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18| How to Get Work Done While Working from Home

Speaker: Teresa Douglas | Website | Book

Discover strategies for handling the distractions, loneliness, and communication issues that arise while working from home. Remote worker of 10+ years and author of the new book, “Working Remotely: Secrets to Success for Employees on Distributed Teams,” Teresa Douglas, gives strategies for making working from home productive and balanced on this episode.

About the Guests

Teresa Headshot largeTeresa Douglas is a People and Operations manager for Kaplan Test Prep. She has worked remotely since 2010 managing staff and processes across North America. Based in Vancouver, Canada, she specializes in strategic analysis and operations management. She is a co-author of Working Remotely: Secrets to Success for Employees on Distributed Teams, published in January of 2020.   


About the Host

Morgan Berna is the host of Olympia Benefits’ podcast, The Small Business Mastermind. Her background is in marketing, journalism, and broadcasting. Passionate about small business, she aims to create content that inspires and educates listeners.


Teresa Douglas: How do you thrive in a remote environment when you do not have experience in a remote environment?



Morgan Berna: You’re listening to the Small Business Mastermind, a podcast created to help small businesses juggle business, finance, health and wellness. I am your host, Morgan Berna. The Small Business Mastermind is brought to you by Olympia Benefits, a leading provider in health and wellness spending accounts. If you are looking to reduce your health and dental costs, visit

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Morgan: Hello, and thank you for tuning in to this episode of the Small Business Mastermind. Before we dive into our topic for this week, I had mentioned on the last podcast episode that I would be giving a shout-out to a small business that sent in some feedback about the podcast. So, the shout-out this week is going to a Calgary-based small business. They are called Bon-A-Pet-Treat. I love that name. They are a pet bakery. You can find their website, or you can find them on Instagram @petbakery. Thank you so much for sending in your feedback.

Now, onto this week's topic, we are going to be talking about remote work. Have you or members of your team been working remotely this year? StatsCan has reported that as of late March 2020, approximately 40% of Canadian workers were now working from home. However, it is now been long enough that that initial excitement I was seeing has been shifting a little bit and articles are coming out about people starting to see the downsides of remote work.

That is why for this episode, I have brought on a long-time remote work professional Teresa Douglas who published a new book in January along with her co-authors Holly Gordon and Mike Webber. It is called "Working Remotely: Secrets to Success for Employees on Distributed Teams". It explores the difficulties many encounter while working from home and how to improve them.

On this episode, we explore in particular issues related to workspace setup, communication and the psychological aspects of being at home. This episode has a lot of practical takeaways for both employees and business owners. I think it is going to be a really helpful one for any of you that are new to this space or just looking for some good reminders about how to be productive and healthy while working at home. So, with that I hope you enjoy this episode. We are going to dive right in and I will be checking in with you again at the end of the episode.


[interview begins]

Morgan: Welcome Teresa. Thank you for joining us on the Small Business Mastermind.

Teresa: Thank you for having me.

Morgan: Teresa Douglas is a people and operations manager for Kaplan Test Prep. She has worked remotely since 2010 managing staff and processes across North America. Based in Vancouver, Canada, she specializes in strategic analysis and operations management. She is the co-author of "Working Remotely: Secrets to Success for Employees on Distributed Teams" which was published in January of 2020.

We are going to start off today with, can you tell us a little bit about your own personal remote work experience, when you got started and where you are at now with it?

Teresa: Sure. I became remote in 2010 when my company that I am still working for decided that we were going to become a distributed company. I walked in one day and they said 'this is what is going to happen. You can stay with us or you can move on. I wanted to stay on so I was a manager at that time. I had about fifty people that I managed for full-timers; the rest part -time staff.

When I went home, I had to figure out how to help the people that I manage, how do I make sure that they can reach me, how do I know that they are working and the things are going well? It was a big change. I have worked remotely ever since managing people. I analyze data in very exciting spreadsheets. I am sure everybody thinks those are exciting too. I look at classes. I look at financials. A lot of different things in my remote journey.

I have moved countries in between from the United States, Canada. So, I have a lot of just sort of different experiences starting and continuing remote. But I love it. I really love working remotely.

