You’ve just granted your people a whole lot of autonomy!

Focus now on ensuring they feel connected to each other and to your purpose, and are on a path of growth and self-mastery, and you’re well on your way to up-leveling your team.

At 15Five, we ascribe to a philosophy called Best-Self Management, based on our belief that high engagement and high performance are results and not things you can manage directly. If instead you focus on managing people to become their best selves, then great culture, engagement, performance and loyalty are the natural results.

As an aside, Best-Self Management is based on principles of psychological safety, intrinsic motivation, growth mindset, strengths and positive psychology. If you or your team are interested in exploring more on this topic, we offer a free 4-hour Best-Self Management Certification Course for managers at 15Five’s Best-Self Academy, which can help to really up-level your managers’ skills whether their team is remote or otherwise.

5) Understand the pros and cons of individual remote-work productivity, have empathy and offer support

Offices, especially open offices can be rife with distraction. While there are certainly benefits to the social interaction, no quality work gets done without focused attention.

On the other hand, science tells us that long commutes have a negative impact on well-being. In addition, recent research by Allen, Golden, and Shockley (2015) shows that remote work increases job satisfaction and performance, and helps to reduce stress and exhaustion.

Another pro of remote working (in many cases) is the ability to intentionally shut off distractions for a period of time and focus on the task at hand.

However, we’re in a unique situation now with employees needing to work from home, many without an effective home office/workstation setup. Some of your employees have roommates. Others are parents needing to balance the demands of simultaneously taking care of both work and their young children.

In a longer-term remote-work strategy, providing resources to help individuals create an effective work space is often a great strategy, and if you can do some of that now, great.

In the current environment, it’s important to have empathy for people’s individual situations, and do your best to provide whatever flexibility that can be provided to ensure your employees are able to take care of their families (especially parents of young children) alongside the needs of the business.

Ultimately, the key to leading a remote team well is to understand that you need to intentionally design communication and meeting rhythms, social connection, and management/work practices.

Thankfully there’s a wide array of easy-to-use tools on the market that help you do exactly this.

Company-wide Tools & Practices

1) Video, video, video, for everything

Video is one of the most critical factors for doing remote well and maintaining a sense of social connection and humanity.

There’s far too much non-verbal communication that gets lost via text or even simply voice, and with fantastic video platforms available like Zoom, there’s zero excuse for not making video the center of your remote-work strategy.

Whenever there’s an opportunity for synchronous communications, whether it’s regular all-hands meetings, individual team meetings or even impromptu 1-on-1s, we opt to use Zoom nine times out of ten.

During all-hands and individual/cross-functional team meetings, video allows everyone to feel more socially connected to one another (which is particularly important at this moment in time), allows you to better “read the room,” and by and large creates a much more cohesive team and experience despite physically being apart. It’s the next best thing to being in person.

To be clear, it doesn’t make much sense to do a Zoom meeting if everyone has their video off. We encourage people to turn their video on whenever possible and in gallery view.

Also, while this isn’t important in this moment, I’d be remiss not sharing it for when things do get back to normal. It’s VERY important that each person be on their own computer with their own camera, even if there are a number of people sharing a conference room (and perhaps just sharing one mic/speaker).

It’s a miserable experience to be on your own laptop and looking at three “faceless” people on the other side who are sitting far from the camera and on the same video screen. The beauty of a platform like Zoom is that they can accommodate large numbers of simultaneous video feeds, and when everyone has their own camera, it lends itself to a much greater sense of connection.

2) Host Weekly All-hands “Boosts”

At 15Five, we have 3 weekly all-hands meetings that we call “Boosts” because they’re designed to boost the energy at 15Five. When we started initially they were called the “Daily Boost” because we did them every weekday, but once we grew beyond 10 people we decided a 3-day/week structure made more sense.

Our Monday Boost starts promptly at 9am PT and runs approximately 30 minutes (sometimes less), beginning with a brief gratitude reflection led by either myself or our Chief Culture Officer, Shane Metcalf.

