How to Start a New Job as a Remote Worker

HR reps say working from home is here to stay. How you start a job virtually, however, presents a new challenge for many.

Written by Nona Tepper
Published on May. 19, 2020
How to Start a New Job as a Remote Worker

You only get one chance to make a great first impression over Zoom.

In 2017, 43 percent of working Americans spent at least some time working remotely. Three years later, the COVID-19 pandemic has quickly scaled that percentage up. It’s safe to say everyone in tech — even those with firms that traditionally eschewed remote work, like IBM — have been working from home for the past couple of months. Post-pandemic, many think the practice is here to stay.

“It’s part of this new reality that we’re in and we just have to find out what works,” said Ally Davis, human resources manager at the Seattle-based Pitchbook Data.

As more people work remotely, the day-to-day of office life has gone home. Developers write code from their dining room. Coworkers build connections over Slack. The LA-based gaming entertainment TV network Venn moved its launch date up a few months to July, aiming to take advantage of social distancers’ demand for content. Human resources reps at the firm are now onboarding talent outside the office, with many new Venn employees finding themselves in the same tricky situation as others right now: navigating for the first time how to start a job remotely.

Theres much less wiggle room to hit the right tone. You have to be more intentional.

“Theres much less wiggle room to hit the right tone. You have to be more intentional,” said Rachel Cougan, head of people at Hiya, a Seattle firm that helps users block spam calls. “What's funny about all of this is, none of this is stuff that you would be doing if you were in an office. You just have to be better at it when youre not there.”

Remote workers may be physically distant from their team, but they still need to keep close ties. Matias Woloski, chief technology officer at Auth0, a Seattle-based identity authentication platform, said empathy is key.

“My biggest piece of advice is to be extra kind, patient and flexible when it comes to remote work transition, and rescheduling meetings in particular,” Woloski wrote in an email to Built In. “If someone doesn’t respond as quickly as you’d like, it might be because they are trying to reconcile a handful of things that have been thrown at them unexpectedly. Be kind to each other.”

Questions Remote Workers Should Ask Their Managers

  • What does success in this position look like in 30, 60 and 90 days?
  • When — and how — should I check-in?
  • How will I be measured? When are performance reviews?
  • How should I get in touch with you in an emergency?
  • Who will I be working closely with, and who should I ask for help?
  • Where are passwords and other information about the company stored?
  • Will you be measuring the amount of time I spend at my desk?


How to Prepare to Meet Your Boss for the First Time

Prepare to meet your new manager like you would prepare for a job interview.

Try to think about everything you will need to know when you start the role, Cougan said, like what success in the position looks like, how the manager prefers to communicate and who in the company can offer help. She recommended writing down employer expectations so they are not forgotten.

“As a new remote employee, its really sort of knowing what you need to know to be successful and being competent in managing up and asking for those things you need,” Cougan said. “A lot of managers dont really know how to onboard. They sorta just wing it and find out four to six weeks in, they should have said something in that first week.”

In addition to learning about the position and company, Davis recommended telling the manager who you are as a professional, explaining your work style and how you like to communicate. Ideally, this should be done over video, she said.

“Reflect on whats worked for you in the past, and start from there,” Davis said. “Make a few must haves, like, ‘Here are the things that make me really successful.’”

Questions Remote Workers Should Ask Their Teammates

  • What do you understand are the responsibilities of my role?
  • How do we currently work together?
  • What’s the best way to work together going forward?
  • What do you wish you knew when you started working here?
  • Do you have any tips about the office that may not be intuitive?


Leading From Your Living Room

As a remote worker, communication can feel transactional.

In a perfect world, a boss will schedule a virtual happy hour or coffee chat for remote workers to meet their new coworkers. If this is not built into a company’s onboarding program, Davis recommended remote workers schedule the event themselves.

“It really gives the new hire a chance to interact with their team on a more social level versus just the projects that theyre going to be working on,” Davis said. “A strong relationship is built on rapport and trust, and I think that’s a neat way to do that in current circumstances.”