Morgan: That was awesome. In my previous position, I had worked remote a couple of years and then now since COVID, I have been doing the remote thing as well. So, looking forward to hearing your tips and your advice. I wanted to start off talking a little bit about the book you have written. It is called "Working Remotely: Secrets to Success for Employees on Distributed Teams". Could you tell us a bit about why you and your co-authors Holly Gordon and Mike Webber decided to write it and what you are hoping readers will get from this?

Teresa: Sure. We wrote this book because it is the advice we wish we had had when we started to work remotely. Mike and I were both in management at that point, Holly was in operations and just trying to figure out how do you check in with people appropriately? How do you work with people in different time zones? How do you feel okay, is the way I would put it? How do you thrive in a remote environment?

If you do not have experience in a remote environment, there are more books out now about working remotely, but at the time we could not really find one that spoke to the employee experience. Even if you are in management, you still have some of the same issues that that an employee has. How do I get ahead in my career? How do I make connections? And this book really was designed to help people answer those questions and figure out how to do a good job if you are in an office of one.

Morgan: Fantastic. Let’s talk a bit about getting set up in our work at home situation. How can we create a comfortable working space even if we have a limited room to work with?

Teresa: I really empathize with that question because I have lived in some of the more expensive places in the world: New York, Los Angeles and now Vancouver. The way you need to think about it in a lot of these limited places is maximizing wall space and pulling out things and putting them away later.

For the longest time when I worked in my bedroom, I had a foldable screen that I would put behind me so that my co-workers did not see my bedroom because that is not something that I liked showing when I was on a professional call. In other times, what I would do is I would set up my desk in the morning, bring everything out for my bookshelf and put it out. At the end of the day, pack it all up and put it away. So, thinking of how to maximize your space that way. But also thinking about how comfortable you find things.

Sitting at the right height so that you can type comfortably is important. Having a nice chair so you splurge on nothing else, having a chair that is comfortable that does not cause injury for me is the big key because you can find tables and desks and things for not that much money. A chair is a little harder. Thinking about that and setting yourself up in a way where you enjoy where you sit.

I need to look out a window. There are other people that need to stare at a wall because if they look out the window, they are not working. So, thinking through those things is really helpful without having to put out a large investment ahead of time.

Morgan: Absolutely. On that note, do you have any tips for minimizing distractions? Lots of people have kids at home, pets. Maybe you are there looking at housework that needs to be done, things like that.

Teresa: We all need to get comfortable with ignoring the housework. This is something that I have had to learn and I feel like now I am a champ at walking over the laundry if needed. Other things, you can think about or how to minimize the noise that you hear. There are noise canceling headphones. I have a pair I am wearing right now. When you are not in a meeting, it may be that you need to go a little higher in the noise cancelling.

I actually have a set of noise cancelling headphones. Those headphones that you wear if you are outside directing airplanes that just really cancel all those noises? That has been amazing, especially during the pandemic time for me when my kids are home and my kids are older. They are not going to put weird things in their mouths so I can ignore them when they are doing other things and working on their own projects. I put those on to help. I also have signs that I employ on my door. For right now example, I have a sign that says 'Stop, I am in a meeting' so my children, my husband understands that when that sign is up and my door is closed, they have to stay out.

On the other side of that, if that is something you are going to use, then you have to be really good about opening the door, taking off the sign, making it clear when it is less bad to interrupt you during your day. Because if people know that you are going to be freed about 30 minutes, usually they will wait. Not always, children are children. But generally, they will wait. So that helps them from interrupting you which makes it easier for you to focus.

Morgan: Absolutely. Do you have any tips for separating work time from home time? I liked your comment of stepping over the laundry. I have been doing that myself. [laughs]

Teresa: [laughs] I do too. I like packing away my things. This may just be a holdover from when I did not have a small dedicated space for my office but I like to shut my laptop screen. I like to stick that in a different room from the one that I am in all the time. In some ways that would be if I am hanging out in the living room in the evening, my computer is not in the living room. It does not mean that I can not just go get it if I feel like I need to work, but just that little bit of friction having to actually leave the room and go get my laptop is enough of a stop for me. I have to think about do I really need to answer that work email because I do not have those emails on my phone. I do not bring that in. That is my own personal boundary. Other people depending on how they work may not be able to do that. But for me, it is keeping things just a little harder to access, help me step away from my desk, turn off my work and say 'okay, I am in my home space now instead of my workspace'.

