Q&A on the Book Working Remotely

In the book Working Remotely, Teresa Douglas, Holly Gordon, and Mike Webber share their experiences from working at Kaplan, a company that changed from being a brick-and-mortar company to becoming a predominantly virtual company.

InfoQ readers can download an extract from Working Remotely.

InfoQ interviewed Teresa Douglas, Holly Gordon, and Mike Webber about their book Working remotely.

InfoQ: Why did you write this book?

Teresa Douglas: This is the information that I wish I’d had when we went remote in 2010. At the time, I was an experienced people manager, but I’d never tried to manage people I couldn’t see in person. We spent a lot of time learning how to thrive in a remote environment through trial and error, and we hope to help others shorten the learning curve by sharing our real world experiences.

Holly Gordon: After working remotely for several years, we initially set out to write an internal guide for new employees to help them adapt to the virtual environment, based on our own experiences. However, we soon realized that with more and more companies going remote, there was a real need for a book like this beyond the walls of just our company. There are so many things you take for granted when working in an office, and similarly, so many things you don’t realize will be different when working remotely. Our book offers remote employees insights and tips so they can hit the ground running.

InfoQ: For whom is this book intended?

Douglas: The short answer is that this book is for any employee, regardless of level. That said, we focus primarily on non management issues and concerns. How can you grow in your career? How can you network in your office of one? How do you get your work done when you’ve never met the other people on your team in person? This is what we talk about in our book.

Gordon: Our book offers guidance to individual contributors working remotely. 

Webber: Adding on to what Holly and Teresa have said, managers can learn a lot by reading our book. We have a section dedicated to managers, which is written in order to help managers better understand their employees' situation, by highlighting what employees need to succeed. 

InfoQ: You stated in the book that people who work remotely work more. What causes this, and how do remote workers deal with it?

Gordon: A typical traditional office is full of distractions that simply don’t exist when you’re working from home. It’s a lot easier to work through lunch or work late when there aren’t any colleagues around asking you to grab a bite or packing up at the end of the day. A lot of these visual and social cues are what trigger office workers to take breaks and keep to stricter working hours. Without these same cues at home, work can easily bleed into other parts of your life and not have a clear beginning or end. That’s why it’s so important to establish some amount of structure while working from home. Even though flexibility is one of the biggest benefits of working remotely, it can easily morph into a negative. Just because you’re home and you can quickly check an email after hours doesn’t mean that you always should. Remote workers should feel empowered to say no.

Douglas: Remote workers generally have more flexibility to create work schedules that match their personal work rhythms. I’m a morning person, so I like to get a lot of work done in the early morning hours when I’m fresh. I get a lot of work done before 8am, which frees me to enjoy the outdoors in the afternoon when I’m less productive. When I come back to my office, I’m charged up and ready to focus on my work again. Remote employees who work when their minds are ready to focus often find themselves in a flow state. We have to make a conscious effort to stop working at the end of the day because we’re on a roll.

Webber: If you are set up well at home, you have fewer distractions. Obviously that's not necessarily the case in a Covid-19 world, where your entire family might be at home with you, requiring more care and attention from you. But in normal times, you aren’t wasting time on non-work tasks. This means that companies will find that their employees are more efficient and therefore can handle more tasks. For the remote worker dealing with this, the first step is understanding that working from home is not a "cushy" job, as those who do not work from home often assume. The next step is to ensure that your work routine and mindset are built around accomplishing tasks in as efficient a way as possible. 

InfoQ: How can we deal with the sense of isolation?

Webber: I'm always reminded of what my mother said to me when I was little and expressed disappointment at not getting letters in the mail like she did. She said that I needed to write letters in order to receive them. So proactive communication is key. Reach out to others and set up meetings to chat. You don't even need to have a specific agenda for those conversations. I did two of those sudden outreaches last week and both of the people I spoke with expressed sincere thanks that I had done so, because they too found value in us getting back in touch with each other. Working remotely is not the same as working in a shared physical space with others, and so some isolation is to be expected. But you can lessen its negative impact by actively connecting with others. Take the initiative!

Gordon: It’s easy to take for granted how simple it is to make friends in a traditional office environment; it’s something most people don’t even really have to think about. When you’re a remote employee, you have to be much more deliberate about connecting with your coworkers. And those connections are more important than ever—because you’re not surrounded by people all day, it’s easy to feel alone. The best thing you can do is actively reach out to people just to chat, not about work. Video calls are a great option, but even a quick IM to ask what someone did over the weekend makes a difference. These smaller casual interactions are the building blocks of remote work friendships.