Davis said new hires should also schedule 30-minute, one-on-ones with their teammates, as a way to learn more about the company, ask for advice and talk up their personal and professional background.

Cougan said introducing yourself with a Slack or an email message can also be effective. When it comes to including personal information, she identifies as an “anti-fun fact person,” since she thinks the subjectivity of the phrase leaves people self-conscious their definition of “fun” may differ from everyone else’s.

“I also think a lot of people have the attitude of like, ‘I don’t have any fun facts,’” she said.

If a company does not ask a new hire a specific question about who they are as a person, Cougan recommended including a fun photo — not a headshot — and a few personal hobbies. For example: Before Game of Thrones ended, she told new coworkers she was a fan of the TV show and asked how they thought the series closed.

“Whether its like, you are a coin collector, you love to run, you have a dog, you have children, you love to travel, write whatever those things are that are important to you and that are going to give somebody a conversation starter,” Cougan said.

If you started a new job with a cohort of new hires, Cougan also recommended creating a Slack channel for the group and sharing something new, encouraging or interesting about the company in the channel at least once a week.

“Try to build some connections with people and be seen,” she said. “My best advice for how you show up as a leader is just like expressing your point of view and listening to others. Its participation.”

As a way to build trust and connections, Woloski recommended starting casual, watercooler conversations with coworkers over Slack, or inviting them to a coffee hangout. At Auth0, the company uses Slack’s Donut app to randomly and regularly pair three coworkers for informal, 30-minute chats.

He recommended a similar strategy for driving trust with your bosses, too, and said remote workers should check in every morning to tell their boss their plan for the day. At the end of work, he recommended reaching out to them with either screenshots or links to what they finished that day.

“Trust is built from the bottom up and from the top down,” he said. “Multidirectional communication is critical.”

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Out of Sight, Out of Mind

New remote workers will mistakenly be excluded from at least one meeting, Davis said. When this happens, she said they should reach out to their manager and gently note how their attendance impacts their ability to do their job.

If it happens once, Davis said not to take it personally. If missing meetings becomes a pattern, however, she recommended telling your boss how being forgotten makes you feel and why it concerns you about the role.

Dont allow yourself to suffer in silence.

“Dont allow yourself to suffer in silence,” Davis said.

“Reach out to your manager, even if its uncomfortable. Conversation can come from a place of, ‘I wanted to make sure that Im getting up to speed appropriately. Im feeling a little left behind in this area. Whats your take on this? How should I move forward?’”


Celebrate the Small Stuff, and Create a Productivity System

Treat working from home like working from the office.

Davis said she uses Microsoft OneNote to organize her weekly and daily to-do lists. She also blocks out specific times of day to complete specific tasks. Once she finishes the item, Davis remembers to congratulate herself.

“Celebrating the small successes when you’re working from home is really important,” she said. “Try not to beat yourself up if you have an off day. Just say, ‘OK, what’s tomorrow gonna look like and what am I going to do differently to set myself up for success?’”

Woloski said he uses the pomodoro method — working for 25-minute stretches and then giving himself a five-minute break — to organize himself. He said productivity lies in building an effective home office too.

He recommends working in a separate place with a door, natural light, comfortable chair, monitor and external keyboard, and a good pair of headphones and camera.

“Remote work introduces the opportunity for countless distractions during the day, sometimes making it incredibly challenging to focus on specific tasks,” he said. “Ideally, you have a separate place in the house to dedicate to your work.”


remote employee
Image: Shutterstock

Tell Your Boss If You Need to Take a Walk

Difficult times draw out difficult conversations.

Whether it’s the coronavirus pandemic, or a presidential election, current events can influence the level of conversation coworkers are having with one another. As a new remote worker, Cougan recommended taking the time to express any stress you’re under and, whether it’s a walk around the block or time to do yoga during the day, asking for what you need.

“Find some sort of stress outlet and be expressive of that,” she said. “Youre cutting to the core of who you are a lot quicker than you might be when all youre talking about is your OKRs, right? Youre going to bond on different levels.

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