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  • Writer's pictureAccidental CISO

AC's guide to remote work

Updated: Mar 17, 2020

Recent events are compelling organizations everywhere to instruct their employees to work from home. Many of these organizations have never embraced remote work. Their employees and leadership are both getting their first taste of working from home full-time. I know first-hand what it takes, as I have many years of full-time remote work experience and have been responsible for supporting home-based workers as an IT leader. Successful remote work requires a combination of the right home-work environment, skills, tools, and company culture.

The Home Office Environment

First, the home office environment is important when we are talking about working from home for sustained periods of time. Working from the couch, laptop teetering on the coffee table as Judge Judy plays on the TV might work for the occasional snow day, but it isn’t going to make full-time remote work enjoyable or productive.

Adequate work space: You will need space to work comfortably without feeling cramped. For some, the kitchen table might suffice, but for most people that isn’t a long-term solution. A proper desk and desk chair are the foundation of a comfortable work space. Pay attention to ergonomics when you chose your desk and chair, and make sure that your keyboard, mouse, and monitor can be placed in the proper locations to eliminate strain. Plan to use a docking station with full sized peripherals at your desk.

A controlled environment: I cannot stress enough how important it is that you are able to control your work environment. When you are deciding where to put your desk, keep in mind that you will need to eliminate distractions and noise, and control lighting. This is important for both focused work and conference/video calls. I recognize that not everyone will have the luxury of a dedicated office space in their home. Creative solutions may be required to define and control the environment. If you are planning to make a long-term switch to remote work, you will probably need to make some difficult decisions about your living space and arrangements.

Secure your network, data, and equipment: Most companies these days have physical and IT security measures in place to protect their data. Examples could include staffed reception desks, key-card access, locked IT equipment rooms, secured wired and wireless networks, and so-on. As a full-time remote worker, you become responsible for the security of your local work environment. We like to think of our homes as secure, but that is not always a valid assumption.

Verify that your wireless network is configured to use encryption and ensure that the default password and WiFi key on your wireless router have been changed. If you frequently have guests in your house, enable the guest WiFi network on your router for them to use. Make sure that you have lockable storage available for any physical documents or removable media that contain sensitive information. If your employer does not enforce security policies on your computer, enable full-disk encryption and screen saver timeouts. Set your computer to require a password or PIN code to resume after the screensaver has activated. If you spend any time working from locations outside of your home, such as libraries or coffee shops, never leave your equipment unattended.

Remote work skills

When you are working from home, you must provide much of the structure of a typical workday yourself. This structure comes in the form of the personal routines and habits that you must form. They are the skills of a successful remote worker.

Maintain a consistent routine: When you work remotely, it becomes critical that you have the discipline to maintain a consistent routine. Set a bedtime for yourself and use an alarm clock, just as you would when commuting to an office. Get ready for work the same way each day. Eat breakfast, drink your morning coffee, walk the dog, listen to a podcast, and so on. Without the structure of a regular routine, working from home can quickly leave you feeling lost and have a surprising impact on your engagement and productivity.

Wear Pants: No, seriously. Wear pants. People joke about remote workers working in their pajamas. The freedom to relax your dress code is a wonderful part of working remotely, but part of your routine needs to be getting showered and dressed, just as you would if you were commuting to an office. Simply getting dressed is an integral part of the discipline and structure that you must establish for yourself to be successful.

Define the workday: Establish regular working hours for yourself. Not only does it reinforce your own personal routine, it helps your coworkers predict when you will be available and supports setting boundaries, which I will talk about later. Beyond simply setting regular hours, it is important to define your workday through your daily routine to help you make the mental switch from home to work, and back home again. When you commute, the drive to and from the office creates a physical and mental boundary for the workday. I suggest that you work a similar signal into your routine. Some people take a walk or a short drive, others meditate. If you have a dedicated room with a door, it could be as simple as closing and locking the door on your home office at the end of the day and unlocking it the next morning.

Keep your calendar up to date: When you work remotely, you will live and die by your calendar. It is an essential part of coordinating collaboration in a distributed workforce. Working remotely eliminates many of the distractions that are present in the office. Most notably, nobody can physically walk up to your desk and interrupt you. Be aware, though, that your coworkers will use other means, such as instant messaging tools or phone calls to interrupt you. Your coworkers can’t know when you are free or busy if you don’t keep your calendar up to date all the time.