Douglas: Build in support structures that give you the personal contact that you need. Like Mike, I reach out to coworkers on an ad hoc basis. But I also have monthly recurring meetings with a few people who I normally wouldn’t “bump into” in the company Slack channel. These 30 minute meetings help me stay connected with my coworkers, and help me work in brain breaks during my work week. I also visit a number of remote work channels on Twitter and LinkedIn. There I connect with other remote workers who don’t work for my company. This helps me feel connected to the world outside my place of employment.

InfoQ: What benefits can working from home bring for the worker?

Douglas: Flexibility to create a bespoke life. One year I ran four half marathons in a year, and I did it by training during my lunch break. Some remote employees talk about pursuing passion projects and activism with the extra time they gained by ditching their commute, while others use that time to connect with family. Remote work can also lead to increased opportunities for people with disabilities, who may not be able to work in a traditional office setting. 

Gordon: Perhaps somewhat counterintuitively, working remotely can actually increase an employee’s visibility within an organization and lead to more opportunities for growth. Of course, this is at least partially dependent on being more proactive, but when you aren’t as heavily tied to a geographic office location and colleagues, it becomes much easier to reach out to people throughout the entire organization. When people are remote, it levels the playing field and opens up cross-functional collaboration on a scale that just isn’t possible in a traditional office. Working remotely has given me exposure to teams and access to projects and opportunities that never would have been an option if siloed to a brick-and-mortar office.

InfoQ: What benefits have you seen at Kaplan after the company changed to become fully remote?

Douglas: There’s a much bigger talent pool available to take on new projects or positions. And if one part of the country is in the middle of a natural disaster (like hurricane season), then employees in other locations can cover for employees who may lose power or have to relocate. We have that fallback system built into our processes now. When this year’s hurricanes took out power for some of our teachers on the East Coast, we had teachers from other parts of the US smoothly step in to teach those online classes. Kaplan also benefits from a higher employee retention rate. Now if someone needs or wants to move, they don’t have to resign from their position. 

InfoQ: How can we discover our daily routine for working remotely?

Gordon: One of the best ways to establish a daily routine is to try different things! I’m someone who has to have a single designated work area in my home, prefers to maintain consistent working hours each day, and blocks out the same time on my calendar every day for my lunch break. But I only know this because I’ve tried doing things the other way and been hopelessly unproductive as a result. Regardless of your working style, I think some amount of structure is important for everyone. Establishing one or two rituals to the beginning and end of your workday or workweek is a great way to achieve that. For example, I have a secretary-style desk specifically for this purpose. When I open it in the morning, that’s my signal that my workday has begun; when I close it at night, that means the workday is over. It’s simple, but having that visual trigger helps me get into the right mindset, whether I’m starting my workday or ending it.

Webber: Well, our book has a lot of suggestions! But experimenting is definitely encouraged, to see what kind of routine works best. You might not have a wide range of flexibility, though. For example, I have to start my day dealing with email because I'm often three hours behind a lot of the people I work with due to the time-zone difference, so I need to prioritize that rather than starting the day with a to-do list. Family obligations might also push you into a certain framework so it's really about looking at what your restrictions are and then experimenting within that range.

InfoQ: How can we deal with a manager who's micromanaging?

Douglas: Don’t assume that micromanagement is about you--it isn’t personal. If your boss is new to managing remotely, he or she may not know how to appropriately support remote employees. Or perhaps your manager hasn’t worked with you before, and is trying to get a feel for how you work. Over communicate with your boss at the beginning. Send messages with status updates. If your manager uses a project management board, keep that up-to-date. If your boss prefers face-to-face meetings, set up a regular check-in, and come prepared with details. Each role in a company comes with performance metrics. Find out what your boss will be evaluated on, and be sure to share the information he or she needs to look good to their boss.

Once you’ve established trust with your boss, you’ll have more opportunities to change the dynamic. Sometimes that’s as simple as asking if you can change the number of check-ins so you can focus on your tasks. For other managers, you’ll want to hold a meeting to talk this through.