Science tells us that practicing gratitude is associated with positive emotions, well-being and health, and that our natural tendency is to trend towards the negative when left unchecked. To counteract this tendency and to experience the positive benefits together as we kick off the week, we take a moment as a company to reflect all together on a shared gratitude.

Our gratitude focus might be on something that we typically take for granted, whether it be running water, red or white blood cells, or perhaps this month, toilet paper! Or it may be something more meaningful, like our parents, families, further back ancestors, the sun, or any number of things you might think of.

The point here is to just take a moment to collectively put our attention on the positive and experience the feeling of gratitude together. And when I say feeling, I mean feeling. We encourage people to not just intellectually consider what they’re grateful for, but to actually cultivate the feeling of gratitude.

For those in an office, we’ll have them turn to one another to discuss for 2 minutes, and for those remote they’ll write a brief share in our #gratitude channel on Slack. (Now that we’re all physical distancing, we’re moving to Zoom’s nifty break-out feature so we can break our team into groups of 3 for a few minutes to share with one another as we kick off the week.)

After that we introduce new hires to the team where people get a short 2-minute slide presentation to share about who they are, as well as things like: who their grandparents were, what makes them feel alive, or any strange hobbies that they keep.

We then share our numbers for the week, department updates on OKRs (rotating departments each week), and announcements.

We err on the side of openness and transparency with our team during these Monday updates, and I get continual feedback from the team that the transparency we espouse during boosts has been a powerful part of building a strong remote culture. In critical times of crisis, sharing freely and openly (within bounds), hosting AMA’s (Ask Me Anythings) with me or our entire leadership team, and providing context that would otherwise be heard through gossip (or not heard at all) goes a long way towards building trust and psychological safety.

Our Wednesday Boost starts with a 5-minute guided meditation by a rotating member of our team who leads these sessions for a month, followed by an in-depth department update or training.

Finally, Friday, which is optional, is Question Friday. A “question master” is nominated each month to ask an interesting, universal, personal question to the group, for example, “If you could relive one experience from your life, what would it be?” We’re then assigned to a breakout room in Zoom with a random set of our peers and share our answers with one another.

15Five was actually selected by the University of Michigan’s Center for Positive Organizations as a Gold Awardee of the 2018 Positive Business Project, specifically for our Question Friday practice.

The Center for Positive Organizations: The Positive Business Project was established to highlight organizations who are leading the way in creating positive change in the world. Gretchen M. Spreitzer, Faculty Director, says “we chose 15Five because they demonstrate the incredible impact that occurs when you establish an employee-first culture, and they’re sharing it with everyone they can. It’s organizations like 15Five that allow employees to be their best professional and playful selves.”

This 15–20 minute weekly ritual, like our gratitude reflections and guided meditations, may seem to serve “no business purpose” but they are precisely the things that create a recurring level of human connection on our team, and are specifically designed to fulfill the lack of natural connection we experience by being distributed. By revealing more of who we are beyond our work roles, people develop deeper connections with their coworkers and experience a greater sense of belonging on the team. That in turn leads to much greater trust and improves collaboration, especially in times of challenge.

Finally, all Monday and Wednesday boosts are recorded and sent out to the entire team for those who were unable to attend.

We also periodically extend Boosts to an hour long or more if we want to host an AMA with the leadership team or communicate any changes in strategic direction. This typically happens after our quarterly leadership retreats (which we do twice per year over Zoom and the other two times in person).

You certainly don’t need to do exactly as we do, or hold as frequent all-hands meetings, but my hope is that you can see how this level of consistency provides our people a greater sense of connection as well as the opportunity for me and my leadership team to demonstrate the leadership presence, transparency and alignment necessary to guide the organization.

3) Encourage daily stand-ups

Some of our teams (e.g. sales, success, support and sales development) opt to also do daily standups to create another point of interaction across offices (and now their homes).

These are quick, light-hearted, focused and designed to ensure people connect face to face.

