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19 Foundational Tips for New Remote Managers

By Ben Congleton, with many contributions from Olarkers and friends

Coronavirus just created a worldwide experiment in remote management.

Almost anyone can work from home successfully a few days a week (or even for a week!), but when weeks turn into months, the tactics and processes you developed working in an office break down for remote teams.

I wrote this guide with our team because we’ve run a remote company for over 10 years and know how hard the transition can be. From face-to-face management to remote management, from in-person employee to remote employee – I want you to be ready to bring your whole self to the challenges unique to working remotely.

Note: This is a living remote guide that most will find helpful when transitioning to remote-first environments. However, we recognize that we're all working (and living) in a particularly sensitive time, worldwide, with COVID-19. Remote work, like everything else, also looks a little different during a pandemic. At Olark, we've found that really honing into our values (especially #speak and #practice) in addition to some added flexibility, has allowed us to elevate our remote environment to our current challenges.

The challenge of going remote

You no longer have any built in physical boundaries between work-life and home-life.

You will need to be creative to create a replacement for your commute - comic by Jeff Koterba

You will need to create a replacement for your commute.

This may feel counterintuitive. Isn’t the lack of a commute one of the biggest reasons everyone is raving about remote work? Sort of. You may not realize this, but your commute is serving a purpose: it is mental space and time between home and work. It is your time. Commuting serves at least one valuable benefit, mental buffer time, and often serves as one of the few periods of personal time we get each day.

Lose the commute, and lose this buffer time. It is not hard to imagine rolling out of bed, showering (or not showering), grabbing breakfast and carrying it over to your laptop to start your day. In fact, is that how you started your day today? It’s more or less how I started my day if I interspersed some anecdotes of taking care of small children.

Some solutions I’ve tried or heard others try: Starting the day off with a great device-free breakfast, taking a solo drive to clear your head, creating a new morning exercise or meditation routine. When not under quarantine, dropping kids off at daycare, commuting to a coworking space, or creating a coffeeshop routine can also help.

Tip #1:
Create mental space and time between work to help you wind up and unwind every day.

Your kids, your pets, your significant other, and your dishwasher will distract you.

When you are an office worker, you likely work from home occasionally to help catch up on life.

Working remotely means work is no longer physically separate from your life. Your pets, children, and significant others will all know you are around. In fact, you will be physically present to help with all sorts of home-related activities, at any time. The dishes in the sink will call out to you. You’re home, so why not go ahead and put those dishes in the dishwasher, right?

Challenges I’ve personally or heard of others dealing with while working from home: flooded basements, dogs that need to go on walks mid-day, children who can’t be brought to daycare due to illness, diabetic cats, windstorms, power outages, tracking down dogs that have jumped the fence, doctors appointments, feeding children lunch, letting a significant other take a nap, grocery shopping, dishes, cleaning up messes pets made, barking dogs, meowing cats, preparing meals…the list goes on.

Your home life is full of challenges. In an office, these challenges are not concurrent with your challenges at home. This is a big transition and there is no silver bullet.

Tip #2:
You must have a door that closes, and is relatively sound isolated from the rest of your house.
Tip #3:
There are real benefits in the act of "going to work" and being surrounded by people working. Coworking spaces and coffeeshops solve many important needs including removing distractions.
Tip #4:
Set and commit to boundaries with your pets, children, and loved ones. Being home does not mean you are available. Specific work-hours can work wonders.

Your work will no longer automatically fulfill your social needs

Say goodbye to regular lunch with your coworkers

More than 90% of us have friends at work (Future of Workplace / Virgin). Over 50% of us report we have a best friend at work. Working remotely will not cause your friends to disappear, but it will change the way you interact with them. Grabbing lunch together starts to involve a commute if your coworkers are local, and becomes more or less impossible if your coworkers are geographically distant.

You won’t run into people in the halls or walking from your car. You may find that you spend most of your day interacting with your cats, and when your significant other returns from work and wants a break from interacting with people, you may find yourself needing social interaction the most. If you have kids, you may find yourself missing the company of adults.

There are many solutions to this problem, but they don’t work for everyone. We’ve heard positive results from coworking virtually, shared group chat rooms, online group fitness classes, scheduling lunches and coffee dates on FaceTime. When not under quarantine, participating in sports teams, trivial nights, attending weekly lunches, and carving out ‘me’ time in the evenings to attend events can help.

Tip #5:
Be realistic about your social needs and create new routines to make sure you fulfilled.

Physical isolation can impact your mental health

Solitary confinement and remote work are not the same, but humans are social beings and need varying amounts of social interaction. It is well known that having a strong community of family and friends creates longevity, it is well known that isolation impacts mental health.

Your coworkers and managers will no longer automatically know how you are doing from informal interactions. If you have a strong informal support system at your office, you will need to build a more formal explicit support system when working remotely.

Some solutions I’ve seen others use: virtual therapist appointments with companies like Talkspace, setting up video chats with coworkers, scheduling team retreats on video calls, being transparent about your mental state with your co-workers or managers, open communication when taking time out of the office for mental health reasons. When not under quarantine, in-person therapist appointments, coworking spaces, in-person team retreats, and building healthy in-person social routines can help.