Gordon: Some managers struggle with trust when they can’t see what you’re doing every day. Err on the side of overcommunication, at least initially. Instead of only letting your manager know when you’re done with an assignment, send one or two updates while you’re working on it. Be prepared for your 1:1 meetings with a list of everything you’re working on and the status of those things. Over time, your manager will see that you’re proactive and self-sufficient, and hopefully they’ll realize they don’t need to be quite as hands on (and in return, you won’t need to check in as often). If things don’t improve, try to have an open and honest conversation (if it’s safe for you to do so) to address the problem directly.

Webber: In a perfect world, you want to be able to have a direct conversation with your boss about how they can better support you. Come to an arrangement as to how they can get the information they need from you without doing so in an overbearing way. If you have that open kind of relationship, great! If not, frame your desire to make changes as a way to increase productivity. Instead of daily updates on your progress, maybe a weekly summary can be provided instead. Five 15-minute chats could be replaced with one 30-minute conversation. While the goal is to get your manager to stop constantly looking over your shoulder, if you can frame it as a productivity topic, you can get the same end result without having to have a potentially awkward conversation. 

InfoQ: How can distributed teams establish a way of working and communicating that works for them?

Douglas: Every company is different, but the principles remain the same. First, think about the team makeup. Is everyone in one time zone, or across several? Does your team work largely independently, or must they collaborate in real time to get things done? Set up systems that allow people to work asynchronously as much as possible, such as sharing google docs, or trello boards. Think of synchronous meetings as the icing on the cake--these should be focused sessions with a definitive purpose.  And above all, discuss livable communication norms with the team as a whole. Some people live for meetings. Others would rather work quietly on their own. A functional team dynamic is one that provides space for both.

Gordon: Agree on a few key expectations early, and then don’t be afraid to revisit and revise them over time. Particularly for teams spread across multiple time zones, it can be helpful (if possible) to establish an overlap period each day: a window of time when everyone on the team is expected to be online and available in real time. Even if it’s only an hour or two, this time is valuable not only for productivity (allowing for meetings or quick responses to questions over chat or video call) but also for a feeling of team cohesion (there’s something to be said for knowing you and your colleagues are all working at the same time).

Webber: Clear communication from the start. Setting up guidelines with input from all groups. Often the mistake made is that the group that works from the office tries to impose its methods universally across the board and the team(s) working outside the office feels marginalized. Start with eliciting feedback from everyone involved and there will be a greater number of positive results. 

InfoQ: What can we do to get feedback when working remotely? And how shall we deal with feedback?

Douglas: Remote workers need to actively seek out feedback. Unlike working in a co-located environment, people can’t stop you in the hall to give you casual feedback. Reaching out to give feedback can “feel” more risky because you’re setting up a time to share it. In a colocated office you might only schedule important news and difficult conversations, but leave positive feedback for more casual interactions. It’s hard to leave that unwritten rule behind when you move to a distributed workforce. Make it easier for the people who can help you grow to give you the developmental feedback you need. Each time you give a presentation, complete a project, or lead a meeting, consider soliciting feedback from the people on the receiving end. 

You may choose to ask a specific person for their feedback, or send a survey or poll to the group. No matter how positive or negative the feedback, thank the people who gave it to you. It’s all too easy to argue with negative feedback, but if you do so, you will find it harder to get honest feedback in the future. Accepting feedback in a positive way will help you build strong relationships with people who can give you more and better information over time.

Gordon: Fewer casual interactions mean fewer opportunities to accurately interpret someone’s reaction via email than in person. To overcome this, you need to build feedback (both soliciting and sharing) into your day-to-day work. Make it a habit to ask your manager for feedback at the end of your weekly 1:1 (and ask them to do the same). Do the same with your colleagues or when working on a project with others. Avoid asking, “Do you have any feedback for me?” Instead, ask specific questions that focus on targeted areas. This makes it easier for the person giving feedback to narrow down what to share, and it also makes it easier for you to incorporate that feedback going forward.

Webber: Be proactive and ask your boss for feedback. Obviously, give your boss some advance notice, and perhaps even provide some guidelines about what specifically you're after. If you don't say what you want feedback on, your boss might end up giving you some generalized feedback rather than anything specific. Once you have some specific feedback, you can incorporate the action steps discussed and set up a follow-up discussion to see how successful your implementation of the feedback was from your perspective and from that of your boss.

InfoQ: What can managers do to build and maintain relationships with their employees?