4) Start all meetings with an emotional pulse check, have a clear agenda, and end with a rating

We host our remote Senior Leadership Team meeting for 1.5 hours every Monday following our Boost.

The very first thing we do is have each member of the team (who then calls on the next) rate how they’re feeling, in that moment, on a scale of 1–10 and then share a few words about their current state, their weekend, or whatever.

Sometimes we’re a 9 or 10, on fire and ready to go. Sometimes we’re a 5 or a 6 and just had a difficult morning with getting the kids to school, or are fighting off a cold.

Whatever it is, this is an opportunity for each person to voice what’s going on for them, get connected with one another, and move into the meeting with greater presence, no matter what mental or emotional state they were in as they joined.

According to research by Harvard Business School’s Tsedal Neely on Global Teams That Work, it’s important to train managers to spend 2–5 minutes at the beginning of every regularly scheduled meeting to talk about non-related work topics that build trust and deepen their relationships.

Further, the practice of “feeling identification” — finding the exact, most specific word that describes your current emotional state — is more critical now than ever. Feeling identification, especially under times of stress, helps people manage their emotions. Both Adam Grant (a top organizational psychologist at Wharton) and Brené Brown (a research professor at the University of Houston Graduate College of Social Work and famed TED speaker) have been promoting this key emotion-management skill during this time.

Doing this only takes a few minutes, but I find that this simple practice is a game changer for building trust, connection, empathy and presence. I’ve even made this a practice with my board!

To maximize the productivity of meetings over Zoom, I recommend always having a clear and detailed agenda in advance. Many of our recurring agendas are planned to the minute to ensure we stay on track and maximize our time together.

A few minutes before we conclude, we ask everyone to rate the meeting on a 1–10, share thoughts about how it could have been even better (if lower than an 8), and also any appreciations they have for anyone else in the meeting. Again, this outro helps us come to a good conclusion, voice any frustrations and feel a greater level of human connection despite often being thousands of miles apart. I also learn in real-time about how well (or not) I’ve led the meeting, which helps me to continually improve as a leader.

5) Use OKRs for alignment and focus

As I’ve already shared, managing a distributed, remote team effectively requires that your people operate with an even higher degree of autonomy, which is one of the keys to intrinsic motivation.

Also, research shows that it’s important to measure performance of remote workers based on results rather than time.

There’s no better system I’ve found for driving alignment around the few objectives that matter most with a group of autonomous employees than OKRs (or Rocks, MBOs, V2MOMs or whatever your flavor of goal / objective-setting may be). Using objectives as a key management structure helps to shift an employee’s focus from task orientation to a results orientation.

To do this well, the first key is to make sure that your objectives are set and cascaded both top down (i.e. set your company-wide first, then department, then individual) but also bottom up, so you have a mix of things your people and teams are also seeing as important to improve that perhaps senior leadership doesn’t have on their radar.

The second key is to make sure you’re setting objectives that are specific and measurable, with clear accountable owners.

Finally, you need a system to keep these objectives top of mind so their owners are reminded to stay focused and continue to move things forward. At the same time, that same system needs to provide each of your managers visibility into the progress their team is making (or isn’t) week to week, enabling them to focus their support and help remove roadblocks in real time. Transparency around everyone’s goals is key, especially in distributed teams. This helps individuals to see how their work contributes to the team and company’s overall success.

6) Implement company-wide chat

If Zoom is your conference room, Slack is your open office. (I also assume Microsoft Teams is a viable option for this, but I don’t have direct experience with it.)

Just like an office, you need to think about leveraging Slack for all the kinds of interactions that you’d normally design for an office, which includes both work and social interaction.

We have two main channels that most of the company utilizes to maintain a feeling of connection.

The first is #working-on which started as a feed for people to post a quick note about what they were working on (so we could all maintain that sense of working together) but has since evolved into a general purpose channel for sharing work-related updates and wins from across the organization.

The second is #water-cooler. This channel offers the team a place to have the conversations you’d normally have in passing at the water cool, kitchen or in the hallways of your office.

