How to Work Remotely

An Orchestration Guide

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First, A Word from the Author

Why hello, it appears that good fortune has brought us together. Welcome to my guide to remote work.

I originally created this guide for a guest lecture at Colorado College, to pass along my knowledge to fresh graduates entering their first jobs. Then, I adapted and expanded it for my marketing agency to guide my team on the best ways to work. Years later, what you see now is the latest iteration, updated and expanded with hard fought lessons learned from 9 years of working remotely. I sincerely hope you find this advice useful & valuable.

Andrew Ishimaru
Founder & CEO, Orchestration

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1) The Basics

Planning Your Workspace

Your "Office"

When working remotely, one of the most important things you can do is establish a designated workspace. This means creating a physical separation between your “work” space and your “living” space, in order to create mental distance between the two. Having a dedicated workspace can help you stay focused and productive, and can also help you maintain a healthy work-life balance.

To set up your workspace, start by designating a specific area in your home that will be used exclusively for work. This could be a spare room, a corner of your bedroom, or even a section of your living room that you can partition off with a screen or divider.

When choosing your workspace, it’s important to consider your surroundings. Make sure you have a reliable and fast internet connection, as this will be essential for video calls and other online communication. Additionally, try to avoid sitting in an area with backlighting, as this can make it difficult for others to see you clearly on video calls.

Another important consideration is comfort. You’ll likely be spending many hours sitting at your desk, so invest in a comfortable chair that provides proper support for your back and neck. Additionally, think about the vibe you want to create in your workspace. Surround yourself with the kind of style that helps you feel focused and productive, whether that means adding plants, artwork, or other decorative elements.

By creating a dedicated workspace that is separate from your living space, you can establish a clear boundary between work and home. This can help you maintain focus, avoid distractions, and ultimately be more productive in your remote work environment.

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Good Habits

Choose a work spot where you won’t be distracted

If you’re working in a cafe or high energy place, get headphones that block noise. You don’t necessarily need expensive noise cancelling headphones as long as you can’t hear your environment when music is playing.

Try experimenting with different work environments to see what you like best.
Sometimes it can be fun to just switching things up a bit.

Tech Recommendations

Basics

Get a fast laptop.

Get a standalone mouse like this one. Your wrists will thank you and your workflow will speed up.

Get headphones with mic like this one that actively cancels background noise around you for mic input so you can take meetings in loud environments.

Home Office

It’s important to create a workspace that supports your productivity and comfort. A key component of your remote workspace is your home office, which should be equipped with the necessary tools and furniture to help you work effectively and efficiently.

One of the most essential tools for remote work is a high-speed wifi router. This will ensure that you have a stable and reliable internet connection, which is crucial for video conferencing, online collaboration, and other remote work tasks. Investing in a high-quality router can also help you avoid the frustration and inefficiencies that can result from a slow or unstable internet connection.

In addition to a reliable internet connection, it’s important to consider your lighting setup. For video meetings, it can be helpful to have a lamp or light rig behind your camera, which will help ensure that your face is properly lit and visible to others on the call.

Another important aspect of your remote workspace is your furniture. Investing in a quality chair that allows you to sit comfortably with good posture is essential for avoiding back and neck pain, which can result from prolonged sitting. Similarly, a good sturdy desk will provide a stable surface for your work materials and can help you maintain focus and productivity throughout the day.

Highly Recommended

• High quality external video camera like this one
• High quality external mic like this one
• Mouse pad - this allows consistent & fast mouse use on all tables including glass. Great for travel.
• Laptop stand (Roost is good)

Nice to Have

• External monitor (second screen)
• Local SIM card if traveling
• High quality backpack with organization system for taking your “remote work setup” out of your home

Your Digital Space

Staying Organized

Working remotely can present unique challenges when it comes to staying organized and on top of your workload. Fortunately, there are several strategies you can employ to help you stay on track and be more productive in your remote work environment.

One of the most important aspects of staying organized is keeping track of your notes and files. Don't use paper notes or random documents. Use digital notes to keep track of your to-do lists, project ideas, and other important information. This will help you stay organized and make it easier to find what you need when you need it.

Another key component of staying organized is keeping your files and documents in order. This means creating folders for different projects or categories of work, and ensuring that everything is synced across your devices so that you can access your files from anywhere. Using cloud-based storage solutions like Dropbox or Google Drive can be especially helpful in this regard, as they allow you to access your files from any device with an internet connection.

