Interview with Teresa Douglas

Teresa DouglasTeresa Douglas is a People Manager at Kaplan Test Prep, analyst during the day, and a writer by night. Theresa is also the Co-Author of “Working Remotely: Secrets to Success for Employees on Distributed Teams”. You can find her through her Website, Twitter, Facebook, and LinkedIn.

1. How did you started working remotely? 

Remote work came to me. Back in the Fall of 2010, my company decided to transform from a brick and mortar business to one where its employees worked remotely. It was either make the switch or find a new job. I liked where I worked, and I suspected that working from home might be a good thing for my growing family.

Also, I’m a terminally curious person, so the fact that I hadn’t worked as a remote employee before was a mark in its favor. I had previous experience freelancing, but I thought working remotely as a manager would be different. It’s been a fun and educational experience.

2. What do you think are the main advantages of remote work?


Two years ago I ran 4 half marathons in a year, and I did all of my training during the day. I would start work early, take a long-ish break in the middle of the day to log some run time, and come back later to finish off my task list. 


It’s been years since I’ve had a boss that lives in the same time zone as me. I am expected and encouraged to get my work done as I see fit, and check in when I need help. I thrive in this sort of environment. 

No Commute

I live in Canada. As I write this, there is a flood warning in effect because of the torrential rain that has been falling for the last 48 hours. I don’t have to go out into that mess to get to work. Nothing makes me feel like I’ve won the employee lottery quite like sitting in the comfort of my office with my warm mug of tea instead of slogging to the bus in the rain.

3. Do you think there are disadvantages or that you’re missing something by working remotely?

I haven’t quite figured out how to replicate the experience of sharing a meal with my coworkers. Sitting in a video meeting while eating lunch just isn’t the same. 

4. From which cities or countries have you worked since you have become remote? 

I have been remote in: New York, Los Angeles, the San Francisco Bay Area, and Vancouver, Canada. Vancouver is my favorite. There’s a huge run culture here, and I love that I can run for miles along the beach, or pound through the trails of an old-growth forest. I see so much wildlife–bald eagles, otters, dolphins, coyotes–I’m never bored on my runs. 

5. From which type of place do you prefer to work?  

I love to work from home. I have a second screen and I haven’t found a socially acceptable way to bring that with me to the coffee shop. While I do go to a local coffee shop when I need to be around people, I much prefer the quiet of my office. If I decide to sing along with the music at home, there’s no one there to judge me. 

6. Which places would you like to travel to while working remotely?

I would love to go to Barcelona and Thailand. More locally, I’d like to visit some of the more remote islands around Vancouver Island. I have a dream of renting a cabin for a month in the summer. I would go exploring via kayak on my off days. My children are almost old enough for this to actually happen.

7. What would you say to the companies that don’t believe in hiring employees who work remotely?

You’re missing out. A remote workforce allows a company a degree of flexibility that is absent in a purely co-located office. It’s more cost-efficient to enter a new market if you don’t have to buy or lease office space first. Existing employees can handle the day-to-day operations in the new market.

If your company needs to pivot, you can reorganize your existing workforce instead of laying people off and hiring new people. Remote work can help you keep your star employees, and develop a more diverse workforce. Don’t knock it until you’ve tried it.

8. What tools do you use to work remotely?

Nearly all of my tools are apps on my computer. I’ll pull out actual paper here and there if I’m having trouble wrapping my mind around something, because sometimes hand writing lists helps me think. The apps I use most are: Google Docs, Zoom, Slack, ToDoist, Trello, Hootsuite, WordPress, and Canva. Sometimes I have to pull out Skype or GChat.

9. How do you manage your business and taxes as a remote working professional?

I am an employee who is legally allowed to work in Canada and the US. Since I am a US citizen Uncle Sam gets a tax return from me every year even though my tax home is Canada. I use H&R Block’s tax software to help me keep everything legal and compliant.

10. What advice would you give to people looking to work remotely and companies making the remote switch?

For people looking to work remotely:

Most folks understand that they need to set up a work space. Few think about setting up their head space for remote success. We spend a lot of our book ‘Working Remotely’ covering this topic. Build in a support structure now.

In Buffer’s State of Remote Work remote workers said that unplugging after work and loneliness were the top things they struggled with. These findings have been consistent for the last three years.

The good news is that you can put routines in place to help with these things. Find a tribe—there are groups for everything—and attend their meetings. Make dinner plans with friends or family.

Find a local coffee shop or coworking space to work in when you need to get out of your home office. Volunteer. Set up a weekly or monthly social call with different people in your company. If you build this support structure now, you will have people to turn to if you’re feeling low. 

For companies considering hiring remote workers:

Remote work isn’t as simple as sending people home with their laptops. Remote workers need a virtual infrastructure. Make sure you have places where they can chat, meet with their colleagues, and get looped in on wider company news.

Make sure you’re compliant with all relevant laws where you hire employees. And if you want happy and efficient remote workers, manage outcomes instead of time in seat. You can be confident that your remote employees are working if they are turning in high-quality deliverables on time. You don’t need to invest in expensive monitoring software, with all the attendant privacy issues.

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