Employees will share any number of things from a simple good morning, suggesting events, inspirational or funny stories or memes, offers for a quick virtual hangout on Zoom before their next meeting in 5 minutes, and recently, great options for things to do after work while being cooped up at home.

In addition to those channels, here are our recommended uses for Slack:

Each team should have their own channel or private group.

  • Depending on the sensitivity, you may choose whether it’s private or open. For example, #marketing is open because anyone from across the organization may choose to go and understand what’s happening in Marketing, or ask questions and offer suggestions.
  • We similarly have channels for #sales, #success, #support, #ios, #outbound_sdrs, #partnerships and #academy that are all open, whereas our @leadership-team channel is private as we may need to hash out ideas before presenting them to the entire company.

Create special-purpose channels for all business-related topics like announcements, triaging topic-specific questions, cross-functional teams, or individual office locations.

  • Some examples of channels we use are #product-announcements, #product-questions, #product-feedback, #pops-triage (for questions for our People Ops team), #billing-triage, #ios, #marketing_updates, #raleigh_office, #sf_office, #nyc_office, #european_team, #winning, #releases, #dev-ops, #dev-lounge, #customer_testimonials, and #best_self_management.

Use channels for social connection as well!

  • Slack is a great place to give your people an opportunity to connect around shared interests.
  • We have a wide array of channels that people can tune into to connect with one another, including #gratitude, #parents-of-15five, #peloton_crew (just created so our team can work out together using the peloton app!), #15five-activists, #disney, #fantasyfootball2k19, #ladies-of-15five, #music, #premier_league and #pets-of-15five to name a few.

In addition to channels, you can start impromptu conversations with any individual or small group of people.

  • These are great for asking quick questions, collaborating ideas and making decisions. In addition, we integrate Slack with Zoom so at any moment either party in the midst of a chat can type /zoom which will provide a Zoom link, and 10 seconds later we’re chatting face to face.

You might be thinking, with all this chat and conversation, when does anyone get any work done?! It’s worth noting that I get almost zero internal email, and treat Slack the same way most people do email.

It comes down to personal practices of both setting boundaries to do uninterrupted work, and checking in on regular intervals. Slack also has a nice feature to suppress notifications during non-work and other blackout periods, which is very useful.

7) Document everything

Being remote-first requires that you have a strong system for both shared files and documentation. We use a combination of Quip for general purpose documentation across all departments (with individual sections for things like Marketing, R&D, People Ops, Revenue Org, Science, Leadership, IT, Academy, Offices, Security and Compliance, etc), Google Docs for some work product, and Dropbox where we need to store actual files and creative assets.

Many teams, including our Revenue Leadership Team and Senior Leadership Team, keep copies of all meetings agendas with notes, decisions, and action items.

The engineering team keeps documentation on processes, practices, onboarding, and post mortems in Quip, logs all new feature tasks and bugs in Jira, and lives in Github where they submit code for review, provide feedback to others and manage our codebase. This also allows new engineers to ramp up in record time.

All of our guidelines, policies, procedures, process and in-progress work product for all departments are clearly documented such that a new employee can easily get up to speed on any project or situation, and have access to whatever they need from wherever they are.

Many companies have moved in this direction already, but it’s even more critical to have impeccable organization with a remote, distributed team, and in my opinion creates a higher standard for operating even if you are all co-located together.

8) Create a culture of appreciation and recognition

While we know that gratitude is one of the most reliable methods for improving well-being and can be practiced alone (e.g., by counting three good things each day, or by doing our Monday gratitude reflections) it can also be practiced in interaction with others. As it turns out, thanking others actually increases the likelihood for helpfulness (pro-social behavior) in organizations. When individuals feel socially valued and that their actions matter in other people’s lives, they’re more likely to engage in helpful behaviors.

People also thrive on being seen and recognized for their work. Giving praise and recognition (yes, even liberally) leads to the giver feeling more positive about their work, the recipient and the company as well.