In addition to digital notes and organized files, using a password manager can help you stay organized and secure when working remotely. Password managers allow you to securely store and access all of your login credentials in one place, making it easier to log in to the various websites and apps you need to access throughout the day.

Finally, adding bookmarks to Chrome for websites and apps you often use, or important links you want easy access to, can help you stay organized and save time when navigating between different tools and resources.

Basic Productivity Tools

• Todo list app
  (Todoist, Google Keep)
• Calendar app
  (Google Calendar, Outlook)
• Project management app (Asana, Monday, etc.)
• File storage app
  (Google Drive, Dropbox, etc.)

Organizing Your Communication

Inbox Zero: In today's fast-paced and digitally-driven world, managing email can be a time-consuming and overwhelming task. This is where the concept of "inbox zero" comes into play. The inbox zero system is a method of email management that aims to keep your inbox empty or close to empty at all times.

The idea behind inbox zero is simple - by processing and addressing every email as soon as it arrives in your inbox, you can reduce the clutter and distractions associated with a bloated email inbox. By clearing your inbox regularly, you can stay on top of your email correspondence, prioritize your workload more effectively, and reduce the stress and anxiety that can come with an overflowing inbox.

One of the main benefits of using the inbox zero system is that it can help you stay more focused and productive throughout the day. By eliminating the distractions of an overflowing inbox, you can devote more time and energy to important tasks and projects, without getting sidetracked by non-essential emails.

Several notable figures in the tech industry, such as Merlin Mann and David Allen, have popularized the concept of inbox zero and are strong advocates for its benefits. While the inbox zero system may not be suitable for everyone, it is a valuable tool for those looking to improve their email management skills and maximize their productivity while working remotely.

By adopting the inbox zero system and processing your email inbox regularly, you can stay on top of your workload, reduce distractions, and achieve greater levels of focus and productivity in your remote work environment.

Slack setup: with so many channels and notifications coming in throughout the day, it can be difficult to stay focused and avoid distractions.

To help manage your Slack channels more effectively, consider using the favorite/star key feature to keep track of the channels that are most important to you. This will allow you to quickly access and prioritize these channels, without getting bogged down by less important messages and notifications.

Additionally, changing your notification defaults can be an effective way to manage the flood of notifications that can come with using Slack. By hiding channels that you don't use frequently, or ones that have no new messages, you can reduce the number of distractions and interruptions you experience throughout the day.

You might like doing things the analog way: writing notes on paper, paper calendar on the wall, etc.
Don’t do that.
Paper is not searchable. You can’t send it easily to your colleagues.
Go digital.

Staying Productive

Organizing your work

There are many different types of to-do lists and task management systems available, from simple pen and paper lists to complex digital platforms like Todoist, Asana, Trello, Monday, and Height. The key is to find a system that you like and that works for your individual needs and preferences. Once you find a system that works, make sure to stick with it to maximize its benefits.

In addition to a to-do list, it can be helpful to use a calendar to organize your time and schedule both work and personal commitments. By scheduling your tasks and appointments on a calendar, you can ensure that you have enough time to complete important tasks and avoid conflicts with other commitments.

Finally, when setting goals, it is essential to use the SMART framework to ensure that your goals are specific, measurable, achievable, relevant, and time-bound. By setting SMART goals, you can ensure that you are working towards tangible and achievable objectives, rather than simply spinning your wheels and wasting time.

Optimizing yourself

In order to work remotely successfully, it is important to optimize yourself by taking care of your physical and mental well-being. One simple way to do this is to drink quality coffee or tea, which can help to boost energy levels and improve focus throughout the day.

Another key aspect of optimizing yourself when working remotely is to prioritize physical activity and movement. Whether you prefer going to the gym, playing sports, or simply going for a walk, it is important to stay active and healthy in order to maintain your physical and mental well-being.

Additionally, it is essential to integrate your work routine with your life routine in order to ensure that you are able to balance your personal and professional commitments effectively. This means planning your meetings and appointments carefully so that you don't miss important events in your personal life, but also making sure that you don't miss important meetings or deadlines because of other commitments.

You don’t want to miss your son’s football game because you didn’t plan your meetings well. You also don’t want to miss an important meeting because you didn’t plan your dentist appointment well.

