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The CEO’s Ultimate Guide To Remote Work, Part 3: Company-Wide Practices

David Hassell, Co-Founder and Executive Chairman of 15Five

As a primarily work-from-home, remote CEO of a company honored to have won multiple awards for its culture, I’ve gained a lot of hard-won expertise over the last nine years building 15Five as a remote-first company, now over 200 employees. 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 transitioning your people to remote work and help you successfully lead your teams.

Here are eight company-wide practices you can implement in your organization that will contribute to building a resilient and productive distributed culture.

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 excuses 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 that 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.

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.

Keep reading The CEO’s Ultimate Guide To Remote Work:

– Part 1: Boosting Manager Effectiveness

Part 2: Individual Work Practices

– Part 3: Company-Wide Practices

– Part 4: Shifting Your Mindset

David Hassell, CEO of 15Five

David Hassell is a business columnist, speaker, and serial entrepreneur who believes that when leaders institute cultural practices that support each person in being and becoming their best self, high performance and uncommon loyalty naturally result. As co-founder and CEO of 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, strengths, and psychological safety. David has been featured in The Wall Street Journal, Inc., Entrepreneur, Fast Company, and Wired. Follow him on Twitter @dhassell.

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