Practicing gratitude is powerful in general, but in a remote environment it’s absolutely essential.

We decided this was so important that we even built a peer appreciation feature right into our product, called High Fives. It’s heavily used by our own team and many of our customers say it’s been an absolute game changer for their cultures.

If you don’t use 15Five, you can accomplish something similar by creating a Slack channel where people can give shout outs or High Fives to one another.

Also, High Fives help to increase the positivity ratio, or the amount of positive communication in organizations. Research shows high performing organizations are characterized by more positive communication than negative. Positive communication is characterized by appreciation, helpfulness, and encouraging words.

Having a company-wide practice like this helps to increase gratitude, recognition, and appreciation in the workplace, which in turn increases performance.

One of the other important benefits of creating a culture of giving public praise and recognition is that you as the leader get to see all of the incredible work that’s happening throughout your organization that you would otherwise have ZERO insight into, especially when your team is distributed.

Finally, not only is it great for both the giver and the receiver, but the positivity builds upon itself for everyone else who gets to witness and share in the appreciation. This is single-handedly one of the most powerful practices for building a strong, healthy culture I’ve ever discovered.

Manager/Employee Practices & Manager Effectiveness

While many of the management skills you normally lean on in a co-located environment are relevant when you go remote, once again it’s critical to have the right set and cadence of practices to do it well.

In my opinion 75% of a manager’s effectiveness, especially when it comes to managing remote teams, comes down to ensuring they’re engaging the right cadence of activities and having the right conversations at the appropriate time. By designing a structure upfront and putting that in place, it ensures these things happen.

Here’s the structure we encourage our managers to use at 15Five.

1) Weekly check-ins

As I’ve said, because you and your managers can no longer “manage by walking around,” you’re forced to grant trust and work in a high-autonomy relationship. In exchange, what you need is transparency, not micromanagement.

A weekly check-in is the best solution I’ve found to accomplish this.

Recurring check-ins ensure frequent and regular communication between managers and their direct reports. Research shows that regular check-ins are shown to improve objective factors such as productivity and goal accomplishment as well as subjective factors such as morale, trust, and engagement.

Each week, every employee reflects on their role and provides a brief update, sharing the following things with their manager:

- A quick pulse on how they’re feeling

A simple 1–5 scale works great, and they can optionally add some commentary about their rating.

- A green/yellow/red on their current OKRs/Rocks/Objectives/MBOs.

The color simply represents the confidence level that the objective will be accomplished by the deadline, along with the status of/progress towards any measurable key results.

This gives you as the manager a near real-time assessment of which of your team’s objectives are on track and which might be at risk, with time to actually do something about it if things get off track.

- A brief list of their top priorities for the coming week.

In addition, they can share the status of the priorities they laid out for the week prior with a simple done or not done.

- Bullet point answers to a few simple questions.

We always include some version of “What’s going well in your role? Any wins you’d like to share?” as well as “Any challenges you’re facing? What’s not going well?”

I find these two questions to be essential, but you can also add another question each week to break up any sense of monotony, get some great information, and spark important dialogues.

While I admit I feel a bit uncomfortable about being self-promotional at this time, I’d be remiss if I didn’t share about our product.

Check-ins is one of the things that 15Five is absolutely the best in the world at. I built our initial product for this very purpose, for myself, to manage my own remote teams. It works extraordinarily well and we now have thousands of customers using our check-in based platform to drive high-performance and engagement in their organizations.

To that end, I’ve instructed my team to make 15Five free for new teams of up to 50 people through June 15 during the peak of this crisis as our way of supporting you through this challenging time.

So far we’re hearing that it’s been a saving grace for many teams. Kristi Faltorusso, VP Customer Success at Intellishift just emailed our team today to share:

I just want to send a quick note to thank you for allowing organizations like mine, to leverage 15Five during this challenging time. I’ve only been using it for a few days but I already see a shift in how my team is engaging with each other. I hope to be able to continue with the service long after this, as I see immense value in it.