Set SMART goals

2) Personal Habits

Looking Good on Zoom

Your Space

When it comes to remote work, creating an appropriate workspace is essential to ensure that you are able to maintain focus and productivity throughout the day. One important aspect of your workspace is ensuring that you have a clean and organized background behind you during video calls or meetings.

If you are working from your bedroom or a shared home space, it is important to clean up the area and make your bed before getting on a call. Additionally, you should avoid backlighting behind you, such as windows, as this can create a distracting glare on camera.

When positioning yourself in the room, it is important to choose a location where people and distractions will not appear behind you. This means placing yourself in a spot where doors are in front of you, rather than behind you.

Finally, adding interesting and visible items to your background can serve as great conversation starters and help make small talk and introductions more enjoyable. Consider incorporating sports equipment, art, family photos, or hobby materials into your background to add a personal touch and make your workspace feel more inviting and engaging. By creating a comfortable and visually appealing workspace, you can enhance your overall remote work experience and achieve greater success in your role.

You

it is important to make sure you present yourself in the best possible way on camera during meetings or video calls. One of the most important aspects of this is the lighting and camera setup. Ensure even lighting across your face and body by putting a light source in front and to the side of you. Experiment with light position to find what works best for you.

Elevate your camera so it is even with your face. This will help you to avoid looking down at the camera, which can be unflattering and give the impression of disinterest. Stacking books under your laptop or using a laptop stand like Roost can help you achieve this. Alternatively, you can use a USB camera like this good one and clip it to an external monitor or other object at face-height.

In addition to the camera setup, good posture is essential. When sitting for long periods, it is easy to slouch or hunch over, which can cause discomfort and fatigue. Sit up straight and make sure your back is supported. This will not only help you avoid pain or discomfort, but it will also help you look more professional and attentive during video calls.

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Meetings with your video on is ALWAYS better than video off.
It’s an opportunity to use your body language to influence the meeting and connect better with your colleagues.

Yes, it’s more work. You need to dress well. Shower. Put on makeup. Clean your space. Look at the screen the whole time. But, that’s the point. You would never make lunch during an in-person meeting. Stay mentally and visually present.

You will be perceived as harder-working, sharper, and better than others who keep video off.

Working Habits

Working at Home

• Minimize distractions in advance of working.
• Make sure to get out of the house from time to time.
• Take walks. Walking meetings can be great to mix things up.
• Separate your sleeping space from your working space.

Working Away from Home

• If you go to a cafe/restaurant/etc. Be respectful to the staff & other guests, and order something to drink/eat.
• Sit at tables close to an outlet
• Use the Speedtest app to check internet speed before you buy anything
• Make sure you have a noise cancelling headset if you intend to take meetings at the cafe

Travel Work Tips

General tips

Reliable and fast internet access is crucial for remote work. Before selecting your workspace, it is essential to prioritize internet accessibility. While searching for apartments or Airbnbs, filter your options by wifi availability and inquire about the up/down speeds in advance. Once you have arrived at your location, ensure that you have a strong internet connection by installing the Speed Test app and running tests frequently. Additionally, it may be worth looking into nearby coworking spaces or coffee shops to have backup options if your home internet goes down. Utilize Google Maps or Yelp to search for reviews that mention "wifi" to find the most reliable spots. By prioritizing internet access, you can ensure that you stay productive and efficient while working remotely.

International travel

• Make sure you have a universal power adapter that works in the country you’re going to
• Get a VPN in case you need to change your IP location or get around national firewalls. Also for security reasons.
• Get a local SIM card with 4G/5G connectivity as soon as you arrive. Americans need to buy an “unlocked” phone for this.
• Take out cash in the local currency ($50+) as soon as you arrive

3) Communication

The Communication Hierarchy

Everything always seems important. Context shows how important it really is.

Least critical to most critical

1. Thinking about saying something
2. Snail mail
3. Open Slack channel
4. Email
5. Project management tool comments
6. Direct Slack message
7. SMS / Whatsapp message
8. Video call (Zoom)
9. Direct phone call

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Levels of escalation

1. “Important, let’s circle back on it” 
2. “Important, but it’s a ways out”
3. “Important, and I’m working on it soon”
4. “Important, and I’m working on it now”
5. “Need help, it’s important”
6. “Urgently need help”
7. “Critical, everything is on fire, call me now”
   
   

The most important rule of remote work

Pick up the phone and call if it’s urgent.