Over-Communicate: When you are not physically present, you don’t get any bonus points for simply showing up. In many ways, your output is all you have, and you must communicate your value. A remote workforce does not have the benefit of local side conversations in the break room, hallways, or most importantly, immediately before or after a meeting when the conference bridge is not active. Constantly reach out to others and maintain open lines of communication. Constant communication is how you ensure that your interests are represented, how others know about your contributions, and how you elicit information from others to keep you in the loop.

Be present: When you work in an office where everyone can see you, there is a natural limit to how much your attention can drift during your workday, especially in meetings. When you are remote, it can be tempting to multi-task, especially during meetings. There are times when that is appropriate and can even be a great benefit, but be very careful. As a remote worker, meetings are your most visible times to others in the company. It is critical that you are present in those moments. Do not be the remote worker that constantly asks someone to repeat something because you “didn’t quite catch that”.

Choose the right tools

Your IT department will need to provide the entire team with the right tools to support collaboration with a distributed workforce. Effective communication is deceptively hard. Successful remote work requires mastery of the collaboration tools that are available to you. You must be aware of the characteristics of each tool and select the right tool for your intended purpose.

Latency: Latency is the time delay introduced by a mode of communication. Some tools are very high latency while others are very low latency or even real-time. Company culture and team norms can impact the latency of a mode of communication. Latency is not a bad thing, so long as it is understood.

Richness: The richness of a mode of communication has to do with how much information can be conveyed through that mode of communication. Rich modes of communication can convey verbal and non-verbal cues such as tone of voice, body language, and facial expressions. Less rich, or lossy, modes of communication, lose much of this additional context, requiring us to adjust how we construct our messages when we communicate over those tools.

Authority: Different modes of communication may carry different levels of authority. Authority, in this case, does not have to mean power or control, but can also refer to the communication as a source of truth or documentation.

Virtual Private Network: A VPN allows remote workers to securely access internal systems. This connectivity frequently comes at the cost of network performance, depending on how the VPN is configured by IT. In recent years, companies are using more and more cloud-based services, reducing reliance on VPN connectivity. As a remote worker, learning which applications do and do not require VPN access will help you to decide how often to connect and let you to stay off the VPN as much as possible. While this seems like a small thing, it will improve your experience working remotely.

Collaboration: Not long ago, we all worked face to face, E-Mail was king, and our phones were used to make calls. Today, we want to work remotely, and E-Mail and phone calls have been supplanted by chat and audio-video based collaboration tools. Chat based tools offer the advantage of near real time communication, allowing them to be less disruptive, while audio-video based tools facilitate screen sharing and rich communications that E-Mail and the telephone can never match.

Documentation: The team needs to define where different types of documentation will be stored, how revisions are tracked, and who owns them. As a remote worker, you must understand where to find the documentation that you need, as well as how and when to update it. It is important to note that E-Mail and chat messages are not acceptable forms of documentation.


  • E-Mail - High Latency, lossy, medium authority Good for: Broadcast messages, formal communication Not so good for: Urgent messages, conflict situations

  • Chat - Low latency, lossy, low authority Good for: 1:1 and small group coordination Not so good for: Formal communication, documentation

  • Audio/Video Conferencing - Real-time, rich media, low authority Good for: Meetings, screen sharing, urgent communication Not so good for: Formal communication, documentation

  • Telephone - Real time, medium richness, low authority Good for: Urgent communication, stop-the-world interruptions Not so good for: Formal communication, documentation

  • Sharepoint/OneDrive/Wiki - Low latency, lossy, high authority Good for: Documentation, revision tracking Not so good for: Urgent communication

Accessories: A good webcam and headset are mandatory. Many laptops today have acceptable webcams built into them, but when you are working at your desk with full sized monitor, you will want a USB webcam to provide the best angle and image quality. The same is true for audio. The built-in microphone and speakers may be OK for occasional use, but you and your coworkers will grow weary of the constant speakerphone experience. A USB or Bluetooth headset will provide rich clear audio quality that is comfortable to listen to on long meetings and regular working sessions. While not required, some remote workers with dedicated home offices eventually move to studio quality microphones, headphones, and USB audio interfaces for optimal quality, comfort, and convenience.

Supportive culture and team norms

The culture and team norms of an organization are very important contributors to the success of a distributed workforce. Since culture is heavily influenced by most senior management, leadership will need to take an active role in ensuring that their remote team members are successful. Managers and team members alike must all hold each other accountable.