Be well and stay safe

To be clear, you don’t need 15Five to do this. You can certainly create a system that models the framework I’ve outlined above where you can have your team email you those updates in that format once each week.

However, if you choose to leverage 15Five as your platform, it will:

- Ensure that check-ins actually get done by managers across your entire company, by managing all the reminders and responses, and allowing your team to respond via the web or on their phones

- Give you the ability to respond in threaded conversations around specific points, even looping in other relevant parties who can help resolve an issue, and add key items to your next 1-on-1. CEOs I’ve spoken with claim that teams that use 15Five check-ins surface and resolve issues far faster than teams who don’t.

- Easily allow both your managers and their direct reports to build out their next 1-on-1 agenda as they interact with feedback from the check-in.

- Give you rich reporting and the ability to run interactive custom reports across your entire organization, allowing you to (optionally) engage with not just your direct reports, but employees and their answers across large cross-sections of your workforce. I relate to this as giving you superpowers as a CEO.

- Allow you to review your entire team’s check-ins quickly and in one place, so you (and your managers) can get briefed on every important project and initiative being led by each of your direct reports.

- Finally, 15Five also invites each of your employees to give their peers “High Fives” as the final step of each weekly check-in, which ensures a constant stream of peer acknowledgement and appreciation across the organization. You and the rest of your team can see a steady stream of those through the High Fives Dashboard or even have them piped into its own Slack channel.

To give you an idea of how customers view 15Five, our newest customers, Alexandra Erman, VP People at StreamSets, just posted on LinkedIn yesterday about her experience.

She shared, “Our teams are very distributed, and we can’t always grab someone in the hallway. 15Five is really helpful for improving communication at StreamSets,”

She also shared,“15Five is definitely an employee-centric product. It encourages employees to take ownership of their individual milestones. It provides an opportunity to check in asynchronously for those who are still building their comfort with a culture of two-way feedback. It allows for agile movement and change.”

2) Regular 1-on-1s

So if I’m doing check-ins, why do I need to do 1-on-1s?

Check-ins are NOT a replacement for in-person (or in this case, video) 1-on-1s, which are an essential management practice, especially with remote teams when face-time doesn’t necessarily happen by default.

That face-time is important for building a relationship and trust, driving accountability and results, supporting an employee in their growth and development, and helping to resolve more challenging issues.

Check-ins do however have the ability to supercharge your 1-on-1s. The reason for this is simple. Because your 1-on-1s are what I consider expensive time (because they’re synchronous and require mutual scheduling), they should be designed for maximal efficiency and impact.

Check-ins get the updates out of the way, and even allow you to converse about, address and even resolve issues in between your 1-on-1 meetings. They also allow you to tee up the most important conversations by adding them to your next 1-on-1 agenda as you move forward. That way, come 1-on-1 time you’re ready to go and able to spend less time getting up to speed, and more time digging in on the few, more critical items that need your time and attention.

I recommend a regular cadence of 1-on-1s on the same time and day so you can set them and forget them. Depending on the situation, they can happen either weekly or every other week, for between 30 to 60 minutes; however, I’ve found that when combined with check-ins they can happen less frequently for less time.

Because I rely on check-ins to keep me informed, I have standing 30-minute 1-on-1s every other week with my leadership team, but we connect for ad hoc work sessions in between. However for many of your managers, a weekly cadence is likely more appropriate.

3) Spontaneous messages or calls to check in and see how your team is doing

It can also be good practice with remote employees to reach out periodically via Slack, text or a phone call just to check in. One of my leaders will often do this during his daily runs or chores and ask his team simple questions like:

- How are you doing?
- How’s XYZ deal going?
- What’s the latest on ABC?
- Anything I can do to help you?
- What do you think about _____?

Sometimes these are just two minute conversations, otherwise 45 minutes. They just talk, no agenda.

4) Office hours

Because you’re not sitting at your desk in the office, your team can’t just walk by and ask you to chat or hop into a meeting they are having with their team in the conference room.