Communicating Like A Pro

Determine the right comms channel to use

• What needs to be communicated? 
• How important/urgent is it really?
• What’s your organization’s policy on what channels to use?
• Are you talking to the right person(s)?
  
  

Consider the synchronicity of your comms channels

Synchronous (Meetings, phone calls, video calls)

• This is best when you need to reach someone quickly, but it can interrupt their work. However, this is the fastest way to collaborate.

Asynchronous (Slack, Email, SMS, Whatsapp)

• Recipients can receive your message and respond when it’s most convenient for them. However, this can add time delays to collaboration.

The Note Agenda System

What is this?

In a remote work environment, it is important to be respectful of your colleagues' time while still ensuring that urgent matters are addressed promptly.

To strike a balance, consider keeping a running list of items that require discussion with your colleagues. This allows you to bring up these topics at a convenient time for both parties, such as during team-wide meetings or scheduled 1:1 meetings.

This practice is particularly valuable for managers and leaders who have the authority to interrupt others for important reasons but don't necessarily need to do so every time something comes up. By keeping a list and bringing up items at appropriate times, you can help ensure that everyone's time is used efficiently and effectively.

How to do it

1. Add a section in whatever document you use to take daily/weekly notes.
2. When something comes up that’s not urgent, add that person’s name and the thing that needs to be discussed as a sub-bullet under it
3. At the beginning of each week, look at this list and check your calendar to see if you need to schedule any extra meetings to discuss important things on the list, or if you can fit your agenda into existing meetings on your calendar.

Empathy: The Sixth Sense

Warning Signals

• Something feels “weird” or “off”
• Someone’s body language is unusual on video calls
• They aren’t communicating "normally"
• No video on Zoom
• Missing meetings
• Someone else on the team comments about them
• This could be internal or external but applies just the same between a colleague and a client

What to Do

DON’T assume you know what’s going on. You don’t.

Reach out to that person immediately to make sure everything is OK. Find out what’s going on.

It’s entirely possible they were just had a bad day and all is well otherwise. But if there’s a work related issue, you and your team need to know about it even if that person doesn’t feel like bringing it up for some reason.

Once you know what’s up, you can proceed with a solution or peace of mind.

What To Do When Things Go Wrong

This will most likely happen at some point to everyone.  Sometimes mistakes happen, expectations are missed, etc. - and in a remote environment, it can be more difficult to resolve these kinds of situations and easier to avoid dealing them.

Here’s how to fix things

1. Deal with the problem as soon as possible. Putting it off will make it worse.
2. Notify anyone relevant on your team ASAP.
3. Take ownership & responsibility - no excuses, defenses, or blame. Even if you don’t feel like you did anything wrong.
4. Be transparent and honest about what went wrong.
5. Come prepared with solutions to move forward.
6. Immediately call anyone external who is involved and let them know there is an issue on a phone call, Zoom, or face-to-face meeting. Do not do this over email/Slack/text. 
7. If they don’t answer, send them a message saying that we have identified a problem, and let them know you are working on a solution.
8. Make it right with the other party(s), and make sure the problem won’t happen again.
9. Check in on your solution after its been in place for a while, is everyone feeling good about the solution & is the problem solved?

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Communicating Across Time Zones

Different policy models

True Asynchronous: Everyone sets their own schedules. Communication in real time is not expected by default.

Meeting Synchronous: Everyone sets their own schedules but must be present for pre-planned meetings.

Partial Synchronous: Everyone must be online together for a few hours regardless of time zone. For example, a US company has 9am - 5pm hours in San Francisco and also New York. Working hours overlap for 5 hours of the day.

Full Synchronous: Everyone must work the same hours regardless of time zone. This requires adjustment of work hours in each time zone. For example, a US company sets San Francisco 9am - 5pm as their working hours. Anyone in New York is expected to work noon - 8pm. In London, that’s 5pm - 1am.

Simple tricks for smoother time zone handling

Block your calendar when you are off work so your team knows when you are not available.

Memorize quick conversion references for your most common time zones.

Prioritize times when everyone is available for meetings.

Plan an extra day or two for back-and-forth unless projects are urgent.

Plan your routine around when people will need you / where most of your team is at. Ex. afternoon/evening in Europe or early morning PST.

Google Calendar offers the ability to set a second time zone on your calendar. Go into settings and enable this for your most common second time zone.