Douglas: Make sure to spend a few minutes connecting on a personal level with your employees. This doesn’t mean prying into their personal lives. Simply asking questions such as, “How was your weekend?” before diving into work tasks can mean a lot. Keep in mind that your employees can’t see the expression on your face when you send an email. Be sure to let them know when you think they’re doing a good job.

Gordon: Regular communication is so important. When you’re working in an office and your employee gives you the assignment they’ve been working on, it’s simple and natural to acknowledge it with a quick “Thanks!” Managers should make a point of doing the same when working remotely. If you email your employee with a request, send a quick note in response after they’ve replied and completed the task (a short “Thanks!” still works here). It can be disheartening as an employee if you feel like you’re constantly sending work into the void. Even if an employee’s email or chat doesn’t have a question or warrant a lengthy response, some kind of acknowledgement still goes a long way.

Webber: Managers should really be having regular conversations with their employees. If you only have a 1:1 call with the person you report to once in a blue moon, it will be very difficult for a strong relationship to be developed. So managers should hold regular calls and they should do regular follow-up from one call to the next about what was discussed. It should also be a two-way street. The employee should be encouraged to lead the discussion and bring topics to go over. If the conversation is solely about the manager checking up on the employee, it's not going to end up working. It should be a conversation about how the two individuals can support each other.

InfoQ: Employees working remotely usually expect flexibility from their managers. How should managers deal with this?

Douglas: Managers need to be careful not to be either too lenient or too strict when it comes to flexibility. Start from a position of trust. Assume your employee wants to turn in quality work on time. There shouldn’t be so many check-ins that the employee is locked into a traditional 9-5 job. On the flip side, there should be enough structure in place so that your employees can get support from you when needed. 

Gordon: Managers need to remember that when an employee works is not nearly as important as whether or not the job gets done. Set clear expectations about communication (when and how they should get in touch), and then trust your employees to do the job. Employees should not have to work to earn your trust. Rather, your baseline as a manager should be to trust your employees until something happens to change that (which very likely won’t).

Webber: Managers should really walk into the situation being on board with the idea of providing flexibility to their employees. Someone who demands a set eight hours a day with no room for change is honestly going to struggle to be an effective remote boss. Let your employees know how/when to discuss changes they want to make to their schedule. As long as you know how to get ahold of your team when you need to and as long as the work is getting done on time with high quality, how, where, and when your people work does not really matter.  

InfoQ: How can we balance between providing stability with a consistent experience and being agile by adapting to change?

Douglas: Work roles, projects, and teams change at an ever-growing pace. While you can’t promise your team that they will have the same role from one year to the next, you CAN promise to be consistent in the way you manage them. Lead with honesty, transparency, and empathy. When your employees know they can count on you to be fair and consistent, they are better able to flex into new roles and ways of working.

Gordon: Establish structure but always leave room for flexibility. It’s impossible to predict the future, and the best way to navigate change is by accepting you don’t have control over everything. Creating a routine that allows for the unexpected gives you agency and a sense of stability when riding out uncertain times.

Webber: This is always the most challenging aspect of any work environment. Change is inevitable these days and the best way to find a comfortable middle ground between consistency and adapting is to build regular flexibility into your work schedule. If you're able to swap around tasks in your day with ease, you'll find it less stressful to adapt to larger changes. Someone who builds their routine in a way that doesn't leave things too close to deadlines is going to be able to handle unexpected events better than someone whose strict routine leaves little room for error. 

About the Book Authors

Teresa Douglas is an operations and people manager for Kaplan Test Prep. She writes primarily about business and parenting from her home in Vancouver, British Columbia. She is a co-author of Working Remotely: Secrets to Success for Employees on Distributed Teams (published Jan 2020 via Simon Shuster). Her work has appeared in The Muse, Forge, CEO World, and Training Magazine. 

She has an MFA in Fiction from Sarah Lawrence College, and an MBA from The University of North Carolina in Chapel Hill.

Holly Gordon is a communications professional who began working remotely in 2010. She is a co-author of Working Remotely: Secrets to Success for Employees on Distributed Teams (Simon & Schuster, 2020). She received both her BA in journalism and her Certificate in Editing from the University of Washington. She currently resides in Seattle, Washington.

Mike Webber has been a freelance writer working remotely since 2008. He has worked in management for three companies that are leaders in their respective industries in Japan, Canada, and the United States. He resides just outside of Vancouver, British Columbia.