Tip #6:
Checking in with a therapist and/or an executive coach can help you catch new mental health challenges quickly.
Tip #7:
Start meetings with "if you really knew me, you would know" to build a practice of disclosure and transparency.

You are now your own IT department

Your internet may not be as reliable as you thought it was

In most offices, there are people in charge of ensuring that your internet is fast, available, and reliable. Having worked remotely for 10 years, I have become accustomed to intermediate outages and slowdowns in internet connections impacting meetings, important conversations, and creating frustration.

Solutions I’ve tried or heard others try include: purchasing a 5G hotspot as a backup, tethering my phone, cutting out video, dialing into meetings using a phone, upgrading my internet connection so that both me and my wife can be on video calls at the same time, upgrading my physical network hardware to reduce latency, using Facetime, and/or calling colleagues directly, or even rapping tinfoil around a USB-C to HDMI connector to reduce interference with WIFI.

Imagine losing your internet connection at the worst possible time during the most important conversation. It will happen, and you’ll need a plan to recover quickly.

Tip #8:
Invest upfront in making sure you have a backup plan for when your home internet connection goes down or becomes unreliable.
Tip #9:
Test your internet speed using a tool like speed test, if you and your significant other are both working from home you may want to upgrade your connection speed if your upstream is less than 5mpbs.
Tip #10:
Subscribe to a business plan with your ISP with an SLA. You'll get better phone support and faster internet recovery in an outage.

Your computer will break and you will be on your own.

When you are in an office and your computer breaks, you can hand it to IT. When you are remote and it breaks, you are lucky if you can drop it off at an Apple store. If you are unlucky, you may need to ship it off for service. Without your primary computer, you will likely be unable to access your VPN without coordinating with IT.

Solutions I’ve tried or heard others try: buying a cheap Chromebook, portable hard drives for backups, as well as assorted connectors to be able to mount and boot from an external hard drive.

Imagine not being able to work for days because your primary computer is hosed while trying to meet a critical deadline. It will happen.

Tip #11:
Have a plan in place for when your primary computer goes down, make sure you have some plan to keep your computer backed up.

The challenge of managing remote employees

You no longer have physical visibility into your team’s emotional or physical state

In an office, you can hear a coworker sneezing and another talking excitedly on the phone. You knew that one of your teammates was going through a tough time by the way they sat at their desk. You know this because you can observe your team and look for physical cues. When working remotely, you are left with few tools to assess the situation on your own and must rely on well placed questions and cultural norms.

Some solutions we’ve seen tried: in depth 1:1s that dig below the surface, building a culture of transparency and disclosure, normalizing radical candor, building trust to create a safe psychological space, and using video calls on a regular basis to bring in more context.

Tip #12:
As a manager you need to normalize disclosure of physical and emotional state so your team acts with the transparency needed for you to do your job. You can do this by starting meetings with "If you really knew me you would know" and modeling behavior that provides more transparency than expected to encourage others to follow your lead.
Tip #13:
Train your team to be explicit about situations where their health or emotional state is impacting their work. They could disclose this in a standup or in a weekly retrospective, but it's important to put the ownership on your teammates for reporting unobservable impacts on their productivity.

It becomes harder for the big picture to be absorbed via osmosis

Imagine working at a huge company where you never see anyone from another department in your building. You never overhear anyone in sales talking to a customer, you never walk past a conference room full of sticky notes where a UX designer is sketching out a new product feature. There’s no impromptu discussions with teammates from other teams at the water cooler.

Siloing is real and it happens naturally. The challenge is that in a remote company, siloing happens quicker and requires explicit process and thought to prevent.

Some solutions we’ve tried: weekly all hands with full status updates from each lead, weekly all hands with deep dives from each team in a quarterly rotation, bi-weekly status update memos, cross functional collaboration meetings, quarterly and annual kickoffs, placing links to our vision and goals at the top of every meeting document, founder AMAs, mid-quarter checkins with each team, putting extra effort into framing the WHY behind our actions in writing.

Tip #14
Overcommunicate the WHY, the HOW, and the WHAT behind decisions you make as a team and as an organization. Repeat until you get tired of saying it.
Tip #15
Create space for lengthy discussions after any public presentations. These calls are big opportunities for creating shared cross functional - understanding.
Tip #16
Encourage your teammates to #speak their mind and ask questions, no questions should be considered a "dumb" question.
Tip #17
Be proactive in collecting questions from other departments and teammates, in a remote company it is likely that messages will get lost and you'll never overhear miscommunications in the break room.
Tip #18
Use All hands meetings for clarity, but do not expect everyone to walk away aligned. Post meeting surveys can help.
Tip #19
When crafting vision, spend less than 20% of the time wordsmithing and 80% of your time creating alignment and commitment.

More Coming soon

This guide is a Work-In-Progress. Want me to email you when we update this guide? Signup for updates here (I promise to only send you an email when I update this guide)

This guide is an Olark collaboration, special thanks to Sarah, Kaitlyn, Mandy, Miranda, and others for their contributions.

Special thanks to Jeff Koterba for permission to include his comic in this post