Looking Like the Hero

Perception, is everything

Perception is a critical aspect of remote work, as it is equally as important as the quality of the work itself. Remote work magnifies this principle because there is no physical presence to demonstrate productivity.

Every day, you are being evaluated by your colleagues, and it is vital to create a positive perception of your work habits. The perception you create can affect your reputation, job security, and ultimately your career growth.

It is crucial to understand that remote work requires trust, and building trust involves demonstrating that you are responsible, dependable, and reliable.

Hence, it's essential to manage your work efficiently, meet your deadlines, and communicate regularly with your colleagues to foster an environment of trust and accountability.

Ultimately, creating a positive perception of your work can go a long way in ensuring the success of your remote work experience.

Remember, work doesn't speak for itself

You do need to actually DO good work, and work hard. 

But your results DO NOT speak for themselves.

Communicate your wins. Own your losses.

4) Team Culture

Work Expectations

Focus on these things

Say/do ratio - If you say you’ll do something, do it. You will be better than 99% of people with this simple trick.

Sense of urgency - Getting stuff done quickly is a hugely valued. If it can’t be done quickly or has to be pushed back, make sure everyone involved in the project knows about it, and why.

Quick confirmations - “I’m on it” - “It’s done”. Everyone you work with should always know where projects are at.

You never want anyone to be thinking… "What is ____ doing?" "Is ____ actually driving results here?"

It is your responsibility to make sure others know you are present in your work environment. When you are remote, others may not know how hard you’re working. In fact, they probably don’t because they’re worried about their own problems.

Getting to Know Each Other Remotely

In Work

When you have internal video calls, get to know each other. Ask questions and share things.

If someone needs something, help them.

Share personal stories & what’s going on in your life.

Casual conversation at the beginning / end of calls.

Make sure everyone is involved in team projects.

Around Work

Call colleagues outside of scheduled meetings from time to time.

Schedule time to get to know each other.

Remote happy hours

Spend time talking about non-work things in Slack & on the phone

Set up fun internal comms channels

5) Work/Life Balance

Building Your Routine

You

Create a routine. It doesn’t need to be “perfect” as long as you create one.

Organize around optimal workflow for YOU.

Integrate your life & your work.

Don’t sweat the details down to the minute. How you spend your hours matters most.

Find ways to integrate new things into your life so your routine doesn’t become monotonous.

Tips & Ideas

Try shifting around your sleep schedule. Perhaps waking up earlier is easier to coordinate with colleagues, or staying up late gives you more time during the day with your family.

Try shifting sports & gym workouts from evening to morning & reverse. It might be easier to fit other things into your life by changing when you work out.

Prioritize your family & significant other. Family should always come first.

Tips for Your Routine

Take breaks: It can be easy to get sucked into work and neglect yourself. Take care of yourself throughout the day.

Keep it consistent: Maintaining a similar schedule each day and each week provides structure to your life, which helps anchor your sense of self.

Set availability expectations: Communicate in advance with your team when you are free & busy.

Respect your meetings: When you do have meetings, respect other attendees by planning other work before/after the meeting, even if it impacts your routine.

Practice Social Habits

Staying sane

It’s easy to fall into your own world when you’re remote. 

Social connection is super important and you won’t get that in the same way that you would in an office.

However, that doesn’t mean that remote has to be lonely! In fact, quite the opposite. By learning and utilizing social habits, you can have a rich social life everywhere you go, both remotely and in-person.

Tips & Tools

Schedule “coffee chats” or catch up time over video calls.

Try always-on audio or video calls you can keep in the background while you’re working to live chat with your colleagues.

Talk about normal life with your colleagues besides just work! Just like you would in person.

Try getting out of the house to work at a cafe, coffee shop, coworking space, library, etc. where you might bump into other cool people.

Utilize social media to keep up with friends & connect with others.

About Us - Orchestration

Remote work, works. However, the world needs to be changed to make this model the norm.

We are here to accelerate this shift by building and operationalizing management systems & infrastructure for the next generation of corporations. 

Here’s how we can help you:

1. We offer free resources, systems, and tools like this guide.
2. You can hire our experts to implement best practice remote work systems.
3. If you’re interested in selling your business, we buy businesses to optimize them for remote work.

One Last Thing

If you want to download this guide as a PDF to save it or share it with someone, there is a download button at the top of the page.

I hope you found this guide useful.

If you have any suggestions on how we can improve this guide, please let us know. We would also love to know if you found this guide valuable!