Having a weekly block of office hours available on your calendar where any one of your managers or team members can book a slot is a great leadership practice. You’re making yourself available for the inevitable issues that come up throughout the week and provide your people another key touchpoint with you.

5) Reviews

Finally, the weekly/bi-weekly cadence of check-ins and 1-on-1s is a great rhythm for reflecting on and staying on top of the work that needs to happen in the near term, it’s not a great structure for reflecting on things happening on a longer trajectory.

For these we do recommend some sort of regular, more zoomed out review. We practice a lightweight form of performance review that we call the Best-Self Review (because it’s designed to not only assess past performance, but also focus on the future growth and development of the employee over time).

We recommend doing these reviews anywhere from 2–4 times per year (vs annually) as they serve as more detailed checkpoints over time to assess performance, growth and an employee’s career trajectory.

Individual Work Practices

It goes without saying that while there are a number of great benefits of working remotely, there are also many personal challenges which can arise for people that include loneliness, family distractions, the psychological implications of not having distinctions between your work time and home time, and an inability to focus or procrastination.

Much has been written about how to be productive working from home and creating clear boundaries, so I’ll just share a few of the most important things I’ve found for myself. Regardless, it’s important to understand that different people experience some, all or none of these challenges, so providing some training, guidance or resources to your employees can be helpful.

1) On time = one minute early

Our standard at 15Five for meetings is that on time means one minute early. For example, our Boosts start at 9am sharp so we ask that everyone be on Zoom by 8:59am.

This isn’t different from your on-time standards at your office, but because there are lots of different links and things that people need to click, it’s important that you’re clear about your standards and practice time integrity to avoid wasting people’s time.

Sure, there are inevitable slips, and we do our best to alert each other if it looks like someone is going to be late, but having this kind of standard makes EVERYTHING work much more smoothly across the board.

2) Slack time vs. Solo Time

It goes without saying, but if you’re ALWAYS available on Slack (or email), you’re always multitasking. Studies show that to be maximally effective and productive, you need time to single task and do deep work.

I recommend a practice of scheduling this time for deep work in advance.

During these times of focus, make sure to manage potential at-home interruptions, close your Slack and email, and put all phone/email/Slack notifications on hold. We encourage everyone to communicate their availability so there’s not an expectation of an immediate response.

At the same time, we need to move fast and that often requires coordination, so we do ask that people check in periodically throughout the day and respond to communications.

3) Dedicated workspace

In an ideal world, each of your employees would have a dedicated space where they can “go” to work, and ideally create privacy and minimize distractions as necessary for work calls and focused work.

This may not be possible at this moment because of how fast these shelter-in-place orders and physical distancing mandates have come online, but I highly recommend that people create a dedicated home office workspace in whatever fashion possible.

In the past week I’ve even seen some really creative ways that our people have made this happen!

One of 15Five’s SDRs getting creative with his “coronavirus” desk
One of 15Five’s SDRs getting creative with his “coronavirus” desk

3) Pomodoros & Music

To create the space of focused work, I’ve found the practice of the Pomodoro Technique (where you set a timer for a work block of say 25 or 50 minutes followed by a 5 to 10 minute break) to be the most effective focusing practice I’ve found.

I like combining those pomodoros with music (as I’m doing right now as I write this), and use a service called focus@will which curates music exclusively designed to increase focus along with an integrated pomodoro timer (they also happen to be offering 50% off to support people facing unexpected challenges during this time — I have no relationship with them, just passing it along).

We also have a #listening-on channel in Slack where our team posts what they’re listening to while working. It’s another really fun way to get to know each others’ interests, have access to new musical experiences, and share something meaningful with others. (Not to mention, sharing with others can be a great mood booster in itself!)

I’ll leave with a few notes about leading in this time of crisis. It goes without saying that it’s very likely some number of your employees are feeling unsettled, afraid, overwhelmed and/or frustrated with the current situation.