Morgan: It is what we would naturally do in an office. You would leave your equipment there and go home. Okay, so we are going to move now into some of the psychological aspects of working at home. For many, this is a new and novel thing. A lot of people have done this previously but then a ton started doing this just over the last year. It has been several months now and I am starting to see articles popping up about people experiencing the loneliness and starting to see some of those downsides. Do you have advice for managing that component of remote work?

Teresa: I do. It can seem counter-intuitive, especially in a pandemic when you can not really go out, mix and mingle with large groups of people. But you have to find opportunities to do that in a socially distanced, appropriate sort of way. What I like to do is during my work day, I build in, even just once a month but generally a couple times a month, social time. I have planned social time. I have on my calendar meetings with people where we get together for 30 minutes to an hour and we talk about whatever. It does not necessarily have to be work things. Some of the folks I talked to are not necessarily working in my company.

We sit, we chat over Zoom. I have slack groups that I also belong to and on Twitter where I will go and talk to people about social things because it may seem like a distraction from work. But if you are filling your tank with the amount of personal contact that you need, it becomes easier and more efficient to actually do your job during the times when you have to work.

If I have already felt personally fulfilled because I had a coffee break with somebody, it is easier to focus on my job. I would really encourage people to think about who you might reach out to because there are other people who are working from home that are in your same boat. They have a lot of things they have to do and it may feel like 'well, I am interrupting them' but we all need just a little bit of relaxation time. Even if you cut it down to twenty minutes and you do this a couple of times a month.

It is a lot easier to feel connected not just to people inside your company but to the world at large at a time when a lot of us are feeling cut off from a lot of the things that we used to do.

Morgan: I think in the office, a lot of people will naturally take that coffee break. Do you essentially do that but you scheduled and with someone to do it remotely?

Teresa: Yes, because I work with people who live across time zones. My morning is their afternoon and it is harder. You can not pop in and look around and see if they look busy. Setting things up ahead of time, you might think 'well, what are we going to talk about?' You are going to talk about the same things you would if you just eyeballed your co-worker in their office and came in to talk about the latest episode of whatever it is you are both watching. It can feel scary but it is really important to do that. Again, it does not take very much time out of your day.

Morgan: I think sometimes there is fear to that because the chats and things are more monitored. It looks more like you are not using your time well, but that is a good point that you need to be taking care of your own self so you can do your job.

Teresa: Exactly.

Morgan: How can we go about making genuine connections with colleagues when we are not face-to-face? It sounds like you are doing this across time zones, across countries. Tips for that?

Teresa: Yes. Look for any justification to make a connection. It does not have to be much. I at one point was in a meeting and before the meeting started, the host had us chat a little bit for about a minute, nothing big. I heard that a co-worker, for example, was going to go later that day to a field trip with their kids. I had no idea this colleague had children. I have children. So, the next day I reached out via slack and said 'hey, how did that feel trip go?' and they told me. There was a connection. Then I mentioned I also have a child that is about the age of your child. It was something small but it made it easier for me to just say hi because that can feel weird that you are reaching out to somebody in the middle of the day and you do not know what they are doing. It is just the small things and it does not have to take long. It is not a video called every single time you reach out to somebody

For example, on Twitter, there are people writing very smart things there. I will read what they write and I will make a comment. If they comment back, maybe next time they write something I will make another comment. Gradually, you are building up those connections with people that you may just not know at all. But even if you are doing it inside your company, you all share the experience of working for that company. So, somebody is going to be a little bit more open if you are reaching out to them when you all share that experience of working for the company.

Morgan: That just made me wonder, do you ever have company-wide remote events? What do you think about those?

Teresa: I love those. We do have company-wide events. We have a couple of things. We have the quarterly meetings where we discuss how the business is doing and things related to that. But there is always some component of social happening. There is the chad and people are saying good morning to each other, good evening, wherever it is they happen to be in the world. Those are the more formal events.

The less formal events, we have these things we do called 'blackout days'. There will be Ted-style talk. Some of them are educational; how to manage part-time staff remotely. Another things are just for fun. Colleagues can apply to give a fifteen-minute talk on anything. A couple years ago, my co-author Mike Weber held a fifteen-minute Ted style talk on board games. He is a big board game fan. It was hilarious. I had no idea how much he was into board games and how fun it was. A lot of us were having conversation around that.