Conference bridges: Whenever a meeting is scheduled, the organizer must always add a conference bridge. This sounds trivial, but it is not. When a meeting organizer omits conference bridge information, it is frequently only noticed as the remote attendees are trying to join the meeting. At best, it creates confusion and delays the start of the meeting. After repeated occurrences, it can begin to alienate remote team members, especially if meetings are continued without them.

Cancelling meetings: In organizations where team members spend time both working in the office and remote, a pattern can develop where meetings are cancelled because one of the stakeholders happens to be remote that day. This is an anti-pattern of remote work, and team norms should be enforced to ensure that the meetings are held as planned. If a conference bridge link is included in every invitation, there should not be any reason to cancel.

Core team communications: Each core team should have a dedicated channel in chat-based tools for their intrateam communication. A team chat provides an easy way to coordinate work and keep everyone up to date on what is happening. It also provides a forum for team members to ask questions, voice concerns, and share challenges.

Off-topic chatter: Off-topic chatter in core team channels can provide a sort of digital water cooler, replacing hallway and break room conversations. Personal stories, links to interesting articles, gifs, and memes, all allow the team to form their group identity, as well as to build and maintain relationships. Mangers should allow it, and participate, provided the topics are appropriate for work environment.

Normalize working sessions: In an office environment, it is easy for coworkers to simply sit together to work through a task or problem together. The same type of experience can be achieved remotely through impromptu working sessions. Teams with remote members should normalize the practice of starting up short on-demand video calls with screen sharing to work through similar problems or tasks.

Document everything: Documentation is critical with a distributed workforce. Many organizations have managed to get by with poor formal documentation, leaning instead on tribal knowledge passed down between team members. When remote workers are involved, this begins to break down quickly. Everything must be documented, and that documentation should be kept up to date reliably. This includes written documentation, as well as change control documentation, and project or task status documentation, and so on.

Over communicate changes: Remote workers are at a distinct disadvantage when it comes to change. When there are changes to policies, processes, and tools, there is usually some amount of confusion and resistance. When everyone works face to face, it is easier for the team to manage the problems and confusion that results from the change. When remote team members are involved, the team has to hold each other accountable to document and over communicate changes.

Respect Boundaries

Boundaries can be particularly difficult for remote workers. When you work from home, relying on adherence to your own routine to create the structure that defines your workday, it is easy to allow that workday to extend into the night.

Respect your own boundaries: With no physical separation between your work and home life, adherence to your routine is the only thing that creates that definition. It happens a little bit at a time. First, there is that one last thing that you need to do today. It will only take fifteen minutes. Before you know it, it is past dinner time. Later in the evening, you notice your computer and think of something else you should have done today. It will be quick, so you log back on. When you do, you see a message from your manager. It will only take a minute to respond. You have now set a precedent that you will work after hours and begun sliding down the slippery slope to burnout.

Honor coworkers’ working hours: If they are not careful, remote workers can set the expectation that they will always be available due to the lack of strong boundaries between work and home. Company culture and team norms must reinforce respecting one another’s working hours, especially for remote workers, as they are conditioned to be responsive.

Use appropriate modes of communication: As discussed earlier in this post, different modes of communication are best suited to certain types of messages based on content and urgency. Team norms will dictate the expectations around each mode regarding availability and response times. Remote teams rely heavily on these team norms to both select the right tool and to know how quickly a response is needed. Email is not an acceptable mode of communication for urgent messages, and remote team members will likely configure quiet hours on notifications for email. If others in the company continually try to send urgent messages via email, it short circuits the remote worker’s ability to enforce their boundaries by turning off email notifications. Conversely, if non-urgent messages are sent using a mode of communication that is typically used when a response is needed quickly, the message will carry an assumption that the remote worker needs to respond right away, again, interfering with their ability to enforce boundaries.

Be considerate about interruptions: Phone, video, chat and IM tools make it easy to communicate with remote employees, but those tools also make it incredibly easy to interrupt them while they are busy. Similar walk-up interruptions occur in an office environment, but they are less likely when it is visually obvious that the employee is in a meeting or deep in focus with their headphones on. Remote workers learn to use their calendars to manage their free/busy time. Team norms should reinforce respecting the busy signal.

If you are considering taking a remote role or implementing a remote work program in your organization, I hope this information has been helpful. I have experienced the magic of fully remote teams and strongly believe that the remote work is the future for most companies. Through careful planning and level setting expectations, remote work is a fantastic way to achieve balance in life. Please click the “follow” button at the top right corner of the page to follow me on Twitter and let me know what you think!

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