As leaders, our teams are looking to us to provide them with a sense of groundedness, clarity and direction, and have an opportunity to help them feel safe, protected and supported.

I’ve also been amazed at displays of human spirit in the midst of this crisis, with Spanish residents under lockdown engaging in aplauso sanitario, coming out on their balconies each night to applaud the healthcare workers, while the Italians come out on theirs to make music.

I’ve been party to conversations of people coming together to serve in any way they can, and seeing so many of our own employees rise to the occasion to see how we can radically help our customers and others during this very difficult time.

I am certain that it is precisely the socially-connected, remote-first culture that we intentionally built at 15Five, the one I have just laid out for you, that has allowed us to communicate, collaborate, support each other personally and professionally, and do some of the best work of our lives these past few weeks. As a leader, I could not be more proud.

One of the best and simplest ways I can suggest to channel and embrace this spirit in your own company, is to invest in putting in place these practices of social connection alongside work productivity. In my experience the levels of trust, camaraderie, and cohesion that this fosters over time only leads to better business outcomes, better companies, and more profound impact for everyone you serve.

I wish you all the best.


P.S. I’ll leave you with a few other offers of resources that my team has prepared on remote work that may be helpful for your efforts:

  • Use 15Five free for teams of up to 50 people through June 15. This is our small way of helping you through this tough time, no strings attached. My hope is that the lockdowns and physical distancing measures will be done by then. If you’re still finding value with 15Five after June, we’d be happy to welcome you as a customer.
  • A recent Webinar, Protecting Productivity: The Shift to Remote Work by Jeff Smith, PhD, 15Five’s Director, Best-Self Academy, for HR, managers and team members shifting to remote work.
  • Join our upcoming webinar on March 31st, Effectively Leading & Managing Remote People & Teams, led by Jon Greenawalt, 15Five’s Chief Performance Officer, who will educate newly remote managers on some proven and practical ways to increase their effectiveness in leading and managing their people remotely.
  • Our Transformational Services group has also designed a remote work workshop, Remote Work Essentials Training for individuals and leaders/managers who have never worked or had to manage people and teams remotely. If that’s of interest, you can download our PDF or reach out to
  • Listen to our most recent episode of the Best-Self Management Podcast, How To Transition To A Fully Remote Team In The Time Of Coronavirus, where I discuss many of these principles with 15Five’s Chief Culture Officer, Shane Metcalf.
  • Finally, I highly recommend Josh Bersin’s post from earlier this week, The Big Reset: Making Sense of the Coronavirus Crisis. He shares his view on how this crisis will likely reshape our world, and writes, “The first big Reset is that we’re going to make digital, remote work thrive… and we’re going to do it in a human way.” I couldn’t agree more.

What are some great remote work practices that your company has implemented? Please leave a response below.

David Hassell is a serial entrepreneur, business columnist, and speaker, who believes that when leaders support their employees in becoming their best selves, high engagement, performance and uncommon loyalty naturally result. As co-founder and CEO of 15Five, David and his team have developed industry-leading performance management software that helps leaders and managers drive high performance and build phenomenal cultures via a suite of features including weekly check-ins, OKR tracking, 1-on-1s, and peer appreciation.

While at 15Five, David created the science-inspired Best-Self Management methodology that helps leaders and managers address the hidden factors that stimulate sustainable growth and development — things like intrinsic motivation, growth mindset, strengths, positivity and psychological safety in the workplace. David and the team practice Best-Self Management and use 15Five internally, which they credit with their near zero attrition, rapid growth, and awards like Inc.’s Best Places to Work and ranking #3 on Glassdoor’s Best Places to Work list for companies with fewer than 1,000 employees. David formerly served as President of the San Francisco chapter of the Entrepreneurs’ Organization and was later named “The Most Connected Man You Don’t Know in Silicon Valley” by Forbes Magazine. He has also been featured in The Wall Street Journal, Inc., Entrepreneur, Fast Company, and Wired. Follow him on Twitter @dhassell.