It was very relaxed but it was structured relaxation, if that makes any sense. We all had an excuse to talk to each other about something and enjoy Mike's delivery of the topic at hand. When you have several of those together, you get to really know what makes your colleagues tick, what it is they enjoy about life. It leads to a more friendly feeling in the company at large.

Morgan: Absolutely. That is why we do things like holiday events and all that in person anyway. We are going to talk now about another topic covered a little in your book, which is communication. This is something that I think is maybe not thought about as much initially. I have heard a lot of people recently telling me their companies either there is kind of no communication happening when they went remote or they are doing like constant meetings for every little thing. Do you have tips for keeping communication open between employees and management in a way that is manageable and not disruptive?

Teresa: That is so important to be manageable not disruptive because we all do need to work. Even if we are talking about remote work outside of the pandemic, folks tend to be on different schedules. So, you never really know when people are on and when they have to leave to attend to other things. Just on the management level, looking at those employee conversations and asking yourself what is the best vehicle for this conversation and what is the purpose of this conversation?

If you need to download a bunch of information that employees need to know, it may be that meeting is not the best time for that. Some people learn by listening, some people learn by reading. In that case, you might ask yourself, can I write an email and then send an audio recording for those that may want to just hear it and send that out instead? Because there are times when that is really the most effective thing that you can do. Especially if it is about policies that everybody needs to follow. That way they can look at that video, audio, email and say, 'okay, am I doing this thing right that I was told that I have to do?'

There are other times when you are looking for a social connection. We do not need a social connection every single day for everybody. Some people do. Some people need to talk to people everyday. Others, they are okay if we can have a day or two of quiet. So, I would say set up those opportunities and then let people self-serve.

If you are on Slack, for example, if there is a channel just for social chitchat then management leadership can go in on there and say 'good morning everybody, hope you are having a great time. Hope you are having a nice day.', whatever it is. Some kind of personal connection. Then step back and let those that need the connection continue the conversation.

I recently read an article where someone was saying that they talk to them boss now more than they talk to their partner because there were so many meetings. That is really not right. We need that connection but we do not need to go overboard because not everything is great for a meeting. Just keep the virtual door open for those that want to talk. Set up some structured one-on-one time with the direct reports and then manage the rest of it on a case-by-case basis on the best way to talk to your team.

Morgan: Those were really great points. It made me think why so many meetings are happening and I wonder if it is because of maybe like a trust issue or just not having a good way to see performance. Do you have any experience with that?

Teresa: Well, it is scary. Right? You have all these employees that you used to be able to look over and see them looking at their computers frowning and typing and now where are they and what are they doing? It is really an easy trap to fall into to say because I can not see you, I need to send you a text message. I need to call you. I need to set you up in a video meeting to prove that you are working.

When A - those employees that you saw in the office, they may or may not have been working. Maybe they are checking their social messages. You do not actually know. The only way you know if somebody is actually working as if you look at the outcomes. So, are people turning in their assignments on time? Are they reaching out to ask for clarifying questions on things that they are doing? Those are how we know the people are working.

If you are a person who is in charge of other people, it makes sense to set up processes so that you can check on your employee without always having to ask your employee. For example, in my company, we have Google Docs. If we are working on a project, we can have a shared document where we are typing a notes, we are doing our work, whatever it is. As a manager, my boss, if he really means to, can go in and take a look at what it is I have done. We also have a Trello board. I can update things there and he can look and see what has to be done. He does not have to micromanage me. He can decide on his own when it is he wants an update on what it is I am doing by just looking at the Trello board on the dock.

For management, set up some things so that you can have some transparency but be very careful not to set up extra reports that actually take away from the work. There is that line. We do not want to set up certain reports and processes so that people have to prove in writing that they are working which takes away from the actual job.

When we are looking at those things, think about how can I be the least intrusive person possible and yet still have a good handle on what it is my employees are doing.

Morgan: Those are some great tips. The next question we are going to go into is about assumptions. I always found when I used to manage a remote team, this was something I would talk about quite early on with employees. I am curious to get your advice. We are working in our own space. We are not necessarily hearing people's tone when they send an email or a message. It can be quite easy to assume that someone is frustrated when maybe they just type a different way or that you are on the same page with the project when maybe you are not. What are your tips around managing assumptions?

Teresa: We should all assume that we read emails more negatively than they are. There is a study out there that talks about that. I can not remember who wrote it, but I believe it was in the Harvard review. If we look at an email we think 'wow, that is a little off-putting.' This is the time when we have to remind ourselves, we are probably reading this morning negatively than it is.

Also keep in mind that our own experiences that day will decide how we are going to be reading things. If for some reason it is a bad day for us, when we look at emails, we are going to be even more negative in our assumptions. So, it is really important to check ourselves and say, 'I might be reading too much into this.'

You may also reach out further to your colleague to see if you can just get a little more context. This is where having made some of those connections on a personal level can really help with that because if you know your colleague well enough to sort of hear their voice when they are emailing you, then you are going to lower the probability that you are going to read a little too much into it. That is just on assumptions and on tone. But assumptions for work, again, we have to assume that people have no idea what we are doing.

Think through how can my colleagues who depend on me know where I am on a project. Maybe that means in slack you say, 'Hey, I am at phase one of the three-phase project we are working on. I am going to go and look up these other questions that I have. I assume that I am going to start phase two in about a week or so,” so the people know where we are on something.

Again, also setting up those shared documents so that people can see where you are is really helpful so that I do not assume that 'you Morgan are completely behind, I have not heard from you. I am a little worried about it.' If you have reached out to me and say 'you are going to hear from me in about three days', then that is something I can check off my list. Keep in mind that we have to do that for each other is to give that little bit of feedback on where we are on things.

Morgan: It sounds like project planning is just an extremely important component. Something you had mentioned to me in our call before this interview was that when we work remote we can have a tendency to see our colleagues as villains. I am wondering if you could expand a bit on what you meant by that and what we can do about this?

Teresa: It is a funny thing if you can not see somebody and there you are trying to work on something. There is just this cascade of assumptions that can happen, right? You may have thought that you told your colleague 'this is where I am at a project' and here they are sending an email and oh my goodness. They copied your boss on the email and you think what are they doing? Are they are they throwing me under the bus, are they trying to get me fired because they have sent this email? It is so easy to think that because we are stuck in our little bubble. We are in our office and it is clear to us what it is we are doing and why is that our colleague is unreasonable. But it is not clear to them and we have to take a moment and just put ourselves in that other person's shoes and say 'alright, that seemed like it was a little off base. What if I am wrong? What does that look like? When we are tired or hungry, it is really hard to do that.

That is why it is really important sometimes when we read those emails to just get up and leave your office for a minute. Even just walking around the inside of your house can sometimes help you get a little bit of perspective on why that person maybe is not Darth Vader. Reach out on a more human level. Now if they have sent an email and it seems stiff and formal, maybe they are not really good at email. Maybe they are somebody who likes to come to somebody's desk and just have a conversation.

If that is the case, that is the time to reach out on instant message and ask, 'Hey, can we just jump in a call and hash this out a little bit?' Then you get a sense of the tone of voice that the person is using when they talk to you. That can give you a lot better instincts on where they are. It may be that they were a little short because their kid has been interrupting them every two minutes for the past three hours and they needed to send that email really fast or it was never going to get out.

If you get into that video call or on that audio call, it does not matter. You can hear that they are stressed out about other things then you can be a little more forgiving.

Most of these problems and communication are people issues . The more that we can regulate ourselves and approach each of these conversations with an open mind, then the better we're going to get on with people and the fewer and more far between these issues are going to be.

Morgan: It sounds like we can have a tendency to be projecting our own stress or just our own mood? I have seen the jokes that go around online that is like, “I am going to add an exclamation point to this email so you know I am not angry.”

Teresa: Emojis. Who knew that those were going to be a part of our professional lives?

Morgan: Absolutely. I think too there is a little bit of a generational gap with how we converse online as well. Is that something you have to you deal with or you notice?

Teresa: I have noticed that. I have, for the past twelve years, managed people who are at least a decade younger than me. I have the leadership obviously in many companies is somewhere between my age in a decade or two older than me. It is important to understand that if you are texting people who are in their twenties or early thirties, if you are using periods, that sometimes makes things seem more negative to that group. It can be very cultural speaking, or all caps is yelling. I think most of us get that. If you are talking to somebody who is older, and these are all stereotypes, that means not all of them are true for everybody. But it may be that a little more formal, full sentences calls across a little bit better.

Keep that stuff in mind. You do not have to know all of that. You have to be into to the idea that if people are communicating with you and they seem stiff, maybe you are committing a generational or cultural faux pas that you are not aware of. Very, very important to check on that and see if that is where the problem may be; that you are just putting your foot in it.

Morgan: Those are great tips to keep in mind. The last question I had for you was around HR issues. For someone that is newer to working remote, we are used to going in in person to talk about things, like maybe needing to take a leave, questions about salary or larger problems. Do you have advice for approaching those types of topics?

Teresa: Yes. There are two sides to that. There is the leadership management side and then there is the employee side. Just putting on that that management hat, we have to think about making sure that our employees are already somewhat acquainted with these folks before they have issues. Someone may have to take an unexpected leave, do they know the name of the person they have to talk to about that?

As a remote manager, my first introduction to HR was when first one I on-boarded. Then not really anything until I had to fire an employee. That is a nerve-racking thing where I am sitting there in the call with the HR representative with me and we are having this conversation with a person who is going to be terminated. It was really nice of the HR person to meet with me ahead of time so that we could discuss next steps and how to do this appropriately for where the employee lived but also just to meet a little bit as a person because we are going to approach this difficult conversation. It was good to have a little bit of knowledge of who this person was. If there are times when in your company, you can make sure your employees know the face and the name of the person they may need to talk to you about leave or resigning or really anything, then that is going to make it a little bit easier for them to use the appropriate channels. That is on the manager side.

On the employee side, remember that a lot of HR professionals are very, very busy with a lot of different things that happen in a company. Reaching out to them to talk about leave, to talk about whatever it is that you need to talk about, I would offer them a series of methods of communication with you. So yes, it is nice to do things in person. Yes, it would be great if you could get on a video call and talk through this. But also leave open the idea that you may just have to do some of this in the email which can feel very crazy when you do not want to write a lot of things in writing, especially if say you have a sick relative and you just do not want to put that out there. But at least offer that as an option because again, you are dealing with a human. It is just a different mode conversation. Leave them that option but being willing to get into a video call or on the phone and just talk through things is really important.

Morgan: So, allowing some flexibility and still treating each other like humans at the end of the day.

Teresa: It really boils down to that in remote work. We are all human and we need to express that.

Morgan: Yeah, especially right now. Lots of people are going through all these challenges and it is great to see resources like your book out there to help guide people through this.

Teresa: Anything I can do to help. That is what I like to do.

Morgan: Well, thank you, Teresa. Those are all the questions I have for you. I was wondering if there is anything you wanted to add or if you feel like we have covered it all.

Teresa: Yeah, I guess the only thing that I would add is that so much of the success and failure of remote work happens in our minds. It is not just about setting up your computer and having internet connection, which is something important and we need. But if we are really going to thrive as people who are working remotely whether we are working remotely by choice or because of current personal circumstances, if we take the time to understand our own emotional intelligence and where we may need to work on things, where our strengths are and project empathy as well as professionalism into our companies, that is going to carry both you and your business through any inevitable missteps that you may make in this new environment for many people. You can all learn together and really thrive in this medium.

Morgan: I love that. That is a great way to look at it. Thank you so much for joining us today, Teresa and sharing all this great information.

Teresa: Thanks for having me.

Morgan: Did you want to share quickly? I am going to put all this in the description. But do you have a website you would like people to go to if they want to reach out to you or any contact info?

Teresa: They can reach me at I am also on Twitter at @teresamdouglas.

Morgan: Awesome. Well, thank you.

Teresa: Thank you.

Morgan: Thank you for tuning in to this episode of The Small Business Mastermind. If you enjoyed this episode and would like to subscribe to the podcast, visit If you are listening to the podcast on a platform that supports rating and reviews, please consider leaving one. It really helps us get the podcast out there and continue to bring on fantastic guests like Teresa. I appreciate you tuning in today. I hope you got a lot out of this episode. I will be talking to you again very soon.